Best Things To Do In Chicago
The Windy City has awe-inspiring skyscrapers, hunger-stomping food and culture to match almost any city in the world.
But what never ceases to amaze is just how much you can do for free in Chicago.
Donations by philanthropists have bestowed the city with superlative museums and more than 700 works of public art, by Picasso, Chagall, Miró the list is huge.
These have turned the skyscraper forest of the Loop and the Millennium Park into one big outdoor gallery.
There are free events too, like Taste of Chicago, the largest food festival in the world, and music festivals to honour the citys enviable music heritage.
Chicago is also great to get around on foot, along the Lakefront Trail or the new Riverwalk, or even underground in the sophisticated Pedway system.
Lets explore the best things to do in Chicago:
Enjoy The Winter Flower Show At The Garfield Park Conservatory
The Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the US. Often referred to as landscape art under glass, the Garfield Park Conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens. Visitors can enjoy the lush flora and tropical temperatures indoors year-round! Their Winter Flower Show, Serenity starts on November 24.
Where: 300 N. Central Park Ave., Chicago, IL 60624
Hours: Wednesday 10am-8pm Thursday Sunday 10am-5pm Closed Monday and Tuesday. Visitors are encouraged to make a reservation online in advance. Walk-ups are welcome if there is space available.
Cost: FREE
Experience An Authentic Italian Dinner At The Rosebud
A winter visit to Chicago would not be complete without a delicious Italian dinner at my favorite restaurant, The Rosebud. This upscale restaurant located in Chicagos Little Italy neighborhood features a spectacular menu, a romantic setting, and impeccable service. This charming restaurant was Frank Sinatras favorite: imagine that!
Address: 1500 W. Taylor St. Chicago, IL 60607
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Take An Architecture Cruise
Taking an architecture river cruise is a must when visiting Chicago. You can also do a combination river and lake cruise. While you can go on an architecture cruise most of the year , they tend to be less crowded and the weather tends to be more pleasant in the fall.
Look for Street Art
Fall is a great time to walk around Chicago looking for street art while also enjoying the beautiful full colors.
One of the most well known Chicago murals is Moose Bubblegum Bubble by Jacob Watts which located at 33 E. Congress . This famous mural is part of the Wabash Arts Corridor and is walking distance to Millennium Park, The Art Institute of Chicago and other tourist attractions.
Another famous mural is the Greetings From Chicago Mural at 2226 N Milwaukee Ave. You can see this mural and other street art on this street art tour.
Other neighborhoods that have a high concentration of street art include Pilsen as well as West Town.
Visit The Neon And Light Museum
The new Museum of Neon and Light pop-up opened in September for limited run. Stand in, under and around 70 professional neon and light-based sculptures in a dazzling and dramatic immersive exhibition. The Neon and Light Museum is an expansion of the successful On Neon show presented here in 2020 by the Ken Saunders Gallery, which, since 1995, has exhibited important and innovative artists working with glass in the world.
When: Ends November 30, 2021.
Hours: Thursday-Friday: 4pm-10pm, Saturday: 11am10pm, Sunday: 11am6pm
Where: 325 West Huron, Chicago
Cost: $40 per person. Online reservations are required.
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Frank Lloyd Wright Home & Robie House Tours
If you know anything about Chicagos cultural scene,then you know that its a city famed for its extensive, diverse, and striking architecture. Among the great names who have built the citys most iconic buildings is one of the most iconic architects Frank Lloyd Wright.
Learn more about this creative giant with a visit to his home and studio. This is where he designed the Robie House, the Larkin Building, and the Unity Temple. Architecture buffs will also enjoy a visit to the Robie House itself, one of Wrights most beautiful private home designs.
Getting In: Frank Lloyd Home Tour tickets and Robie House tickets are both included with the Go Chicago pass.
Make A Mental Health Pilgrimage To The Shit Fountain
If youre in the Ukrainian Village area and looking to do the whole public art thing, you may not find as dense of a concentration of murals as Pilsen or as many fine art sculptures as downtown. But you have one thing those other places cant touch: the one and only Shit Fountain. The human feces-shaped sculpture is located on a residential front lawn just off Augusta and Wolcott, created by a Chicagoan fed up with dog poop. After you get your fill, amble over to some of the citys best dive bars, conveniently located a mere stone’s throw away.
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Take An Architecture Cruise On The Chicago River
The architecture in the Windy City is unique, historic, and complex, and theres no better vantage point to admire it all than the waters of the Chicago River.
As you cruise under the citys skyscrapers, youll pass the East Bank Club, the old Post Office Building, the Willis Tower, and plenty more.
Tours typically last an hour and a half, and the guides are notably informative and entertaining.
Race Against The Clock At An Escape Room
Race against the clock and put your teamwork and puzzle-solving skills to the test with an epic escape room challenge.
Visit The Escape Game and choose from gold hunting, prison breaks, heist mysteries, even rocketing to Mars, all within 60 minutes of non-stop excitement.
Think you have what it takes to bust out? Sign up for one of the most fun things to do in Chicago and find out!
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Apple River Canyon State Park
Nature lovers looking for respite from city life will find it at Apple River Canyon State Park in the rolling hills of northwest Illinois. Inside the park, visitors can see the Apple River carving its way through a limestone canyon.
Anglers will appreciate early spring trout fishing along with summer sunfish and small-mouth bass fishing. Four picnic areas along the scenic river give visitors an opportunity to barbecue and make use of park grills, tables, and nearby restrooms. Hikers are advised that the five rugged trails crisscrossing the woods present potential hazards. Flora and fauna are abundant in the park.
8763 E. Canyon Road, Apple River, IL, Phone: 815-745-3302
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Catch A Baseball Game
Take a trip to Chicago’s South or North Sides to catch a White Sox or Cubs game as fans can now fill the stands.
Wrigley Field announced it would allow full capacity for Cubs games starting June 11, with Guaranteed Rate Field still seating a limited number of fans until further notice. Both teams continue to have some COVID mitigations in place, with more for those not vaccinated.
Find out more about White Sox and Cubs tickets.
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Emily Oaks Nature Center
A thirteen-acre break from urbanity, Emily Oaks Nature Center is home to coyotes, flying squirrels, water snakes, and other animals that can seem like living myths to little kids. The three-acre pond is a perfect place to rest and enjoy the scene. The Woodland Wander Inn is a great spot in the park to help kids learn about the surrounding environment.
Price: Free
The visitors center and restrooms are only open to program participants and rental groups. The trail is only open from Monday to Saturday from 8 a.m until sunset and on Sundays from 10 a.m. until sunset. Gate closes at sunset daily.
Tip: This is a great place for birthday parties in summer and early fall!
Support Chicagos Black Community
Whatever else you do this fall, be sure to continue to do your part in making the community we live in a better place for all its residents. Aid in the fight for racial justice and social equity taking place across the city by supporting Chicagos Black community via everything from BIPOC-focused nonprofits and community organizations to Black-owned restaurants and bookstores. Here’s how to get get started.
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Get Even Artsier At The Museum Of Contemporary Art
Easily one of the worlds largest contemporary art venues, this popular Chicago attraction has been welcoming curious guests since 1967.
The MCAs ever-changing exhibits span paintings, sculptures, photography, and film, all educational and often interactive.
Under-18s get in free year-round in July and August, admission is free for everyone. Even if youre not an art fan, during the scorching summer months, its a welcome respite from the beating sun.
Fun Things To Do In Chicago In The Winter With Kids
Winter weather can be atrocious, but in Chicago we are used to it, and try to have a supply of fun winter activities for kids ready to go at any given moment. As locals know, it is important to have plenty of activities at your disposal to entertain the kids on snow days, cold days, and good old school holidays. Here are some of our favorite things to do in Chicago in the winter with kids.
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Let Your Imagination Run Wild At The Legoland Discovery Center
No matter if youve just turned 5 or 50, everyone loves Lego! The large complex offers Lego-themed rides, building sections, a 4D cinema to delight the senses, and a gift shop to buy all the Lego sets you could possibly fit in your suitcase.
The Discovery Center is situated outside of the main Chicago area, so make a day trip out of it and explore the adjacent Ned Brown Preserve while youre there.
Skip The Lines At Au Cheval Restaurant
People wait in line for hours to try Au Chevals famous no-frills cheeseburger, which should tell you just about everything you need to know about this restaurants popularity and quality.
Despite only opening a few years ago, Brendan Sodikoffs diner has quickly found its way into the spotlight.
To avoid the lines, visit during the week, outside of peak lunch and dinner lines.
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Immerse Yourself In The Office Experience
The Office Experience pop-up opened October 15 in Chicago for a three month run. Visit Schrute Farms, walk through the Dunder Mifflin set, and relive Jim and Pams iconic romance. The world of The Office will come to life with iconic set recreations, original show costumes and props, and opportunities for fans to engage with the show in new ways. Timed tickets are now on sale online.
Where: 540 N Michigan Ave on the Mag Mile.
Cost: General admission is $37.50 plus taxes + fees for off-peak times or $45 plus taxes and fees for peak times. Children 3 and younger are free. Groups can also purchase private access tickets or book the space for a private party.
The Escape Game Chicago
Can you escape? Test your skills, smarts, and ability and see if you have what it takes at The Escape Game Chicago. Escape games were made for rainy days and they are fun for both families with older kids and groups of friends. You will have just one hour to work as a team and solve a series of clues. Can you escape the room before time runs out? Take your pick from a variety of games, including the espionage-themed The Heist, out-of-this-world Mission: Mars, and ultra-daring Prison Break. Good luck!
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Go Rock Climbing Outdoors At Maggie Daley Park
Rock climbing outdoors might seem like a luxury reserved for rural areas and national parks, but theres actually an opportunity to do it right in the heart of Chicago. Located in Chicagos Loop, Maggie Daley Park boasts a 40-foot outdoor climbing wall, which has a total of 19,000 square feet of climbing space.
At Maggie Daley Park, theres bouldering, top roping, and lead climbing for budding climbers, from beginners to intermediate enthusiasts. There are crash pads in the bouldering area and employees on staff to ensure a safe and fun environment. You can also hire a private belayer if youre new to climbing or came without a belay partner.
For $30, you will get admission, a short lesson on belaying, and all of the necessary rental equipment shoes, ropes, belay devices, helmets, and chalk. Also, Chicago residents get 20% off climbing admission .
Catch A Performance Of The Chicago Symphony Orchestra
As the Chicago Symphony Orchestra edges its way toward 13 decades of captivating performances, it solidifies its reputation as one of the worlds best.
With brass, percussion, string, and woodwind instruments, coordinated by renowned Italian conductor, Riccardo Muti, its quite literally music to our ears.
Performances regularly take place at the Symphony Center in the Loop area.
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Unleash The Youngsters At Pirates Cove Childrens Theme Park
Specifically designed for kids aged two to nine, the Pirates Cove Childrens Theme Park is a formidable way for the youngsters to burn off some energy while imaginatively exploring the parks attractions.
They can climb aboard Petes 18-century Pirate Ship, go round and round on the Captains Carousel, watch an interactive show at the Swashbuckler Wharf Fun Stage, and plenty more.
Pirates Cove is only open in the warmer months of June through August.
Adults Night Out: Lincoln Park Zoo
Adults Night Out: The Great Pumpkin Glow is a unique adults only after-hours experience at the Lincoln Park Zoo takes that takes place annually right before Halloween. This your chance to explore the zoo after the gates close while also enjoying seasonal activities such as a pumpkin walk, a haunted trail, themed food, and seasonal cocktails. This is the perfect event for a fall date.
These are some of the best things to do in Chicago during the fall. I suggest bookmarking this post as I plan to update it with any new fun fall activities and events I find.
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