How to Spend 24 Hours in Chicago (During COVID-19)

Chicago is one of those cities that we cannot believe we haven’t visited until now! We didn’t expect Chicago to be surrounded by so much water (which we loved), and as a lesbian couple it was a place where we felt extremely welcomed. We only got to spend 24 hours in Chicago (but recently went back in 2022 so we’ve updated this post!) so here are all of our tips to get the most out of your day!

Where to Stay

We recently went back in Chicago in 2022 and stayed at The Godfrey Hotel. It was in the perfect location and the hotel was trendy & clean. They also have a rooftop bar that was very popular and was always crowded! We would definitely stay here again next time we go to Chicago.

Find other Chicago accommodations here!

We stayed at a Sonder location in the South Loop area of the city. If you don’t know about Sonder, it’s kind of like Airbnb where you get an entire space to yourself, usually including kitchen & laundry. They are also taking amazing measures to make sure the spaces are extremely clean & sanitized. The apartment we stayed in had an open layout with a lot of natural light and it was in a great location! We were in walking distance to a lot of things we wanted to visit. The only negative was that there was only street parking available but there were a ton of garages nearby that weren’t too expensive.

Best Things to Do with only 24 Hours in Chicago

Head to Millennium Park and see Cloud Gate/The Bean
Snap a photo outside the Chicago Theater
Take a stroll along The Riverwalk
Try some deep dish pizza
Visit Navy Pier
Rent a Divvy Bike and cycle along the Lakefront Trail
Pop into some shops in Lakeview
Stop by the iconic Wrigley Field
Walk along the rainbow crosswalks in Boystown
Walk along the North Avenue Beach Pier

Book other Chicago activities here!

Where to Eat& Drink in Chicago

Sam & Gertie’s
Goddess & The Baker
Can’t Believe it’s Not Meat
Standup Burgers
Handlebar
Gino’s East for deep dish (they also have a vegan option!)
Lou Malnati’s
Stan’s Donuts & Coffee
Do-Rite Donuts
Jeni’s Ice Cream
Pie Pie My Darling
The Chicago Diner

Check out our Vegan Guide to Chicago post for more!

The LGBTQ+ Scene in Chicago

Boystown aka the queer area of Chicago is extremely welcoming. The second you get nearby there are pride flags everywhere, rainbow signs, and even rainbow crosswalks! It’s very obvious that it’s an LGBTQ area and you instantly feel at home.

Andersonville is also a great LGBTQ+ friendly neighborhood in Chicago. It’s known by the locals as a lesbian neighborhood, but we definitely felt like all members of the LGBTQ+ community are welcomed there. Andersonville had cute shops, thrift stores, and great bars/restaurants!

If you want to see how we spent our 24 Hours in Chicago make sure you check out our YouTube vlog! We detail everything we did in there & give you even more tips on how to spend your time.

Also if you want to see what we did on our most recent trip to Chicago in 2022, then watch our YouTube video from that trip below!

Some links on this post are affiliate links of which we receive a small commission, but the price is the same for you.

24 Hours in Chicago