Fortunately for us, many of our team members get to spend part of their day outside already giving food tours, such as our Iconic Foods of Chicago Tour and our Gateway to the West Loop Food Tour. But outside of tours, there’s so much this city has to offer in summertime Chicago that usually we can forgive those long, harsh winters.
So let’s all enjoy the warm weather while we can! Below is our list of favorite Chicago summer activities to do outside, along with some updated resources to help you plan your perfect sunny day.
As official Chicago foodies, we definitely put a priority on outdoor eating when the weather is warm. There are a variety of amazing patios and beer gardens out there to satisfy your cravings, no matter what they are. Below are some of the best guides and a few recommendations for summertime in Chicago.
Beer Gardens, Rooftop Bars, and Outdoor Dining — TimeOut Chicago
Time Out Chicago has some of the best guides to the city, and this one is no exception. Check out their updated list for the 2026 season to find new patios, dog-friendly spots, and the best rooftops for a view of the skyline.
Chicago Rooftop Bars with Breathtaking Views — Thrillist
If drinking outdoors is more your style, here’s the ultimate guide from Thrillist Chicago, covering the best outdoor drinking spots in the city spanning several different neighborhoods.
A more specific kind of outdoor food adventure we love is visiting the many farmers markets that pop up around the city when the warm weather hits. They are great places to grab fresh produce, and many make a splendid day out where you can try local artisan foods and take a seat in the grass for a picnic.
Chicago Farmers Market Guide — WTTW
A comprehensive breakdown of farmers markets by day of the week, including favorites like the Green City Market in Lincoln Park and the Logan Square Farmers Market.
DCASE Citywide Markets — City of Chicago
This is the official guide to city-run markets, including the historic Maxwell Street Market and the Daley Plaza market, which are staples of summertime Chicago.
A classic favorite among Chicago summer activities, Movies in the Parks is put on by the Chicago Park District every summer. They host hundreds of outdoor screenings throughout the season in parks all across the city. The best part? It’s completely free! You can just show up with a blanket and a picnic basket for a perfect night under the stars.
You can search all the screenings on the Chicago Park District website. From family-friendly animations to 80s classics like Ferris Bueller’s Day Off, there is something for every cinephile this summer.
Walking and taking a day for exploration is squarely on our must list of summer activities. The Bloomingdale Trail is an elevated trail that connects several vibrant Chicago neighborhoods, including Humboldt Park, Bucktown, and Wicker Park. There are 12 different access points and plenty of art installations to enjoy along the nearly three-mile route.
In fact, we often enjoy a short walk on part of the trail during our food tours that stop in Bucktown and Wicker Park.. The best place to figure out how to explore it is the official Bloomingdale Trail website, which lists yearly events like the Bloomingdale Trail Run.
How have you been gearing up for your summertime in Chicago? Let us know your favorite Chicago summer activities! If you're looking for a delicious way to spend a sunny afternoon, check out how Chicago Food & City Tours can help you explore the city's best flavors.
