Lead Contributors: Brittany W. and Lilly H.

For the girls with the gold hoops and fly hair…

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!

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:

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

Persona Lounge

408 S Wells St

Streeterville Social

455 N Park St

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2. Bottomless Brunch

Note: MAKE RESERVATIONS WELL IN ADVANCE

80 Proof

1500 N Wells St

Truth*

56 E Pershing Rd

Beatnik On The River

180 N Wacker Dr

Fremont

15 W Illinois St

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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

Hyde Park Brew Fest

Chosen Few Picnic & Festival

The Taste of Randolph

900 W Randolph St

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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.

Emporium Chicago

1366 N Milwaukee Ave

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5. Hit the club

Club LITE Chicago

215 W Ontario St

Reverie

414 N Orleans St

Joy District Day Party

112 W Hubbard St

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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.

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7. Explore the city from an aerial view

Chicago Helicopter Experience

The Ledge- Skydeck Chicago 

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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.

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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.

Portillo’s

For Chicago style hot dogs and Italian beef

And for the infamous Chicago Pizza

Giordano’s

Lou Malnati’s

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

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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.

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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.

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!

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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.

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.

Play volleyball or just lay out on the beach-

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

All businesses with an asterisk* are Black owned.