Visit The Walnut Room
It doesnt get much more festive than a meal from the Walnut Room. Located inside Macys on State Street, the historic restaurant is an essential holiday destination. The stately interior is adorned with elegant decor and sparkling chandeliers, with the towering Great Tree in the center of it all. And dont miss the famed holiday window displays that line the exterior of the historic building.
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.
Tour The Chicago River By Kayak
In either a solo or tandem kayak, soak in the famous skyline views with a peaceful paddle along the Chicago River.
All the equipment is included with the tour, likewise the knowledgable guide wholl spill architectural, cultural, and historical tidbits throughout the journey.
For something a little more spooky, glide down the river by moonlight on a ghost-themed outing.
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See More For Less With A Chicago City Pass
Many of Chicagos biggest attractions have entry fees.
While you do pay for a tourist discount pass, it can give you a bulk discount and free admission into some interesting tours and museums, saving you up to 55%.
They can also save you time with skip-the-ticket-line privileges.
Each Chicago tourist discount pass includes a variety of fun activities and attractions.
Here are a few examples of what you can visit with a tourist pass, for a discount or for free.
For more details, make sure to read our full post covering Chicago tourist passes.
Millennium Parks Hidden Garden Aka Lurie Garden
Hidden Gem in Chicago
Millennium Park is a hot tourist attraction in Chicago but Lurie Garden is a less-visited hidden gem in the city. The garden, often called Millennium Park’s Hidden Garden, is hidden from the city by a 15-foot wall of trees to keep it a beautiful, relaxing oasis in the middle of the city’s hustle and bustle.
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Cheer On A Sports Team
No matter what time of year, theres a game going on somewhere!
Be part of the Crosstown Classic, where Northsiders cheer on the Cubs at Wrigley Field and Southsiders root for the White Sox at U.S. Cellular Field.
Baseball not in season? The Blackhawks hit the ice at the United Center fighting for another Stanley Cup!
And who can deny a chance to see the Chicago Bears play at Soldier Field?
Hop Between Chicagos Rooftop Bars
After soaking in the views from Tonys Rooftop Bar at the Time Out Market, continue the rooftop adventures by hopping around some of Chicagos very best patios and terraces.
Try the Elderflower Collins cocktail and take in the sweeping panoramic vista at Z Bar sample a flight of local beers at the garden-themed Raised or sit around a fire pit at Offshore, the largest rooftop bar in the world.
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Things To Do At Night In Chicago
Mentioned below are some activities that you can take part in when you next visit Chicago and need a little entertainment in the night. Some are more on the affordable side. However, some are expensive yet worth every penny if you genuinely wish to enjoy Chicagos nightlife to its full extent.
Take part in Chicagos ultimate city bike tour.
You would not ordinarily think to hop on a bicycle as soon as it gets dark. However, it is the ideal chance to take in the lakefront and get the best view of the horizon. Beginning daily at 7:00 p.m. whats more, leaving from our central command in Streeterville, your Bobbys Bike Hike Chicago local area expert will lead you through a more than two hour, eight-mile circle that grandstands a few of the sights and hints of downtown Chicago. During the ride, you can appreciate the enlightened horizon and take in sights like Olive Park, Oak Street Beach, Millennium Park, Buckingham Fountain, Museum Campus, and Soldier Field.
Visit the Skydeck
Get acquainted with the Adler After Dark
Catch a show at the Chicago Theatre
The Chicago Theater opened in 1921 as the principal luxurious film royal residence in America and has become one of downtown Chicagos most darling live amusement scenes. Inhabitants and successive guests can see the venues famous six-story vertical C-H-I-C-A-G-O sign at the side of State Street and Chicago.
Enjoy a shift in altitude
Catch the Blue Man Group
Spend The Night At Museum
Many of the museums offer special events where the kids can spend the night amongst the exhibits – whether it is dinosaurs or butterflies depends on the museum.
They offer kid-friendly activities and tours of the museums and an unforgettable way to experience some of the iconic sites of Chicago.
Closest L stop: State/Van Buren Brown LineRecommended ages 8 and up
Games at Room Escape Adventures include escaping a room with a zombie, and cracking a code on New Years Eve 1999 before Y2K hits!
Tip: Book your spots at their website, and Free Tours By Foot customers can enter the code FREEFOOT for $5 off their booking!
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Order A Slice At Vito & Nicks Pizzeria
Contrary to Chicagos deep-dish pizza reputation, Vito & Nicks Pizzeria has been dishing up Cracker Thin Crust Pizza since the 1950s, and theyve yet put a foot wrong.
A visit to this adored eaterie and youll feel like youve stepped back in time into an old-world Chicago dive restaurant.
This isnt luxury nor sophistication, its just darn good pizza.
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.
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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.
Make Sightseeing Competitive With A Scavenger Hunt
With limitless attractions scattered across the city, walking around from A to B can get a little repetitive. Why not spice it up a bit with a little extra adventure?
The professionally-orchestrated Scavenger Hunt games combine sightseeing with interactivity, sending players all over the city to solve puzzles and complete tasks, Amazing Race-style.
Sign up for a city-wide adventure, or get specific with a hunt centralized to the Magnificent Mile or the Chicago Zoo.
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Go On The Ultimate Chicago Outdoor Mural Crawl
One thing the pandemic cant stop is the citys thriving street art scene, which can best be enjoyed IRL via an urban mural crawl. Start your excursion in Pilsen, where dozens of vibrant works turn the neighborhoods streets and alleys into an outdoor feast for the senses. Trackdown standouts like the Hector Duarte Studio at 1900 W. Cullerton before making your way to Logan Square to marvel at the famous Robin Williams mural outside Concord Music Hall and the nearby Greetings From Chicago mural at 2226 N. Milwaukee. Finish the crawl with a trip up to Rogers Park, where you can see a mile-long stretch of wall art along the Red Line path as well as the brightly colored seawall of murals off the lake at Tobey Prinz Beach Park.
Hold Your Event At Navy Pier
Planning a special event in Chicago? Wow your guests with a private event venue unlike any other in the city: Navy Pier.
From weddings to corporate retreats to festivals to trade shows, Navy Piers breathtaking venues and unmatched service provide an unparalleled private event experience, ensuring that no detail goes unnoticed.
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Skating Ribbon At Maggie Daley Park
When: Opens November 19th, 2021
Nothing says white Christmas more than a snow-filled ice skating session at one of Chi-towns best ice skating rinks. The Skating Ribbon at Maggie Daley Park is unique in that its curved serpentine structure makes it twice the length of a traditional ice skating rink.
View The City From Above
See the Chicago skyline from a birds-eye view and marvel at the architecture as the city lights up.
The main Observation Decks in Chicago are:
All three are included for free on at least a few of the tourist discount passes.
If you arent sure which of the three to visit, weve put together a list of the pros and cons of each of them.
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Late Night Chicago Restaurants And Shopping Options
The Windy City is home to one of the largest shopping areas in the country. Known as the Magnificent Mile, the region stretches for about a mile on Michigan Avenue just north of the Chicago River. The Mag Mile encompasses more than 450 retailers of all kinds.
Water Tower mall on the Magnificent Mile, which offers shopping opportunities until 9 pm everyday.
The large Water Tower Place mall is open until 9 pm everyday except Sunday. As for the shops not located in malls, each store on the Mag Mile sets its own hours. Most close by 9 pm, but you can find exceptions. The Macys at Water Tower is open until 10 on weekends
While youre in the area, walk past the Tribune Tower, which has become a quirky attraction thanks to the chunks of famous worldwide structures embedded into its exterior.
When it comes to food, Chicago has some of the most incredible culinary destinations in the country, many of which are open into the late evening. I couldnt even begin to describe all of the award-winning Chicago restaurants, but this article from Eater is a good start.
The line at the Wieners Circle, a popular late night food spot.
And for very late dining after the bars close, theres always the Wieners Circle the wacky hot dog stand where the employees berate and insult the customers.
Let The Kids Run Wild At The Chicago Childrens Museum
Located at Navy Pier, the Chicago Childrens Museum is regularly considered the premier kids museum nationwide.
The immersive attraction features a plethora of hands-on exhibits that the youngsters absolutely love perhaps none more so than the Dinosaur Expedition, where they can dig for bones and pretend to be archaeologists.
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Holiday Theater Shows To See This Winter
Planning something special for Christmas in Chicago this year? Consider an evening at the theater. After a year of mostly virtual productions in 2020, Chicago theaters are bringing some of the city’s most beloved holiday plays, musicals, ballets and variety shows to the back to the stage for in-person performances this season, offering audiences plentiful opportunities to get dressed up and see a festive show or two. Whether you prefer to keep it classic with the Goodman Theatre’s A Christmas Carol or check out something entirely differentlike a musical parody of the holiday rom-com Love Actuallyyou’re sure to find something to put you in the holiday spirit on our list. FYI: Many of these venues require proof of vaccination or a negative COVID-19 test to attend shows, so be sure to visit the venue’s website for health protocols before snagging a ticket.RECOMMENDED: The best things to do during the holidays in Chicago
Experience A Traditional Christmas Market
Christkindlmarket is back! The beloved Chicago tradition turns the downtown Daley Plaza into a bustling holiday market, filling the air with the smell of roasted nuts, fresh pretzels, and hot spiced wine. Admission is free to come in and peruse artisan goods, imported German gifts, and handmade holiday decorations. You can even catch cultural activities and family-friendly events. The market opens for the season on Nov. 19, 2021.
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Take A Sunset River Cruise
Architecture river cruises in Chicago are an absolute must. Not only will taking a river cruise help you get your bearings and help you better understand the layout of the city, but youll also learn so much about the citys inspiring past.
And did we mention youre going to be an architecture pro after your cruise? Trust us, they are a lot of fun.
While a daytime river cruise is a fun activity, the architecture river cruises at night, held after dark or at sunset, are even more beautiful. Youll get the added perk of seeing the city skyline lit up, from a really unique perspective!
There are also dinner cruises available which include either a 3-course meal or a buffet, music, drinks, and more.
Head To Logan Square For Free Music Comedy Or Djs
The Logan Square neighborhood is a trendy scene for nightlife, and two bars in particular have no-cover events almost nightly.
Coles Bar is always free and hosts comedy, DJs, and live music.
Just down the street is the Whistler, which also hosts DJs and music that often caters to the jazz crowd.
Info: Coles Bar is located at 2338 N Milwaukee Ave. Visit www.colesbarchicago.com for more details. The Whistler is located at 2421 N Milwaukee Ave. Visit whistlerchicago.com for more.
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Slather Yourself In Chicagos Bbq Scene
It aint quite KC or Memphis, but Chicagos barbecue landscape has certainly come a long way, baby. From iconic haunts like Lems and Earls to more modern outposts like Lillies Q and Smoque, BBQ is enjoying something of a Renaissance as newer spots like Babygold continue to push the envelope.
Take A Bike Tour Of The City
With so many interesting things to see and do in Chicago, it can be difficult to get around and discover all the sites.
Thankfully, there are bike rental services which offer bicycles for both adults and children.
All bike rental companies provide helmets and other protective gear to keep everyone safe.
Kids love to ride bikes, so this is a fun way to explore the city and see some of the most notable landmarks as a family.
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Check Out The Public Art Downtown
Looking to get out of the house? Yes, you can go see The Bean, but dont stop there. Swing by the Chicago Picasso, or Calders Flamingo, then head down to the southern end of Grant Park to walk among the giant, headless sculptures that make up Agora. Take a selfie with the Art Institute lions, and be sure to check out the installations along the Chicago Riverwalk between Lake and Franklin. The concentration of world-class public art downtown is astounding and not to be missed. And, even better, Art on theMARTthe worlds largest permanent digital art installationcontinues its screenings on the south façade of the Merchandise Mart through November 25.
Explore The Harold Washington Library
One of the nations largest and most impressive libraries is located in downtown Chicago and open until 9 pm.
Be sure to take in the architecture on the outside and inside of the building, as well as the glass roof of the Winter Garden on the 9th floor.
You can also create some art for free in the Maker Lab on the 3rd floor, and there is usually free art exhibits for the adults and storytimes in the Childrens Library.
Info: Harold Washington Library is located at 400 S. State St. Check out www.chipublib.org/locations/34/ for events and visitor info.
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Free Halloween Events In Chicago
Halloween in Chicago is so much more than just trick-or-treating. Theres magical nighttime parades, authentic Day of the Dead celebrations, ghosts tours, and more plus many of the events are free. Here are just a few of the free events and celebrations in Chicago for Halloween this year.
Check our Halloween guide for more things to do around the city.
Pay A Visit To A Speakeasyall The Cool Kids Are Doing It
Theres a reason why the speakeasy never goes out of style. Sometimes you just need to hide out in a dark hole and drink cocktails like its illegal. Whether or not our own 20s turn out to mirror the Roaring ones of yore, Chicago still offers plenty of options to unleash your inner Capone. Heres our full roundup of local speakeasies and secret bars, since you asked. Shh.
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