Tips for how to spend your first weekend in Chicago

Wondering how to spend your first weekend in Chicago? With fancy restaurants, bars, museums, and green parks, this city has it all.

Editorial Team

By Editorial Team

downtown chicago crowd

The Windy City is an exciting place to be, whether you’ve lived here for years or have just arrived in town. Blueground wants all of our guests to feel at home as soon as they move into one of our turnkey furnished Chicago apartments.

Our fully furnished apartments come standard with everything you need to get started. Our guests love our fast Wi-Fi, well equipped kitchens, and comfortable work-from-home setups.

the chicago skyline at dusk

The beauty of choosing to rent with Blueground is that you can spend your first weekend exploring. Here are some of our favorite things to do in Chicago.

Friday: Deep dish and deep cuts

Chicago-style pizza is controversial. Some people love the thick, flaky crust and homestyle sauce. Others, especially New Yorkers, balk at eating their pizza with a knife and fork. However you may feel personally, trying Chicago-style deep dish pizza is a rite of passage.

Lou Malnati’s, a chain that originated in Chicago in 1971 and has now expanded to several states, is an easy introduction to deep dish-style pizza. There are Lou Malnati’s restaurants throughout the city, so find the one closest to your apartment. If you’re not sure what to order, you won’t regret sampling the Malnati Chicago Classic.

After dinner, head back to your apartment and fire up your Smart TV to stream High Fidelity. The 2000 movie is a love letter to the city from native John Cusack. This snarky film has too many pop-music references to count. (We also love the 2020 TV show with Zoe Kravitz, but that’s set in NYC.) In the course of 1 hour and 53 minutes you’ll come to feel like you were a part of the city’s music scene in the 90s.

Saturday: A fine time for fine art

Chicago is home to one of the oldest art museums in the US, the Art Institute of Chicago. The museum has more than 300,000 works of art in its permanent collection, and also hosts a variety of traveling exhibitions each year.

Starting this Friday you will be able to view The Obama Portraits, an exclusive showing of Kehinde Wiley’s painting of former President Barack Obama and Amy Sherald’s portrait of former First Lady Michelle Obama. But don’t wait too long, because the show ends on August 15.

The Art Institute of Chicago is located within Grant Park, a lovely greenspace that is perfect for a late-day picnic or even just a quick selfie break. The Adler Planetarium and several other notable Chicago museums are also nearby.

gold coast, one of chicago's best neighborhoods for young professionals

Sunday: Day trip to Woodstock

Summer is the perfect time for exploration, and Chicago’s first-rate public transportation means that it’s just as easy to get out of town as it is to get from one neighborhood to another.

We love Woodstock, Illinois for its cute, walkable downtown. That said, many choose to visit this hamlet because it’s the setting for the 1993 movie Groundhog Day starring Bill Murray and Andie MacDowell.

Local sights include the Woodstock Opera House and the Illinois Railway Museum. This is quite fitting, since Woodstock is just a one-hour ride on the Metra commuter line from Chicago. (If Woodstock isn’t quite your style, here are some other quick getaways from the city.)

Blueground wants all of our guests to feel at home in a new city right away, whether you’re staying for a month or a year. We set up our furnished apartments in Chicago and other cities around the world with absolutely everything you need to live, play, and work. Find out more about the Blueground experience.

Editorial Team

Editorial Team

The Blueground editorial team covers the best things to see, do, and experience in our cities around the world.