How to spend the summer in Chicago

09 March 2026

For an incredible nine years in a row, Chicago has been crowned the ‘Best Big City in the U.S.’, and it’s not hard to see why. This Midwestern metropolis, set on the shores of Lake Michigan, offers a holiday experience that feels endlessly exciting. With its welcoming spirit, world-class attractions, and a cultural scene that is constantly evolving, Chicago makes everyone feel right at home. Whether you are seeking artistic inspiration, family adventures, or simply a new city to explore this summer, your Travel Counsellor can craft the perfect itinerary to help you discover this exceptional city.

Kick off summer with football and festivals

The summer of 2026 is set to be an unforgettable one in Chicago, especially for sports fans. The city will come alive with excitement, hosting a variety of thrilling sports events and engaging experiences, welcoming football fans traveling to North America. You can join locals at live viewing parties across the city, soaking up the global spirit of the beautiful game. Chicago Fire FC will host a huge fan zone at Recess from 11^th June until 19^th July, featuring live matches, guest appearances from players, and special food and drink offerings. Beyond the football, the city’s summer calendar is packed with festivals, concerts, and cultural events that bring its diverse neighbourhoods to life.

Family adventures in the Windy City

Chicago is a fantastic playground for an all-ages adventure. At Navy Pier, you can ride the 200-foot-tall Ferris wheel for amazing views of the city skyline and lakefront. For a truly unique experience, head to Maggie Daley Park, where children can scale an outdoor rock-climbing wall or enjoy the whimsical play gardens. Chicago’s museums, including the Field Museum and the Museum of Science & Industry, offer hands-on exhibits that bring learning to life for curious minds of every age.

Dive into Chicago's cultural scene

Chicago's cultural landscape is bold, daring, and always innovating. The city is the birthplace of artistic movements like improv comedy, house music, and amplified blues, and its creative spirit is still very much alive. You can explore this rich heritage in world-class institutions like the Art Institute of Chicago or in the many galleries dotted throughout the city’s neighbourhoods. A major highlight for 2026 will be the much-anticipated opening of the Obama Presidential Center in June. Located on the city’s South Side, this new museum and community campus will offer a journey through the legacy of President and Mrs. Obama, with dynamic exhibits and interactive activities for all visitors.

Celebrate pride in an LGBTQ+ friendly city

Chicago’s reputation for warmth and inclusivity is well-earned. The city is one of the most LGBTQ+ friendly destinations in the country, with welcoming communities and year-round Pride celebrations. Northalsted, the first officially recognised gay neighbourhood in the United States, is the heart of the community. Here, you will find historic landmarks like The Legacy Walk alongside lively gay bars, clubs, and fantastic drag shows. While the famous Chicago Pride Parade takes over the city in June, the spirit of Pride is felt all year long, making it a welcoming place for all travellers to explore and be themselves.

Savour the flavours of Chicago

No trip to Chicago is complete without indulging in its legendary food scene. From iconic deep-dish pizza and classic Chicago-style hot dogs to Michelin-starred dining experiences, the city’s culinary offerings are as diverse as its population. You can explore global cuisine in lively neighbourhoods like Pilsen, known for its authentic Mexican food, or Uptown’s ‘Asia on Argyle’ for incredible Vietnamese dishes. Whether you are looking for a casual bite from a neighbourhood eatery or a tasting menu from a celebrated chef, Chicago’s restaurants provide a delicious way to experience the city’s character.

To design your summer getaway to Chicago, contact your personal Travel Counsellor today.

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How to spend the summer in Chicago

Where to stay, eat, and explore in Bermuda

Jumeirah’s resort experience is being reimagined in Dubai and the Maldives

Where to stay in Kruger National Park

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