The Haute Seeker

101 Of The Best Things To Do In Chicago Year Around


Chicago has an endless amount of things to see, do, and experience throughout the year. Yes, our summers are dreamy, and our winters are a bit harsh, but we are a city that has something to satisfy every visitor and local alike, no matter the season.

We’ve rounded up the best of what Chicago in this guide. From visiting Chicago’s most unique museums to exploring urban parks, now, it’s your turn to seek and experience what the city has to offer for yourself.

Are your favorite things to do year around missing from this list? Let us know by submitting your favorites to us here. 

Reminder: While we encourage you to enjoy one or all of these activities, we recommend keeping yourself and others safe by practicing safe social distancing rules and regulations.

  1. Support local artisans and makers by shopping small during an in-person or virtual market.
  2. Pass the time with a scenic drive through rural Illinois byways or backroads.
  3. Catch a new film at a drive-in theater.
  4. Cheer for your favorite Chicago sports team at home or in the stands all year long.
  5. Volunteer for a Chicago grassroots organization.
  6. Visit a neighborhood coffee shop and sample the best items on the menu.
  7. Rejuvenate your mind and body with a trip to the day spa.
  8. Bake your favorite dessert using ingredients from a Chicago farmer’s market.
  9. Find chic vintage pieces at a North Shore estate sale.
  10. Grab the best seat in the house at an iconic movie theater.
  11. Hit the great outdoors by hiking a nearby trail solo or with friends.
  12. Observe the celestial landscape by stargazing during your next date night.
  13. Plan an urban scavenger hunt with your closest friends.
  14. Venture overnight 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. Cruise the historic commercial district of a nearby town.
  18. Rest in a hidden park on the South or West side of Chicago.
  19. Catch a cool breeze with a walk on the lakefront.
  20. Admire ornamental architecture on Terra Cotta Row.
  21. Expand your at home library with books from local bookstores.
  22. Take a quick trip to the land of OZ in Lincoln Park.
  23. Get some Dim Sum as you taste your way through Chinatown.
  24. Step beyond Western culture with a trip to Roger’s Park.
  25. Delight in delectable dessert from a famous bakery.
  26. Host a Chicago-themed holiday party.
  27. Savor an icy treat from a local ice cream shop.
  28. Order your favorite Chicago style pizza.
  29. Practice your swing at a local golf course.
  30. Observe a virtual tour of historic Chicago landmarks, and then safely visit them in person.
  31. Take a day trip to an Illinois nature preserve.
  32. Grab a drink from your favorite neighborhood bar. 
  33. Adopt a pretty plant for your home from a local nursery.
  34. Learn something new at a cultural institution.
  35. Check out an under the radar museum.
  36. Interpret art while visiting local art galleries.
  37. Find famous land sculpture art in the Chicago Loop.
  38. Go mural scouting in Chicago’s coolest neighborhoods.
  39. Shop for trendy threads at a local boutique.
  40. Take insta-worthy photos in one or all of the 77 neighborhoods.
  41. Reach new heights at a hip rooftop bar.
  42. Take a charming stroll on the Chicago Riverwalk.
  43. Elevate your outdoor run on the 606 Trail.
  44. Watch fowl in their natural habitat at the bird sanctuary at Montrose Beach.
  45. Create a DIY taco tour through the infamous Pilsen neighborhood.
  46. When the season is right, pick your own fruit and other seasonal goodies at statewide orchards.
  47. Take a heroic photo in front of the Big Monster Toys Door.
  48. Find serenity and notoriety at Graceland Cemetery.
  49. Hunker down and warm up with a bowl of ramen from a popular noodle shop.
  50. Check out a play from a Chicago community theater.
  51. Laugh out loud to witty jokes at a local improv or comedy show.
  52. See the best views in the city from Willis Tower and the John Hancock Tower.
  53. Admire the architecture of a Frank Lloyd Wright home on the North, South, and West sides of Chicago.
  54. Get your seafood fix at Calumet Fisheries.
  55. Travel back in time with a visit to the Pullman Historic Neighborhood.
  56. When the temperature drops go ice skating at Midway Plaisance Ice Rink.
  57. Add to your vinyl collection from a local record shop.
  58. Renew your romance at the Obama kissing rock in Hyde Park.
  59. Visit the birthplace of famous Chicagoans.
  60. Grab coffee in an alley at HERO Coffee Bar in the Loop.
  61. Pick up a meal from restaurant masters in the making at The Hatchery incubator.
  62. Spot your favorite exotic animal at a zoo
  63. Witness the golden age of meatpacking at the Union Stockyards.
  64. Marvel at large scale street art on the Wabash Arts Corridor.
  65. Grab microgreens from The Plant in Bridgeport.
  66. Sing your favorite song with a musical artist at an online or offline festival.
  67. Stream a cultural event online with your family or friends.
  68. Experience all that your neighborhood has to offer at a community festival (virtually).
  69. Order a basket of gourmet goods from a fancy market.
  70. Shop on the famous ‘Magnificent Mile’.
  71. Take your booze to go from a pick-up window at a bar.
  72. Go see some live music (virtually as well).
  73. Grab macarons while waiting for the Metra train at the Chicago French Market.
  74. Cruise through a cool neighborhood on a bike.
  75. Get an informal education at Chicago Museum Campus.
  76. Pick up a jibarito from an authentic Puerto Rican restaurant.
  77. Scarf down dishes that you can only find in Chicago.
  78. Order in from a Michelin-ranked restaurant.
  79. Reserve a table for dinner at a sidewalk patio or rooftop bar.
  80. Go house hunting for Gilded Age mansions in the South Loop.
  81. Pamper your palate with an afternoon of wine tasting.
  82. See the latest luxury fashions on Rush Street in the Gold Coast.
  83. Plan a stay-cation at a swanky hotel in downtown Chicago.
  84. Escape the cold with a stroll through the pedway in the Loop.
  85. View a dazzling display of lights with your entire family during the holiday season.
  86. Keep your neighborhood thriving by shopping and supporting small businesses.
  87. Find the perfect gift for a child or even yourself at a local toy or hobby store.
  88. Explore your inner botanist at the Garfield Park Conservatory.
  89. Admire the waterfront at Navy Pier.
  90. Arrange a romantic picnic in a historic park.
  91. Scout the location of well known movies films in Chicago from ‘Home Alone’ to ‘Love Jones’.
  92. Find new things from locals with Free Tours by Foot.
  93. Save on designer brands with a trip to the Fashion Outlets in Rosemont.
  94. Rummage through odd and mysterious trinkets at a quirky novelty shop.
  95. Get your ‘om’ on and meditate at the Garden of Phoenix.
  96. Pursue the spectacular selection of books at the Harold Washington public library.
  97. Play tourist and take a photo in front of the ‘Cloud Gate (The Bean) at Millennium Park.
  98. When summer lands in Chicago, hit the waves of Lake Michigan on a pontoon, sailboat, yacht, or jet ski.
  99. Savor international flavor at a Joong Boo Market.
  100. Pick up a new skill at Chicago’s Mosaic School.
  101. Top off your weekend with a bottomless and boozy brunch.
Accomplished everything on the list and Still find yourself in complete boredom? No worries! Be sure to checkout our guide to hidden places to hangout, at-home date night Ideas, and other things to do to stay busy while in Chicago.