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.

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

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 

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

Make sure you eat at & cheers at:

I’m not very competitive in regular life but there’s something about putting on an amazing, jaw-dropping costume that suddenly empowers every part of me. In that moment, I do feel like I am the best dressed ever and if anyone tries to get in the way of that then I’m fully prepared for my own live action reenactment of the waterhole scene from Mean Girls. What I’m trying to say is that I LOVE costumes, costume contests, and any reason to dress up. So, of course, I love winning them.


I’ve won four costume contests to date, six if you count spirit week from my high school days - I don’t because wow was that amateur hour. With each win, I can’t help but get a little more cocky. It’s kinda like my version of cocaine. Each win comes with it’s own high. It’s addictive. It’s exciting. ​

The second costume contest I won basically by just showing up. I went to an Oscars watch party at this swanky rooftop bar, The J. Parker, in Chicago. It was me and a bunch of older ladies watching the Oscars and drinking champagne. It was incredibly fun, but nobody else even dressed up. So I won. It was fun, but the excitement wasn’t quite there. However, I did appreciate the $50 gift card. ​

My third costume contest win was in Salem, MA on Halloween. This party took place in the middle of Salem at the famous “Rockafellas” bar. This win of “Best dressed” was maybe the most impressive of all because people in Salem take Halloween very seriously. The competition was high. But, so was the thought I put into my costume. Wearing a wedding dress I bought on Craigslist for $50, my Catherine D’Lish dressing robe, and a custom $150 feather masquerade mask from New Orleans, I won “Best Dressed” Halloween 2017. It was a helluva time. ​

The last won was less of a formal "win". My mother and I dressed up as princesses to attend/watch the Royal Wedding of Prince Harry and Meghan Markle. We had a front row "seat" from our VIP window at Bluegrass BBQ across from Windsor Castle. We saw Prince Harry & Meghan in their horse-drawn carriage as they left their nuptials. It was an amazing, historic day. We were interviewed for our costumes by Brad Blanks of CBS Radio, Telemundo, and featured in TMZ. 

After all of these wins, a few losses, and just enjoying dressing up - I have gained a lot of knowledge in the costume contest world. I figured why not share what I’ve learned to help others *hopefully* win a contest they enter?! It's a blast to enter any competition, especially one where your imagination can run wild. So, here are my tips. Take ‘em or leave ‘em. ​

You need to make sure you arrive early, as many parties or bars/restaurants pick contestants to qualify for the contest near the start of the event. Also, the earlier you arrive the more people you can meet and impress. ​Make sure to not only get to the party early but also to stay late. Don't leave as soon as the win is announced, rather you win or lose. Celebrating after the costume contest ends is a great way to enjoy your win, or to still have a fun time even if you didn't. 

Winning a costume contest is incredibly fun, rewarding, and exciting. However, if you don't win you should still try to have an amazing time. This is something I'm still working on, which is strange because as I mentioned earlier I don't normally feel too competitive. However, for some reason when I lose a costume contest I feel personally attacked. 

The truth is that dressing up and attending a party of any kind should be fun enough. You don't need to win in order to enjoy the moment. There will always be more costume contests to enter!

I'm SO excited for 2020 because I'm ready to party like Gatsby for the next ten years! 2020 is going to be a big year for me. I'm getting married (YAY!), continuing my business degree, entering my upper-twenties (not sure how I feel about that), traveling to some new places, and pursuing my career path even more. 

I've been creating this annual list since 2016. It's become a major part of my life. Over the Christmas holiday in 2015, my cousin committed suicide. It was an incredibly difficult time for me. I had just published my first list: "216 Things To Do in 2016" a few days before she passed away. Unbeknownst to me, the list went crazy viral. Once I found out how inspired people were by my list, I was given this newfound hope amidst so much sadness that maybe there are always ways to feel purpose. 

​I hate resolutions and bucket lists. For one, they are extremely hard to keep. They are also insanely unrealistic. I wanted my annual list to be something that basically anyone anywhere could participate in. This list isn't about keeping resolutions or striving for perfection. It's about creating, learning, trying, and experiencing new things. I think when we can make the time to do one or all of those things then we can find personal growth and satisfaction. 

Each list varies from year to year, and I have made sure to never repeat an item- which is getting to be quite difficult lemme tell ya. I'm super excited because this year I've created a planner + calendar + checklist package that can be purchased through my blog! This is the perfect gift for yourself or anyone looking to feel a little more inspired starting this new year! It's also art deco themed because I'm really trying to bring back the 1920s vibe! 

​Without further adieu, here is my list of "220 Things To Do In 2020":

52. Choosing a word for the year and living by it (For example gratitude, simplicity, etc.)
53. A ghost tour of your city
​54. Living for each day instead of living for tomorrow
​55. Sleeping with your phone in a different room (& using an old school alarm clock)
56. Waking up early every day for an entire week and either working out, reading, or doing something productive to start your day
57. Learning a new language by dedicating 1 hour each week
58. Cooking with plant-based ingredients
59. Writing a song
60. Planning out your outfit each day for an entire week
61. Getting a suntan tattoo 
​​62. Topgolf
​63. Running a marathon
​64. Buying something you normally would buy online at a local, family-owned store instead
65. Tracking the amount of time you spend online (& learning to limit it)
​66. Olive oil tasting
​67. Talking on the phone more (I know, cringe, right?!)
​68. A new hairstyle thanks to Wigdot
69. Being on time to all commitments 
70. The 30 Day Squat Challenge
​71. Going one month without any impulse purchases
72. Sticking to a new healthy habit with the app Streaks
73. Being more transparent
74. Ordering the impossible burger instead of a regular burger
75. Cutting down on food waste by purchasing less and cooking more
76. Alcohol-alternative drinks, such as Kin
77. Negotiating for a higher salary or job position
78. A new snack that catches your eye at the grocery store
79. Goat Yoga
80. Joining a roller derby league
81. Becoming a polymath (someone who excels in multiple areas of life) 
82. Drinking more drinks that have no alcohol or caffeine
​83. Being a leader more often than a follower
84. Entering a short-story contest
85. Cooking seasonally with seasonal fruits, vegetables, etc
86. Joining Vinyl Me record club
87. Reading more investment / financial magazines, books, and journals
88. Giving more genuine comments on your family & friend's social media posts - because even though it can be fake, it's amazing we can connect with so many people
89. Seeing the other person's perspective in an argument or heated moment
​90. Learning, networking, and creating new relationships through online community forums
​91. Surrounding yourself with people who are smarter, wealthier, and have more life experience - so you can educate and grow yourself to their level (or beyond!)
​92. Being an ambassador for a club, organization, product, or business that you look fondly towards
93. Studying more - even if you're not in school!!
94. Rewiring your brain
95. Being more deliberate
96. Conserving more
97. Turning the page on chapters in your life that no longer need to be read
98. Different types of coffee
99. Supporting local bands/artists by attending local shows or art fests
100. Riding on the scooters that are poppin' up everywhere!
101. Geocaching
102. Cutting back on your water usage 
103. Writing a book or creating something with your partner or a friend
104. Setting up an automatic bank transfer to your savings - so you at least always save something! 
105. Reading an entire book in one sitting
106. Blind Wine/beer tasting