Refresh & recharge for the coming week!
Searching for the top Chicago weekend activities?
Want to get the most out of Saturday & Sunday and emerge refreshed on the other side, raring to take on the workweek?
Things to do in Chicago to make your weekend come alive
From iconic downtown adventures to hidden outdoor gems, we're rolling out the ultimate guide to make every moment count.
Whether you're planning a solo adventure, looking for that perfect date idea, or aiming for memorable times with family and friends, our list has something for everyone.
Let's dive into Windy City’s top weekend adventures, beginning downtown.
10 must-visit weekend attractions in downtown Chicago
Hitting up these downtown spots is how we make every Chicago weekend feel like a mini-vacation right in our backyard!
The Art Institute: Wander among the works of Monet and Picasso in Chicago’s iconic art museum, a treasure trove for art lovers and history buffs, and a top downtown Chicago attraction.
Millennium Park & The Bean: Grab your coffee and catch the morning glow on The Bean - our own shiny beanstalk minus the giants.
Skydeck Chicago at Willis Tower: Dare to stand on the glass and look straight down - Chicago sprawls beneath you like a giant, intricate map.
Navy Pier: Beyond the tourists, Navy Pier's fireworks and festivals make them our city’s way of throwing a weekend party.
Chicago Riverwalk: Perfect for a lazy weekend stroll or a kayak adventure - watch the city's history glide by from the best seat in town.
The Magnificent Mile: Not just for window shopping - hit The Mag Mile for some of the best eats and people-watching spots in the city.
Grant Park & Buckingham Fountain: Chill in Grant Park for a music-filled picnic or catch the fountain's light show - a classic Chicago weekend move.
Museum of Contemporary Art: A spot where the art's as bold and innovative as our city - drop in to see what's pushing the envelope.
Chicago Cultural Center: For a slice of culture, the Cultural Center's free exhibits and stunning Tiffany domes are our little secret and a top tourist attraction in the Loop.
360 CHICAGO Observation Deck: Elevate your weekend with a visit to 360 CHICAGO. It’s like seeing the city for the first time, every time.
Top outdoor attractions to rev up your weekend outing
Get those muscles working with a kayak adventure over the weekend!
Chicago isn't just skyscrapers and deep-dish pizza; our outdoor game is strong too. Here's where to soak up the sun and fresh air during the weekend break.
The 606: Next time your NYC colleagues boast about the High Line, tell ‘em about The 606, our elevated walking trail perfect for bikers, joggers, or anyone craving an urban escape with a view.
Kayak on the Chicago River: Begin your weekend on a kayak, gliding past the Willis Tower and under the Michigan Avenue Bridge, experiencing Chicago's skyline from a unique vantage point.
Lincoln Park Zoo Nature Boardwalk: Stroll or jog this scenic garden boardwalk to spy turtles sunning and red-winged blackbirds flitting about - some even describe the experience as “magical”.
Montrose Beach: A sandy retreat for volleyball enthusiasts, sunbathers, and anyone looking to dip their toes in Lake Michigan - ideal for weekend outdoor activities in Chicago.
Weekend fun with family & friends in the Windy City
Looking for some epic Chicago weekend activities to enjoy with your squad or fam? Hit the jackpot with these Windy City gems.
Wrigley Field Tour & Game: No better time to feel the Chicago spirit than the weekend, and no better place to feel it than the iconic Wrigley Field (a top draw in August). Get a tour or catch a Cubs game!
Chicago Architecture Foundation River Cruise: Glide through the city's Insta-worthy architectural marvels, like the Willis Tower and the Wrigley Building, on this cruise.
Second City Comedy Show: Laugh your socks off with friends at a show that's launched comedy legends like Tina Fey and Bill Murray. An indoor favorite and a hilarious addition to any long weekend plan.
Green Mill Cocktail Lounge: Sip on classic cocktails in Al Capone's old haunt. A jazzy, vintage vibe that's ideal for a laid-back Sunday night out.
Chicago Food Tours: Weaving through culinary hotspots like Chinatown, the West Loop, and Pilsen, a food tour is a very satisfying weekend family activity in Chicago.
Ways for Chicago couples to enjoy a weekend together
Wow your partner with an amazing itinerary
Having trouble finding a weekend getaway that’s the perfect blend of romance and fun? Don’t worry - we got you!
Chicago Botanic Garden: Wander hand in hand through its varied landscapes from the Rose Garden to the Japanese Island. A picture-perfect setting for a peaceful weekend retreat.
The Signature Room at the 95th: Sipping cocktails sky-high transforms any Saturday evening into a spectacle, with Chicago sprawling beneath you like a dazzling, urban tapestry.
Garfield Park Conservatory: Explore tropical paradises and ancient fern rooms together. A lush escape that's ideal for adding some warmth to a couple’s weekend in Chicago.
Adler Planetarium: Dive into the cosmos together; it's where the awe of the universe makes for a uniquely stellar date night, blending romance with discovery.
The Riverwalk: Strolling by the river as the city lights dance on the water, creating the perfect backdrop for those weekend moments you wish could last forever.
North Avenue Beach: Share a picnic or dive into beach volleyball. It's a sunny spot for couples looking to stay active during the weekend break.
Popular weekend destinations in the Chicago suburbs
Craving a break from the city vibes? The Chicago suburbs are brimming with hidden gems perfect for that weekend getaway you've been dreaming of.
Frank Lloyd Wright Home and Studio in Oak Park: Explore the birthplace of Prairie-style architecture with a visit to this historic home and studio.
Brookfield Zoo: Wild encounters await in one of the best weekend family activities in the Windy City suburbs, where nature meets conservation.
Morton Arboretum in Lisle: Lose yourself among 1,700 acres of trees and breathtaking landscapes. Ideal for a peaceful and memorable Sunday picnic. Also a popular Thanksgiving destination in Chicago.
Illinois Railway Museum in Union: Experience the golden age of American railroading with a visit to the nation's largest railway museum, featuring historic trains and a journey through the past.
Anderson Japanese Gardens in Rockford: Discover a slice of tranquility and beauty at one of the most authentic Japanese gardens in North America.
Kids’ corner: Weekend fun for the little ones in Chicago
Looking for places in Chicago to refresh the little ones before classes resume on Monday? Here's the scoop on the best kid activities in Chicago on weekends.
Chicago Children's Museum at Navy Pier: From dinosaurs to water play areas - there’s plenty at this museum to engage children on a weekend outing.
Lincoln Park Zoo: Animals ranging from polar bears to gorillas & seals, a carousel, a Ferris Wheel, and many other attractions make Lincoln Park Zoo an awesome place for a kid’s day out! And did you know that entry is completely free of cost?
Field Museum: Unleash your child's inner scientist with mummies, dinosaurs, and precious gems. An educational weekend outing that’s quite thrilling - and not just for the kids!
Peggy Notebaert Nature Museum: Where nature and fun meet, this museum offers hands-on exhibits and the famous butterfly habitat. It’s a delightful place in Chicago for kids to have fun during the weekend.
See if any events or festivals are going on
Chicago thrives on events and festivals; every weekend could be an opportunity to dive into something unique and exciting.
Whether you like amping up for the electric vibes of Lollapalooza or geeking out at C2E2 (Chicago Comic & Entertainment Expo), there are so many options to choose from.
So, before you set your end-of-the-week in stone, Google what's happening around town.
You never know - you just might find the perfect way to rev up your weekend and help you beat those damn Monday blues!
Fox in a Box Escape Room - a top weekend destination in Chicago
Looking for an epic weekend activity to freshen up before facing deadlines and whatnot again on Monday?
Say no more!
Ranked as the #1 Escape Room in Chicago and a favorite for office outings, we at Fox in a Box offer a variety of game themes, from a bank heist to a serial killer faceoff.
Whether for an outing with your partner or some quality time with friends and family, our doors at the historic Dearborn Station beckon!
FAQs
From things you can do for free to weekend-only events - here are the FAQs for weekend planning in Chicago.
What are the best free weekend activities in Chicago?
Chicago is brimming with adventures that don’t cost a dime!
Lace up for a scenic jog on the 606, meander through the Lincoln Park Zoo, or immerse in culture at the Chicago Cultural Center.
Ideal for planning your weekend on a budget.
How can I make the most of a long weekend in Chicago?
Pack your long weekend with diverse Chicago weekend activities.
Start with downtown Chicago attractions, add a splash of outdoor fun at Montrose Beach, and wrap up with a unique event or festival.
And if you’re looking for an immersive movie-like experience, hit us up!
What are some unique weekend activities in Chicago for couples?
Here are some of Chicago's top weekend adventures for you and your significant other:
Stargaze at Adler Planetarium for a cosmic journey.
Enjoy a romantic walk through the Chicago Botanic Garden.
Sip on cocktails at The Signature Room at the 95th.
Catch a breathtaking sunrise at North Avenue Beach.
Explore the art-filled streets of Pilsen for a colorful day out.
Are there any weekend-only events in Chicago I shouldn't miss?
Absolutely!
Dive into the local scene with neighborhood street fests like Wicker Park Fest or Logan Square Arts Festival, catch exclusive weekend shows at Second City, and don't miss the Sunday farmers markets.
They're the quintessence of Chicago weekend vibes and a fantastic way to experience the city's heart and soul.
How early should I book attractions for a Chicago weekend visit?
For a smooth Chicago weekend getaway, book top attractions like Skydeck Chicago or the Architecture River Cruise 2-3 weeks in advance.
Spots fill up fast, especially during the summer or long weekends, so plan ahead to avoid FOMO!
The best ways to enjoy your weekend in Chicago - Final thoughts
Hope you got the inspiration you were looking for to plan a stellar Saturday & Sunday.
From art-soaked streets to the tranquil waves of Lake Michigan, there's no shortage of Chicago weekend activities to explore.
And hey, if you've never tried an escape room, Fox in a Box is the perfect twist to add to your weekend plans.
It's all about seizing the moment to recharge and inspire.
Let's make this weekend unforgettable.
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