Chicago in 24 Hours: A Quick Girls Trip
Chicago is less than 2 hours from Boston, and it was the perfect opportunity to explore a new city during a quick getaway.
Here’s how we made the most of our whirlwind trip to the Windy City!
First Stop: LH Rooftop
We kicked off our adventure with a visit to LH Rooftop, where we grabbed a refreshing beverage and a snack. The views from the rooftop are absolutely stunning, offering a fantastic overlook of the city. It was the perfect spot to unwind and start our day in Chicago.
A Visit to The Bean
Next, we made our way to one of Chicago's most iconic landmarks—The Bean. Yes, it’s a touristy stop, but it’s a must-see when you’re in the city. We took plenty of photos and enjoyed the unique reflection of the skyline in the shiny, sculptural surface. It’s just one of those things that you have to experience in person.
Lunch at Au Cheval
After soaking in some city sights, we wandered around the city and headed to Au Cheval, a place everyone recommended for its burger. Let me tell you, they weren’t wrong. The burger was absolutely delicious—juicy, flavorful, and all-around perfection. Definitely worth the hype!
Coffee at Ralph’s and Donuts at Stan’s
The next morning, we started our day with coffee at Ralph’s, a cozy spot with great brews. After fueling up, we swung by Stan’s Donuts for a sweet treat. I opted for the blueberry gluten-free donut (delicious!), while Tiffany went for a frosted donut. Both were fantastic and the perfect start to our morning.
Customizable Chicago Hats at Alice and Wonder
We couldn’t resist a stop at Alice and Wonder to grab customizable Chicago hats. You get to choose your patches, making each one unique. They’re super cute, and of course, I had to wear mine out of the store as we headed to our next stop.
Architectural River Tour
Next up, we boarded an architectural river tour. I absolutely love the buildings along the river, and it was fascinating to learn more about the history of Chicago’s iconic architecture. The tour offered an up-close look at some of the city’s most famous buildings, and it was a great way to take in the skyline from a different perspective. Book here!
Classic Chicago Hot Dog at Portillo’s
After the tour, we were hungry and headed to Portillo’s for a classic Chicago hot dog. Let me tell you, this was delicious. The hot dog was everything you’d hope for—packed with flavor and served with all the classic toppings. A must-try for anyone visiting the city.
One Last Meal: Pequod’s
Before heading to the airport, we stopped for one final meal at Pequod’s. It came highly recommended, so we were excited to try it. Unfortunately, we were a bit disappointed. While it looked like it was going to be amazing, it didn’t quite live up to expectations. Still, it was a decent end to our trip.
And that was it! Our 24-hour adventure in Chicago was packed with great food, iconic sights, and plenty of fun. It’s a city that’s definitely worth exploring, even if you only have a short time to visit.
Here are some recommendations on where to eat based on asking my audience:
Downtown / Loop / River North / Near North Side
Cindy’s rooftop at Chicago Athletic Association
3 Dots and a Dash!
The Aviary
The Purple Pig – (Michigan Ave near the river)
Le Colonial
Lou Malnati’s Pizzeria – (multiple locations, one near River North)
Alinea – (technically Lincoln Park but often grouped with nearby neighborhoods)
Sparrow
The Drifter
Redhead Piano Bar – “close and my favorite for a nightcap”
Gibsons
Devil Dawgs
Goose Island Brewery – (original brewpub is in Lincoln Park; other locations exist)
West Loop / Fulton Market
Girl and the Goat
Duck Duck Goat
Rose Mary’s!
Monteverde is really special!
Ciccio Mio best Italian or Rose Mary’s!
Beatnik on the River has such good food and very aesthetic
Put your name in at Au Cheval for the best burger of your life!
Go to Parlor Pizza Bar in West Loop – “for brunch and they have a make your own Bloody Mary bar – you can’t miss!”
Aba
J.P. Graziano Deli
Bavette for steak house and martinis – “Same owner as 4 Charles in NYC”
Gretel – (technically in Logan Square but often grouped with West Loop recs)
Trivoli Tavern if you can get a rez!
Ukrainian Village / Wicker Park / Logan Square
Rainbo in the Ukrainian Village
Happy Camper – (location in Wicker Park)
Chefs Special – (Wicker Park)
Armitage Ale House… – (Lincoln Park, near Armitage Ave, but listed here for neighborhood crossover)
Lincoln Park / Old Town
Cafe Ba-Ba-Reeba for tapas!!! – “I still dream of this restaurant”
Chicago Pizza and Oven Grinder Co. – “for a pizza pot pie”
Pequod’s Pizza – (often considered Lincoln Park)
Stan’s Donuts – (location on Clark in LP)
South Side
Justice of the Pies (Southside)
Harold's Fried Chicken – (South Side staple, but has locations all over)
Gold Coast / Streeterville / River East
Foxtrot – (multiple locations, one in Gold Coast)
Blind Barber – “absolute cutest speakeasy ever”
Bub City – “above 3 Dots, country bar that’s also fun”
Royal Palms Shuffleboard – (technically Bucktown, but grouped here for nightlife recs)
Miscellaneous / Multiple Locations / Notes Not Specific
Kasama for the breakfast sandwich – “Order ahead of time and you'll cut the line” (Located in East Ukrainian Village)
Pizza parlor – “the ‘you make me corny’ pizza is amazing!!” (exact spot unclear)
Tzuco (River North)
Galit, u will thank me later. (Lincoln Park area)
Roscoe’s (Lakeview, Boystown area)
Ava, Rossi’s (unclear – possibly Ava in Fulton Market and Rossi’s Liquors downtown)
Do-Rite Donuts – (various locations)
Go to Portillo’s and get a Chicago dog and the chocolate cake shake! – (flagship location in River North)