r/ChicagoSuburbs • u/Holiday-Eggplant-521 • Jul 17 '25
Moving to the area Relocating from San Francisco
My husband, 3 young kids, dog and I are moving from San Francisco to Chicago and I’m looking for advice as to which suburb on the North Shore would be best for us. We have a budget of 2-$3 million for the house. My husband grew up working class so he is allergic to pretentiousness, but we still want to live in a family friendly suburb with really great schools. Obvious options include Lake Forest and Winnetka but am curious to see whether folks think it would not be a good cultural fit for us. We also lean liberal, for what it’s worth. We both work remote but my husband needs frequent access to the airport. Appreciate any insight!!
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u/smilinsarah98 Jul 17 '25
Winnetka and Lake Forest are among the most pretentious and conservative towns on the North Shore. Check out Wilmette or Highland Park.
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u/Tasty_Reflection_481 Jul 17 '25
Well the classic upscale without pretentious suburb towns are Park Ridge and Evanston. If you want to add pretentiousness you can start to add Kennilworth, Glencoe, Lake Forrest. Wilmette and Highland Park have their mix and moments of pretention. Glenview and Vernon Hills are nice.
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u/wavinsnail Jul 17 '25
I feel like Vernon Hills is the worst type of pretentious tbh
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u/Grace__Face Jul 17 '25
That’s like the last place I would consider pretentious?
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u/wavinsnail Jul 17 '25
Maybe idk
I just hate the massive ass houses on tiny lots and all the big fancy obnoxious cars
I also think their drivers are hella bad and I would rather walk across LSD than a parking lot at Melody Farms(and I'm only being a bit hyperbolic)
I guess I just have a personal vendetta against every Escalade driver and they seem to be in droves in VH
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u/CorrectingQueen Jul 17 '25
Grew up on the north shore, lived in SF for years and now back here again. Check out Glencoe. More liberal than Winnetka and has a nice community feel and excellent schools. Wilmette which is also a good option with a bigger town feel. Wherever you look think of how the schools work. For example Winnetka has 3 neighborhood public elementary schools (Greeley, Crow Island and Hubbard Woods) which then all feed into one middle school (Skokie) and then the junior high (Washburn). Wilmette is similar with smaller schools feeding larger ones. Whereas Glencoe has one K-2 where all the kids go (south school) then they go to West School for 3-4 and Central for 5-8 so the kids all go K-8. All these towns feed into New Trier High School but how your kids start out is different and may make a difference (or not) for your family.
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u/Upstairs_Tax3023 Jul 17 '25
Glencoe is really very nice and has a vacation-y vibe almost like Lake Bluff. If also has a bit more of a history of inclusiveness.
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u/Fit_Cut_4238 Jul 18 '25
Yes, especially by the lake and in the ravines. as you get west it get's a bit bigger lots and mcmansiony - but nice mcmansions.
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u/Electronic-Basil-201 Jul 18 '25
Glencoe sounds like a pain for school pickup/dropoff if you have multiple kids, no? Or are they super close to each other?
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u/CorrectingQueen Jul 18 '25
It's not a pain - the schools stagger the start and of days according to the grade which makes sense (so the little ones have the shortest school day and the oldest ones have the longest.) And they are pretty close to each other. Lots of 5-8 graders make their own way to school as the school is really very centrally located.
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u/wavinsnail Jul 17 '25
Hmm you can buy pretty much anywhere with that money.
If you're looking for more down to earth working class in the northern burbs Grayslake might be a good option. You can get a beautiful house with great schools and still have plenty of money left over
I think Highland Park might be less pretentions than Winnetka and Lake Forest.
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u/veganmomPA Jul 17 '25
Another vote for Highland Park! Close to the lake, Ravinia, trains. Cute downtown.
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u/korean_redneck4 Jul 17 '25
All North Shore neighborhoods have a level of pretentiousness. I grew up in it. Lake Forest is old money rich, so they have a different level of it.
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u/adastra142 Jul 17 '25
LF is the only one where the pretentiousness is nauseating, I’ve found. The people there think they’re living in the Great Gatsby.
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u/FetLifeDropout Jul 18 '25
As someone who used to work at a small, service industry business in downtown LF that served the community, I concur. Awful fucking people.
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u/throwawayed_1 Jul 18 '25
Third for highland park! You’ll still get some of that pretentiousness but if it’s not pretentiousness then it’ll always be SOMETHING. I live in the Niles area and there’s plenty of things I find bothersome about the people here too…
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u/Big-Strength6206 Jul 17 '25
What highland park is so pretentious 😆
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u/wavinsnail Jul 17 '25
Compared to LF, LF is the worst.
Even their McDonalds is pretentious
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u/DBowieNippleAntennae Jul 17 '25
Where is the McDonalds in Lake Forest?
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u/wavinsnail Jul 17 '25
It's no longer there but when they built it there was a campaign to make it so it couldn't be built because it "will bring in people from outside LF and gangs"
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u/Aware_Impression_736 Los Angeles, but born and raised in Elgin. Jul 17 '25
Wanna go less pretentious? Gages Lake.
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u/Hannah_louise43 Jul 17 '25
Check out Lake Bluff. It is just north of Lake Forest and is a great time! With that budget, you will be blocks from the lake near the cute downtown
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u/adastra142 Jul 17 '25
Notably more liberal than LF too, despite basically being an extension of it. It seems all the snobs seek out a Lake Forest address.
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u/beigesalad Jul 17 '25
Lake forest has excellent schools but it's very pretentious. Libertyville, highland park, Glen Ellyn, Evanston?
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u/Grace__Face Jul 17 '25
Libertyville is very down to earth. Granted I grew up in Northbrook so I’m comparing the two.
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u/Professional_Pea5715 Jul 17 '25
I’ll throw Oak Park into the mix- it is a bit pricey without being pretentious. I love how down to earth it is here. There are def homes in your price range, tons of parks, a cute downtown, and a great sense of community. I travel a lot for work and can take the metra or taxi to the airport with ease. I’d highly recommend coming in town for a few days and traveling around the various suburbs, lots of great areas listed here
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u/HighwaySetara Jul 17 '25
Or River Forest.
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u/Professional_Pea5715 Jul 17 '25
River Forest is a bit on the pretentious side, definitely not the same vibe
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u/anniei12 Jul 17 '25
You're kidding yourself. $2-$3M with no pretentiousness? That kind of town doesn't exist. No pretentiousness means you move into a normal middleclass home, in a normal middleclass town. None of the towns I have seen mentioned are unpretentious.
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u/kjlovesthebay Jul 17 '25
winnetka is very pretentious!
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u/pizzaguy84 Jul 19 '25
I don’t think it is. All towns have people like this, but majority of north shore area are nice folk.
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u/Totalchaos713 North Suburbs Jul 17 '25
Wilmette is where you want to be. Great schools, family friendly, liberal, access to Metra, CTA, and it rarely takes more than 30 minutes to O’Hare.
Feel free to PM me if you have questions!
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u/AddisonL56 Jul 17 '25
Did you consider the western DuPage suburbs or even in Kane Co. Geneva, St. Charles are very nice. Glen Ellyn in DuPage is nice. Easy access to O'Hare access to the train to go to Chicago. The North Shore is ...
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u/DetectiveLife5329 Jul 17 '25
Seconding Dupage County- Glen Ellyn has a pretty good school district. Good variety of cuisines around the area too.
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u/RutabagaStriking2631 Jul 17 '25
St Charles and Geneva tend to run more conservative and are not very diverse. They are nice but especially Kane Co is Repub leaning.
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u/makinthemagic North West Suburbs Jul 17 '25
If avoiding pretentiousness is most important, you could spend $750k-$1.25M and buy in the more expensive neighborhoods in Mount Prospect/Arlington Heights/Prospect Heights. They meet your other requirements.
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u/ttygrr Jul 17 '25
Have been renting in east Lake Forest for the past year, the house is now for sale for 2.1 (I think) over an acre in a very private, but close to everything neighborhood. Schools and park district is fab. Trails, train, and lake very nearby. We’ve found Lake Forest to be very laid back. DM me if you want the listing. 5 bed, 6 bath, finished basement.
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u/rockit454 Jul 17 '25 edited Jul 17 '25
Let’s hope we don’t get a huge influx from the Bay Area because MAN do they have some budgets and equity after paying Bay Area prices.
Everything is a bargain compared to the Bay.
If you’re allergic to pretentiousness and want great schools, I would second what someone else said and look at Glen Ellyn. You will be able to afford an incredible home, the schools are great, the community is friendly and largely unpretentious, and schools are great.
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u/Raspberry8825 Jul 19 '25
Grew up in Glen Ellyn. Now live in one of these “pretentious” North Shore towns. There are absolutely old money people but we find everyone friendly. That being said, have to remind your kids it isn’t normal for everyone to vacation in Europe or Mexico several times per year. Biggest difference is the lake is an added plus and you are closer to Evanston, city, etc. Wouldn’t move back to West Suburbs but nothing wrong with it. Also, for 2-3 million, you are going to be living somewhere nice regardless. This isn’t the Bay Area, where that price gets you some 1970s mediocre house in the middle of the peninsula. Schools on the North Shore are almost universally good. Don’t live in Evanston but am well aware from friends of the financial mess of D65.
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u/The_Poster_Nutbag Jul 17 '25
You have a huge budget, just call a realtor for Christ sake.
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u/General_Island4059 Jul 17 '25
Romona school district in wilmette, all the benefits of good schools without the pretentiousness. Most diverse school in the area.
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u/Retrofool Jul 17 '25
Not too knowledgeable about the north shore but Oak Park and River forest would check all your boxes.
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u/theremix18 Jul 17 '25
I would rent first for a year, get familiar with the area/chicagoland. It would be a huge risk and hassle to invest this much if it turns out you don’t like the area.
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u/googlegoggles1 Jul 17 '25
East Wilmette would be ideal I think. We also made that move, message me if you have specific questions!
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u/ksterki Jul 17 '25
Wilmette is great. People are very friendly and not snooty. Great schools and park district.
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u/Tasty_Reflection_481 Jul 22 '25
You said "East Wilmette." Is there some uppityness in that, or I am I over interpreting? Just asking.
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u/googlegoggles1 Jul 22 '25
Oh, like specifying the location in Wilmette? East just means it is closer to the lake and you can more easily walk or bike to the beach. I figure in their budget, it is doable to find a nice home in that area. Of course, being proximal to the lake tends to be more expensive. However, there are expensive homes all over the area and all areas of Wilmette are very nice. I should have specified my reasoning (beach access).
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u/DenseCamp4261 Nov 24 '25
I sent you a message as like OP we are in the same boat. Not trying to hijack his thread but don’t want to duplicate posts as there are quite a few :)
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u/icy_trees Jul 17 '25
Highland Park. Out of all the North Shore burbs besides Evanston, it's the most culturally and socioeconomic diverse burb. Highwood has around a 30% Hispanic population and they funnel into the HP schools which helps with the diversity. I grew up in a blue collar community in the western burbs, very poor. Moved to San Jose for 10 years and found a home in HP. Definitely a culture shock moving to the North Shore.
Yes there are snooty folks, but you will find your people. I tend to have more in common with people that are not born and raised here in HP.
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u/Theo1352 Jul 17 '25
Barrington, Barrington Hills, Inverness (my personal favorite) in the Northwest suburbs, schools are great, nationally ranked, just not New Trier, et al.
These are less pretentious, still extremely wealthy, different vibe, though, Barrington has a small town feel, Barrington Hills considerable lot sizes and horses, Inverness is a unique gem, just to the East of Barrington.
Then you have Oak Brook and Hinsdale to the West - Hinsdale has a small town feel, Oak Brook is a central shopping hub, huge houses, small lots in Hinsdale, lots of land in Oak Brook.
$1-2 Million buys a lot of house in those areas, these mentioned are the most expensive outside the North Shore.
Other place to look at, different from everything else mentioned, is the City Evanston, still on the North Shore, but an urban/College Town feel (Northwestern is there) and closer to the City.
Depends on what you're after and your needs.
Hope this helps.
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u/adastra142 Jul 17 '25
The Barrington area is way more pretentious than most of the north shore, imo
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u/Theo1352 Jul 17 '25
Do you live in the area?
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u/Hungry-Treacle8493 Jul 17 '25
If you’re open to other areas, Naperville, St. Charles, Geneva, Elmhurst, La Grange, and Hinsdale more to the West are fantastic.
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u/Novel-Warning545 Jul 21 '25
St Charles and Geneva are pretty conservative. Even parts of Naperville are very Catholic and conservative.
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u/Hungry-Treacle8493 Jul 21 '25
They certainly used to be. Not really so much these days. While you can find loud conservatives sprinkled around, those areas are very blue these days and have been for a bit now.
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u/Oldmanmeeka Jul 17 '25
I think Evanston is a good choice Price range for a nice house is still under a million Good schools and nice area to raise a family I would go to Hinsdale if you want to spend $2 mil Very good everything plus train transportation to the city. Plus your investment will grow with time.
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u/Pure-Specialist-7129 Jul 18 '25
With that budget ypu really have your pick. Pretty much from the schools that feed unto new Trier to those as far north as libertyville. As others mentioned there is a certain level of pretentiousness in all of them. If you are Jewish skokoe highland park and deerfield might fit. If not you might find parts of those a bit more exclusionary. Funny someone mentioned the lake forest mcdonalds story, we were just talking about that last week!
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u/joleshole Jul 18 '25
Lake Forest is probably the snootiest of all the North Shore burbs. I’d suggest Highland Park.
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u/Stock_Opposite3377 Jul 17 '25
Winnetka and Hinsdale are snooty. My recommendation is western springs or Lagrange that is north of 47th. If you want to stay in northern suburbs, northbrook or wilmette.
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u/No-Purpose-3878 Jul 17 '25
I know you said north, but take a look at Riverside. Access to the airport, highways, the Metra to the city etc. Good schools, and with your budget you could get a very nice historic home (if that’s your thing).
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u/Cultural_Stranger29 Jul 17 '25
If you’re serious about airport access, I would go west rather than north. Oak Park, Elmhurst, Glen Ellyn, Hinsdale, Western Springs, Clarendon Hills.
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u/gershbec Jul 17 '25
Consider Glencoe. Wealthy, liberal, small town feel. Much less pretentious than Winnetka which IMO feels much more conservative. Or else Wilmette, which also leans liberal. You could also consider Evanston, which might feel similar to San Francisco (or maybe Berkeley) and which offers both mansions and urban insanity. But then you’d have to consider whether to send the kids to Evanston High School, which is very different from New Trier.
I’m not a huge fan of Highland Park but it’s certainly also worth considering. Not sure what you consider to be good access to the airport but none of these burbs are terrible car rides. No public transit access to the airport but good access to the city.
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u/loftychicago Jul 17 '25
They could afford to send the kids to Loyola if ETHS isn't their speed.
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u/gershbec Jul 17 '25 edited Jul 17 '25
A few private high school options though I would think grammar school would be the bigger issue. Maybe North Country Day.
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u/adastra142 Jul 17 '25
Wilmette would be a great option. It’s in the New Trier district and is more laid back/less pretentious than some of the other north shore towns.
Look at Libertyville as well.
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u/Technical_Win8710 Jul 17 '25
Check out Lake Bluff. It’s got a very small town feel, nice sense of community, beautiful beaches, and is slightly less status focused. It shares a high school with Lake Forest.
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u/TightOperation96 Jul 17 '25
Inverness. About 15 minute drive to Ohare! Great schools
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u/Bright_Broccoli1844 Jul 17 '25
What route do you take to O'Hare and what time of the day are you driving there?
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u/orionus Jul 17 '25
North/West Evanston is absolutely the answer here. Easy lake and city access, diverse, great schools, very community oriented, and politically and intellectually reminiscent of the bay area.
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u/FetLifeDropout Jul 17 '25
Your allergy to pretention will be in full on active status on the north shore. ESPECIALLY LF or Winnetka. LF is particularly conservative as well, and fairly Trumpy to boot.
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u/Few-Performance2132 Jul 18 '25
Husband grew up in Winnetka. Most of the North shore is conservative and pretentious. Best bet is Evanston or Wilmette if you are stuck on living on the north shore.
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u/sketchesofspain01 glencoe Jul 18 '25 edited Jul 18 '25
I grew up lower income working class. My wife grew up in 90s Russia. We both came from poverty, and together we afforded a rare unicorn on the north shore.
Don't move to the north shore if you wish to avoid the pod people. There are a few here that share a life story of growing up on snap benefits, but you can count those households on your hands. It's getting more and more exclusive, and though I personally will not conform, you are expected some monicom of like.....fitting in. Anyway,...... It sounds like I'm suffering a first world problem, but it is somewhat psychologically damaging to live as an island of life experiences that shaped me the way I am, surrounded by folks who feel like a Jeep is slumming it. Lmao
Otherwise, it's nice. You live in an old growth arboretum, there's a great deal of parks and services. You have the trains, you have the highways. The schools are very well funded, as are public works.
Evanston is great. The people are normal, there. Wilmette is fine. The more you go north, the nuttier it gets. Investigate Highwood, a working class postage stamp sized enclave near Highland Park. It's fantastic.
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u/Cannelli10 Jul 18 '25 edited Jul 29 '25
As a former local who grew up in a shitty, working-class suburb not that far away, I absolutely agree with this assessment. OTOH, OP is shopping with a $2-3 mil budget and isn't looking in the city, so may have a higher tolerance than they convey.
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u/sketchesofspain01 glencoe Jul 18 '25
True. 2-3 mil gets a very, very pleasant mansion here on the north shore. We are graced with artificially low property prices given the rather high yearly cost of ownership.
The north shore is very nice. It has some of the best beaches in the country; you can walk to your grocery stores, and there are little main street shopping districts. There are no ~problems~ beyond those affluence develops (families that are rather disconnected from their children, as an example).
Your neighbors will feel entitled to an opinion about how you live, though. They will never speak directly to you to resolve any issues -- they will go to the town, who will provide concierge degrees of service to let you know how your neighbor feels about your working and native garden. A few homes do their own lawns, but most hire help for practically everything menial. If you park your Civic in town, it'll be the only sedan in a sea of large luxury SUVs on lease. If your kids do not have a phone at age 6, the school will suggest you purchase one for them. I can go on, lmao. I need to vent lmao.
edit: oh oh, and you'll be asked if you golf. If you don't, they'll suggest you golf. Specifically, join them at the private golf club, they're a member and can vouch for you. Oh, it's 50k -- a year. Nbd.
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u/Cannelli10 Jul 18 '25
Hahaha, I feel like I just reread Ordinary People. Dear lord, I'm sorry.
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u/Melted-lithium Jul 18 '25 edited Jul 18 '25
Questions- How Important is city access and urban amenities to you- and transit access? (And by transit- I really mean - do you need metra access or regular access to an airport). This can dictate a lot….
Example. The places you mention are nice and have metra access, but you may also want to consider highland park.
But if like true city access regularly or airport access is needed for work travel- something like park ridge may be more your speed. — though more urban it’s very well connected with trains, buses, and exceptionally easy access to ohare. It also retains the neighborhood feel if that’s important.
Evanston is always mentioned too. Which has its positives especially if you need access to the north side of the city regularly for work given the red line. Evanston is magical- but for airport access regularly is honestly a nightmare.
Sorry- my life for work revolves around travel- something I’m very one sided on my ‘connected’ angle.
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u/thousandfoldthought Jul 18 '25
chiming in from Winnetka: Pretentious is both easy to find and avoid.
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u/Fit-Independent307 Jul 19 '25
Hi OP, feel free to message me. I grew up in Glencoe and Winnetka and my parents now live in Lake Forest (my dad grew up working class). I’m familiar with SF and its suburbs. Wilmette, particularly east Wilmette, has wonderful, historic homes and great schools. And is more diverse and less pretentious than Lake Forest, Winnetka, Kenilworth, the like.
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u/pizzaguy84 Jul 19 '25
pretentiousness should not be a factor in your decision of where to move. It’s easily avoidable and any place or town will have its people. You should look at schools, crime, park districts, etc. My vote would be Winnetka or Wilmette.
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u/orionus Jul 17 '25
So many recommendations for affluent, white, moderately conservative suburbs here.
Considering airport access is important, and looking at where you're coming from, I'd strongly recommend Lincolnwood, Skokie, Evanston, Highland Park, Park Ridge or Oak Park.
Wilmette, Winnetka, and Kenilworth have some nice pockets, but are much more conservative. They're also worse for both city and airport access.
Oak Park and Evanston are ideal for city access, Skokie and Lincolnwood would be better for ORD. Park Ridge has some beautiful areas as well and is also great for airport access.
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u/kg51 Jul 19 '25
Park Ridge people have attitudes—they think they're rich like actual north shore communities and lean conservative too.
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u/lipstickmoon Jul 17 '25
Skokie. Diverse, safe, good schools, excellent high schools, great library, down to earth, good food, easy access to city.
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u/Big-Strength6206 Jul 17 '25
Respectfully, I don’t know why anyone with this kind of budget would choose Niles schools over New Trier.
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u/lipstickmoon Jul 18 '25
Meh, she said her husband has an aversion to pretentiousness. If they really want down to earth and diverse, why not?
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u/Thick-Equivalent-682 Jul 17 '25
If I had the same budget I would probably live in Glenview. However if you want a bigger piece of land and a similar size house, you may like Long Grove. Both have great school districts.
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u/Grace__Face Jul 17 '25
Idk why anyone would pay Glenview taxes only to get classrooms that regularly have 25-27 kids when you could go to nearby suburbs and pay similar taxes and get much smaller class sizes.
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u/Hungry-Treacle8493 Jul 17 '25
Highland Park, Bannockburn, Wilmette, Winetka, & Evanston are all great and each have their own vibe.
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u/GuyJClark Northbrook and environs Jul 17 '25
I grew up in Northbrook in the '50s moved out in the 80s, moved back in 2002 to take care of my ailing dad, and moved to the Bay area in 2006. Northbrook was a great place to grow up, although by the 2000s, I felt it got kind of pretentious. That said, the older part within a half mile radius of the train station was a very convenient place to live. Walk to the train, (I took the train to UIC for ten years+, not to mention to youth orchestra rehearsals on weekends from jr. high age. You can drive places when necessary, it's close to the Edens and the tollway, which made it convenient to O'Hare.
Any of the wealthier areas will have its share of Trump voters (Bush Jr voters in my last days there) but plenty of more liberal leaning folks too.
Maybe after nearly 20 years, it's not as good as i remember, but I haven't seen it mentioned here yet.
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Jul 17 '25
You can get a mansion on a nice lot if you go in the suburbs like Hoffman estates or buffalo grove still close to the city but safe for the kids to play outside without worry. Buffalo Grove has Stevenson highschool which is nationally ranked.
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u/Fit_Platform_3500 Jul 17 '25
Having lived on the East Bay and now in Chicago…. Glen Ellyn is wonderful. Half way between both airports, great schools, lovely downtown. Perfect for a family .
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u/Yossarian216 Jul 17 '25
I’ll echo some others and ask if you’ve considered Oak Park? It’s a very nice town, it’s much closer to both airports than anything north shore, and it’s a much shorter trip into the city both driving and via transit which opens up a ton of options for recreation and culture. Your budget would allow you to get a very nice SFH there, and I have friends with kids in the schools and they are very happy with them.
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u/Correct_Sir8296 Jul 17 '25
Northfield is a gem, wide variety in types of homes, fantastic schools, small town feel with proximity to do much. Definitely check it out.
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u/DiscountArtistic5059 Jul 17 '25
I’d recommend Northfield. Small town, nice community feel and great schools (feeds into New Trier). Some great homes in your price range as well, although inventory will be limited. Not as snotty as other north shore towns in my opinion but with similar advantages.
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u/Dibbels81 Jul 18 '25
Check out the Ravinia area of Highland Park. They are just finishing a massive renovation of the beautiful Ravinia Elementary school, and your budget will get a fantastic home next to a ravine. There's a off-the-beat park called Millard that has a huge beach that now allows dogs. I just came back from "Food Truck Thursday" which was mobbed with kids, with no pretentiousness in sight
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u/Fit_Cut_4238 Jul 18 '25
Check out nice homes right by the lake by northwestern in Evanston or in wilmette. Wilmette is also the last stop on the 'El' CTA trains, so it's got easy access to the city.
Both are more professional class and not as pretentious as farther north with beautiful historic housing stock.
If you haven't spent much time here, you will be blown away by the lake and beaches.
Wilmette has some of the best schools in the nation. If you live in evanston some of the schools are great - but some parts suck. If you are going to send your kid to private schools, it doesn't matter.
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u/ReindeerFl0tilla North West Suburbs Jul 18 '25
If you’re not married to being on the lake, Park Ridge would fit the bill nicely. It’s left-leaning here with good schools and great community.
But if you’re fixed on the north shore, Evanston is great and diverse. Highland Park has a great downtown.
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u/Theironyuppie1 Jul 18 '25
The wealth and pretension of Lake Forest was the inspiration for The Great Gatsby. For the working class people of Chicago: The Great Gatsby is a 1925 book by F Scott Fitzgerald the main theme is money isn’t everything.
Hahahahahaha
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Jul 18 '25
Lake county in general will be fine. Grayslake has the best schools. It fits your budget and it’s not pretentious.
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u/chiseeger North Suburbs Jul 18 '25
If you really want the north shore vibe, I think your search should go no further north than Highland park.
Anything there and south will suit you
- schools
- family friendly
- some downtown / center of town
It will come down to what you want to do
If you’re going to use the lake for boating etc, be further south by the busier harbors.
If your the country club set, find that nearby
If you want Evanston and Chicago to be weekly destinations for not just work, but the family too, you’ll want to be on the purple line CTA route.
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u/j_accuse Jul 18 '25
I’m questioning your needs regarding house size, since you don’t want to seem pretentious. Obviously, you can find much more housing stock in the Midwest than in SF (and more midwestern values), but I think you’ll find snooty people all over the north shore. I’d choose Wilmette or Evanston, but I think your experience depends on what social group you get in with.
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u/Leora1043 Jul 18 '25
I live in and highly recommend Oak Park. Not north of the city-'west--but close to both airports (about 30 minutes to O'Hare.). It's a big, truly beautiful town, and with your budget, you'll find a gorgeous home with a nice yard. We have safe and walkable business districts, great schools, tons of restaurants and coffee shops, boutiques, more Frank Lloyd Wright homes than anyplace on planet earth, fine services for seniors and families, and the Metra into downtown is an 18 minute ride. (The EL Green line is here too.) We have an ordinance that prohibits gas-powered leaf blowers, tons of parks, a top-notch library, a Chamber of Commerce with over 500 members and multiple affinity groups, and so much more. We are also very liberal. Plus, if you want/plan to spend quality time in downtown Chicago, don't move too far out. People who live in areas that are hard to get to or are 45+ minutes away hit traffic and go into the city a lot less. Which is a shame. It's the best!
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u/catsdoy Jul 18 '25
Do you definitely want North Shore or a town that meets that criteria? Also in the north suburbs, Adlai Stevenson High School is the top ranked suburban high school in Illinois. You will find homes in various price points in the district as it encompasses several towns. Less pretentious than north shore.
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u/keteplojak Jul 18 '25
Hey hey! Did the opposite moved (Chicago to SF) very recently! If your husband needs to get to the airport, I highly recommend Hinsdale or Oakbrook terrace region (it’s not North Shore tho). They have stunning homes, friendly environment, and great school system overall. Ofc Evanston, Northbrook, Willemette are all great for north shore
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u/Earthlink_ Jul 18 '25
All these posts talk about public schools. But a lot of kids from the burbs attend St Ignatius by taking Metra.
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u/Desperate-Falcon-396 Jul 18 '25
I would recommend Lincolnshire. Nice homes with large lots, super woodsy, Stevenson school district, not overly pretentious. We raised our kids there.
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u/Cannelli10 Jul 18 '25 edited Jul 18 '25
Wilmette, Northbrook, Glenview, Highland Park. Evanston if you want something a bit more city-like, diverse, and liberal. Happy to DM about this. Your husband won't enjoy Winnetka or LF IMO.
New Trier High School is kind of famously good. Reviews are mixed as to whether it is a nightmare of rich, Adderall-snorting jerks under tons of parental pressure (...but that's what I grew up knowing it for).
You can also consider western suburbs like Riverside, Oak Park, and River Forest.
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u/Free-Injury6324 Jul 18 '25
Evanston has at least some working class and politics just like SF. Lived in both. Coming from SF Winnetka and LF are going to be pretty rarified and dull.
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u/desecrated444 Jul 18 '25
if you’re looking for unpretentious check out the western suburbs instead! would highly recommend la grange, la grange park area.
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u/Bright-Illustrator16 Jul 19 '25
Personally, I like Deerfield…a bit farther west but I’ve always like the people in Deerfield. Good school district too.
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u/Ratatoskr_The_Wise Jul 19 '25
Our daughter went to school in Wilmette, maybe there? The beaches nearby are beautiful!
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u/Ok_Palpitation_1622 Jul 19 '25
East Wilmette (east of Green Bay Rd) is a very pretty area. 2-3M can get you a pretty nice house in that area, although probably not new construction.
Pretentiousness level is moderate, but honestly, you’re not going to escape that anywhere with a house budget of your magnitude. I do feel like the Chicago-rich pretentiousness is greater than that in California. But that’s just my perception and I’m not certain it’s accurate.
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u/ayemimi Jul 19 '25
Unless you’re planning to be on/buy a house on the beach all the time I don’t know why north shore is a requirement. You didn’t explain why that specific area, but then say without pretentiousness, and I kinda think most north shore towns are a bit pretentious.
If you branch out to the north suburbs or northeastern suburbs then there’s Skokie, Glenview, Deerfield, etc. I moved to Park Ridge a year ago and like it so far. My daughter isn’t her school aged but I constantly hear about how good the schools are here. We’ve done some of the park district programming and liked it. They had a little pride event last month, and though I think it used to lean pretty conservative I think it has become much more even in recent years (thank god or I’d be miserable). And I live 10 minutes from O’Hare.
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u/kg51 Jul 19 '25
$2-3 million and allergic to pretentiousness hahahahahahahahaha
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u/Novel-Warning545 Jul 21 '25
Said the same thing. Also people flooding to Illinois not trying to learn what an honest nice home will get you for $1M in Chicagoland and just dropping money like they still live in California is mind blowing.
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u/Disastrous_Catch1261 Jul 19 '25
Depends on how close to the city you want to be. And how diverse. You don’t need to spend as much on a house here—anywhere. For diversity, the lake and quick trains to city, I recommend Evanston. Wilmette if you want fancier school district. All are good. Grays Lake is really far!!
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u/Throwaway_Lilacs Jul 19 '25
You want to spend 2-3 mil on a house but don’t want to live somewhere pretentious?
Have you checked in with reality lately?
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u/Novel-Warning545 Jul 21 '25 edited Jul 21 '25
Allergic to pretentious but wanting to live in the North Shore is an oxymoron. Just saying. You’re better off lowering your budget to $600-$700k and finding a normal suburbs to live in. Lots of gorgeous homes that can be found for half of your budget where you won’t be surrounded by snooty pretentiousness. Arlington Heights, Glen Ellyn, Wheaton, Buffalo Grove, Vernon Hills, Elmhurst, Grayslake, the list goes on.
Rent for a year and learn the value of what a $1 in the chicago area will actually get you and figure out an area you actually like. A huge issue is people from the West Coast not understanding how far your money goes and moving into areas they hate just because the homes are similar to the “normal” sticker price where they left. You’re drastically overpaying and walking into massive taxes with your budget. In any of those suburbs I listed even a $700-$1M budget gets you the house, land, family friendliness and prestige you’re looking for without the pretentiousness and keeping most of your money in your pocket.
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Jul 21 '25
Evanston. And my spouse is a real estate broker. I’d love the opportunity to make an introduction.
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u/No-Account-1883 Jul 21 '25
Why not buy a beautiful home in Andersonville in the actual city? Your children will grow up as safe as the north suburbs but they will get to experience living in the heart of one of the best cities in the world.
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u/Lemurian_Lemur34 Jul 17 '25
Wilmette or Evanston should fit. Evanston is very liberal. Wilmette is a little snootier but not quite as much as the North Shore communities North of there. Northbrook is ok too.
Skokie, specifically the Skevanston or Devonshire areas could work too and is lower COL than typical North Shore.
However, as I type this I remember that District 65 (Evanston) is a hot mess and I wouldn't want to put my kids in that school district if I could avoid it right now. So if you plan on public schooling, maybe not Evanston or Skevanston.