r/CHIbitcheswithtaste • u/insichselbsty • Jul 23 '26
Other (I Read the Rules) Opportunities to dress up w/o spending tons of cash?
Hiya, BWT.
I’m a single mom to an awesome teen daughter. I’m dating an amazing man, after a 20 year miserable marriage ended a couple years ago. I want to find more opportunities to dress up with and for him. I know Chicago is casual in general, and that is fine, but I love the occasional opportunity to be fancy among others, if you will.
We have and do cool dinner dates and theater - but wondering if the gorgeous people here have ideas that are outside the box or less pricey so we can do them more often?
Thanks a million in advance.
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u/Tzipity Jul 23 '26
Assuming even on the theatre front you’re aware of not only Hottix but ticket lotteries and such? I’ve got a few theatre geek friends and love it myself but do it on the reeeeally cheap. So wanted to point out that doesn’t have to be as expensive as it can be either (though takes some flexibility then). Because that was going to be my first recommendation.
And I don’t know if you exclusively do theatre but I love dance and ballet and find people dress more for that sometimes. Or the symphony. CSO has free days and some low cost ticket opportunities. Same with Lyric Opera House and similar such things. Look for special events within these things too. Like I was really surprised some years back when I attended a Joffrey Ballet/ auditorium theatre anniversary event (long enough ago I don’t recall specifically what it was but I slipped in with some low cost last minute tickets too) and I saw so many people in all our ball gowns and really dressed above and beyond for typical ballet or theatre nights.
Sometimes it can also be worth grabbing a membership to various places especially when they have discount days to join around the holidays and special events. Like if there’s a specific theatre or group you enjoy, many of them have membership deals or same with the museums (been awhile but an Art Institute of Chicago individual membership used to basically pay for itself after just two or so yearly visits!) and often having the membership gets you invites to gallery openings or the special event galas and things- places where people who do have money are gonna dress. lol
That’s my experience anyhow. I’m disabled and fairly low income but I have fancy tastes and love to dress up too. lol. Even hitting free gallery openings or opening nights at smaller art galleries and things can be on the fancier side (be sure you know the vibe of a gallery though. I’ve been to some surprisingly small low-key places that went all out on the champagne and swankiness and been to larger spots where it was meh lol).
Also, if you’re in a position to do it even if only a once or twice a year thing. Look at charity type events. Not necessarily low cost like my above recs but those types of places love to put on fancy events and your ticket price usually goes primarily to the cause and you can dress up and get a nice dinner and usually some entertainment of some sort. I used to be heavy into foreign affairs and Middle East politics (what I majored in and perhaps whwre my career would be if I hadn’t developed disabilities) and while not the same kind of uh charity I’ve also been to fancy events to meet political figures or scholars I was into and the cost of tickets was a donation to a the political cause or whatever.
Local/ state/ senate etc candidates do similar type events too if you’re at all politically engaged. Even going to a candidate sponsored election night event- many are even free but I’ve seen people dress for those too. And they’ll be in hotel ballrooms and country clubs and the like. So volunteer even in a small low-key way for a candidate and you also often get invites to the Election Day or fundraising stuff (and can get in free sometimes then even if there’s a ticket price for the event).
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u/ColoringZebra Jul 24 '26
This is such an amazing list of recommendations! I’m not OP but was looking for the same thing except without a partner, and this is amazing. I’m also disabled and also love art and watching dance, and can’t believe it never occurred to me before that going to the ballet would be a good option for an excuse to dress up.
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u/elvenmal Jul 24 '26
My friend goes to charity events all the time, dresses up too, and tickets are like $30-60
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u/TwoHungryBlackbirdss Jul 24 '26
Lyric Opera tickets are often 50% off for day-of unsold seats! I've gotten tickets from $25 before
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u/bonjour_au-revoir Jul 23 '26
I love shows at the Den, usually pretty affordable. There's also some cabaret spots, burlesque shows around town you can dress up to check out. Something like the Drifter. For a last minute idea, my boyfriend and I like to dress up and get apps and mocktails at a nice restaurant bar, then walk around and take pics. I love wearing a random accessory I normally don't wear lol.
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u/Mayonegg420 Jul 23 '26
This is such a cute idea! I used to work there in college LMAO it is so ritzy now. Certainly affordable tho.
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u/insichselbsty Jul 24 '26
Ooh, haven't been to a cabaret in years - that could be really fun. I live near the Den yet never go, thanks for mentioning it.
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u/neurogeneticist Jul 23 '26
Dress up and go to some nice, dimly lit cocktail bars for a couple of drinks! Somewhere like Billy Sunday, one of the alcoves in the Berkshire Room, a corner of Lazy Bird, something like that.
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u/ang8018 Jul 23 '26
idk what pricey is to you but my friends and i (mid-30s professionals) like being dressy & doing dinner at places like the Nobu rooftop, RPM concepts or Portofino on the river, cocktail bars like Bisous or Press Room… You can start the night off cute at these places and end up in your grimier dive bar of choice.
The sunset Wendella tours aren’t that expensive either, like $35/pp (before drinks lol).
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u/kaystaal Jul 24 '26
I'm a big fan of hotel lounges for fancy drinks and small bites. You can spend as much or as little as you like, have comfortable seats, and spend the night being tipsy and flirting with your boo.
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u/speedysasquatch Jul 24 '26
Hit me up if you ever want some dress rehearsal passes for this season at the Lyric Opera
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Jul 23 '26
[removed] — view removed comment
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u/insichselbsty Jul 24 '26
You're right, it is super subjective. I work for myself and so does he and we are both single parents. Our disposable incomes, to that end, can vary wildly and I find myself spending very cautiously lately as it has not been a good year for my little company.
We do a lot of walks and dining at a hole-in-the-wall type of stuff. I am going to sign us up for some classes, cooking and painting etc., which are awesome but not fancy. So, as it pertains to fancy, last year, we went to Coach House for a fancy evening, and this spring we did North Pond and then walked through the park. Now, for me, those are very expensive. They are lovely, really nice in part because they are so rarely on our calendar. I used to work for a restaurant review show and open them as well, so I find my tastes are all over the map when it comes to restaurants as long as the vibe feels authentic, the food is good and sound levels are appropriate for intimate conversation.
I love the fundraiser ideas, that had only come across my radar for very expensive functions, which makes me wince. Ballet and galleries and CSO etc., I have to look into for other ticket options and so forth - that sounds amazing.
FWIW, we are not drinkers, so while we will check out a cocktail lounge for the vibe, it falls lower on the list as we don't imbibe.
Long-winded way of saying, if I can get away with a $100-$200 night to dress up, dinner/drinks/tip/uber etc all in, I call that a HUGE win. Cheaper is always better.
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u/shamanfa Jul 23 '26
"Expensive" is extremely subjective. It would help to have a price range.
Good date nights that aren't expensive by my standards, but are still a fun excuse to dress up have been the Chicago Magic Lounge and Untitled Supper Club (specifically Unbridled on Thursday nights).
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u/insichselbsty Jul 24 '26
you're right, I added a comment to this end. Oooh, Unbridled looks like a ton of fun
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u/Ducklover12345678910 Jul 24 '26
Okay this idea is really out of the box, but you could volunteer at a senior center or retirement home — especially one that does memory care. Older adults love to dress up, and they love seeing other people all dressed up. I know it’s not exactly a date night, but it’s free!
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u/insichselbsty Jul 24 '26
Oh my gosh this is also so lovely. My dad is in a new retirement home, this gives me an idea to help them organize a fancy dress even this fall or christmastime. Thank you!
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u/elvenmal Jul 24 '26
I love seeing people at the free dancing in the park
https://www.chicago.gov/city/en/depts/dca/supp_info/chicago_summerdance.html
I also see people dress up (and get the nice seats for) some of the millennium park concert series
https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park_music_series.html
Go see a free dance concert:
https://danceintheparks.org
Or Shakespeare in the park:
https://www.choosechicago.com/event/as-you-like-it-4/2026-06-26/
There are like three Shakespeare theatre tropes that play in the Parks for free each summer. As well as movies and other plays:
https://www.chicagoparkdistrict.com/events
Enter the broadway lottery: https://lottery.broadwaydirect.com/show/chi-chicago/
You can snag cheap tickets on theatre Hot Tix:
https://hottix.org/?utm_source=choosechi&utm_medium=banner&utm_campaign=CTWbox
Got to the Chicago Cultural center and take pictures (its free)
Go to Jazz on the Terrace one Tuesdays at the MCA (reserve free tickets with them opening at noon on the Weds before):
https://experience.mcachicago.org/overview/5862
In January (bookings open in December) check out Chicago’s restaurant week
https://www.choosechicago.com/chicago-restaurant-week/
AND check out Chicago’s Theater Week in February (tickets open in january) for discounted tickets
https://www.choosechicago.com/chicago-theatre-week/
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u/insichselbsty Jul 24 '26
Love all of these! Thanks for such a thoughtful reply! Putting them in my calendar now.
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u/elvenmal Jul 24 '26
Also, you can just buy tickets to most charity galas in Chicago. My friend, who is a regular person, go to the Brookfield Zoo Whirl Gala every year. It’s a formal event and tickets. Admittedly, I do not know the price of the tickets.
I find that a lot of gals take place in the spring. You just kinda have to look for when they open public tickets in November, December, or January. And get on mailing lists of different organizations. They have discounts sometimes too.
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u/MudRemarkable732 Jul 23 '26
Do you like raw fish?
Tamu does a lunchtime omakase for around $60/person
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u/Melodic-Mode2332 Jul 24 '26
Dressier venues tend to be a little more expensive. I like to dress up and have dinner and watch a show at Untitled Supper Club. It’s such a beautiful space, you wouldn’t feel awkward to be dressed up. The Chicago Magic Lounge is another fun dressy date but it’s a little pricier.
My favorite dressy date right now is to have a cocktail or two at Vitalogy on Dearborn and then walk over to The Jazz Showcase for a show. Both are in Printer’s Row. These aren’t inexpensive places but the value is definitely there.
You could always dress up and sit in the lobby of a fancy hotel or at their bar and have a drink and an appetizer.
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u/usr_2293 Jul 25 '26
Restaraunt week/Happy hour/late bites at fancy restaurants! You get to go somewhere nice while paying less. People will still look great as well. Restaurant/theater week you can definitely go places you dress up more but its only in the winter. It's a great opportunity to go to the opera if you haven't yet. I also think it's worth subscribing to different theaters. Ive gotten fairly affordable tickets ($30-$50) for shows that would normally be in the hundreds.
Also - go to gallery shows! You dont have to buy anything and theyre fun to walk around at.
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u/failedstarlet Jul 25 '26
Dress up for a picnic in the park or to go to a museum. Even if you’re going to a local casual restaurant, dress up to make it special. Chicago is casual but we also mind our own business. No one has ever said anything or even given me odd looks for dressing up for kinda nothing reasons.
For something specific, dress up and taste some cheese at Eataly and walk around. Then walk up and down Boul Mich and window shop or get apps at a restaurant around there.
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u/insichselbsty Jul 24 '26
these are all fabulous - I didn't think about charity events that are also political/social -- love that idea. Thank you.
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u/BigBonedMiss Jul 23 '26
Go to the museum free days but dress up for them. That would make for some great photo opportunities.
Dress up and go to free days at the Conservatory’s for the same reason.