Things to Do in Chicago This Weekend

Whether you live in the city, are planning a day trip from a nearby suburb or are coming into town for a weekend getaway, Chicago offers a variety of great activities to keep you entertained. While most of Chicago’s well-known tourist sights are concentrated in the loop (downtown) area of the city, there is no shortage of great local spots and sights to check out as well. We will highlight some of our favorite things to do in Chicago, but leave us a comment below if you have questions or want to share your own favorites!

Things to Do in Chicago This Weekend

Things to Do in Chicago

Many of the places on this list of things to do are in the Chicago neighborhoods north of the loop where we have lived. The rest are places we have stumbled into while exploring the city. Although most of them wouldn’t show up on a ‘Chicago must see’ list, each offers something unique that we haven’t found in our travels elsewhere and keeps us coming back. The list is structured to follow the flow of a day, so pick a couple from each section to explore and enjoy the weekend!

Breakfast & Coffee

Coffee shops chicago

  • The Wormhole Cafe 80’s sci-fi themed coffee shop, with a delorean on display (Wicker Park)
  • Osmium – A Dark Matter coffee location, check out any of their locations in the city for cool vibes and great coffee (Lakeview)
  • Chicago Bagel Authority – Tasty steamed bagel sandwiches of every variety and solid coffee (Lincoln Park and Lakeview)
  • Batter and Berries – My favorite is the chicken and waffle, but they offer a host of creative french toast and waffles (Lincoln Park)


Things to do in chicago entertainment

  • The Second City – Chicago’s most famous comedy troupe, the Mainstage sells out well in advance but E.T.C. and Up stages often have availability (Old Town)
  • iO Theater – Another great comedy venue with a number of themed improv shows, often with great availability (Old Town)
  • Museum of Science and Industry – Chicago has lots of cool museums but the Museum of Science and Industry often gets missed due to its location south of the city, which is a shame because it has a captured WWII German submarine inside (Hyde Park)
  • Lincoln Park Zoo – A really cool zoo in the middle of the city, check out the conservatory too! (Lincoln Park)


things to do in chicago food restaurants

  • 90 Miles Cuban Cafe – BYOB Cuban restaurant, so bring a bottle of red wine and enjoy table-made sangria (Roscoe Village, Lincolnwood and Logan Square)
  • Vienna Beef Factory Cafe – Grab a Chicago dog straight from the source, a no frills place but worth a stop if you’re in the area (Roscoe Village)
  • Chicago Pizza and Oven Grinder – Their pot pie pizzas are worth waiting for but check in with the owner and kill the couple hour wait at the nearby Lincoln Park Zoo (Lincoln Park)
  • Sapori Trattoria – Quaint, chef-owned Italian restaurant. One of our favorite date spots (Lincoln Park)
  • Kuma’s Corner – Heavy metal bar that serves up gourmet burgers (three Chicago locations, but go to the original in Avondale)

Drinks & Nightlife

things to do in chicago bars nightlife

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