Chicago: Things To Do Around The City (with 2021 updates!)


For the girls with the gold hoops and fly hair…

[Scroll all the way to the bottom for the 2021 hot foodie picks!]

Whenever I’m visiting a new city, I do what we all do, I search Google to see which places are the must sees. Most of the time I end up stumbling upon a list that some well-meaning person has created and while helpful, there’s one problem: this person is not like me or into the same things as me. So, after having relocated to my favorite city, Chi-City, I decided to make the perfect list, made just for girls, and guys, like me. This is thee most beautiful city in America- just look at these photos! You can also check out videos of me hopping around the city right here –> LINK!

photo credits: @taemichelle_
photo credits: Instagram | @ricp2206

Now, because I am not a Chicago native, I have enlisted the help of two of my best homegirls, Brittany and Lilly, both born and raised in Chicago (Lilly on the North side and Brittany on the South side) to help me make this list.

The list at a glance:

[Lead Contributors: Brittany W. and Lilly H.]

  1. Sip on a drink at Vu Rooftop, Persona Lounge, or Streeterville Social
  2. Brunch at 80 Proof, Truth*, Beatnik, or Fremont
  3. Go to a festival
  4. Play at an adult arcade like Punch Bowl Social or Emporium
  5. Hit up Club Lite, Club Reverie, or Joy District’s day party
  6. See a movie in the park
  7. Take a helicopter ride or visit the Skydeck
  8. Party on the lake or cruise on the river
  9. Eat at Harold’s*, Portillo’s, Giordano’s, or Lou Malnati’s
  10. Go to a local market and shop at Boxville*
  11. Support a local business like Sip & Savor* or Shawn Michelle*
  12. Hang out on the lakefront!

So, let’s get into the details and remember, all of the business names listed below are clickable links.

1. Sip 

Vu Rooftop

133 E Cermak Rd

photo credits: Instagram | @vurooftop
IMG_4123 2
photo credits: Instagram | @vurooftop

Persona Lounge

408 S Wells St

photo credits: Instagram |@personalounge

Streeterville Social

455 N Park St


photo credits: Instagram |@steetervillesocial

2. Bottomless Brunch


80 Proof

1500 N Wells St

photo credits: Instagram |@80proofchi


56 E Pershing Rd

photo credits: Google Images

Beatnik On The River

180 N Wacker Dr

photo credits: Instagram |@beatnikontheriver


15 W Illinois St


photo credits: Instagram |@fremontchicago

3. Go to a street festival

Chicago has a street festival every week of the entire summer. There are more than 150 festivals and the dates differ by a few days to a week each year, but you can find two different lists here and here. Notable favorites are:

Silver Room Block Party


photo credits: Instagram | @thesilverroom

Hyde Park Brew Fest

photo credits: Instagram | @hpbrewfest

Chosen Few Picnic & Festival

photo credits: Instagram | @chosenfewdjs

The Taste of Randolph

900 W Randolph St

photo credits: Instagram | @tasterandolph

4. Play (and have a drink) at an adult arcade

Skee-ball, giant jenga, bowling, foosball, darts– they’ve got it all!

Punch Bowl Social

310 N Green St.


photo credits: Instagram |@punchbowlsocial

Emporium Chicago

1366 N Milwaukee Ave


photo credits: Instagram |@emporiumchicago

5. Hit the club

Club LITE Chicago

215 W Ontario St

photo credits: Instagram |lite.chicago


414 N Orleans St

photo credits: Instagram |@reveriechicago

Joy District Day Party

112 W Hubbard St


photo credits: Instagram |@joydistrict

6. Catch a movie in the park

You can catch a free movie in Bronzeville at Armstrong (Lillian Hardin) Park located at 4433 S. St. Lawrence Ave. Also, downtown in Millennium Park- The Millennium Park Film Series is every Tuesday, June through August at 6:30p. This Summer they’ve shown Black Panther, The Wiz, Fences, and Moonlight.IMG_4129

photo credits: Google Images

7. Explore the city from an aerial view

Chicago Helicopter Experience

photo credits: Instagram |@chicagoheli

The Ledge- Skydeck Chicago IMG_4681IMG_4132


photo credits: Instagram |@skydeckchicago

8. Get on a boat!

Party on Lake Michigan 

Lake Michigan’s boat scene gets WILD. On almost every warm day, people on boats tie their boats together and then hop from boat to boat for one enormous party, notoriously dubbed as the “Playpen:”


Cruise the Chicago River

The Chicago River goes right through the center of downtown, so these boat cruises give you incredible views of Chicago’s famous architecture.

photo credits: Instagram |@espetersen

9. Eat Chicago style

Harold’s Chicken Shack*

When I asked the question ‘Which Harold’s is the best?’ the answer was a unanimous “Depends on who you ask.” I linked up a list, but my personal friends believe that the very best locations are: 103rd & Halstead and 100 W 87th St.

Harold’s Chicken Shack \ Image belongs to Chicago Mag


For Chicago style hot dogs and Italian beef

photo credits: Instagram |@portilloshotdogs

And for the infamous Chicago Pizza



photo credits: Instagram |@giordanospizza

Lou Malnati’s


photo credits: Instagram |@loumalnatis

And these restaurants aren’t “Chicago foods,” but they’re some of my faves: EatalyCantina Laredo, and Mercadito

10. Visit an outdoor market

Boxville Marketplace*

320 E 51st St

Boxville is a street food market and container mall that runs every Wednesday and Sunday June through October. Boxville is made for you to support the local community by shopping local and purchasing unique pieces and every day essentials.


11. Grab coffee or ice cream at a small business

Sip & Savor*

5301S Hyde Park Blvd

This cute coffee shop’s slogan is “Where coffee and community meet” and they specialize in fair-trade coffee from around world.


photo credits: Instagram | @sipandsavorchicago

Shawn Michelle’s Ice Cream*

46 E 47th Street

Shawn Michelle is serving up HOMEMADE ice cream with flavors like Jamaican rum raisin, melanin magic, honey cinnamon graham cracker, black walnut, and banana pudding! And they don’t just serve ice cream, they also serve our most beloved peach cobbler….WOW!

Melanin magic and honey cinnamon graham cracker ice cream | Photo belongs to

12. Hang out on the Lakefront

Chicago has 26 miles of sand beaches with the most popular probably being North Ave Beach, Ohio St Beach, and 12th St Beach.

Aerial image north Avenue Beach Chicago
photo credits: Google Images

You can run, walk, or bike the lakefront- this is one of my favorite things to do! It is just so pretty! There are 18 miles of Lakefront Trail and our suggestion is to start at either 31st Beach, 41st St Beach, or The Museum Campus and head north from any of those points.

photo credits: Google Images
photo credits: Google Images

Play volleyball or just lay out on the beach-

photo credits:

You can listen to live music, from house music to jazz to blues, on 31st Beach in the Summer. Here is a link to their Facebook page for the lineup.

Also, my favorite neighborhoods are:

Hyde Park, Bronzeville, Lincoln Park, the Riverwalk downtown, and Michigan Ave- The whoooole street (my preference is starting at Water Tower and heading south) is made for SHOPPING!

This list was made with the girls like me in mind, the ladies with the gold hoops and fly ass hair, so thank you for reading and I hope you fall in love with The Windy City
photo credits: Instagram |@whereisweatherby
photo credits: Instagram | @sekrety
photo credits: Instagram | @ry_guy_chi


UPDATE: 2021 Quick Picks

All businesses with an asterisk* are Black owned.

13 Comments Add yours

  1. kellbell6470 says:

    OMG!! THIS 👏🏽 WAS 👏🏽 EVERYTHING 👏🏽 !!
    Definitely my next trip. Thank you for this! ❤️

    1. Tae says:

      You’re welcome!

  2. Olivia says:

    Ahhhh! Thank you so much! I’m in the midst of planning a trip here and you’ve literally made planning so much easier! 🙌🏾

    1. Tae says:

      I’m glad! I hope you have fun!

  3. Brittany says:

    Ahh there’s so much rich Black history in Chicago I love it! I have a good amount of family there and I remember when I was younger and visited for the first time and tried the pizza, I was actually impressed! Coming from the state of New York I was shook by how good it was! 🍕Oh and by the way, I’m a huge Bulls fan! These pictures are great! 🤩

  4. Nia says:

    Thanks for this list!!! I want to visit and this list is a life saver!

  5. Kylie says:

    Thank you for this!!! I’m hoping to visit one day and you have given me insight on how awesome Chicago is!!! 💕💕

  6. Pia Walker says:

    I can’t wait to visit one day! You make Chicago seem like a dream!

    1. Tae says:

      It’s my favorite US city! Here and Wash, DC

  7. Briana says:

    I love that you’re always speaking life over your city. I’ve never visited Chicago but more often than not, I hear people speaking negatively about it. I’ve always wanted to visit for a number of reasons. Seeing the pictures you post from the food to spending time in the city with your hubby makes me that more eager to spend a few days there. Also, to know that you were raised by a black women and to see where you are now gives me hope. Thank you!

  8. Traci says:

    Your pics make me wanna relocate!! I’m definitely booking a trip here… Thanks for all the recommendations!!!

  9. Kayla Brewer says:

    Chicago is definitely on my list of places to visit! This post increased my excitement! Thank you for all the gems!

  10. Sherita Rooney says:

    This was very helpful and it inspired me to plan a trip to Chicago with me and my two babies. Thanks, Tae.

    From: __cerebellum

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