220 Things To Do In Chicago In 2020

I've lived in Chicago for 4+ years and STILL find myself saying "I need to try (insert realllly famous restaurant) soon" - every. single. day. 

I think 2020 should be the year I change that! While Chicago is home now, it might not always be. I would like to get out there and finally experience, try, learn, & sink my teeth into all of the amazing places and spaces that make the Windy City so great! This is my list of 220 Things To Do in 2020 - the Chicago version! Who needs a resolution when you can instead try, learn, and create new memories to help you grow as a person? That's how I look it at least.

Read my list & let me know what you think! I would love to hear your comments & recommendations to keep in mind as I attempt to be a tourist in my own city this year.

To Experience...

Get out there & try something new - or check something off your Chicago bucket list:

1. A Cubs Game at Wrigley Field
2. Attending a Sox Game 
3. A relaxing Spa Day At Aire Ancient Baths
4. Practicing your swing with Topgolf at the Chicago Athletic Association 
5. Shopping & vintage finds on Clark Street in Andersonville
6. Friday the 13th at L&L Tavern
​7. Scottish beer at Duke Of Perth's
8. Game night at Replay
9. Karaoke at Mom's Place
​10. Dancing at Beauty Bar
11. St. Patrick's Day In Chicago & seeing the river dyed green
12. Drinking wine & perusing the furniture at Restoration Hardware
13. Music & libations at the Redhead Piano Bar
​14. A night out at Untitled Supper Club
​15. Concerts / Movie Nights at Millennium Park
16. High views from The Ledge @ The Willis
17. Jazz at the Green Mill
​18. Reggie's Rockclub
19. A Sofar Sounds Show
​20. A fun time with friends at Punchbowl Social
​21. Zoo Lights at the Lincoln Park Zoo
22. Comedy at Second City
23. A Steppenwolf Theater Play
​24. New music at Empty Bottle
​25. Drag Brunch In Boystown (Kit Kat is super fun!)
26. Movie night at Music Box
27. Seeing a Bulls Game
​28. Spring at the Chicago Botanical Gardens
29. An Improvised Shakespeare show at iO
30. The Renaissance Festival
31. Dancing at The Hideout
​32. Kingston Mines live music
33. The magic shows that take place at Chicago Magic Lounge
​34. Riding the swings or ferris wheel at Navy Pier (+ see the fireworks!)
35. A historic homes architecture tour by carriage horses off Oak Street
36. A beach day at North Ave Beach
​37. Searching for the perfect book at Myopic Books
38. The views of the city from the London House rooftop bar
39. Let loose & dance all night at Smart Bar
​40. Lollapalooza
​41. Amazing views of the Air & Water show
42. Thrift store hopping off Milwaukee Ave in Wicker Park
​43. Seeing the sunrise at Cloudgate 
44. A Chicago gangster + ghost tour
​45. Reading books & playing games over coffee + beer at kibbitznest
46. A relaxing weekend getaway in Lake Geneva
​47. The beauty of the Chicago Cultural Center
48. Touring the Richard H. Driehaus Museum
49. A Blackhawks game
​50. Getting splashed at Crown Fountain
51. Admiring the Robie House architecture by Frank Lloyd Wright

To Try...

Trying new things is one of the best ways to enjoy a city & get out of your comfort zone:

52. Cooking Classes At Read It & Eat
53. The 14K Chocolate Cake at RPM Steak
54. Biking the 606 trail
​55. Visiting ALL of the museums
​56. Taking a wine tasting class at wineHOUSE
57. Swing dancing classes at Big City Swing
58. Mermaid swimming at Aquamermaid
​59. Axe throwing at Bad Axe
​60. Making new friends at a Meetup group (hello , check out mine!)
61. Running the Chicago Half Marathon (or full marathon!)
​62. City Mini Golf
63. Winning bowling with your friends at Pinstripes
​64. A shot of Malort
65. Drinks at Rite Liquors
​66. Making your own perfume at Aroma
​67. Ceramic painting at Glazed Expressions
68. The taxi water boat on a warm summer day
​69. Getting photos at all of the Chicago Instagram spots!
70. Capturing a gorgeous night photo of the Buckingham Fountain water display
​71. Running / Walking / Biking the entire Lakefront Trail
72. A mob & crime bus tour
73. Escaping your comfort zone & feed sharks the Shedd!
74. Finding all the famous landmark stonework pieces at the Tribune Tower
75. New food finds at The Taste
76. Trapeze class at TSNY Chicago
77. Indoor skydiving at iFLY
78. Finding & drinking inside Janitor's Closet Speakeasy
79. Enjoying a Vaudeville show at Bordel
​80. Bowling at The Pink Squirrel
81. A river boat cruise
​82. Yoga at Gallagher Way
83. All of the Christmas themed bars that pop up around Chicago
84. Speaking of Christmas, a Santa crawl
​85. Renting a heated dome at City Winery with your close pals
​86. Finding a new local artist you love at a Pancakes & Booze art show
87. Turtle Racing at Tin Lizzie's 
​88. Joining a Skee-Ball League (Sluggers!)
89. Staying out until 4am at all of the local late-night bars!
​90. A cooking party at Get In The Kitchen
91. Seeing a show that peaks your interest at The Vic
92. All of the sandwiches at Cheesie's Pub 
​93. Enjoying a $7 Long Island & finding a quaint spot at Lilly's Bar
94. Finding new books at The Book Cellar 
95. Alcohol infused cupcakes at Intoxicakes
96. Spanish tapas at Cafe Ba-Ba-Reeba!
​97. Bar hopping the Chicago Riverwalk
98. The 2020 Chicago Polar Plunge!
99. Getting your blood pressure up at Tilt 360Chicago!
100. Getting a fun photo in front of the big door at Big Monster Toys
101. Visiting the Home Alone house
102. Afternoon tea at The Drake
103. Karaoke at Trader Todd's 
104. Seeing an artist that interests you at Bottom Lounge
105. Eating at & ranking each Chicago deep dish pizza restaurant (at least the top 5!)
106. The night tubing & brewery tour by Sourced Adventures 

To Learn....

Expand your mind & maybe even pick up a new hobby:

107. Archery at Archery Bow Range
108. Learning cheer + dance moves to your favorite songs thanks to PomSquad
109. Ice curling at Kaiser Tiger
​110. About the planes, boats, & history behind the Air & Water show
​111. All about wine and which wine you should add to your collection at BottlesUp!
112. Improv with classes at Second City
113. Burlesque dancing at Chicago Academy Of Burlesque
114. Pole dancing at Bombshell Movement
115. The art of aerial silk at AIR Aerial Fitness
116. How to push your body at GOAT Chicago
117. Glass blowing at ignite glass 
118. Cooking new recipes at The Chopping Block
119. How to sew with Anastasia Chatzka 
​120. How to ice skate at one of the local + popular rinks that pop up around town in the winter
121. To make beautiful bouquets at an Alice's Table event
122. Painting at a wine & paint night event
123. Mixology at Hollow Leg
124. How to improve your golf swing at the Diversey Driving Range
125. Crocheting at Firefly Fiber Arts Studio
126. All about VR at the Kyrpton VR Lounge
127. Horticulture at the Chicago Botanic Garden
128. More about your favorite animals at the Lincoln Park Zoo 
129. Calligraphy at the Flying Dolphin Studio
130. Print making at Spudnik Press
131. Rock climbing at Brooklyn Boulders
132. To improve your writing at StoryStudio Chicago
133. Indoor skydiving at iFly
134. Screenwriting at Chicago Filmmaker's in Andersonville
135. Enhancing your photography skills at the Chicago Photography Academy
​136. How you can give back to your community by volunteering some place that inspires you
137. More about the fascinating & strange history of Chicago on a walking tour
138. About a subject that interests you thanks to Dabble
139. All about beer at a local brewery (Mousetrap, DryHop, etc) 
140. Everything you could ever want to know about coffee at Intelligentsia Coffee Chicago Roasting Works
​141. About powerful women on the Badass Bitches Tour
142. To create your own perfume/scent at the Aroma Workshop
143. How to enhance your food + pantry at the Savory Spice Shop
144. To not color outside the lines by joining an adult coloring group! It's super fun & relaxing! 
145. Kayaking / paddle boarding on the lake
146. How to gain entrance into all the famous Chicago secret bars + pubs
147. The best ways to update your closet & look with Chicago stylist & Instagrammer @shoppinggirlxoxo
148. Magic at the Chicago Magic Lounge
149. Gymnastics at Aloft Loft 
150. Fencing at Redstar
151. Salsa at American Legion
152. The two-step at Chicago Honky Tonk
153. How to code with Generalassemb.ly
154. Business networking with WeMeet
155. Cake decorating with Give Me Some Sugar
156. Scuba Diving @ Sea Lions Diving Center
157. Martial arts with Chinese Martial Arts
158. Bonsai workshops, soap making, adult toy making (wow!), and or one of many fun & unique classes at Color Cocktail Factory
159. Painting at VIP Paints
​160. Random facts you can keep in your brain forever by attending one of many trivia nights around the city 
​161. To refresh your bingo skills with adult bingo - such as the PBR bingo night at the Boiler Room

To Sink Your Teeth Into...

Make sure you eat at & cheers at:

162. Lowcountry
163. Funkenhausen
164. Smoque BBQ
165. Shore Club
166. Honey Butter Fried Chicken
167. Fat Rice
168. Mindy's Hot Chocolate
169. Au Cheval
170. Girl & The Goat
171. Alinea
172. Spiaggia
173. Pacific Standard Time
174. Summer House Santa Monica
175. Cindy's 
​176. Carnivale
177. Happy Camper
178. Chicago Diner
179. Handlebar
180. The Purple Pig
181. Big Star
182. The Publican
183. The Berghoff
184. Parson's Chicken
185. Lonesome Rose
186. Bang Bang Pie & Biscuits
187. Mott Street
188. 90 Miles Cuban Cafe
189. The Radler
190. Furious Spoon
​191. Geja's Cafe
192. Longman & Eagle
193. Lost Lake
​194. Giordano's
195. Lou Malnati's
196. Gino's East
197. Portillo's
198. Sunda
199. Three Dots & A Dash
​200. Goose Island 
201. Maple & Ash
202. Fig & Olive
203. Velvet Taco
204. Homeslice
​205. XOCO
206. Pequod's
207. Sushi Para II
​208. The Walnut Room
209. Chicago Q BBQ
210. RPM Steak
​211. Tanta
212. Le Colonial
213. Athena Greek Restaurant
214. Wrigley BBQ
215. Prost!
216. Milk Room
217. Lillie's Q BBQ
218. Devil Dawgs
219. Oiistar
220. Any of the THOUSANDS of restaurants in the Chicagoland area - all of which are unique and feature so many amazing dishes. We are lucky to live in a city with great cuisine and customer service!