5 Best Things To Do In Chicago This Summer That Locals Swear By

I moved to Chicago at the tail end of Summer 2025 and got a taste of the magic this city has to offer when the weather is glorious. It entails lazy afternoons spent by the lake, glasses of rosé on riverfront patios, and long strolls through the Division Street farmers market. Autumn came far too quickly for my liking. Now that Memorial Day is behind us, I cannot wait to start taking part in all of the Chicago summer activities that I have been dreaming about for nearly a year.

Like many beloved northern hubs dotting the United States, Chicago winters are notoriously brutal, but summers make the chilly wait worth it. I spent a large portion of my winter cozy on my couch in Old Town doing one of my favorite activities — planning. This time, I wasn't planning for travel, but for everything that I was going to do as soon as the temperature rose above 70 degrees and the bundled up joggers on the lakefront were replaced by swimmers and jet skiers enjoying the crystalline waters of Lake Michigan.

I may still be new to the city by Chicago standards (e.g., I wasn't born and raised in the 'burbs, and I moved here for college. I'm a twenty-something transplant through and through). That said, through research, friend accounts, and one glorious late summer month last year, I'm excited to share the top Chicago summer activities that locals swear by, from getting out on the lake to strolling the city's farmers markets. 

Every morning on my runs down the lakefront trail, I spot jet skiers gliding across the waters of Lake Michigan. Last summer, I put renting my own as the number one thing on my Chicago summer bucket list. Jet ski aside, I was able to enjoy some magnificent paddleboard trips before the water got too icy. The best time of year to get out on the lake is in July and August, when water temperatures are at a comfortable 65 to 80 degrees Fahrenheit. 

There are a handful of spots along the lake and river where you can rent jet skis, stand-up paddleboards, kayaks, Duffy boats, and other watercraft. One of the best rental joints is Jet Ski Chicago, conveniently located at the intersection of Lincoln Park and Old Town on the North Avenue Beach. A 30-minute jet ski ride starts at just $55. From there, you can speed along the skyline and take in the iconic sites, from the opulent waterfront apartments lining Lake Shore Drive to the Hancock Building and Lincoln Park.

If you'd rather stand up paddleboard, Chicago SUP is right next door to the North Avenue jet ski rentals. It offers rentals starting at $45 per hour, as well as classes and group activities, such as sunset paddles, nighttime fireworks expeditions, and SUP yoga classes. This is the perfect rental if you are new to paddleboarding or simply want to join a community of other paddlers.

Leaving Chicago without visiting Chinatown is on my personal list of red flags. The neighborhood is in close proximity to downtown, has some of the best food in the city, and is considered one of the best Chinatowns in America. Although you can use the Red Line train or a rideshare, the best way to enhance your journey is to take the seasonal water taxi.

The water taxi has been running from downtown to Chinatown for over 50 years and is a cost-effective way to see the city skyline (it follows a similar route to the architecture cruise for a fraction of the cost). The water taxi picks up passengers at the dock at 400 N Michigan Ave, right next to downtown's most iconic sites, and it continues down the river to the Chinatown river entrance at Ping Tom Memorial Park. Before you head into town, I recommend spending time strolling around this glorious park.

After exploring Ping Tom Park, head over to Chinatown Square Plaza and check out the statues lining the pavilion. Then, peruse the shopping along the pedestrian route until you've built an appetite. It's hard to go wrong with food, but two of my favorite joints are MCCB (Modern Chinese Cookbook) and Qing Xiang Yuan Dumplings. After lunch, head over to South Wentworth Avenue for more shopping, and grab a sesame ball at the famous Chiu Quon Bakery. If you have time, check out the 88 Marketplace, too — it's the largest Asian market in Chicago.

Chicago has over 26 miles of public lakefront and an expansive Riverwalk. There are few things better on a hot summer day than lounging at an outdoor table, ordering a spritz, and watching the boats meander by.

Starting with the lake, one of the places you're most likely to find me enjoying a waterfront drink is at Castaways on the North Avenue Beach. The menu features a range of tropical cocktails, as well as shareable buckets, wines, and even bottle service. You can also order small bites and casual eats if you're hungry. The Offshore Rooftop is another popular place located on iconic Navy Pier. Be sure to book in advance, as it does fill up, especially on a beautiful day. There's also a lovely brunch service if you want breakfast with a view.

Plenty of joints in Chicago serve a delicious cocktail or bite to eat on the river, and some of the most popular are located up and down the 1.25-mile Riverwalk. I like to grab a glass of wine at City Winery Chicago, a frozen concoction at Tiny Tapp, or a beer and a gigantic pretzel from the Northman Beer and Cider Garden. The river also runs alongside some of the best restaurants in the Loop, like Pizzeria Portofino and RPM Seafood in the famous Mariano Towers, aka the corncobs. Some other great options can be found on this list of the Chicago Riverwalk's 5 best restaurants.

The Botanic Gardens are a stunning north side urban escape filled with magnificent flora. The Chicago Horticulture Society founded the gardens in 1890 and even hosted a Chrysanthemum showcase at the 1893 Chicago World's Fair. The gardens opened for public enjoyment in the 1970s and have since been considered one of the premier public gardens in North America.

Today, the gardens cover over 385 acres of lakefront property and exhibit an impressive array of 27 gardens. With over 2.5 million plants, it is one of the largest public gardens in the world. I love to visit on a cooler summer day when the sun shines high, and I'm in the mood for a long, luxurious stroll. The lands include islands, bridges, forests, prairies, and greenhouses, and there are seasonal activities and showcases. At the time of writing, some activities include pickling classes and a potted herb workshop.

It's hard to choose a favorite garden here, but if I had to, I'd go with Spider Island. It isn't overflowing with colorful flowers like other parts of the garden, but the intimate setting — away from the hustle and bustle of more popular gardens — is a fantastic place to roam among the trees and enjoy the ferns and natural vegetation of Illinois. The towering birch trees also make this garden an excellent respite from the summer heat.

Farmers market season is finally back, and I could not be more thrilled about it. There are few things I love more than strolling through a market with a cup of coffee in hand and picking out fresh produce to use for the night's dinner. I often find myself grabbing a bouquet of fresh flowers and a tamale for the walk. There are a number of fantastic markets in the city, but I have the privilege of living right next to the Division Street Farmers Market, located at the intersection of Old Town and Gold Coast.

A list of some of the most popular markets in the city is available here. One of the best is the Green City Market in Lincoln Park. It includes an array of vendors selling everything from fresh Illinois produce to breakfast pizza (I recommend). Each entrance also has a coffee vendor, and local farmers from across the Midwest convene here to showcase their products, such as fine cheeses, meats, and seasonal produce. One of the most centrally located markets is the City Market at Daley Plaza in the Loop. This is the perfect market to visit if you are touring the city on a weekend and staying in a downtown accommodation.

Many of the farmers' market vendors rotate between the various city markets. Smits Farm makes the rounds, attending up to six markets a week and offering a range of produce like fresh herbs, eggplant, and juicy Illinois tomatoes. Stamper Cheese Company is one of my personal favorite vendors — it would be criminal to leave the market without a bag of their garlic dill cheese curds or the orange-hued, funky red rock cheese.