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Enjoy Labor Day in the Loop

Posted  31 days ago  in  Trending

5 MIN READ – For many, Labor Day offers one last three-day weekend to enjoy summertime weather, so you’d better make the most of it! Spend the day in the Chicago Loop enjoying major events, great outdoor public space, world-class museums, delicious dining, an iconic shopping district, and more. If you’re having way too much fun, turn it into a vacation with an overnight stay in one of the Loop’s luxurious hotels. No matter what you’re into, the Loop’s got you covered.

Sundays on State

For one final chance this summer, join Chicagoans from every neighborhood and beyond for Sundays on State, a free interactive block party in the Chicago Loop. State Street is closed to traffic from Monroe to Lake as you experience art, culture, active recreation, shopping, food and drinks. Be a part of everyone’s neighborhood, the Chicago Loop! The event is free and open to the public, but those register to attend here are automatically entered to win a $1000 Loop staycation package. #SundaysOnState

Chicago Jazz Festival

The Chicago Jazz Festival is a Labor Day weekend tradition that promotes all forms of jazz through free, high-quality music programming. The festival showcases Chicago's local talent alongside national and international artists to raise awareness and appreciation for one of the city’s most beloved art forms. Learn more.

Enjoy “Urbs in Horto”


Labor Day weekend is not complete without a round of mini golf at Maggie Daley Park’s Chicago-themed course, where you can tour the entire city. Chicago may not have mountains, but we do have one of the largest outdoor climbing walls in North America. No matter what level of climber or boulderer you are, Maggie Daley has a route for you. If you would rather keep your feet on the ground, rent one of their Micro Kickboard Scooters, and scoot or rollerblade the quarter mile ribbon with incredible views of the Chicago skyline. If all this activity has made you hungry, stop by the Rink Café for a bite to eat and a cool, refreshing ice cream treat. Don’t forget their 3.5-acre Alice in Wonderland and Charlie and Chocolate Factory-inspired one-of-a-kind playgarden, recommended for children 12 and under. If you are looking for more of a respite, visit their Cancer Survivors Garden’s pillars of hope, and enjoy a peaceful moment.

There are plenty of options for hanging out outside in the Loop, including Millennium Park, the Lakefront Trail, the Chicago Riverwalk and more. See all public parks and plazas here.


Don't let the sun set on your summer without a trip on the Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady. Voted the #1 Boat Tour in North America by the USA Today 10Best Readers’ Choice Awards, this 90-minute cruise explores some of the city's greatest architectural wonders across all three channels of the Chicago River. Experience this award-winning boat tour for yourself, with multiple departures taking place every day. Then, continue your exploration of the city’s built environment with a trip to the Chicago Architecture Center, just $5 with your purchase of a river cruise ticket.

Don’t miss out on the other museums in the Loop—everything from specialized spots like the American Writers Museum and Museum of Contemporary Photography, to huge, iconic museums like the Art Institute of Chicago, to immersive, Instagrammable experiences like the Museum of Illusions, Skydeck, Medieval Torture Museum and more. All your options await you here.

High in the Sky

Chicago boasts some of the best rooftops in the country (we’re not just saying that ‘cause we’re biased.) From impeccable skyline views to scrumptious drinks and bites, Loop rooftops take the cake. Try a round at Raised, an urban indoor/outdoor bar that offers unparalleled service and breathtaking views of Chicago. Face the Chicago River and the iconic Marina City towers while you enjoy indulgent food, delicious cocktails, and the fabulous energy of a Chicago summer. Or take in the sights and delicious tastes of Cindy’s, Aire Rooftop Bar, ROOF on theWit and many more. Spend some time Labor Day weekend floating above it all. See your options here.

Shop shop shop

Macy’s State Street flagship store is a Chicago icon. Meet your friends under the giant clocks for a selfie, peek at the gorgeous Tiffany glass ceiling, dine at the Walnut Room to enjoy old-world elegance with a modern twist, and, of course, shop ’til you drop. After all, the seasons are changing, and your wardrobe could probably use an update. There’s no better place to find all you need than Macy’s on State Street.

State Street, “that great street,” is an iconic shopping destination. Check out the fanciest Target you’ve ever seen (also famously known as “Goth Target”), plus newer additions like UNIQLO and Primark. Swing into Block 37 if you’re looking for a mall experience in the city. The possibilities are endless; find them all here.

Staycation in the Loop

With a busy Labor Day weekend, full of things to do and see, wouldn’t it be great to spend the night at a fabulous Loop hotel? The Loop is one of the best places to see and be seen, so book your stay today! Check out Loop hotels here.