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The Best Chicago Festivals This Summer

The Best Chicago Festivals This Summer

This summer, enjoy a full season of senseational music festivals in the Windy City. Chicago is known for Lollapalooza, but check out all of the great musical festivities happening this year:

Chicago Blues Festival (June 7 – 9, 2019 in Millennium Park)

Chicago and blues music goes hand in hand, so it is not a surprise that Chicago boasts the country’s largest free blues festival. Entering its 36th edition, the Chicago Blues Festival attracts some 500,000 fans who come from around the world to enjoy performances from a wide range of blues musicians from Grammy Award-winning performers, like Bobby Rush, to up-and-comers.

Where to Stay: The Hotel Julian, named after St. Julian who was the patron saint of hospitality and travelers, sits just a few blocks from Millennium Park and all the festival’s blues performances.


Chicago SummerDance (June 27-August 24, 2019 in Grant Park)

The 23rd year of Chicago SummerDance is returning every Friday through Sunday this summer at Grant Park’s Spirit of Music Garden. The festival brings together people of all ages and musical persuasions together for dancing and free instructional lessons. Of course, those who don’t want to dance can always sit back and enjoy the music from 48 different live bands and DJs who will perform over the course of the summer.

Where to Stay: The Blackstone Hotel, a storied architectural icon within the city, is located in Chicago’s Loop district, just a short walk from Grant Park. From here, visitors will have easy access to the park with its music and dance lessons taking place during the festival.


Windy City Smokeout (July 12-14, 2019 at the United Center Parking Lot)

Beer, barbecue and coutry music is the perfect weekend. The Windy City Smokeout  features major country music superstars and up-and-coming talent to perform while attendees sample barbecue from some of the world’ best BBQ pit masters and beers from some of the country’s best breweries. The 2019 music line up will include performances by Ashley McBryde, Old Dominion, Lanco, Chris Young and more.

Where to Stay: The Hoxton Chicago made its highly anticipated debut to the city’s hotel scene in April 2019 in a newly constructed building in the West Loop/Fulton Market neighborhood, which boasts one of the most dynamic food and drink scenes in the city.


Year of Chicago Theatre in Millennium Park

As part of the 2019 Year of Chicago Theatre, the Department of Cultural Affairs and Special Events (DCASE) will present original theatre performances at Millennium Park beginning this summer. Between July and October 2019, DCASE will commission up to 12 theatre companies to complete a one-week residency in Millennium Park and produce a minimum of three performances that are free and open to the public. Proposals are currently being reviewed from Chicago’s diverse theatre and performance community and an announcement of the final program will follow.

Where to Stay: In the heart of Chicago’s theatre district, the Kimpton Allegro hotel is perfect for theatre enthusiasts coming into town to catch a show in Millennium Park or at one of the city’s over 225 theatres.



Chicago Jazz Festival (August 30 – September 2, 2019 in Millennium Park & Chicago Cultural Center)

For over 40 years, the Chicago Jazz Festival has been closing out the summer music season as the oldest free lakefront festival in the city. The shows at Millennium Park and the nearby Chicago Cultural Center feature jazz legends, influential modern masters and new voices over the course of 10 days. The 2019 line up has not yet been announced, but updates will be available at on the Choose Chicago website.

Where to Stay: There’s nothing that says “jazz” quite like Art Deco architecture. For travelers looking to visit Chicago for the annual Jazz Festival, the Loop’s St. Jane Hotel is a study in Jazz Age design.