Cultural & Sightseeing · Tomorrow

(21 activities)
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    Southwest Michigan Wine Country Day Trip from Chicago

    Is your palate parched for a new pinot? Well then why not taste the best of the Midwest? A tour of four wineries is waiting for you in the picturesque hills of the Michigan countryside. You’ll have the chance to taste over 20 different kinds of wines, receive a hearty lunch with vegetarian options at Founders Wine Cellar, and take home your own customized wine glass. Bring some extra cash, because specially discounted bottles will be available along the way. The wineries of the Heartland of America are calling for you.
    Southwest Michigan Wine Country Day Trip from Chicago

    640 N Wells St, Chicago

    • Enjoy tastings at Founders Wine Cellar, the Lemon Creek, St. Julian, and Round Barn Wineries
    • Discover the variety of wines grown from grapes right in the Midwest
    • Taste over 20 different wines from 4 of Michigan's most charming wineries and enjoy a hearty lunch
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    Haunted History Tour

    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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    15 positive reviews
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    The Original Chicago Pizza Tour

    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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    Sunset Paddle

    If you seek a titillating twilight tour, look no further. This kayaking journey will give you a whole new perspective of city of Chicago. You’ll be making your way along the Chicago River, surrounded on all sides by reflections of gold as the sun drops below the horizon. You’ll paddle for six miles with a licensed guide who will point out some of the unique sites as you pass by, offering up nuggets of architectural fact and history. Whether you have years of experience kayaking, or are picking up the paddle for the first time, you’ll find plenty to enjoy during this adventure. That is, if you’re not too busy being titillated by the views.
    Sunset Paddle

    1220 W LeMoyne Ave, Chicago

    • Kayak across the city on the Chicago River during this energizing twilight adventure tour
    • Learn about the history and architecture of Chicago as you paddle by several famous sites
    • Let a certified instructor show you the ropes during a safe row
    • Feel the adrenaline of adventure consume your senses and fuel your sense of wonder
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    5 positive reviews
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    Mini Bus Tour

    On this tour you'll see Chicago's world renowned architecture and learn about the city's colorful history, including gangsters like Al Capone and John Dillinger. Drink in the beautiful views of a lake that looks more like an ocean, and a river that now runs backwards! Downtown, you'll see Millennium Park, The Loop, Museum Campus, Soldier Field, The Willis (Sears) Tower and more. Then it's up north, to the fashionable Gold Coast (including the original Playboy Mansion), Lincoln Park, and Wrigley Field (legendary home of baseball's Chicago Cubs since 1916). Of course, you'll stop a few times along the way, so that you can get out, stretch your legs and take some pictures of Chicago's many fantastic sights.
    Mini Bus Tour

    300 East Ohio St, Chicago

    • Explore the sights and sounds of Chicago in style, aboard a climate controlled, large-windowed mini bus
    • You'll see some of Chicago’s most interesting and popular downtown sights and neighborhoods
    • Snap beautiful pictures at the photo-ops along the way
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    6 positive reviews
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    Sports History and Landmark Tour

    See the homes of Chicago's iconic sports teams as you are escorted in a comfortable van to the city’s top sports parks, learning the history of each during your journey. Begin by visiting the home of the Chicago Cubs—Wrigley Field. Originally built in 1914 as Weeghman Park for the Chicago Federal League baseball team, the Chicago Whales, the stadium name was changed when chewing-gum titan William Wrigley Jr. purchased the team in 1921. Next, stop at the United Center, home of the Chicago Bulls basketball team and Blackhawks hockey team, to see the bronze Michael Jordan statue, officially known as The Spirit. A tourist favorite, the statue was created shortly after Jordan’s retirement to commemorate his 3-consecutive NBA championships as a Chicago Bull. Your next destination is the oldest NFL stadium, Soldier Field. This lakefront field is home to the Chicago Bears.
    Sports History and Landmark Tour

    Hotel pickup, Chicago

    • If you are a sports fanatic, this tour is for you!
    • This tour shuttle you and your friends to the top sports parks in Chicago for the ultimate photo op
    • You will visit Chicago's historic Wrigley Field - built in 1914, the United Center - home of the Chicago Bulls and Blackhawks
    • End the tour at the Harry Caray's Water Tower with admission to the Chicago Sports Museum!
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    Interior Architecture Loop Tour

    Step inside magnificent lobbies, corridors, and the underground Pedway System for an in-depth look at architecture and a personal, cultural approach to experiencing downtown. Great for any time of year, you'll stay indoors for most of the walking tour. Highlights include a historic department store, a skyscraper church, the infamous Block 37, and the sparkling mosaics of the Chicago Cultural Center. You will also engage with photos and video clips on shared iPads, while a live tour guide shares expert commentary on this architectural and historical tour.
    Interior Architecture Loop Tour

    10 S Dearborn St, Chicago

    • Take an in-depth look at the architectural interiors of several Chicago landmarks
    • Explore the famous underground Pedway system
    • Engage with photos and video clips at each location
    • Uncover Chicago’s marvelous history through architecture
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    13 positive reviews
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    Mini Bus and Boat Tour

    On this tour you'll see Chicago's world renowned architecture and learn about the city's colorful history, including gangsters like Al Capone, and John Dillinger. Drink in the beautiful views of a lake that looks more like an ocean, and a river that now runs backwards! Downtown, you'll see Millennium Park, The Loop, Museum Campus, Soldier Field, The Willis (Sears) Tower and more. Then it's up north, to the fashionable Gold Coast (including the original Playboy Mansion), Lincoln Park and Wrigley Field (legendary home of baseball's Chicago Cubs since 1916). Of course, you'll stop a few times along the way, so that you can get out, stretch your legs and take some pictures of Chicago's many fantastic sights. At the conclusion of your Chicago mini-bus tour, you'll visit Navy Pier. From there, you’ll enjoy a 75 minute cruise along the scenic Chicago River, while learning a thing or twenty about architecture, Chicago history, and even how to reverse the direction of a river!
    Mini Bus and Boat Tour

    300 East Ohio St, Chicago

    • Enjoy Chicago sights and sounds on a mini-bus tour and a River Cruise
    • See all of the famous downtown sights, as well as some of Chicago's distinct neighborhoods
    • Explore the sights and sounds of Chicago in style, onboard a climate controlled, large-windowed mini bus
    • Relax and enjoy the city's world-renowned architecture, on the Chicago River
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    6 positive reviews
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    Lake Paddling (North Avenue Beach)

    Chicago life has its conveniences. Deep dish pizza, for one. But let’s face it: concrete gets tiresome. So how about leaving the city behind for a spell during this kayak paddle along the shore of the Lake! You’ll start off the trip with an introduction to the basics of paddling, so even if you have zero experience manning a kayak, you’ll be able to take part in this rousing open-water exploration. Out on the Lake, you’ll be treated to perfect views of the urban skyline, attaining an appreciation for its immense scope. In addition to this eye-opening perspective, you’ll be getting a light upper body workout, and introducing yourself to what very well might be a lifelong hobby! Besides, doesn’t absence makes the heart grow fonder? That’s gonna be some really delicious pizza when you get back!
    Lake Paddling (North Avenue Beach)

    1600 N Lake Shore Dr, Chicago

    • Escape the city and embark on an open water kayak exploration of Lake Michigan
    • Enjoy water-level views of Chicago from afar that will alter your perspective of the city
    • Let a certified instructor show you the ropes during a safe row
    • Allow an energizing adventure to consume your senses and fuel your sense of wonder
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    Chicago Grand Tour and Hancock Observatory

    You’ve arrived at the Grand Tour of Chicago, the tour of all tours! This comprehensive half-day tour is the perfect introduction to the Windy City. Explore Chicago’s North South sides on this comprehensive guided city tour! See Chicago’s highlights and visit the impressive Hancock Observatory in the Hancock Center for magnificent views of the Windy City! A narrated coach will guide you through the city’s finest sights, uncovering the unique art and architecture that make Chicago’s streets beautiful. At the tour’s end, you’ll hop on over to the Hancock Observatory, where you not only gaze at the skyline but also see the states of Indiana, Wisconsin, Illinois, and Michigan. Quite the view, eh?
    Chicago Grand Tour and Hancock Observatory

    The Loop, Chicago

    • Embark on the perfect introduction to the Windy City on this half-day tour
    • Visit the highlights of Chicago’s North and South sides as you’re guided by a city expert
    • Experience Hancock Observatory and witness one of the prettiest city views you can see
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