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10 Jul - 10 Reasons to Summer in Chicago


The summer solstice has hit The Windy City and we’re soaking up the sun with our favorite outdoor festivities. Whether you’re one for nature, or a culture seeker in search of the newest exhibit, Chicago is a one stop shop for all things summer.

1. Music Festivals

From Pitchfork to Lollapalooza, Chicago is known to throw a rockin’ party. Check out the list of festivals here, and then head here to save 15% off your stay with us.


2. Food

Chicago’s food scene is just as diverse and unique as the city itself. Hot dogs, doughnuts, deep dish pizza, tacos and BBQ adorn some of the hottest eateries in town. Don’t believe us? Check out all the #eeeeeats here.


3. Movies in the Park

Chicago Parks District puts on more than 240 outdoor screenings every summer! Grab a blanket, pack a picnic and indulge in cult classics with your crew. Get the full lineup here.


4. Street Festivals

Every summer, our favorite Chicago neighborhoods close their streets for community gatherings composed of art, music, and fashion. Get in on the excitement here.


5. Bike the 606

Over 17-feet above the ground, the 606 is a three-mile long park that was once an elevated freight train. It draws comparisons to NYC’s Chelsea High Line, but this public hangout spot has a trail just for bikers in addition to lounge space for local pedestrians.


6. Museums

Chicago’s culture spots may be local, but they’re rich in the world’s art, music, and history. The Art Institute of Chicago has held the number 1 spot for top museums in the world, but MoCA Chicago and the Field Museum of Natural History are also top contenders.


7. Kayak / Paddle Board on the River

Hit the waterway for an afternoon/evening of kayaking or paddle boarding. Guests of the Freehand save 25% all kayaking excursions!


8. Farmer’s Market

Chicago Farmer’s Markets aren’t just about stocking your fridge with the good stuff, you can upgrade your cooking skills with specialty classes and even get a fresh floral arrangement to top off your dinner party. Our favorite markets are here.


9. Jazz

It don’t mean a thing if it ain’t got that swing, and Chicago’s got it. Little do people know that Chicago has its own distinct style of jazz different from that of the rest of the country’s. Check out Chicago’s jazz clubs and festivals for a taste of Chicago’s vibrant and diverse music scene.


10. Freehand Chicago

We saved the best for last! We’ve recently set up shop in River North and we’re shaking things up in The Windy City. Come hang for an afternoon cup of jo’ at Café Integral, or get hooked on late night eats at the Broken Shaker. Summer isn’t complete without a full lineup of events, so be sure to check out our weekly Industry Night, Saturday Morning Walking Tours and Friday Run with locals. Discover our events/activities here.