Although Chicago’s frigid breezes may have won the city its nickname “the windy city”, it’s an attractive summer destination for tourists from all corners of the world. With its distinctive vibrancy and rich culture, Chicago offers a ton of amazing festivals, beach activities, and culturally enriching experiences during the summer season. If you’re planning a trip to this world class destination, you’ll want to make sure you’ve organized everything in advance. Arrange your Chicago airport transfer or airport car service, book your stays, and most importantly – plan your activities during your stay. 

Let’s see what some of the best summer activities are in Chicago and help you make a list of must-try events and must-visit destinations. 

Spend a few romantic hours on a boat cruise

If you’re into boat experiences, Chicago is the perfect place to be during the summer. The city offers a range of different boat cruises and tours which take place in the waters of Lake Michigan and the Chicago River. No matter whether you’re looking for a relaxing or romantic  boat dinner cruise, an architectural tour, or an adventurous and adrenaline high-speed boat ride, there’s something out there for everyone.

Visit one of Chicago’s outstanding summer festivals

Chicago is renown for many things and its diversity of summer festivals is certainly one of them. You can visit practically any type of festival, with more than 70 festivals organized in the city during the warm months of the year. Some of the most popular ones include the Chicago Pride Fest (18-19 June), Summerfest (dates available in both June and July), the Grant Park Music Festival (15 June – 21 August), the Chicago Jazz Festival (1-4 September), and much more. 

If you’re into music and festival adventures, it’s worth synchronizing your travel dates with a festival of your choice to get the most out of the city.

Explore Chicago’s beautiful beaches

What’s a summer trip without some beach time? Luckily, you don’t have to go very far, as Chicago offers it all. The city has miles of stunning sandy beaches, where you can enjoy the sunrays and get the tan you’ve been dreaming of, play volleyball, enjoy cocktails, or build sandcastles. Some of the must-see beaches are Rainbow Beach, Oak Street beach,  North Avenue Beach, and Foster Beach.

If you want to enjoy daybeds and cabanas, make sure to reserve your spot in advance, the summer season is a busy one! 

Get wet with Chicago’s water activities

Speaking of water, Chicago also has a wide range of water activities to offer tourists. If you’re into adventure and thrilling water experiences, you can try jet skis and paddle boards on the lakefront of Lake Michigan or take part in kayaking on the Chicago River. Not to mention the diversity of boats you can rent, including electric vessels, pontoon party boats, and others. 

Visit Navy Pier

When in Chicago, you simply can’t miss Navy Pier – the city’s top attraction. Although this is a must-see spot throughout the whole year, Navy Pier is perhaps even more exciting to visit during the summer season. This lakefront treasure offers a multitude of exciting and spectacular experiences like summer firework displays, live music, theatre events, a waterfront beer garden, bike tours, dancing, Centennial Wheel, and more! Oh, we forgot to mention that it’s also host to Chicago’s largest rooftop bar and offers splendid views that you won’t be able to forget.

Discover the city’s public art 

Public works of  artwork is a big deal in Chicago and it won’t take you long to notice that. You can spot amazing art at different locales throughout the city, like train stations, skyscrapers, sidewalks, office lobbies, and more. If you are inspired by art, Chicago will certainly refill your creative pool. For example, the world famous Art Institute, Wabash Arts Corridor district won’t disappoint. You can also take amazing  art tours and discover the second to none variety of art presented throughout the city. 

Have a meal under the stars

Chicago’s restaurant scene  is a major focal point for all visitors, with  delicious cuisine, amazing cocktails, and fine wines to satisfy every taste. The  best part is that there are a ton of places where you can enjoy a tasty dinner outside, under the stars. You can check out some of the city’s top-rated local patios and rooftop restaurants, enjoy a meal with a lakefront view from one of the restaurants at the beachfront, or perhaps dive into the a plethora of diverse and award winning restaurants across the Chicago Riverwalk and throughout the city.

Explore the 606

The 606 is Chicago’s urban oasis that merges together so many different experiences and things to explore. You can discover biker and running trails, art exhibits, breathtaking landscapes, and more. You can find The 606 Trail in the city’s Logan Square area. Walk down the 2.7-mile track and prepare to expand your mind and broaden your horizons. 

There we have them – some of the best summer activities to try in Chicago on your next visit to the city. Don’t forget to organize your travels ahead of time to maximize the fun and have the time of your life in Chicago, one of the greatest travel destinations in the world. At Bus Connection, we can support you with a range of different transportation services that will enable you to enjoy your stay in Chicago without having to worry about missing out on anything. Get in touch and let’s discuss how we can help.