Eat And Admire On The Spirit Of Chicago Dinner Cruise
Take the riverfront experience to the next level by combining pristine Lake Michigan views with a delicious all-you-can-eat buffet dinner.
The menu includes entrees, salads, and desserts, ensuring that you disembark entirely stuffed and satisfied.
A DJ will spin the tunes all the way through, while the crewmates coordinate a few interactive games.
Remember How To Laugh Again
If Netflix reruns of The Office arent quite as funny as you remember, you might need to turn to the experts for your comedy fix. Comedy clubs across the city are doing their best to keep you laughing through Americas still-not-over pandemic, including live stand-up shows at Zanies and, of course, the world-famous improv-sters at Second City. In the meantime, head over to Lincoln Lodge to bask in the oddball glory of the nations longest running independent comedy showcase, recently back from hiatus. For even more options, check out this handy rundown.
Explore Chicagos Famous Downtown
There is so much architecture and unique landscape to see downtown.
The Bean and nearby Crown Fountain in Millennium Park may be the most well-known attraction, and you can also stroll through Lurie Garden and Maggie Daley Park.
Head south a few blocks and visit one of the worlds largest fountains, Buckingham Fountain, in Grant Park.
If you are at or near Navy Pier, you can also enjoy a fireworks display every Wednesday and Saturday night all throughout the summer, and right on the lake!
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Try And Spot The Sculpture By Actual Picasso
Dan DeLuca
Did you know that theres a secret Picasso statue in Chicago? We bet you didnt. But there is. And its an interesting statue with an interesting story. An Chicago architect wrote Picasso a poem asking him to create a piece. A rare commission for the artist, he accepted because it fit with another gangster city he was producing some work for .
An untitled piece, its one of the coolest things to do in Chicago because its sort of interactive people slide down the bottom of it. Another fun thing to do is guess what it is: Picasso never explained, and todays eyes see everything from a baboons head to an aardvark. Fun fact: its in The Blues Brothers chase scene.
Enjoy Live Music At The House Of Blues Chicago

You know those moments during a concert when time seems to stop and youre just present, right there in the moment? Yeah, me too. No matter how many times you listen to your favorite artist, nothing compares to seeing them live. Going to a concert is an experience everyone should have, especially at the House of Blues. Founded in in the 1990’s, the House of Blues is chain of live music concert halls that strive to bring all kinds of genres to its local communities. If youve got friends in town, be sure to make a stop at the House of Blues to experience live music like no other.
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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.
Top 6 Things To Do In Chicago During Christmas
by Chicago Traveler | Entertainment, Top 10 in Entertainment |
If anyone knows how to celebrate the holidays, its Midwesterners. More specifically, its Chicagoans. Every year during Chicagos winter wonderland, visitors are drawn like magnets to the citys festive energy. It seems everyone wants to visit Chicago during Christmas.
Millions of twinkling lights glow among the buildings, trees, and silhouettes of the downtown atmosphere. Animated window displays charm onlookers of all ages, and the frigid, icy air actually feels hospitable in the midst of holiday magic. And it is frigid, and icy, but oh so welcoming!
Thousands visit Chicago during Christmas and the other winter holidays, and they revel in the enchantment of the Windy City. What do they do? Where do they go? Here are some ideas.
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Visit The Adler Planetarium
Enjoy a live, guided tour of Chicagos night sky in Chicagos oldest planetarium! Every month, Adler Planetarium holds a 21-and-up after-hours event that invites adults to explore the Museum Campus while enjoying themed drinks and live entertainment.
Usually, the drinking is paired with music and featured vendors, all while guests learn about space, the future of deep space exploration, and a featured topic of the month.
With after-hours admission, youll get full access to museum exhibits and galleries, unlimited sky shows in their state-of-the-art theaters, access to special guest lectures, andhands-on educational activities.
Wet Your Whistle On The Barrel Run
With a thriving craft beer scene thats only advancing with every passing year, it would be a sin to visit the Windy City without sampling a few local brews.
But this isnt your average barhopping walking tour thirsty travelers whiz around town in the one-of-a-kind Barrel Bus, sampling plenty of cold beer from start to finish.
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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.
Halloween Edition Night Bike Tour
Only in Chicago can you be scared witless while enjoying a rip-roaring entertaining bicycle tour of Chicagos hauntings! This haunted Chicago tour is a 3 hour guided adventure through the citys spookiest spots.
The haunted tour takes guests to the haunted John Hancock Center, past the lingering spirits of the SS Eastland and the trapped souls of the Iroquois Theater, and to the ghastly elegance of the Congress Plaza Hotel. This night time activity in downtown Chicago during October is perfect for thrill-seekers, ghost-hunters, Halloween parties, or anyone looking to have a chilling good time!
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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.
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.
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Spot The Holiday Train
A beloved Chicago tradition, the CTA holiday train will make its way through the city this December. Marvel at the six-car train decorated with holiday scenes and thousands of sparkling lights then hop on board to meet the elves handing out candy. Dont forget to wave to Santa, whose sled replaces the head car. Theres also a holiday bus that will traverse the city streets.
Toast At The Top Of Londonhouse Chicago
Perched at the very top of the LondonHouse Hotel is the LH Rooftop, offering panoramic views of the city, The Magnificent Mile, and Lake Michigan. For many Chicagoans, rooftop season is the best season and by the time youre 30, you should claim your favorite outdoor dining spot. LH Rooftop is a top competitor with picture perfect views from the best vantage point, says Don Barnett, LH Director of Sales and Marketing. Guests can choose to sit outside on the patio or venture back inside to the LH Lounge on floor 21, all while enjoying specially crafted cocktails.
Despite the rooftop being open seasonally from May to October, guests can still order winter menu items like hot chocolates or ciders from the main bar and take them up to the top to enjoy. The best time for visitors is during the Happy Hour rush or during peak nightlife at around 9 p.m. The busiest nights of the week, however, happen to be on Wednesdays for Ladies Night, with a Christian Louboutin raffle every week. Im not biased, but nothing beats a free pair of shoes, Instagram worthy views, and signature cocktails all in one night.
85 E. Upper Wacker Dr. | 357-1200
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Enjoy Beautiful And Interesting Street Art
Youll find a lot of unique artwork sprinkled across this city, including both planned out sculptures and original graffiti work from street artists.
Consider using our guide to public art in Chicago to find some of the most well known and high quality artwork which is entirely free to experience.
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!
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The Signature Lounge At The 96th
Located on the 96th floor of the John Hancock Center there is no doubt that the lounges main attraction is not just the outstanding drinks menu, but the breathtaking views across Chicago.Gazing out on dazzling 360-degree views of the entire city skyline, while sipping on a selection of specialty cocktails and wines, is guaranteed to be an unforgettable experience. From a classic Long Island iced tea to the Chicago-inspired Magnificent Mile Manhattan the Signature Lounge has it covered. Make an evening of it by dining in the adjoining restaurant on the 95th floor for seafood and steaks.
Greet The Animals At The Lincoln Park Zoo
Since its opening in 1868, Lincoln Park Zoo has developed a reputation for excitement and prestige.
One of the most established zoos in the country , the 35-acre complex houses animals of all shapes, sizes, colors, and origins amphibians, birds, mammals, reptiles, and more.
Its a fantastic excursion for the whole family just remember to wear comfortable shoes.
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Stop : A Tiffany Jewel In The Crown
On the corner of Michigan Avenue and Randolph Street, youll encounter the Chicago Cultural Center, a neoclassical landmark that houses the largest Tiffany stained-glass dome in the world. This stunning building is a humanities haven, with concerts, dance performances, theatre productions, films, lectures, art exhibitions, tours, and family events scheduled throughout the year and all for free.
Go To A Free Concert Or Festival

During the summer months, there are often several free festivals held at various public squares and parks throughout the windy city.
Many of these events will also include free concerts, allowing you to enjoy some live music without worrying about ticket prices!
Check our monthly TTD posts to see whats on the schedule when you plan to visit Chicago.
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Soak In The Skyline From A Lake Michigan Sightseeing Boat Tour
Get off your feet for a while sit back and relax on a boat as the captain takes you down the Chicago River, pointing out the iconic landmarks and delving into the citys rich history along the way.
If youre fed up with the crowds, take the experience to the next level by booking a private, luxury tour on your very own sailboat, or grab a two-person pontoon.
Night Activities Included In Tourist Passes
As we mentioned above in the FREE section, getting a tourist attraction discount pass can save you considerable money, especially when it comes to night activities.
Be sure to read our post comparing the different tourist discount passes.
All passes include night attractions and activities, though some passes have more than others.
In general, tourist passes include at least a few, if not nearly all, of these Top Ten nighttime attractions that stay open daily until at least 9 or 10 pm, if not later.
- Navy Pier Centennial Wheel & Ride
- The Escape Game Chicago
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Stupidly Exclaim How Bout Them Apples At An Area Orchard
There are few events as fall-centric as apple picking, which is why this is the season to actually make it happen if youre ever gonna do it. Get out of the city and explore the picturesque surrounding farms in Illinois and Wisconsin for a fresh taste of what the season is all about. Remember, you can always DVR the Bears game. Chart a crunchy course with help from our lowdown.
Public Parks & Beaches
Chicago boasts hundreds of free public parks that cover over 8,000 acres of the city. Many feature wildlife havens like Northerly Island and North Pond Nature Sanctuary incredible landscape designs such as Alfred Caldwell Lily Pool and Humboldt Parks prairie river and boathouse and athletic facilities such as the kayak boathouse in Ping Tom Memorial Park. You can also spend the day at one of the free public beaches, open Memorial Day to Labor Day. Various locations
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