Haute & Cool Things to Do This Weekend in Chicago

Rupi Kaur on Haute and Cool Things to do in Chicago

This weekend, we are back with another list of curated events for you to enjoy this weekend in Chicago. From bottomless and boozy brunches to artistic performances expressed through spoken word, dance, and even writing.

Check out the full guide of Haute and Cool things to do in Chicago this weekend below.


An Evening With Rupi Kaur

Thursday, May 12th // 8:00 p.m.

Cost: $39 – $49

Enjoy a captivating evening with the popular poet, artist, and performer Rupi Kaur this weekend at the Chicago Theater. The captivating performance is an all-new spoken word poetry experience. Audiences are taken on a journey of personal loss and love, growth, mental health, community, friendship, and strength. These universal themes take center stage as original music scores the show and projections immerse audiences.

No Cap Comedy Tour

Friday, May 13th & Saturday, May 14th // 8:00 p.m.

Cost: $99 – $600

Enjoy some laughs this weekend with a live comedy show at the Arie Crown Theater. The No Cap Comedy Tour features DC Young Fly, Chico Bean, Karlous MIller, B. Simone, Blaq Ron, and Mojo Brookzz.

Cerqua Rivera Dance Theatre by Photo by Fernando Rodriguez Photography

Cerqua Rivera Dance Theatre

Saturday, May 14th // 7:30 p.m.

Cost: $36

Experience an explosive display of theater for one night only at The Beverly Arts Center in Chicago. Cerqua Rivera Dance Theatre is a company proudly and visibly multicultural in both its art and artists, that engages audiences in magnetic human stories at once new and deeply familiar encapsulated through dance, story, and music.

Guests with mask at the Field Museum Chicago

Free Admission Days at the Field Museum

Saturday, May 14th & Sunday, May 15th // 9:00 a.m. – 5:00 p.m.

Cost: Free

Spend a day at the Field Museum for free this weekend in Chicago. Free Admission Days are available to all Illinois residents and are the perfect opportunity to explore the general admission exhibitions with family and friends. Haute Tip: You cannot take advantage of Free Days when buying tickets online.

American Writers Festival

American Writers Festival

Sunday, May 15th // 10:00 a.m. – 5:00 p.m.

Cost: Free

Check out a free literary festival in downtown Chicago this weekend. The inaugural American Writers Festival will be held on four stages inside the Chicago Cultural Center and one stage at the American Writers Museum, and feature more than 75 beloved contemporary authors, artists, and playwrights. Participating writers will address their perspectives on many of today’s most timely and controversial topics through themes within their literature. Haute Tip: Proof of vaccination and masks are required to enter the American Writers Museum and all event spaces at the Chicago Cultural Center.

Indulge in a Bottomless Brunch

Saturday, May 14th & Sunday, May 15th // Time Varies

Cost: Varies by Location

Sip and savor bottomless drinks and brunch items from various restaurants in Chicago. From unlimited low-priced bottomless options to all you can handle boozy beverage and food packages—these bottomless brunch options will help you kick off your weekend the right way. Bottomless and boozy.

check out our events calendar for more things to do in Chicago this weekend.

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