8 Things to Do in Chicago in Summer

Chicago is brimming with music during the summer and fans flock to the green grounds of Grant Park for the city’s top music festivals. Soak up hot local and national blues acts in late June at the Chicago Blues Festival, the world’s largest free blues festival. Or relish in the joyful sounds at the Chicago Gospel Fest held in early June. The Chicago Jazz Festival closes the summer with 4 days of top jazz players from around the world.

We can’t talk about Chicago music festivals without mentioning the extravaganza that is Lollapalooza. Hosting the biggest music names across all genres and studded with celebrities, this is a summer concert you don’t want to miss.

There’s nothing that epitomises summer better than the sun beaming down on the glittering water. The majestic Chicago River winds its way past some of the city’s most stunning buildings and scenery. A sightseeing cruise gives you a close-up view of it all. From Navy Pier, take a sunset cruise out onto the blue waters of Lake Michigan and watch the skyscraper-filled skyline silhouette against an orange-hued backdrop. 

Alternately, rent a boat or canoe and enjoy the freedom of rowing out yourself. You can even spend an afternoon fishing in the Chicago River. Just make sure you have an Illinois fishing licence before setting up your gear at Lake Shore Drive or the Jetty at Wacker Drive.

When you need a break from the summer heat, shop in air-conditioned comfort at one of the lavish shopping centres on Michigan Avenue, or the Magnificent Mile, as it’s also known. The 900 North Michigan centre houses a dazzling list of couture shops like Gucci and Michael Kors, but also entertains shoppers with live piano performances, art installations and virtual golf. 

At Water Tower Place, 7 floors of boutiques and international stores include Lacoste and Akira, as well as family-friendly workshops and events. A few blocks away, The Shops at North Bridge give space to stores like MAC, Hugo Boss and Lola + The Boys. Check the centre’s website before you visit for details about sample sales.

After a busy day of shopping and sightseeing, relax at one of Chicago’s many gorgeous riverside patios or gardens and drink and dine under a sunset sky. Splurge on a romantic dinner on the swanky, candlelit terrace at Boka, or dig into steak frites in the cheerful garden at Le Crêperie. 

Alternatively, enjoy the lake at city skyline views at the Waterfront Café as you’re serenaded by live jazz and blues music. If you’re looking for something a little more bohemian with a party vibe, check out Beatnik On The River’s Mediterranean menu from their scenic terrace and with a tropical cocktail in hand.

Most weeks throughout the summer, you’ll find the streets bustling with fairs and filled with live music and events. From local artists selling unusual crafts and souvenirs to food trucks serving tasty snacks, there’s always something to discover. 

Lincoln Avenue regularly hosts artisans and pop-up markets, while Daley Plaza is known for cultural performances and celebrations. Northhalsted Market Days offers block after block of vendors and wild and colourful entertainment including music, drag and dance. For mouth-watering street food, the Windy City more than delivers. Check out Ribfest for sticky, smoky BBQ ribs, the Tacos y Tamales Festival for traditional Mexican fare and the Taste of Randolph for festival food provided by the city’s top chefs and restaurants.

Lincoln (Abraham) Park provides a serene yet playful haven of lush, expansive greenery, tranquil ponds and lakefront paths. Sunbathers can soak up the rays or find zen at an alfresco yoga session at North Avenue Beach, while history buffs can find exhibits inside the fascinating Chicago History Museum.

The Lincoln Park Zoo attracts wildlife lovers of all ages, and we recommend visiting endangered species such as the Western Lowland Gorillas and the Eastern Black Rhinos. On Wednesday and Saturday mornings, the Green City Market hosts dozens of vendors selling fresh fruit and veggies, vibrant flowers and artisan bread and honey. Why not fill a basket and enjoy a picnic on the park’s verdant banks?

A quick trip on the Blue line subway to the Damen Street stop puts you in the centre of one of city’s most creative hubs. An eclectic mix of artists, families and professionals cluster in the adjoining neighbourhoods of Bucktown and Wicker Park. 

Spend a sunny afternoon strolling the blocks that sprout from where the Damen, Milwaukee and North Avenues intersect. Browse the cool art galleries, groovy boutiques and vintage record stores or chill out and people-watch from one of the hip outdoor cafes.

875 North Michigan Avenue, located in the Magnificent Mile district, is an incredible 100-storey skyscraper. It's the type of destination that you can spend an entire day exploring thanks to the diverse range of surrounding tourist attractions, shopping and cafés.

The Observation Deck, which is 1,030 feet above Chicago, offers incredible skyline and Lake Michigan views. On clear days, you can see as far as 80 miles, which includes 4 different states. Refresh yourself with a cocktail from the CloudBar, check out the immersive displays in the concourse and visit the gift shop for iconic souvenirs. You can even take a sky-high yoga class. Top tip: buy a Chicago CityPass to save money on Chicago’s top attractions.