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Labor Day Weekend in Chicago

Labor Day marks the unofficial end of summer, yet that doesn't mean there won't be plenty to do this weekend! From food and music festivals to architecture river cruises and much more. Check out some great activities this weekend.

The Chicago Jazz Festival is an annual citywide tradition showcasing local and national talent. Performances take place Thursday to Sunday in Millennium Park and at the Chicago Cultural Center.

1. Visit the Art Institute of Chicago

The Art Institute of Chicago is one of Chicago's premier attractions, and a must-visit destination. Boasting one of the world's largest collections, this museum is sure to have something for everyone!

Since 1879, this museum has housed more than 260,000 works of art. Some highlights include Asian statues dating back millennia; European masterpieces spanning from Renaissance to modernity; as well as American and Impressionist paintings.

The museum features special exhibitions and educational programs. Weekends may prove particularly busy; so plan ahead.

Flowers, food, and drinks (excluding water ) are prohibited at the museum. To reduce crowding for children's visits, an Architecture River Cruise may be more suitable. Museum admission tickets cost $39; students with ID can enter free on certain days during the year while Illinois residents and active-duty military personnel can visit for free during wintertime.

2. Take a Bike Ride

Chicago offers an expansive bike path network and impressive commuter rail system for biking enthusiasts to take advantage of over holiday weekend rides, whether retracing one of Chicago's iconic landmarks or cycling loops along lakefront trails. Get on your wheels for some self-guided fun this holiday weekend and ride!

Join Bike the Drive this Sunday, September 4 for something truly different: this event closes Lake Shore Drive to cars for an epic 30-mile bike ride showcasing incredible views of Chicago skylines and Lake Michigan from 8 am until noon in Grant Park.

Labor Day weekend presents music lovers with plenty of chances to experience live tunes throughout Chicago's rooftop bars and open-air venues, from free jazz festivals like Millennium Park's Jazz Festival honoring legendary and contemporary jazz greats, or the Northerly Island North Coast Music Festival showcasing regional musicians.

3. Head to Millennium Park

Millennium Park offers visitors an amazing architectural spectacle - the "Bean", "Cloud Gate" Crown Fountain and Jay Pritzker Pavilion to name just a few - perfect for an ideal family outing this long weekend. Additionally, free public cultural programming such as concerts, exhibitions and tours await them here.

This outdoor amphitheater hosts the Summer Concert Series of rock, jazz and world musicians as well as annual festivals like Chicago Blues Festival and Grant Park Music Festival. Pack up a picnic and take in Chicago's beautiful outdoors!

Visit their website for a complete schedule.

4. Head to the Jazz Festival

The Chicago Jazz Festival is an iconic Labor Day weekend tradition that brings all forms of jazz together for free music programming. Showcasing local talent alongside national and international artists to raise awareness for one of Chicago's beloved art forms - this year the Festival takes place this Thursday through Sunday!

Bitter Jester Music Festival promises a concert competition between emerging artists in Navy Pier's Beer Garden for those seeking an additional exciting way to end the weekend. Don't miss this fun family-friendly way of ending it all.

Labor Day weekend in Chicago offers the ideal way to soak up the last moments of summer fun. Festivals, concerts and the final fireworks display at Navy Pier offer endless entertainment. When planning your visit to Chicago's Windy City make your stay at The Rose Hotel Chicago O'Hare one to remember by booking its Fashion Outlets of Chicago Shopping Package featuring a Savings Pass, Complimentary Coat/Bag Check Service, Late Checkout Time and Continental Breakfast service - plus many other amenities!

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Originally published: 

June 6, 2023

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Jason

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I enjoy designing and curating experiences both virtually and in 3-dimensional reality.
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