If you moved to Chicago in the past nine months, maybe you’ve heard about this thing called summer. Those of us who have been here a while promise it exists — and that it’s worth waiting for.
Now that daffodils are tentatively opening and restaurants are removing the wind covers from their doors, it’s time to start scheduling your outdoor time. Pro tip: It’s a bad idea to leave the city between June and September. Instead, lure your out-of-town friends with our ultimate Chicago summer bucket list. How many items can you cross off?
Choose your own festival adventure
Chicago’s cultural, musical, neighborhood, food, and beverage-focused street festivals are so numerous, we won’t even attempt to list them all here. Every resident should experience at least one of the city’s Big Three music festivals — Pitchfork, Lollapalooza, and Riot Fest — once in their lives. But for a truly Chicago festival experience, think smaller: Andersonville’s community spirit shines through during Midsommarfest (June 8-10), a celebration of the neighborhood’s Swedish roots, which features music, dancing, crafts, beer, craft beer, and everything else that makes a Chicago street festival great. Or drown out the swan song of the end of Summer Fridays with some sweet notes at the Chicago Jazz Festival (August 29 to September 2). The Millennium Park mainstay features legends and newcomers alike, as well as art, food, a New Orleans-style second-line procession, and tons of adorable dancing children.
Enjoy the city’s architecture by water
If you think Chicago’s architecture tours are just for visitors, you’d be dead wrong. There’s really no better way to see all of downtown in an afternoon than by water. We recommend Wendella’s Signature Lake and River Tour ($39), which takes passengers on a 90-minute journey through the locks and into Lake Michigan for an unparallelled view. In true Chicago fashion, the tour boats have bars. If you’re looking for a slightly more budget-friendly option, the Chicago Water Taxi connects commuters and tourists alike to locations from North Avenue and Sheffield Avenue in Lincoln Park to Chinatown. An all-day pass will run you just $9.
Find your summer cocktail
Chicago is lauded as one of the top culinary cities in the world, which, duh. But the cocktail scene is world-class in its own right. Pick your signature cocktail of summer and taste-test it at bars throughout the city, or try different ones depending on your mood. At Estereo, try the Breezy — the permanent menu option features a base of yerba mate, house falernum, lime juice, and bubbles; customers then choose their add-in spirit. Devereaux, the newest project from former Billy Sunday beverage director Lee Zaremba, features a spread of creative signature cocktails and daytime sippers; we’re itching to try the Pineapple Collins (tequila blanco, pineapple, lemon, mineral water). If you like your summer cocktails frozen, Parson’s Chicken & Fish does a slushy version of a negroni, along with a rotating daily slushy special (like a margarita and Dark & Stormy). In search of a dive bar that’s not really a dive? Maria’s Packaged Goods & Community Bar is the answer to your quandary, where our go-to is the Hornswagglers High Tea, a blend of Earl Grey-infused vodka and cream soda. It’s yours for the low, low price of $7.
Hit the patio circuit
We’ve never seen a group of humans more excited about sitting outside than Chicagoans in summer. A great patio is the sprinkles on the soft-serve cone of the Windy City. A couple new options this summer: Nine-year-old taco haven Big Star, the gold standard of Chicago patios for years, recently gained a sibling; Big Star Wrigleyville opened in early April in a massive space at Hotel Zachary with some fresh menu items to go with the same old honky-tonk soundtrack. And Avondale’s Ludlow Liquors, located in the former Orbit Room space, is bringing picnic tables, two-tier stadium seats, and lounges to its revamped outdoor area. (Has someone invented a word for a patio makeover yet? We’ll call it a pati-over.) Create a drink sampler with cocktails served by the ounce.
Go Bar-Hopping in Boystown
If you like pitchers of vodka-lemonade and dancing, there’s Roscoe’s. If you’re looking for some less innocent dancing, there’s Berlin Nightclub. There’s truly a bar to fit every mood in Boystown, and on a hot summer night, the hours fly by so fast, you won’t believe it’s 3am. The neighborhood is especially lively during the annual Pride festival and parade (June 16-17 & 24), and Northalstead Market Days (August 11-12).
Make a friend with a boat
One of the surest signs summer is on its way: The return of private boats to Chicago’s harbors. Whether you’re part of the party-hard “playpen” scene at Ohio Street Beach or looking for a calmer afternoon of sailing, there’s a ship life for every Chicagoan. But before you can live out your aquatic fantasies, better make sure you’ve got a boat friend lined up to help make them come true. (Even better if it’s a friend-of-a-friend, so you’ve got an easy out in case of a summer romance gone sour.)
Navigate the air & water show — Or Don’t
There are two groups of Chicagoans: Those who hate the annual Air & Water Show, and those who are either from the suburbs or have a friend who lives in a lakeside high-rise. If you’re in the latter group, you know how to play this one. (Step 1: Ply your high-rise friend with lots of bubbly.) But for those who have HAD IT with the noisy fighter jets and lakefront crowds, Air & Water Show weekend (August 18-19) is a great time to check out all those places on the West and South Sides that you keep missing. Head down to Calumet Fisheries for legendary smoked seafood, or, if ribs are more your style, check out the barbecue at Smoque.
Play Hooky in Millennium Park
Across the street from the Loop business district, it’s almost as if Millennium Park was planned to taunt office workers during the summer. Take a break for an afternoon (or just for your lunch hour, if you can’t get away), and spread out on the lawn next to Pritzker Pavilion. Read a book, listen to a podcast, or just people-watch as friends chat and kids chase each other across the grass. We’ll also let you in on a little secret: At the southeast corner of the Pavilion is the entrance to Lurie Gardens, where visitors can take off their shoes and dip their feet in a man-made stream.
Take an extra-long bike ride
With miles and miles of lakefront, and even more parks and trails outside the city to explore, Chicago is best seen on two wheels, and summer is the perfect time to do so. Rent a Divvy bike if you don’t own one (but don’t forget a helmet) and hit the pavement. Biking can also be a great way to make new friends. Join Critical Mass as riders take over the streets for a massive group ride the last Friday of every month, or strip down for the World Naked Bike Ride on June 9.
Shop your local farmers market
While you’ve certainly enjoyed more than your fair share of local produce in Chicago’s restaurant scene, the city’s plethora of farmers markets mean it’s time for you to become the chef. Check out this schedule to find your neighborhood market. We’re particularly fond of Lincoln Park’s Green City Market, which features chef demonstrations, live music, and more dogs per square foot than a humane society.
Visit the original rainbow cone
This Chicago classic’s sole location is so far south, you’d swear you’re in the suburbs. (They actually start across the street.) But the cone’s layers of chocolate, strawberry, Palmer House, pistachio, and orange sherbet have kept Chicagoans young and old making the journey for decades. You can get the cone at select festivals like Lollapalooza, but nothing compares to the 92-year-old storefront.
