How to Spend a Girls’ Weekend in Chicago, Illinois

millennium park sprinkler

My girlfriends and I try to get together once a year. While Adriane, Amy, and Jen are all in the D.C. area, Jamie is in North Carolina and of course, I’m in Austin, so these annual trips are a much-needed chance for us to leave behind our husbands, boyfriends, kids, dogs, and jobs and catch up like we used to when we all lived in a two-block radius of each other. This year, we settled on a late June weekend in Chicago! Though I’ve been to Chicago a few times already, the great thing about a place like the Windy City is that there’s always more to do and new things to see.

Day One

I took an early flight Thursday morning, getting into O’Hare around 11am. I’d read it was pretty straightforward to take the L train from either airport, and since the rest of the ladies weren’t arriving until late afternoon, I had plenty of time to figure it out for myself. From the gate, I just followed the signs for “Trains to City” which eventually got me to the trains (about 15 minutes of walking from the United terminal). Since O’Hare is at the end of the Blue Line, there’s only one line at the station and one direction to go so you don’t have to worry about getting on the wrong train. A single-ride pass was $5, saving about $30 over a Lyft/Uber trip. 45 minutes later, I got off the train at Clark/Lake, the closest stop to our hotel, Aloft Chicago City Center, in the River North neighborhood, and walked the last few blocks.

Jen flew into Midway and also took the L downtown. Midway is at the end of the Orange Line and her single-ride pass was $4.

I was able to check into our room early so I dropped off my bags, freshened up, and set off for lunch and an explore. I ended up at LYFE Kitchen where I had the buffalo cauliflower tacos, which were pretty good, and a refreshing cucumber mint water. Wanting to practice some photography, I walked about a mile down to Millennium Park and tooled around there for an hour or two. I also squeezed in a SoulCycle class at the Loop location before the girls arrived.

Once the girls were settled in, it was time for dinner. We didn’t have anything planned but it was a gorgeous summer evening so we were in agreement on wanting to eat somewhere outside along the river. We stumbled upon a hoppin’ place called River Roast which looked promising so we joined the 90-minute wait list and posted up in the bar area. I realized a bit belatedly that it was a very meat-centric restaurant (“River Roast”…duh) but it was too much effort to find somewhere else and I figured I would manage, which I did. Given our long wait to be seated, we closed the restaurant down around 10pm.

Day Two

Jen and I started our morning with an Orangetheory class at the Streeterville location then neutralized (if we’re being generous) our calorie burn by hitting up a few donut spots. The first one, Do-Rite, was out of vegan donuts by the time we arrived, so we also went to Stan’s where I got both a sugar and cinnamon sugar donut (they tasted pretty similar but were both quite good).

Stan's Donuts

Like any good trip, a lot of our activities were focused around food and drink and our next activity was no different: lunch at and wandering around Eataly. Jamie had been dreaming about Le Cucine di Eataly‘s braised brisket tagliatelle since her visit to Eataly’s L.A. location and we were more than happy to oblige. I had a really fantastic ziti dish which I requested without cheese, but I’m pretty sure some still got in there so it’s probably not a reliable choice for those with dairy allergies.

We then pampered ourselves with $35 mani/pedis at Center Nails & Spa before going back to the hotel to get ready for our pre-theater dinner at The Marq in the Theatre District, followed by an evening at Hamilton! The Marq had a pulled vegan BBQ sandwich on its menu which I was super excited about, not just because it made dinner ordering easy but also because it was made with jackfruit, something I’ve been wanting to try for ages and hadn’t gotten around to it yet. And it didn’t disappoint. I also munched on the beer tempura battered fried pickles.

Speaking of things that didn’t disappoint…back to Hamilton. We purchased the tickets a few months in advance – once we’d planned the dates for the trip – from the main Chicago Hamilton website, so we paid face value for them. If you want to see Hamilton but don’t want to wait forever or sell your kidney to pay for tickets, a trip to Chicago is the way to do it. I loved it! I made a point of listening to the soundtrack a few times before the trip so I’d be at least somewhat familiar with the music. Hamilton also made me realize just how little I know about American history (#expatproblems); I was frantically reading tons of Alexander Hamilton/Aaron Burr/American Revolution Wikipedia articles during the intermission. I’ve continued to listen to the soundtrack since the show in preparation for the next time I see it!


We walked back from the Theater District to River North, where Jen, Jamie, and I decided to go for an after-Broadway drink at Bub City, a country bar just down the street from our hotel. We’d noticed its fun vibe and loud country music while walking past the night before. Our one drink turned into a few more as the live band, Casee Allen, kept playing cover after cover of hit country songs. Finally, at last call, we called it a night.

Day Three

Time for more donuts! Needing some fuel for our morning on the Chicago Architecture River Cruise, we stopped at another Do-Rite location on our way to the boat (and I called ahead to reserve one of each of their vegan donuts before they sold out – spiced maple chai, orange olive oil, and double chocolate…all delicious). Despite the heat wave hitting Chicago that weekend, the architecture cruise was a fun way to spend the morning – and if you weren’t having a good time, you could just go below deck to the bar and get a cocktail to ease the pain.

Following the architecture cruise, Jen, Jamie, and I took a quick walk over to Millennium Park, stopping at Garrett for some popcorn, before meeting Amy and Adriane for brunch at Beatrix (which was conveniently located in our hotel). After a killer Bloody Mary and some avocado toast, we were facing an afternoon without any planned activities. What to do? We settled on Cindy’s, a stylish rooftop bar across from Millennium Park. After a 15-minute wait for the elevator, I was sipping on a Scoby Snack made with a delightful combination of gin, kombucha, grapefruit, and sparkling rosé. We were even lucky enough to get some couch space on which to enjoy our cocktails.

Terrace at Cindy's

While Adriane, Amy, and Jamie did a bit of shopping after Cindy’s, Jen and I spent some time at City Winery on the Riverwalk which was a lovely way to enjoy the (hot) afternoon sun.

Then it was time for our night on the town! Showered and refreshed, we had time for pretty cocktails in the hotel bar before walking a few blocks to Sunda for dinner. It had a fun vibe, friendly staff, and fantastic food, including a dedicated vegan menu. It was hard not to order one of everything, though we definitely came close! Next up: Three Dots and a Dash, a super cool hidden tiki bar just around the corner from Sunda. We waited in a tiki torch-lined alley for about 20 minutes before being invited to walk down the dimly-lit staircase into the bar where we ordered a round of tropical elixirs; I opted for the Painkiller: rum, tangerine, pineapple, and coconut. The only negative was that the bar area was super crowded and there wasn’t anywhere else for our group of five to stand or sit. They do have small tables but they were all taken or reserved. Perhaps it would have been easier with a smaller group (or a reservation!).

Our last stop of the evening was The Signature Room & Lounge. We only spent about 10 minutes waiting for the elevator that whisked us up to the 95th floor of the John Hancock building. While the views from the top were fantastic – and I’d love to go back and see them during the day – the style and service of the place wasn’t quite what we had expected, especially given the prices! We were seated around a small, crowded table in the dark, back corner of the lounge and the service was very slow. After a drink, it was time to call it a night.

Once inside, the lounge looked incredibly familiar to me and I finally realized I had visited on a previous trip to Chicago to visit my friend Anna. We sat at a window table and I just loved it. So, it seems seating location is key to the experience!

Day Four

Amy, Jen, and Jamie flew out mid-day so before they left for the airport, we had breakfast at LYFE Kitchen then walked a few blocks to Lou Malnati’s so the girls could get their deep dish pizza fix. Adriane and I both had evening flights so after we said our goodbyes to the others, we took the L the 20 minutes to Wrigley Field and spent the afternoon watching the Cubs take on the Minnesota Twins.

Adriane ended up having to leave earlier than planned due to a rescheduled flight but I enjoyed the rest of the game on my own and snuck into a lower section for the last few innings. I ducked out in the bottom of the 9th to beat the crowds to the L so I could shower and check out of the hotel, then get back on the L to the airport. Though we had a late check-out regardless due to Amy’s SPG status, the folks at the Aloft had hooked us up and extended it until 6pm!

My flight home kept getting delayed due to storms in the area and eventually I just opted to change it for one the next afternoon to avoid sitting in the airport for who knew how long. I used some points to stay at the Aloft by O’Hare and had a quiet little evening. I was able to fly standby on the first flight to Austin the next morning (hello exit row and no one in the middle seat!) and was home by 11am to celebrate Juno’s fifth birthday!

Any recommendations for future trips to Chicago?