Curator’s statement
I grew up in Chicago, and there’s truly no better time to experience the city than summer. The energy is electric. Rooftops are buzzing, lakefront paths are packed, and every neighborhood feels like its own little celebration. Yes, it gets hot, but between patio dining, beach days, and unbeatable skyline views, it’s the kind of heat you’ll want to lean into. From legendary food to loyal sports fans (even when the teams let us down), summer in Chicago is pure magic.
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Things to do in Chicago
Catch a Cubs game at Wrigley Field
There’s nothing like cheering on the Cubs with a cold drink in hand and the Wrigleyville buzz all around you... even if they’re not winning, the vibes are immaculate.Rent a yacht and drop anchor at the Playpen
Chicago’s version of a floating day club. Gather your crew, bring snacks and swimsuits, and soak in skyline views from the lake.Boutique shopping in Southport or Lincoln Park
These walkable neighborhoods are full of charm and unique shops, perfect for a lazy afternoon of browsing with an iced coffee in hand.Ride a Divvy bike along the Lakefront Trail
Hop on a bike and cruise past beaches, parks, and skyline views on one of the most scenic urban trails in the country.Free concerts and movies at Millennium Park
Pack a picnic and enjoy live music or a classic movie under the stars at Pritzker Pavilion... it’s one of the city’s best-kept summer secrets.Architecture boat tour
Even locals love this one. Glide down the Chicago River and learn how the city’s skyline came to be. It’s equal parts relaxing and fascinating.Explore Navy Pier
From the Centennial Wheel to fireworks and family-friendly fun, Navy Pier brings out your inner kid (in the best way).Beach day at Oak Street, North Ave, or Ohio Street Beach
Whether you want to tan, swim, or people watch, Chicago’s lakefront beaches offer the ultimate urban escape.Hit up a summer festival
From Lollapalooza to Windy City Smokeout and the legendary Blues Fest, Chicago knows how to throw a party.Wander Through the city’s parks
Take a stroll through Maggie Daley Park, bike the elevated 606 trail, or pop into the Peggy Notebaert Nature Museum for a dose of greenery and calm.
Places to eat & drink in Chicago
Daily pastry options at Kasama
Sushi Dokku
Trendy, intimate, and always fresh... perfect for sushi lovers who want serious flavor in a speakeasy setting.Duck Duck Goat
Stephanie Izard’s funky Chinese spot in the West Loop brings bold dishes and big vibes. Don’t skip the scallion pancake.Aba
Mediterranean small plates, dreamy decor, and one of the best rooftop scenes in the city. Ideal for date night or group hangs.Beatnik on the River
Boho-chic and globally inspired, this riverside gem serves cocktails and small plates in a setting that feels like a summer escape.Tzuco
A French-Mexican fusion that works. This Michelin-starred stunner in River North delivers flavor, flair, and a killer mezcal list.Broken English Taco Pub
Colorful, casual, and always a good time. Grab tacos and margaritas before heading out for the night.Happy Camper Pizza
Lively, dog friendly, and loaded with neon signs... come for the pizza, stay for the party vibes (and maybe a slushy cocktail).Kasama
Filipino fine dining meets casual daytime café. Get the pastries (truffle croissant if available) and Longanisa breakfast sandwich.Café Ba-Ba-Reeba!
A classic for a reason, this Spanish tapas spot is great for groups, sangria pitchers, and sharing everything.Cindy’s Rooftop
Sky-high views of Millennium Park paired with seasonal cocktails and elevated comfort food, come early for golden hour magic.
Need to know
Getting around
Chicago is incredibly easy to navigate. You don’t need a car—grab a Divvy bike, hop on an electric scooter, or take the L (our subway). Ubers are handy, but not essential.
Reservations are a must
Popular restaurants book up fast, especially on weekends. Make those reservations early, especially for patios and rooftops.
Pack for the weather
June can bring quick midday showers, so toss a small umbrella in your bag. July and August get hot, so lightweight clothes and sunscreen are key.
Beach day basics
If you’re heading to the beach, come prepared: towels, chairs, snacks, water. Rentals are rare (only a small setup at North Avenue Beach), so bring your own setup.
Festival season is real
From massive music festivals to neighborhood street fests, there’s something happening every weekend. Check what’s on during your trip—it might impact traffic, crowds, or be the highlight of your weekend.
Lakefront = Life
Whether you’re running, biking, picnicking, or just people watching, the lakefront path is a must. It’s where the city comes alive in summer.
BYOB is still a thing
A handful of casual spots still allow you to bring your own wine or beer. Always worth checking before you go.
Keep an eye on the fireworks
Navy Pier does summer fireworks on Wednesday and Saturday nights. You can watch them from the Pier, nearby rooftops, or even a boat!
Travel Advisor
Meghan Irle
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For more inspiration and insider recommendations, visit our Chicago page.