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Chi-Town Breakdown - My Favorite Bars in Chicago

Updated: Sep 4, 2021

I’ve been totally itching to write something a little different lately, and seeing as I had an absolute BLAST in Chicago I figured I should give the deets! Like where I went, what I loved, what I hated, and what I wish I hadn’t run out of time for.

So the background of why we picked Chicago goes a little something like this – It was my roomie’s 24th birthday and we decided we should try something a little different. The Ancient Aire Baths had a little (or a lot) to do with our decision on where in the world to go but the rest of our plans were only roughly planned out. We thought we had it down with every day planned out down to the outfits – outfit changes and Instagram-able spots with the cutest photo ops, Duh. But upon arriving we were swarmed with recommendations of things to do from friends.

We took all the lists we were given and sat down to narrow it down – naturally, the places that were recommended on more than one list were our MUST visit places! Our trip went as follows-

Ancient Aire Baths

First, stop Ancient Aire Baths! I cannot recommend this place enough! Upon arrival, we quickly dropped our bags at the hotel and took an uber straight to the spa. Everything was booked in advance, of course, and I’m so glad we did! Not a moment was wasted sprawled out on the hotel beds before we set off to explore the city! The entrance to the baths is in an ALLEY y’all, and come to find out that’s pretty common in Chicago but at the moment we were hesitant as to where in the F our Uber was dropping us off. The whole experience was so cool and I won’t bore you with all the tiny details but just know that I got hands down the best massage EVER here. 10/10 recommend! Our bath time was split into two sections, one before and one after our massage and it was so so nice to let our muscles warm and loosen up in the hot baths before going into our treatment. Also, force yourself to do the cold water plunge – I promise you won’t regret it! The only advice I have for coming here is to bring your own hair/skin products for after. We did not and wished we had. They provide a few complimentary products and while the showering supplies were perfectly fine, the hair products available were very cira 2002 (I’m talking hair mouse and Garnier hair gel, like what) Oh, and before I forget, your time in the baths is timed and supposedly there is a bell sounded every 30 minutes but I don’t remember hearing one at all while I was there… You are able to ask the attendant how much time you have remaining but that’s kinda stress-inducing so I’m not sure what exactly the solution is here… Maybe they can be convinced to put a chic low-profile analog clock on the wall? This is my only complaint

The Beatrix

Next up, dinner! For our first night in Chicago, we went the no makeup, leggings route and found our way down to the hotel restaurant for dinner which turned out to be excellent! What I find funny about this is that we ate at other hotel restaurants during our stay but for some reason, your own hotel restaurant always feels less glamorous, am I right? Anyway if you ever stumble upon The Beatrix while in Chicago, the hummus and kung pow cauli are musts!

Corey's Bagels

Day 2 started with bagels at Coreys Bagel’s – YUM We actually went here twice while we were in town because we have a serious weakness for a good bagel!

Skydeck .... kinda

Next, cue failed Skydeck experience. The original plan was to get to the Skydeck right at opening and hopefully before the crowd but we couldn’t tell you if that plan worked or not as it didn’t happen… Already set to arrive late, we were advised by our Uber driver to get a drink or two before conquering the sky deck and If you know me you know that I’m TERRIFIED of heights so this sounded like a great idea! Once we were slightly tipsy we trekked our way back to the sky deck and got in line – WOWZA y’all that line is no joke. I mean Adele was ready to bail almost before we got in line but I was like “no no no, we will regret this if we don’t do it” Fast forward 30 minutes I spot a sign that says groups of 3 or less are restricted to 60 seconds on the Skydeck as a courtesy to other visitors waiting in line… Now I already know that it’s going to take my scared ass 60 seconds just to CRAWL out there and then I need at least another 60 seconds to gather my composure and take a photo. PLUS my buzz is already wearing off so at this point I’m ready to bail as well. I still want to do the Skydeck at some point and I definitely want to go back to Chicago but $25 apiece for a minute of deck time after waiting for what was surely going to be at least an hour was not what either of us had in mind for this trip!

The Hampton Social

The Hampton Social, cute atmosphere, v v picture-perfect Rose All Day sign (if you get lucky enough to arrive when people aren’t eating in front of it. Decent oysters but do not come with crackers? Is that a thing?

Joe and the Juice

Joe and the Juice, adorable coffee and juice bar! Pink cups are adorable! (also for some reason the entire block in this part of Chicago smells like a brownie and apparently, the wonderful smell comes from the Chocolate Factory, I didn’t get a chance to go but it’s on my list for next time!)

Two Dots and a Das Tiki Bar

Two Dots and a Dash Tiki Bar – So here’s the thing, if you like Tikki bars then definitely check this one out but if a super sweet hangover in a glass isn’t your alcohol of choice then maybe skip this one – You’ll be standing in a small roped-off section unless you come early enough for dinner and a table. On a positive note, however, the cups are cool!

The Boss Bar

The Boss Bar – Just a good ol regular bar, you know what I mean? The music was poppin’ the drinks were how you’d expect them to be and the crowd was happenin’ and sometimes that’s just exactly what you need!


Celeste – Go here!! This bar is 4 floors that all have a completely different vibe! The Disco floor and the top Greenhouse floors were my personal favorite!

The Pizza Window

The Pizza Window – Look, this pizza is nothing special but seeing as you’ll probably be hammered when you stumble your way to this spot, will you even care? The answer is no, you’ll just be so happy for a late-night slice.

Cindy's Rooftop

Cindy’s Rooftop – This place is a must yall! It overlooks Millenium Park and the Bean so after you get your classic Chicago pic, come here for a yummy cocktail. The rooftop view is something you just can’t miss!

Flight Club

Flight Club – Flight club wasn’t on any of our lists but I’m so glad Chadd and Adele found it! This was one of the most fun bars if not THE most fun bar we went to. Craft cocktails here are a must, I got the Honey Bee and loved it. Playing darts was just good energy! I do have to say though, this is a day-drinking spot strictly! Also, unless you plan on flirting your way into a dartboard spot like Chadd did for us, plan ahead and book a reservation! You’d be surprised but apparently it's a hot commodity!

Punch Bowl Social

Punch Bowl Social – By far the best punch bowl social I’ve ever been to and everyone I talked to agreed! This PBS was huge and we had an absolute blast bowling! Plus there are lots of photo-op spots, so what more could you really ask for??


Emas – We had a boozy brunch here and nearly missed our flight back… oops! I highly highly recommend the hummus sampler! And if you are looking to get a HYPE buzz the espresso martini is delish but if too much caffeine makes you anxious then maybe pass on this one!


Giordano’s – This is where we went for deep dish pizza and it was PACKED so as you can imagine the pizza was delicious! Also, yall listen up! Get the Italian dressing to dip your pizza into – thank me later.

Aloft Hotel

Aloft Hotel – Wait before I go, let me tell you where I stayed! The Aloft is nothing crazy but for what we paid we couldn’t have gotten a better deal! Aloft River North was in the perfect spot and everything we did was very walkable or just required a short Uber! Also, I have to say I’m usually not impressed with the hotel bed/pillow situation (I’m just that person that majorly prefers their own bed) but Aloft had some of the fluffiest most heavenly pillows ever!

All in all, I had a great time and I will definitely be back! There is so much we didn’t get to explore and I’m sure my next trip will have a whole new set of places to check out for eats drinks and adventures. I would love to know where you went to in Chicago! So if you’ve been, hit me with all the places I’m missing in the comments!


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