Chicago in the summer is an experience like no other. Maybe because we know how punishing the winter can be, Chicagoans savor every last drop of the summer months — there is no shortage of things to do. And because there are so many options, it can be overwhelming to zero in on where to start. Next thing you know, the days are turning crisper and you wonder where all the time went. What you need is a plan! We love lazy summer days but if you don’t want them to melt into a long blur of inactivity, here’s a few suggestions for designing a summer filled with activities, experiences, and events to help make the most of these warm Chicago days.
Alfresco only, please!
Whether you grab a table with lake views or perch on a rooftop amongst the skyscrapers or nestle in at a street-level bistro, enjoying a meal outside is one of life’s greatest pleasures. Some restaurants lean into their prime vistas, while others have carved lush green spaces into the urban jungle. The Covid pandemic forced restaurants to get creative with their seating, and now, post-pandemic, many have kept their outdoor solutions so diners can still make the most of a beautiful day. Since so many restaurants and bars offer some sort of alfresco option, a good way to narrow down options is to set fun parameters. Perhaps it’s your “rule of summer” to only dine outdoors, or meet at a new rooftop each week for happy hour. Consider taking your lunch break on the steps of the Riverwalk or even a bench in the corner park. Trying a new patio/picnic spot/rooftop/sidewalk café in a different neighborhood each week of the summer is an easy way to soak up the mood-boosting sunshine while you can.
Go green.
Chicago’s history with nature and green space is as storied as its big shoulders. In 1837, Chicago adopted the motto Urbs in Horto, a Latin phrase meaning “City in a Garden.” In the 1850s, real-estate speculator John S. Wright suggested a ring of parks linked by boulevards (or “pleasure drives”) for public use, later dubbed Chicago’s Emerald Necklace. The 1893 World’s Columbian Exposition invited famed landscape architect Frederick Olmstead to design beautiful parks and green spaces that are still maintained today. And now, thanks to a city-wide Green Roof program, Chicago boasts 5.6 million square feet of green roof coverage, helping cool the city naturally and keeping the ecosystem more balanced for pollinators and native animal species. Chicago is indeed a “City in a Garden,” so it’s a no-brainer to find ways to enjoy it!
Some ideas: Grant Park—Chicago’s Front Lawn—is one of the most beloved, iconic, and pedestrian-friendly spaces, as is its newer sibling, Millennium Park. Meander through the sprawling Lincoln Park, stroll around Logan Square’s pocket parks and green medians, lounge by the lagoon in Humboldt Park, take in the Japanese Gardens of Jackson Park, dip your toes at Osterman Beach, or picnic at Promontory Point. Point is: Chicago is bursting with natural beauty—go check it out!
Be a tourist.
One of the city’s favorite sons is the fictional Ferris Bueller, who spends one day living his best life in the city. What Ferris gets right is that Chicago always has something happening. Play hooky from work to catch a baseball game, have a leisurely stroll through world-renowned art collections at the Art Institute, check out Big Sue at the Field Museum and gaze at galaxies far, far away at the Adler Planetarium. Take one of the many insightful and fun walking tours of Chicago history or climb aboard a famed architecture tour to get a new perspective on the skyscrapers that built the city. You don’t have to eat a deep-dish pizza to be a Chicagoan (in fact, most residents only do so when visitors are in town), but embracing all the different ways Chicago is a toddlin’ town is a great way to re-appreciate your hometown.
Get on the water.
Lake Michigan has been the shining epicenter of Chicago since the first settlers set up shop at Fort Dearborn on what is now the corner of Michigan Ave and the Chicago River. While it’s easy to take its presence for granted, spending some time on or near the water is a summer rite of passage, and the opportunities are nearly endless.
If you’re feeling sporty, gather a crew and rent a fishing charter to catch all the bluegill, bass, and salmon you can handle. For an upper body workout, rent a kayak or paddleboard and explore the Chicago River and any of the tributaries off the North and South Branch.
Hopping on a water taxi will always beat riding the El on a hot day. Gather your friends to rent a duffy boat, the electric boats that run like golf carts, and motor up and down the Chicago River, maybe catch the weekly fireworks at Navy Pier. Chicago’s First Lady is a high-class cruise to tour around the lakefront with dinner, dancing, and glittering lights of the shoreline. Thanks to efforts from forward-thinkers like Montgomery Ward, who fought for 20 years to keep the lakefront from being commercially developed, Chicago’s coastline is free and accessible to everyone.
Soak up some culture.
A picnic in the park, complete with live music, is a Chicago summer staple. Sprawl out on the Millennium Park Great Lawn every Monday and Thursday for live performances or learn a new dance at the weekly Summerdance events at Grant Park. Chicago Shakespeare in the Parks brings the Bard to neighborhood parks, including Chinatown, Austin, West Pullman, and Little Village. And the Night Out in the Parks program, put on by the Chicago Park District, has a rotating line-up of music, shows, theater, and of course, movie screenings in every neighborhood. Download the MyChi App to have every event at your fingertip.
Chicago’s Department of Cultural Affairs and Special Events (DCASE) really shines in the summer, putting on a wide variety of free or low-cost programs in areas all over the city. Join or summer workouts on the Great Lawn at Millennium Park, and pop-up markets and festivals in neighborhoods.
Try a new commute.
Maybe you can’t walk the entire trip from your home to the office, or the prospect of arriving sweaty is what keeps you from biking to work. But the weather is too nice—and fleeting!—to spend any extra minutes in a steamy El car or cramped bus. Consider your usual route to work and see where you can hop off and walk for a portion. Or try using a Divvy to get you from the office to home at a leisurely pace. If you’re in the Loop, consider taking a water taxi from Ogilvie or Union Station for a welcome change of scenery.
If you work from home, spend your morning working from a park or a coffee shop with café seating. Take a lunch break by strolling down a leafy street or browse the local farmers market. And if you’re lucky enough to have summer hours, make sure you use them because come winter, you’ll be missing those lazy sun-filled days.
To paraphrase Ferris Bueller, summer moves pretty fast and if you don’t stop and look around, you’re gonna miss it. For more ideas and tips on places to check out, check out the Grotto Chicago Instagram page.
