Things to do in Chicago Tomorrow

(102 activities)
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    The Prison: Room Escape

    (20)
    Contain yourself. You're about to be contained. Stuck in a fictional prison for a fictional crime you're pretending you didn't commit, the choice is clear: bust out or spend the rest of your fictional life locked behind imaginary bars. It may all be a game, but the suspense and sense of urgency are all too real in this gripping escape-room event. It's you against a maximum-security prison. Using the cover of a tumultuous riot, you've got to scour your surroundings, build your plan of escape, and put it into effect. But as any film buff knows, busting out of the Big House is rarely a one-brain deal. Assemble your smartest friends to play along with you and up your odds of success! But work fast, because you've only got sixty minutes before the riots are quelled. Beat the clock, or do the time!
    The Prison: Room Escape

    47 W Polk St, Chicago

    • Immerse yourself in an escape-room game based on a daring prison escape
    • See how far your observational and critical-thinking skills will take you
    • Bring your friends to increase your odds of busting out before your 60 minutes are up
    • Spark your imagination and thrill your inner child with a nail-biting escape from reality
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    20 positive reviews
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    Chicago Skyline Cruise

    (14)
    Sailboat, water, skyline: that sounds like a recipe for the perfect day of relaxation. See Chicago's skyline the way it was meant to be seen from the water. On this beautiful tour of Chicago, hop on a sailboat to kick back and forget about all worries. You'll tour Lake Michigan as you enjoy the gorgeous skyline in front of you. This optimal vantage point is truly one of the most unique and best ways to see the city. So, whether you're a tourist or a local, sit back, relax, and experience Chicago in a new light.
    Chicago Skyline Cruise

    700 E Grand Ave, Chicago

    • Enjoy Chicago's beautiful skyline from a unique vantage point
    • Take a leisurely trip around Lake Michigan on a sailboat
    • Relax with the wind at your back and gentle waves rocking you back and forth
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    14 positive reviews
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    Earn Your Wings in Naperville

    (9)
    Have you always wanted to feel the thrill of free falling without having to, well, jump out of an airplane?! What if you could feel the adrenaline rush of skydiving MINUS your totally understandable fear of heights? Well, here's your chance! iFLY is an indoor skydiving facility that creates true free fall conditions. You'll float inside iFLY's 1,000 hp vertical wind tunnel -- with absolutely NOTHING attaching you to planet earth. And with the Earn Your Wings package, you'll get the ultimate beginner-level package for a great introduction to indoor skydiving: 2 unforgettable one-minute flights, plus hands-on assistance and a comprehensive training session from your personal flight instructor. You'll even get to take home a personalized flight certificate to show off to your friends. This is one indoor aerial experience you don't want to miss! Note: The total duration of the activity is 2 hours, which includes 1 hour of training. Includes use of all the flight gear. If you have had a prior shoulder dislocation, back, or neck problems or if you are pregnant, you should not fly. Those less than 6 feet tall must weigh less than 230 pounds, and those over 6 feet must weigh less than 250 pounds. Flyers can be as young as 3 years of age; there is no upper age limit. Participants under 18 years must have parent or legal guardian present to sign Release of Liability.
    Earn Your Wings in Naperville

    1752 Freedom Dr, Naperville

    • Experience the adrenaline rush of skydiving without having to jump out of an airplane
    • Benefit from the ultimate beginner's package, with everything you need to have a great first flight
    • Feel safe and prepared with hands-on assistance from your personal flight instructor
    • Channel your inner super hero as you float in iFLY Chicago's 1,000 hp vertical wind tunnel
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    9 positive reviews
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    Spirit Ships & Haunted Harbors Tour

    (14)
    The Great Lakes hold spooky mysteries, many of which still continue to haunt these waters today. On this storytelling adventure, learn about the many ghost ships and souls that roamed Lake Michigan and the other inland waters. As night falls and the seas grow dim, you'll uncover the history, legend, and lore behind these mysterious beings. Ever wonder what happened to all those souls that perished with their ships? You're about to find out!
    Spirit Ships & Haunted Harbors Tour

    700 E Grand Ave, Chicago

    • Hear chilling tales about ghost ships on the Great Lakes
    • Discover the mystery, history, legend, and lore of these ships, and the harbors they haunted
    • Learn about the dark souls that sailed these shorelines
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    14 positive reviews
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    Haunted History Tour

    (20)
    Boo! Scared? No? Oh. How about a ghost tour? But, wait, this isn't just another run-of-the-mill ghost tour your family dragged you through. Explore the exciting thrills that mix ghosts with gangsters, and more! It's like Mario Puzo meets Ghostbusters, but in Chicago! Experience the strangeness and haunted history first-hand on a tour that does so much more than just drive past spooky places. See them up close and personal for an experience in the Windy City guaranteed to send chills up your spine. Scared now? You should be.
    Haunted History Tour

    600 N Clark St, Chicago

    • See some of the scariest and spookiest sites in Chicago with a tour that gets up close and personal
    • Learn the history and background that make these locations so seductively sinister
    • Take a ghost tour that has access to unique places and all-around strangeness
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    20 positive reviews
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    Twilight Riverwalk & History Tour

    (22)
    Join Free Tours by Foot for a leisurely stroll along the northern reaches of the Chicago River to take in the surrounding beautiful architecture! Following your expert local guide, you'll learn the fascinating histories of Chicago icons, such as the Tribune Building, Trump Building, and Wrigley Building, and hear the stories behind the men and women who built them. The tour even ends right around the corner from Municipal Pier #2 (better known as Navy Pier), where you can easily stroll over to see the sites including the Ferris wheel, the Stained Glass Museum, and tons of food vendors. Chicago may be known as The Second City, but on this tour you'll discover exactly what makes it first rate!
    Twilight Riverwalk & History Tour

    175 N State St, Chicago

    • Explore the northern reaches of the Chicago River on this informative guided walking tour
    • Snap great photos as you pass the Tribune Building, Trump Building, and Wrigley Building
    • Follow your expert guide to learn the fascinating stories of the men and women who built these iconic buildings
    • Stroll over to Navy Pier to see the Ferris wheel, the Stained Glass Museum, and tons of food vendors
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    22 positive reviews
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    The Original Chicago Pizza Tour

    (10)
    Experience an unmatched culinary experience on the only bus driven pizza tour! You'll explore several of Chicago's neighborhoods in search of tasting Chicago's most defining food... PIZZA! Along the tour, see interesting and historical sights and landmarks as you see Chicago one bite at a time! Each tour will visit a mix of culturally significant and neighborhood pizzerias, enjoying a full serving at each restaurant. Of course, all 4 pizzerias visited are very different in taste and style to ensure the ultimate dining experience. At some restaurants, you even get a "backstage pass" into their kitchens to check out the ovens, ingredients, and overall process. Stops vary from day to day, but rest assured every place selected has a dynamite slice and a friendly atmosphere. Make sure you're ready to eat and experience how these magnificent pizzas span more than a mile.
    The Original Chicago Pizza Tour

    61 E Madison St, Chicago

    • Taste your way through several Chicago neighborhoods with delicious pizzas
    • Visit interesting historical sights and landmarks as you take a bus around the city
    • Eat at four different pizzerias and uncover the varying styles and tastes of each pizza
    • Dive into the kitchen and check out the ovens, ingredients, and processes behind each pie
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    10 positive reviews
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    The Railcar Escape game

    (2)
    It was just another normal day in the city. You rub the sleep out of your eyes as you struggle onto the train. Ugh, Mondays. All of the sudden -- the lights cut out and the train comes to a screeching halt! A screen flickers to life and a face appears. A crazed hacker has commandeered your train and has programed it to slam into the center of Chicago! You and your team members will have to use your wits to avert this catastrophe and save your own lives. You have 60 minutes to outsmart the hacker or you'll be blown to bits and the city of Chicago will be left with a gaping wound that may never heal. Good luck!.
    The Railcar Escape game

    1579 N Milwaukee Ave #350, Chicago

    • Prevent your train from hurtling into the center of Chicago killing all the passengers and innocent civilians in the process
    • You and your fellow passengers will have to work together to thwart an evil hackers plans
    • Use your brains and your creativity to find clues and solve puzzles
    • Immerse yourself in an exciting adventure and beat the hacker before your time runs out
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    2 positive reviews
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    Chicago Dinner Cruise (Weekday)

    (35)
    What's better than a three-course meal? A three-course meal on the water! Newly renovated, this luxury vessel features a newly furnished rooftop lounge, posh atmosphere and stylish interior. Upon boarding, the Captain and crew will greet and escort you to your private table. From there, you'll be able to check out the observation decks, filled with understated Art Deco accents and reminiscent of the classic ocean liners. Next, you will feast on a splendid 3-course meal with celebrity-chef inspired dishes prepared from fresh ingredients right on-board. Finally, dance the night away to DJ entertainment or simply relax in the elegant ambiance and admire unparalleled views of the famed Chicago skyline as you glide along the shores of Lake Michigan. Why eat at your usual restaurant spots when you can dine in style... on the water!
    Chicago Dinner Cruise (Weekday)

    600 E Grand Ave, Chicago

    • Board a luxury vessel that features a newly furnished rooftop lounge, posh atmosphere, and stylish interior
    • Dine on a three-course meal prepared with fresh ingredients
    • Enjoy the nighttime entertainment, including DJs, unmatched views of the skyline, and an elegant ambiance
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    35 positive reviews
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    BYOB Painting

    (12)
    A little wine, a little love, and a whole lotta paint are coming your way. Are you ready to loosen up and uncork those creative juices -- along with those of wonderfully aged grapes -- in this painting party? It doesn't matter if you can't paint a straight line or if you're an amateur van Gogh, this class teaches you how to tune into your inner-artist and create a beautiful painting for your home (or gallery!). You'll learn brushstroke techniques, color mixing, composition, and texture. All the while, you will relax and enjoy the lively environment. Keep calm and paint on!
    BYOB Painting

    1907 S Halsted St, Chicago

    • Sip wine and create a painting perfect for your home
    • Learn painting basics, including color mixing, brushwork, composition, and texture
    • Relax with a drink in hand and a brush in the other during this social, creative environment
    • No experience necessary
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    12 positive reviews

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