31 of the Best Things to Do in Chicago This August

Make the most of the final weeks of summer with the Chicago Air and Water Show, Chicago Hot Dog Fest, Lollapalooza, The Great American Lobster Fest, and more.


July 31 to Aug. 4: Northbrook Days 2019

This annual festival has been moved to Northbrook Court this year, but you can still expect tons of family fun, live music, and food and drinks. Northbrook Court, 1515 Lake Cook Road, Northbrook

Aug. 2-4: Squeeze’s Birthday Weekend with the Chicago Dogs

Chicago Dogs: Squeeze's Birthday Weekend
Photo by Daniel Boczarski.

Celebrate Chicago Dogs mascot Squeeze’s birthday as the Dogs take on the St. Paul Saints. On Aug. 2, the first 1,500 fans will receive a Squeeze bobblehead and kids can run the bases after the game. On Aug. 3, all fans will receive a birthday dessert and there will be a post-game fireworks show. And on Aug. 4, enjoy $3 bottomless popcorn and soda and meet the players and Squeeze before the game. Impact Field, 9850 Balmoral Ave., Rosemont

Aug. 3-4: Art at the Glen

This free festival will showcase the work of more than 150 juried artists throughout the Glen Town Center. Plus, enjoy live music, food, and kids activities. The Glen Town Center, 2030 Tower Drive, Glenview

Aug. 4: Drake Challenge Cup & Horses and Harleys

Enjoy a day of polo as well as a bike rally of roughly 100 Harley-Davidson motorcycles. Before you go, find out why this is a can’t-miss event. Oak Brook Polo Club, 2606 York Road, Oak Brook (Better is a proud sponsor of this event.)

Aug. 7: Taste of Andersonville

Taste of Andersonville: Stone Fox Chicago
Stone Fox Chicago’s Frozen Paloma (Photo courtesy of Stone Fox.)

This progressive dinner crawl will feature two routes this year with 17 tasting stops each. Check in at 5217 N. Clark, Chicago

Aug. 9-11: Chicago Hot Dog Fest

Join the Chicago History Museum for this celebration of the Chicago-style hot dog, which will also feature live music, family-friendly activities, and more. Stockton and LaSalle Drive, Chicago

Aug. 10-11: Kite Festival

Watch stunt-kite performances by the Chicago Fire Kite Team and the Kite Society of Wisconsin & Illinois before flying your own kite (bring your own or make one on-site) and enjoying lunch and ice cream (both available for purchase). Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe

Aug. 15: Craft Cocktail Festival

Sip cocktails and dine on food samples from Nando’s PERi-PERi, The Hampton Social, Roka Akor Old Orchard, and more while supporting Fight2Feed. Westfield Old Orchard, 4905 Old Orchard, Skokie

Aug. 16-18: Evanston Art & Big Fork Festival

Evanston Art & Big Fork Festival
Photo courtesy of Amdur Productions.

This free festival will feature art, food and drink, live music, and activities for kids. Downtown Evanston, 800 Church St., Evanston

Aug. 17-18: Chicago Air and Water Show

Look up — one of Chicago’s biggest summer events will take place high above Lake Michigan. North Avenue Beach, 1600 N. Lake Shore Drive, Chicago 

Aug. 22: 2nd Annual River Boil

Enjoy andouille sausage, potatoes, fresh sweet corn, and summer cocktails with a stunning view of the Chicago River. River Roast, 315 N. LaSalle Drive, Chicago

Aug. 23: Chicago Sky vs. Washington Mystics

Cheer on Diamond DeShields (winner of the 2019 WNBA All-Star Skills Challenge) and the Sky as they take on Elena Delle Donne and the Mystics. Wintrust Arena, 200 E. Cermak Road, Chicago

Aug. 23-25: Taste of Greektown

Taste of Greektown in Chicago
Photo by Mike Lyons.

Sample fare from local restaurants, rock out to Greek bands, play games, and more. Halsted between Van Buren and Jackson, Chicago

Aug. 23-25: Skokie’s Backlot Bash

Say goodbye to summer at this event featuring two music stages, carnival rides and games, the Backlot Dash 5K, movies, a classic car show, food and beer, a farmers market, and more. Downtown Skokie

Aug. 24-25: Heirloom Fest: Tomatoes & More

Get expert tips for growing tomatoes and heirloom veggies at home as well as cooking ideas. Plus, visit the market to purchase items like pepper jams and heirloom popcorn. Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe

Aug. 24-25: Port Clinton Art Festival

Shop paintings, jewelry, photos, and more from 260 artists at this festival, one of the best in the country. 600 Central Ave., Highland Park

Aug. 30 to Sept. 1: The Great American Lobster Fest

The Great American Lobster Fest in Chicago
Photo courtesy of The Great American Lobster Fest.

Lobster will be flown in from the East Coast for this lobster and seafood festival, the largest in the Midwest. As you dine, enjoy live music, family activities, shopping, drinks, and more. Navy Pier, 600 E. Grand Ave., Chicago


Opens Aug. 23: Melanie Parke and Richard Kooyman, “New Paintings”

Melanie Parke at Anne Loucks Gallery
Melanie Parke, “Amethyst Pine,” oil on canvas, 30×30 in.

Anne Loucks Gallery’s newest exhibit will highlight paintings by Melanie Parks and Richard Kooyman, both Michigan-based artists who have been represented by this Glencoe gallery for 15 years. Meet the artists at the opening reception on Aug. 23 from 5-7 p.m. Anne Loucks Gallery, 309 Park Ave., Glencoe


Aug. 8: Play for Free at Chicago Children’s Museum

Enjoy a free day at this museum as you explore exhibits and take part in special events like Ring Around the Parachute and a dance party. Chicago Children’s Museum, 700 E. Grand Ave., Chicago

Closes Aug. 25: Purchased Lives: The American Slave Trade from 1808 to 1865

As this Illinois Holocaust Museum exhibit nears its closing date, the museum will host a lecture titled “The Lingering Impact of the American Slave Trade” on Aug. 8. Illinois Holocaust Museum & Education Center, 9603 Woods Drive, Skokie

Closes Sept. 8: Manet and Modern Beauty

Don’t miss your chance to view this exhibit, the first to focus on Manet at the Art Institute in more than 50 years. The Art Institute of Chicago, 111 S. Michigan Ave., Chicago

Ongoing: Nature Cat: Backyard and Beyond

Nature Cat exhibit at Kohl Children's Museum
Photo courtesy of Kohl Children’s Museum.

Tally Ho! Join PBS Kids’ animated hero Nature Cat and his friends as they explore the marsh, the cave, and the forest while learning important lessons about the great outdoors! Exhibit created by Kohl Children’s Museum in partnership with WTTW Chicago and Spiffy Pictures. Kohl Children’s Museum, 2100 Patriot Blvd., Glenview


Aug. 1-4: Lollapalooza

Lollapalooza in Chicago
Photo by Roger Ho/Lollapalooza 2018.

Some of the biggest names in the music industry (The Strokes, The Chainsmokers, Childish Gambino, Tame Impala, Twenty One Pilots, J Balvin) will descend upon Chicago for this four-day festival. Grant Park, 337 E. Randolph St., Chicago

Aug. 6: Barbra Streisand

Legendary singer, actress, director, author, and activist Barbra Streisand will return to Chicago for one night only. United Center, 1901 W. Madison St., Chicago

Aug. 8-11: Out of Space

Evanston concert hall SPACE goes outside for four concerts with Cake (Aug. 8), Mandolin Orange and I’m With Her (Aug. 9), Jeff Tweedy with Ohmme (Aug. 10), and Bruce Hornsby & The Noisemakers with guest Suzanne Vega (Aug. 11). Canal Shores Golf Course, 1030 Central St., Evanston

Aug. 10: Gladys Knight

The Empress of Soul returns to Chicago for a can’t-miss concert. The Chicago Theatre, 175 N. State St., Chicago

Aug. 12: Broadway in Chicago’s Summer Concert

This free concert will feature performances from “Come From Away,” “Dear Evan Hansen,” “Frozen,” “Hamilton,” “Mean Girls,” “My Fair Lady,” “The Phantom of the Opera,” and more. Jay Pritzker Pavilion at Millennium Park, 201 E. Randolph St., Chicago

Aug. 17: Laurie Berkner

Laurie Berkner, who you may know from Nick Jr., Sprout, and NBCUniversal Kids, will perform at Ravinia as part of the Kids Concert series. The KidsLawn will also feature an instrument petting zoo and crafts for young music fans to enjoy. Ravinia Festival, 418 Sheridan Road, Highland Park

Aug. 23 to Sept. 2: Chicago Jazz Festival

Chicago Jazz Festival
Photo by DCASE, City of Chicago.

Enjoy concerts around Chicago before the main shows at Millennium Park, which will feature a tribute to Nat King Cole by his brother Freddy Cole. Various

Aug. 24: Hip-Hop Orchestra in Chicago

You don’t want to miss Thee Phantom & The Illharmonic Orchestra, which combines hip hop and classical music. Auditorium Theatre, 50 E. Ida B. Wells Drive, Chicago


Opens Aug. 14: Into the Woods

Into the Woods at Writers Theatre
Photo by Saverio Truglia.

This Stephen Sondheim classic brings your favorite fairy tale characters to life in a whole new way. Writers Theatre, 325 Tudor Court, Glencoe

Anna Carlson writes the weekly Weekend 101 column and monthly Recommended Events. A graduate of the University of Missouri, her work has been published in Chicago Parent, Inside Columbia Magazine, and Central California Parent Magazine. She is a proud supporter of St. Jude Children’s Research Hospital