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Summer Happenings!


August Rocks Chicago


Rooftop bars, al fresco dining, a boat ride on the lake or strolling through Millennium Park are just a few way Chicagoans make the most of summer’s glorious weather. From Lollapalooza to the Chicago Air Show, August is jam-packed with massive fun for people of all ages. August is a thrill ride from start to finish so rest up before you come and be ready for some incredible music, shows, meals, and general good times. Pack the sunscreen and the umbrella (just in case) and get ready to snap some memorable selfies.


Grant Park Music Festival Tchaikovsky Romeo and Juliet

August 1

6:30-8 p.m.

Carlos Kalmar returns to lead the orchestra in a Shakespearean-inspired program, which includes the tales of Othello, Macbeth and Romeo and Juliet, as well as the classic Tristan und Isolde. Just one of many incredible and not-to-be-missed concerts in this summer soiree. 



August 2-5

11 a.m. – 10 p.m.

Grant Park

Soak in the sounds of summer at this four-day music festival headlined by Bruno Mars, The Weeknd, Jack White and the Arctic Monkeys, but just a taste of what you’ll get. Over 200 acts will be performing over the four days, with a lot of Chicago’s best hip hop artists in the mix. And who wouldn’t want to attend just for the novelty of seeing LL Cool J? 


Arlington Million

August 11, 2018

Gates open at 10:30, first race at 12:15 p.m.

This one of worth leaving the city limits. Pack your Derby pastels and get ready for an exciting ride. 2018 marks the 36th running of the Arlington Million, the first stateside horserace to offer a $1 million purse to the winner. Don’t miss this all-day affair with live music before and after the main event, including a free concert by Eric Pasley, and, like always, a chance to be a part of the winner’s circle if you place your bets right.


Jazzin at the Shedd

Wednesdays, August 1-29

5-9 p.m.

Take a sip of summer at Jazzin’ at the Shedd and move to the rhythms of Chicago’s top jazz musicians. Combine a cocktail with great music, the city skyline, and fireworks. 


The Taco Crawl

August 11, 2018

11 a.m. – 7 p.m.

River North’s finest watering holes

Crawl from bar to bar and sample awesome tacos and enjoy beer and tequila! Your $10 ticket includes admission, seven Tacos (one per hour), drink specials, giveaways, and more. Can’t think of a finer way to waste an afternoon in the Windy City. Bars include AceBounce, Bar Louie, El Hefe, Hubbard Inn, Ironside, Moe's Cantina, Old Crow, Taco Joint, Kerryman, Theory and more.


Chicago Air and Water Show
August 19-20, 2018
10 a.m. – 3 p.m.
North Avenue Beach

Get ready for some daredevil thrills on the water and in the air in this free show, now in its 60th year. Featuring some of the top civilian and military pilots and aircraft, it’s nothing short of awe-inspiring. Camp out early on the beaches at Oak Street and North Avenue or head to your favorite rooftop for the best viewing spot. 

Chicago Triathlon
August 29, 2018
Monroe Harbor, 6 a.m.
With more than 10,000 participants, this is one of the largest triathlons in the world. Sign up for this challenging event or enjoy watching the athletes compete against the backdrop of the Chicago skyline. Race weekend consists of five stand-alone triathlons, including the Life Time Kids Tri Chicago (two distances), Chicago Tri SuperSprint and the Transamerica Chicago Triathlon Sprint and International races. 


Dream Freaks Fall from Space

Tuesdays, Wednesdays & Thursdays at 8pm
Fridays & Saturdays at 8pm and 11pm
Sundays at 7pm

Second City

This Old Town comedy venue is and always will be the bomb. Head to the mainstage to take in Dream Freaks Fall from Space, which holds a funhouse mirror up to the already bizarre times in which we’re living. The powerhouse cast delivers a show that’s surreal, musical, maniacal, and utterly entertaining all at the same time. 


Music on the Lake

July 1 - Sept. 3, 2018 

Reggae, disco, swing, 80s cover bands, and more! Enjoy live music and dancing in the Miller Lite Beer Garden at Navy Pier. Some evenings also offer free dance lessons. Free for all ages.


John Singer Sargent and Chicago’s Gilded Age

The Art Institute Chicago

111 South Michigan Avenue

From July 1 through September 30, the Art Institute of Chicago presents an exhibition of American Portraitist John Singer Sargent with a focus on his numerous Chicago connections. Featuring nearly 100 objects from the Art Institute’s collection, private collections, and public institutions, John Singer Sargent and Chicago’s Gilded Age examines Sargent’s impressive breadth of artistic practice and the network of associations among the artist, his patrons, his creative circle, and the city.


The 606

Head off the beaten path and walk, run, or bike the 606, an art and nature-filled 2.7-mile multi-use recreational trail and park created on an abandoned rail line. Hop on and off at any point and explore restaurants, cafes, shops, and watering holes along the way. Dogs on leash welcome. 


Movies in the Park
Hollywood stars return to Chicago skies this summer, as Movies in the Parks brings big-screen entertainment to local parks for the eighteenth season. Featuring everything from classics from the Golden Age of Hollywood and retro childhood favorites, to the best family-friendly box office favorites from recent years.  All movies begin at dusk. Check out the full lineup in the My Chi Parks App.

Mystic Blue’s Fireworks Dinner Cruises 

Wednesday: Board 6:30 p.m. Cruise 7-10 p.m. 
Saturday: Board 7:45 p.m. Cruise 8:30-11:30 p.m. 

Memorial Day through Labor Day

There are so many dinner cruises out on Lake Michigan we can’t begin to name them all. This 3-hour cruise is a sure bet for a good dinner, heart-pumping music, and the best views of Chicago’s skyline, including the nightly fireworks over the lake.

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