41 things to do in Chicago this weekend: Windy City Hot Dog Fest, Do Division Street Fest & more

Your toughest decision this weekend might be choosing between a concert, a comedy show or an outdoor festival. 

Here's your guide to events in Chicago May 29 – 31. 

Concerts around Chicago this weekend

May 29: Roy Blair at Outset

May 29: Summer Walker at United Center

May 29: Rilo Kiley at The Chicago Theatre

May 29: Dumpstaphunk at Garcia’s Chicago

May 29: Belle & Sebastian at The Salt Shed Indoors

May 29: WGCI Tone Kapone and Jacquees at House of Blues Chicago

May 29-30: Jeff Tweedy at Vic Theatre

May 30: Lee Burridge and Oliver Koletzki at Castaways

May 30: Of the Trees at The Salt Shed Outdoors

May 30: Hemlocke Springs at Thalia Hall

May 30: The Knocks x Dragonette x Aquaria at House of Blues Chicago

May 30: Cody Johnson at Allstate Arena

May 30: Laura Pausini at Rosemont Theatre

May 31: Bluegrass Brunch at Garcia’s Chicago

May 31: Deep Dish at Castaways

May 31: The Toadies at Vic Theatre

May 31: Romeo Santos & Prince Royce at Allstate Arena

 

Sporting events around Chicago this weekend 

May 29: Chicago Sky vs. Minnesota Lynx

May 29: Chicago Dogs vs. Winnipeg Goldeyes

May 29: Chicago White Sox vs. Detroit Tigers

May 30: Chicago White Sox vs. Detroit Tigers

May 30: Chicago Dogs vs. Winnipeg Goldeyes

May 31: Chicago White Sox vs. Detroit Tigers

May 31: Chicago Dogs vs. Winnipeg Goldeyes

 

Theatre and comedy shows around Chicago

Monty Python’s Spamalot 

Finesse Mitchell

Going Bacharach 

Bobby Lee

Deeply Rooted

House of Burlesque 

We Them One’s Comedy Tour

 

Things to do in Chicago May 29 – 31 

13th Floor Chicago Halfway to Halloween

13th Floor Chicago is bringing back its "Blackout" haunted house experience May 29-30, where guest navigate the attraction in near-total darkness. Tickets for the immersive pop-up event start at $29.99. 

 

Do Division Street Fest 

Do Division Street Fest returns to West Town from May 29-31 with live music, fashion shows, local vendors and family-friendly activities along Division Street between Damen and Leavitt streets. 

 

Arte Agave Chicago

Arte Agave Chicago returns May 29 to Artifact Events with tastings of more than 100 tequilas and mezcals, craft cocktails and live performances. 

 

Windy City Hot Dog Fest 

Windy City Hot Dog Fest takes over Portage Park May 29-31 with hot dog vendors, live music and a hot dog eating contest. 

 

Dino Dash at Brookfield Zoo 

Dino Dash returns May 30 with a two-mile run through Brookfield Zoo Chicago during the zoo’s new dinosaur-themed experience. 

 

BARK: Walk for Chicago’s Animals

The Walk for Chicago’s Animals returns to Lincoln Park on May 30 with a lakefront dog walk, agility courses, games and pet-friendly activities. 

 

Magnificent Mile Spring Art Festival

Magnificent Mile Spring Art Festival will showcase work from more than 60 juried artists May 30-31 outside 875 North Michigan Avenue. The free festival features jewelry, paintings, photography, fashion and glass art. 

 

Maifest Chicago 

Celebrating German heritage, Maifest Chicago returns to Lincoln Square May 28-31. The longtime festival features German food, beer, live music and traditional maypole celebrations. 

 

Vintage Sheffield Sip & Shop

Vintage Sheffield Sip & Shop debuts May 31 in Lakeview with vintage vendors, DJs, cocktails and outdoor patio experiences along George Street near Sheffield Avenue. 

 

Nathaniel Mary Quinn Exhibit 

Nathaniel Mary Quinn: A Love Letter to My Mother is now on view at the National Public Housing Museum, marking his first solo museum exhibition in Chicago. The free exhibit is inspired by Quinn’s childhood growing up in public housing. 

The Source: The events in this article were gathered by FOX Chicago's Justine Baker. Email justine.baker@fox.com to suggest an event. 

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