Watch The Blue Man Group
This troupe has set up a semi-permanent residence in Chicago, which means that you can reasonably expect them to be performing whenever you choose to visit the windy city.
In addition to being an excellent nighttime activity, the Blue Man Group is also appropriate for kids and teens, which makes it a good choice for families as well.
Enjoy Dinner And A Show At Tommy Guns Garage
So long as you recall the entry password, a night of glamour, history, laughs, and intrigue awaits at Tommy Guns Garage.
As soon as you step through that front door, youll be transported back to the roaring 20s, a time when gangsters, flappers, and jazz ruled the streets.
While the dinner is delicious, the selling point is undoubtedly the entertainment. Song, dance, comedy, and even audience participation ring through the evening.
Delve Into The History Of The City
Chicago wasnt always a big, shiny metropolis. Not at all. Rollback the years to as recently as the 19th century and Chicago was pretty much just a pioneer outpost, and an important stop-off for trappers and fur trade buyers. What happened between then and now? We wont bore you with it, because its much more interesting to learn about it first hand at the fascinating Chicago History Museum.
This aint no dull and dusty prison of artefacts. What you get here is a lot of hands on, interactive exhibits that makes history fun! Step inside a recreated old jazz club, a restored L train car , and clap eyes on a giant, Chicago-style hot dog. A super interesting thing to do in Chicago even if youre no history buff yourself.
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Catch A Show At The Chicago Theatre
Besides sitting down for a show at the world-famous Chicago Theatre, visitors are blessed with the opportunity to go behind the scenes and explore the grand history and intricate architecture of this iconic entertainment venue.
Step on stage, visit the rehearsal space, admire the ceilings, and more, all with an expert guide leading the way.
The theatre is centrally located to countless bars and restaurants, which makes planning the evening outing a breeze.
Explore The Lakefront On A Segway Tour
As the third-largest city by population across the entire country, Chicago is unquestionably massive. That means seeing everything on foot is next to impossible. Why not speed things up and tick off a few more attractions by joining a Segway tour?
Glide through downtown, the riverfront, or a number of other routes on offer, all while learning about the city from a seasoned local. These smooth-moving machines are fun for the whole family.
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Detroit: The Rise Fall & Renewal Walking Tour
Fly to Detroit, where you can explore the very different American city with a walking tour before setting out on your own. On the tour, youll explore the social and economic upheavals of Detroit through its architectural landmarks, learning all about the city and its complex history!
The tour is a great introduction to the city. Youll see some of the worlds tallest vacant buildings, and most beautiful modern landmarks. Chat with fellow tourists and a knowledgeable local.
See The Light Show At Buckingham Fountain
Once the sun starts to set, head over to the Clarence Buckingham Memorial Fountain in the center of Grant Park.
Before Cloud Gate came along, this historical landmark was Chicagos most-visited attraction, thanks largely to its mesmerizing nightly light show.
The majestic attraction uses as much as 15,000 gallons of water per minute, and it all illuminates up after dusk.
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Final Thoughts On The Coolest Places To Visit In Chicago
Chicagos reputation has suffered a bit over the last few years, but this doesnt mean that you should avoid the city. As long as youre careful and stay away from certain key areas, your visit to Chicago should be safe and filled with great food, entertainment and amazing sites! So make sure you visit some of your favorite sites on this list, and youll see why people say that Chicago is one of the most exciting and interesting cities in the world.
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Cheer On A Chicago Sports Team
As weve mentioned before, Chicago is home to several great teams in multiple sports including baseball, basketball, hockey, and football.
No matter which sports your kids love, chances are youll have a chance to take them to a game during your trip to the windy city.
Check this list of sporting events in Chicago to find one that your children will enjoy.
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Smoke Some Of Illinois Most Essential Legal Green
Who knew that just a few months after Illinois became the 11th state to legalize recreational marijuana, a full-blown public health emergency would bring our society to its knees? And, furthermore, can you imagine dealing with the past year-and-a-half without a little green? We dont even want to think about it, and you dont have to either. Deemed “essential” businesses with more than $1 billion in sales in 2020, legal weed is clearly here to stay in Illinois. Check out our full dispensary guide for all the hairy details.
Appreciate Jazz At The Green Mill
Known across the city for its eclectic jazz performances and poetry readings, The Green Mill is a Chicago treasure.
Its the oldest jazz club in the U.S., welcoming tourists since way back in 1907.
Celebrities and mobsters alike frequented this prohibition-era speakeasy over the years, and travelers continue to do so to this day.
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Hit Up Some Of The Seasons Finest Events
Event season certainly isnt as predictable as it once was, but there are still a few fall classics you can count on. From the annual Halloween spectacle that is Arts in the Dark and the family-friendly Chicago Thanksgiving Parade to the cosplay-drenched C2E2 and the drunk-before-noon TBOX Christmas bar crawl, theres something for every kind of reveler.
Laugh At The Faces Of Crown Fountain
While far less extravagant than the Buckingham fountain, the Crown Fountain takes the cake in the entertainment department.
Its become famous for its Faces of Chicago element, where anonymous people are projected onto two identical 50-foot towers, appearing as though theyre spitting out a stream of water.
Youll often spot kids running around in the fountain, trying to cool off on those sizzling summer afternoons.
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Check Out A Comedy Club
Fill Your Night With Smiles and Laughter
Chicago is known for creating and incubating the improv and sketch comedy scene. You can catch rising talent perform every weeknight before they head off to a different city. There are plenty of comedy clubs and theatres across the city for every type of humor. Chicagos comedians are raw and unique when it comes to their humor.
Chicago is home to The Second City an improvisational comedy enterprise. Some of their most notable alums include Tina Fey, Amy Poehler, and Steve Carell.
Bilal and I have watched several stand up and improv shows throughout the city and each one has lived up to its hype. Its always impressive to see how the comedians are able to pivot on the spot based on the interactions with the audience!
Laugh Factory serves as the epitome of what the Chicago comedy scene stands for. Listed as Americas #1 comedy club with multiple locations across, you can attend any show and find a diverse mix of seasoned and rising talent. Each show usually has a surprise special guest as a headliner
If youre ever looking for fun things to do in Chicago, check out the comedy scene as its sure to set you up with a night full of laughter.
Museum Of Contemporary Art Chicago
- A smaller, but no less impactful art museum than others in the city.
- Has a permanent collection that showcases Andy Warhol, Francis Bacon and Alexander Calder.
- The venues eatery is well worth checking out for the food and the ambiance.
Why its so awesome: This imposing building fits perfectly with the contemporary art that it showcases. It houses a smaller collection thats absolutely fascinating for art lovers and people who are curious about modern art. The restaurant also has a range of startling dishes for brunch, lunch and dinner, so whatever time you go make sure that you check it out!
What to do there: If youre an art lover then youll probably recognize many of the famous names that showcase their art in this museum. But if you dont know as much about contemporary art then its a chance to wander and maybe find some new favorites! Make sure you check out the rotating display as well as the regular one to get the full effects. And grab a snack or a meal at the Marisol restaurant to experience some truly innovative dishes while youre there.
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Take A Tour Or See A Game At Wrigley Field
Wrigley Field, home to the Chicago Cubs, was built in 1914 and is the second-oldest Major League Baseball park in the US, second only to Fenway Park in Boston. The park has seen some legendary moments in baseball history, including the 1917 no-hitter pitching duel between the Cubs’ Jim Vaughn and the Reds’ Fred Toney, and Babe Ruth’s “called shot” during game three of the 1932 World Series.
Ballpark tours are conducted in-season, when you can visit the press box and field, as well as the dugouts if there is no game that day.
Nicholas Conservatory & Gardens
Nicholas Conservatory & Gardens is located in Rockford, Illinois, along the Rock River. It showcases 11,000 square feet of indoor tropical plants, flowers, and trees interspersed with benches, garden sculptures, a koi pond, and an infinity pond. Outdoor paths connect to a Monarch butterfly garden, Riverview Terrace, Eclipse Lagoon, two teahouses, two waterfall gardens, the Sinnissippi rose garden, Trolley Car 36 station, and Forest City Queen Riverboat dock.
An onsite indoor garden café serves light fare as well as Wednesday night rooftop dinners on their green roof viewing deck during summer. The conservatory hosts temporary exhibits like Lorikeet House and events like Family Botany Labs and Breakfast with Santa.
1354 N 2nd Street, Rockford, IL, Phone: 815-987-8858
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Visit The Chicago Childrens Museum
The Chicago Childrens Museum has a lot of fun, hands-on exhibits that are designed to help kids learn about the world around them.
If youre looking for an activity that will engage the imaginations of your children, this is an excellent museum where they can go on a hunt for dinosaur bones, create art, play in a treehouse, and more.
Best of all, admission is free for children 15 and under on the first Sunday of every month, and they offer late hours every Thursday!
Obsess Over Famous Wordsmiths At The American Writers Museum
With an abundance of interactive displays detailing all facets of the nations literary history, the American Writers Museum in the heart of Downtown is a bookworms delight, and one of the most unique things to do in Chicago.
In addition to blurbs about tens of revolutionary wordsmiths, the museum also displays artifacts like typewriters, hand-written notes, and old-school quills.
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Why You Should Go
Searching for fantastic free things to do in Chicago? Do yourself a favor, and put this riverside walkway to your list of places to visit in Chicago. Not only is it a terrific place to stroll, but it also offers splendid city views.
Furthermore, it has a ton of arts displays, public gardens and water-based activities, like kayaking.
Museum Of Contemporary Art
Dedicated to art from 1945 to the present, the Museum of Contemporary art is endowed with a serious collection, spanning surrealism, conceptual art, pop art and minimalism.
Youll get to see works by Chuck Close, Andy Warhol, Jasper Johns, Francis Bacon, René Magritte, Alexander Calder, Ann Hamilton and Richard Serra.
When we wrote this article in 2018 there was a haunting exhibition by the Nigerian multidisciplinary artist Otobong Nkanga, combining installations, photography and textiles.
From June to September, Tuesdays on the Terrace is a programme of summer performances by members of Chicagos dynamic jazz community.
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History & Natural History Museums
History fans, especially those with a taste for local history, will also get a lot out of a trip to Chicago. Visit the Chicago History Museum for a specific focus on the heritage and history of this marvelous city. Why not stop in at one of their fantastic temporary exhibitions and soak up some culture together?
With its convenient location in the south part of Lincoln Park, the Chicago History Museum is also right near Old Town, a trendy neighborhood with plenty of great food and drink options. We love Broken English or Old Town Pour House .
Or, head to the Field Museum for a fascinating perspective on the natural history around the globe. Here you’ll find everything from SUE, the iconic T. Rex skeleton, to gorgeous gemstones of all varieties to Ancient Egyptian artifacts.
Getting In: Chicago History Museum admission and Field Museum admission are both included with the Go Chicago pass.
Richard H Driehaus Museum
Youll step back into Americas Gilded Age at the refined Nickerson House, built in 1883 for the banker Samuel M. Nickerson.
Close to the Magnificent Mile, on the Near North Side, the house looks a little out of place, dwarfed by the citys bold Neoclassical monuments and glass-clad skyscrapers.
In 2003 the Chicago fund manager and philanthropist turned the Nickerson house into a museum, blending the original furnishings with luxurious Art Nouveau glazed tiles, stained glass, onyx, carvings and marble all sourced from other places.
The museum is heaven if you like decorative arts.
Youll find some lovely pieces by Louis Comfort Tiffany, like a large fire screen, a set of vibrant stemware, a blown-glass humidor and a peculiar centrepiece lamp.
The ballroom has Edward Colonna furniture you can sit in, while some other exceptional pieces include Sèvres vases, a suite of George A. Schastey neo-Empire chairs, pre-Raphaelite paintings and a rare Chickering and Sons grand piano.
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