Haute & Cool Things to Do This Weekend in Chicago

Looking for something fun and unique to do this weekend in Chicago? Instead of doing the same old routine, which can get boring, why not check out some of amazing new events in the city? Whether you want to explore a new restaurant at a great price or finding new goods at a vintage market, you’ll definitely find something that’s perfect for you.

Here, we’ll give you the inside scoop on the best haute and cool things to do in Chicago this weekend. Read on to find out about some of the most interesting activities in the city for an experience that’s definitely different from the ordinary.

Dine at Chicago’s Best Restaurants during the final days of Chicago Restaurant Week

Thursday, February 2nd – Sunday, February 5th // Time Varies

Cost: Varies by Location

Sample the city’s best eats during Chicago Restaurant Week, a 17-day celebration of the city’s award-winning culinary scene. The 16th annual event brings together more than 300 of the city’s top restaurants, representing a near-endless array of cuisines.

Experience Black History Month Events Across the City

Thursday, February 2nd – Sunday, February 5th // Time Varies

Cost: Price Varies by Event

Black History Month is here in Chicago! And, the events this year are bigger and bolder than ever. Check out these awesome events this weekend in Chicago:

Freedom Fridays at Haji Healing Salon

Black History Month Tours every Saturday with Dilla

MOB(Moments of Blackness) Part One: A short film and conversation

Saturday Youth West African Dance Class with Mama Aluna

 Black x Art at the Museum of Contemporary Art Chicago

Fall in love with vintage pieces at A Valentine’s Day Vintage Market

Sunday, February 5th // 11:00 a.m.

Cost: Free

Head over to Epiphany Center For The Arts in the West Loop for a vintage and handmade market. This event will feature over 50 vendors and hosted by Vintage House Chicago.

Sample Delicious Donuts at Donut Fest in Evanston

Sunday, February 5th // 1:00 p.m. – 5:00 p.m.

Cost: $25 – $50

Love Donuts? Who doesn’t? Enjoy beer? They’ll have that too at Donut Fest this weekend in the suburbs of Evanston of Chicago. Sample donuts enjoy beer, coffee, and more with a fun-filled tasty event.

Sponsors include Temperance Beer Co. and Food + Travel. Proceeds will benefit the Hospitality Fund.

Catch Adam Sandler at the United Center

Sunday, February 5th // 7:30 p.m.

Cost: $125- $160

Adam Sandler will bring his outstanding and renowned tour to Chicago this weekend. A successful actor, writer, producer, and musician, Sandler has also performed on stage to live audiences on a sold-out tour across the U.S. and Canada. In 2018, 100% Fresh was released on Netflix which was Sandler’s first comedy special in twenty years and was filmed during his last concert tour. 

PLEASE NOTE: This show is recommended for mature audiences or adults 16 and older. 

Opening weekend of New Releases: Neptune Frost

Saturday, February 4th // 7:00 p.m.

Cost: Free

Catch the opening of NEPTUNE FROST this weekend in Chicago. Hosted by Doc Films is the Afrofuturist tale of a hacker collective in Burundi. NEPTUNE FROST is a colorful, gripping story that is equal parts acerbic social critique and joyful ingenuity.

For more things to do in Chicago, check out the daily events calendar.


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