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Travel Lemming: Where to Stay in Chicago, By a Local (Best Areas & Places)

Wondering where to stay in Chicago? Then you’ve come to the right place! There are plenty of great options for areas and places to stay in Chicago as it’s such a vast and action-packed city.

But where you choose to book your accommodations should depend on what you plan to do and see – with regular events, museums, the new Maxwell Street Market, a rich music scene, and much more, you’ll be busy during your visit. I should know – I’ve lived in Chicago for almost five years!

Whatever you seek in Chicago, this guide details a variety of options for where to stay. And while you’re here, be sure to bookmark this guide to the best day trips from Chicago.

Let’s dive in!

Wicker Park

If you like unique, artsy areas, then you might want to consider a stay in Wicker Park. It’s a great area for people who are on the unconventional, eclectic side, with indie music venues, speakeasies, unique art galleries, and more. To see this entire cool area from above, I recommend using the 606, a repurposed rail line for pedestrians.

Wicker Park is also the place to stay in Chicago for travelers who want to experience indie culture. It’s full of thrift stores and bookstores, and it has a flourishing gallery scene. It’s also the home of the Around the Coyote Fall Arts Festival if you happen to be there in September.

If you’re a foodie, you’ll love this area for the artisan drinks at the Violet Hour, noodle joints, trendy coffee houses, and other small eateries that are some of the best-kept secrets of the area.

Pros of Staying in Wicker Park:

  • Eventful, eclectic nightlife
  • Many fun bars, restaurants, and cafés
  • A very distinct and fun culture
  • Easy access to public transportation
  • Lots of parking spots

Cons of Staying in Wicker Park:

  • Lodgings and shopping can be expensive
  • The area can be congested, especially at night
  • Some areas are not the safest places to be walking around at night

📚 Wicker Park Mini Guide 📚

Best Area for Hipsters
Google Map

Escape Artistry

The Time Gallery: 1342 N Milwaukee Ave, Chicago
The Railcar: Flatiron Arts Building, 1579 N. Milwaukee Ave. Ste 350, Chicago

Choose Your Mission! 

At Escape Artistry, our escape rooms are "Chicago Original." All 6 of our games are handcrafted by local Chicago artists with custom puzzle games you won't find anywhere else! 

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