There is no better time to explore Chicago than summertime. The weather is beautiful. The sun is shining. You’re ready for an adventure.
There’s no way we could list all of the awesome things to do in Chicago during summer, but you can hopefully discover your new favorite spot in the city by following these suggestions thanks to Do312 and Line 39 Wines.
Evening Excursions
Photo: Shedd Aquarium/Brenna Hernandez
Free movies and music in Millennium Park: Millennium Park isn’t just the crown jewel of Chicago’s downtown area and home of the forever photographable “Bean” sculpture. It’s also a great place to find awesome free things to do during the summer. The park hosts free movie screenings on Tuesday nights and free concerts on Thursdays. Check this summer’s schedule.
Music festival Aftershows: If you think festival fun has to end at 10 p.m., you need an attitude adjustment. Find out where the artists playing your favorite fest will be playing a late night set. Win tickets to Lollapalooza aftershows while you’re at it.
Go dancing: You can really showcase your moves now that you don’t have a bulky coat weighing you down! Hit up one of Chicago’s best dance floors like Beauty Bar, Smart Bar, Studio Paris or Late Bar.
Shedd Aquarium: The Shedd is already one of our favorite places to spend a day. In the summer you can spend your evenings there, too! “Jazzin’ at the Shedd” brings live jazz to the outdoor terrace every Wednesday night through October and “Shedd After Hours” is an adults-only opportunity to explore the aquarium after its normal hours.
Foodie Paradise
Photo via Revivial Food Hall
Chicago pizza tours: Quick, name the first food that comes to your mind when you think of Chicago. Pizza! Jinx! Take a walking or bus tour of some of Chicago’s most pizza-plentiful neighborhoods with Pizza City, USA tours. Come hungry. You’ll get a slice at each stop!
Revival Food Hall: Love food but can’t ever make up your mind? You don’t have to at Revival Food Hall. It’s home to a dozen eateries. Try a little something at each (or as many as you can stomach). Plus, hit Curbside Books & Records for some post-lunch shopping.
Wicker Park Farmers Market: If you want to make the freshest home cooked meal you can, plan to do it on a Sunday. That’s when the Wicker Park Farmers Market pops up in its namesake park every week.
The Plant: Home to non-profit group, Plant Chicago, the facility hosts farmers markets, workshops and more focusing on self-sustaining, circular economies—that means nothing goes to waste here! It’s also home to Chicago’s most environmentally friendly brewery, Whiner Beer. Co.
Stylish & Skillful
Photo via Facebook/Randolph Street Market
SAIC At Homan Square: School of the Art Institute of Chicago hosts community programs and classes with topics ranging from t-shirt alteration to zine publishing to quilting. This is where you find your new hobby.
Randolph Street Market: Chicago’s largest antique market is at its best during the summer when it all moves outdoors. Even if you’re just “window shopping,” it’s a great way to spend an afternoon.
Handmade Markets: Ukrainian Village’s Empty Bottle and its sister venue The Promontory in Hyde Park host two of our favorite handmade markets in the city once a month. You’ll come home with a bag full of candles, jewelry, beauty products, other goodies made by your fellow Chicagoans.
Fat Tiger Workshop: These local street style specialists started from the ground up and have built a brand in Chicago that’s now knocking on the doors of mainstream fashion. Visit their retail space in Noble Square.
Game On
Photo via Flight Club/The Door Idea House
Flight Club: Darts is the newest “bar sport” to receive its own bar in Chicago. Flight Club opened in the spring and is elevating the social element of darts. You can rent your own private “oche” (rhymes with “hockey”) with your own board and throwing area for up to 20 friends.
Royal Palms Shuffleboard Club: Shuffleboard isn’t just for retirement communities in Florida. Revisit this classic game in a hipster space in the heart of Logan Square. This New York transplant opened its Chicago location earlier this year and the place has been packed ever since.
St. Lou’s Assembly: St. Lou’s backyard outdoor space is a summertime classic in Chicago. In addition to a separate bar and patio seating, you can also get in line for a round on the bocce court. We recommend getting a game in before partaking in the restaurant’s food coma-inducing Southern comfort classics.
Emporium Arcade Bar: It’s getting tough to throw a stone in Chicago without hitting a new location of Emporium arcade bar—not that we’d ever do that and risk damaging those beautiful vintage video games. Visit the arcade bar in Logan Square, Wicker Park, and Fulton Market and see how your pinball skills have held up over the years.
Refreshing Escapes
Photo via Flickr/damiavos
Miko’s Italian Ice: Miko’s is a Chicago summer tradition if there ever was one. You’ll want to make multiple stops by the Logan Square, Bucktown or Irving Park locations as new fruity flavors like kiwi and grapefruit are always popping up on the menu.
ACTIVATE: Chicago Loop Alliance’s monthly summer series takes over alleyways in the downtown area and transforms them into some of the coolest party avenues you’ve ever visited. Live performances, music, art and more are usual suspects at these pop-ups.
Go to a beach: Welcome to the Third Coast. Chicago’s beaches will make you forget you’re in the Midwest. Our favorites are Oakwood, Osterman Beach (aka Hollywood) and Montrose beaches.
Bike ride on the Lakefront Trail or The 606: Cruising south alongside Lake Shore Drive is one of our favorite views of Chicago. The new(ish) 606 Trail is an elevated view of the West Side. Both make for awesome two-wheeled urban adventures.
You, Rediscovered
Photo via The Catcade
Take an improv class: Has anyone ever mentioned what a quick wit you possess? Have you ever thought about putting that to use? Register for improv classes at iO Theater or The Annoyance Theatre and hone your funny bone.
Daybreaker: Should you choose this path, your day will start early but it will be worth it. Daybreaker parties kick off when the sun rises, starting with a round of yoga followed by an intense, but totally sober dance party. When things wrap at 8:30 a.m., you can ride those good vibes into the rest of your day.
Bad Axe Throwing: Looking for a new form of stress relief? Well, here it is. Visit Bad Axe’s West Loop or Lakeview locations. Make an appointment or just the walk-in schedule and get ready to learn about this Canadian pastime firsthand.
The Catcade: Need a break from companions of the human species? Stop by The Catcade in Lakeview—an arcade-themed, non-profit cat cafe that’s provided hundreds of new forever homes to kitties of all ages. If you’re not in the market for a new roommate, just stop by for a soft drink and get some good, soul-healing pets in.
Relax & Restore
Photo via 3 Arts Cafe
Humboldt Park: Humboldt Park is one of Chicago’s most diverse public parks and offers a variety of restorative activities like fishing, swimming, paddle boat rentals, art installations and more.
3 Arts Cafe: One of Chicago’s most zen destinations is in one of the most unlikely locations. Inside Restoration Hardware’s Gold Coast store, 3 Arts Club Cafe occupies the central most space with a beautiful all-seasons courtyard. Enjoy an afternoon with a cup of coffee, a good book and constant people watching.
Chicago Cultural Center: From the magnificent 38-foot Tiffany Glass dome ceiling to rotating exhibitions from internationally recognized arts and innovators to an always agreeable price point ($Free.99), the Chicago Cultural Center is a calming escape from the urban bustle that surrounds it.
Museum Of Contemporary Art: The MCA is always a top pick for a reflective afternoon but in summer, Tuesday mornings and nights are the top times to visit. Shop the SOAR (Streeterville Organization of Active Residents) Farmer’s Market from 7 a.m. to 2 p.m. or swing by after work for Tuesdays On The Terrace—a free after-hours look at the museum and the opportunity to stroll the outdoor gardens while enjoying live music.
Dare To Explore
Photo via Do312
Street Festivals: Looking for a crash course on a neighborhood you’re not familiar with? We bet there’s a street festival for that. Chicago’s street fest scene continues to grow each year. Almost every neighborhood hosts at least one major bash with local restaurants, performers, vendors and more! Check out every Chicago summer festival here.
The Best Rooftops: Get a different view of your city from a new vantage point this summer. A good rooftop bar is a classic seasonal source of fun and we think it’s time you find your new favorite.
Willie Dixon's Blues Heaven Foundation: The former home of Chess Records (Chuck Berry? Muddy Waters? Etta James? That Chess Records) exists today as a music and tribute to the building’s historic past. Take a tour and hang out in the studios some of music’s most iconic tracks were recorded in. On Thursday evenings during the summer there is free live music in the museum’s adjacent garden.
Chicago Magic Lounge: Abracadabra! We’ve just found your next adventure. The Chicago Magic Lounge is currently Chicago’s only operating magic club, but it pays tribute to notable magician havens of years past. With two performance spaces hosting internationally touring talents and a cocktail lounge, you’ll need a full evening to discover all the magic this place has to offer.
No matter which adventure you seek, Line 39 Wines are the companion...now get out there & Find Your Summer!
