43 Awesome Things To Do in Chicago this Summer

Lincoln Square summer festival in Chicago

Summer in Chicago—most people refer to it as “Summertime Chi” and there is nothing quite like it. All summer long, you can experience beautiful sandy shores, endless outdoor patios, and countless cultural activities, making Chicago the best place to be all season long. Here’s your guide to awesome things to do in Chicago this summer.

  1. Hit the waves of Lake Michigan on a pontoon, sailboat, yacht, or jet ski.
  2. Top off your weekend with abottomless and boozy brunch.
  3. Catch a cool breeze with a walk on the lakefront.
  4. Hit up your favorite Chicago beach.
  5. Get in the game by joining a softball, volleyball, or flag football league.
  6. Host an outdoor gathering at your home.
  7. Shop small at an in-person or virtual artisanal market.
  8. Catch a new film at a drive-in theater.
  9. Cook your favorite summer dishes with produce from a Chicago farmer’s market.
  10. Take a hike at a nearby state park or city trail.
  11. Support a Black-owned business on and after Juneteenth.
  12. Hop on board an architecture cruise or tour.
  13. Root for the Cubs or White Sox all summer long.
  14. Plan a summer road trip to a small town or cool city near you.
  15. Quench your thirst with beer from a local brewery.
  16. Spot something new on a long bike ride through your city.
  17. Reserve a seat at your favorite outdoor patio.
  18. Practice self-care in a hidden park.
  19. Create your summer reading list with selects from local Chicago bookstores.
  20. Order in from a Michelin-ranked restaurant.
  21. Savor an icy treat from a novelty ice cream shop.
  22. Cut a slice of your favorite Chicago-style pizza.
  23. Practice your swing at a local golf course.
  24. Learn something new at a cultural institution.
  25. Go mural scouting in one of Chicago’s coolest neighborhoods.
  26. Shop for trendy threads at a local boutique.
  27. Reach new heights at a hip rooftop bar.
  28. Elevate your outdoor run on the 606 Trail.
  29. Discover the eastern culture and hidden gems in Chinatown.
  30. Add to your vinyl collection from a local record shop.
  31. Sing with your favorite music artist at a summer festival.
  32. See exotic animals(for free) at the Lincoln Park Zoo—or neighboring suburban zoos.
  33. Stream a cultural event online with your family or friends.
  34. Experience free entertainment at a park near you.
  35. Buy a print from a local artist at a gallery open house.
  36. Upgrade your home with vintage housewares from shops in Andersonville.
  37. Experience Costa Rican, Puerto Rican, or Cuban food in Chicago’s Westside neighborhoods.
  38. Take a bite out of your favorite Italian Beef sandwich.
  39. Pamper your palate with an afternoon of wine tasting.
  40. Keep your neighborhood thriving by shopping with small businesses.
  41. Catch the fireworks at Navy Pier.
  42. Arrange a romantic picnic in the park.
  43. Soak up the sun at Promontory Point.
Find more events and activities to experience this summer, thanks to a few influential locals. Check out Seek Like a Local for weekly guides on things to do from a local perspective.



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