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History of the Jazz Age at Chicago Art Deco Architecture Tour

from $ 67

Dive into the center of the architectural boom of the roaring 1920s and take a chance to enjoy the grand facades of the Art Deco skyscrapers on this guided walking tour. Go back ... more detail

1.5 hours Free cancellation

More activites to help you explore Chicago

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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour by Open-Top Bus

Discover Chicago's best on our Big Bus tour. Board our open-top, double-decker bus and see the city's iconic landmarks, from the Magnificent Mile to Millennium Park. Utilize our convenient stops to explore vibrant neighborhoods and attractions, including Willis Tower, the Chicago Riverwalk, and more. Spend your day shopping on Magnificent Mile, enjoying Navy Pier's Ferris Wheel, or tasting authentic Chicago Deep Dish Pizza. Our flexible tour lets you create your own itinerary, with a free app to track bus arrivals. Listen to digital commentary in multiple languages, offering expert insight into Chicago's history and culture, while recommending the best places to eat, drink, and shop. Offering comfortable seating and panoramic views, our Hop-On Hop-Off Sightseeing Tour is an ideal way to explore the city. Hop off as often as you like within your ticket's validity period, and simply hop on again when ready to continue.

2 hours Free cancellation
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$ 49.5

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Chicago City Minibus Tour

Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town) and The Buckingham Fountain. You'll also see The Magnificent Mile, Lincoln Park, The Chicago River, Millennium Park, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational and at times humorous commentary about the area and its many attractions. The small-group atmosphere with maximum of 10 people ensures a more personal experience.  

2 hours Free cancellation
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$ 47.95

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Chicago Pizza Tour

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias.  In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.

3 hours Free cancellation
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$ 89

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Lake Michigan Skyline Cruise in Chicago

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views of Chicago's renowned skyscrapers from a unique vantage point. This tour offers an amazing opportunity to admire the city's breathtaking skyline and architectural wonders. Feel free to bring your lunch and savor drinks from the onboard bar as you relax and take in the scenery on this delightful sightseeing cruise. Highlights: Spectacular views of Chicago's famous skyscrapers Onboard bar serving refreshing drinks Relaxing and enjoyable sightseeing cruise Experience Chicago like never before on this serene and scenic Lake Michigan boat tour. Remember to bring your camera to capture those social media worthy photos!

30 minutes Free cancellation
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$ 32.5

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Private 45-Minute Chicago Skyline Helicopter Tour

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is the total for all 3 passengers (saving you money compared to other operators who charge per person.)

45 minutes Free cancellation
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$ 849

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Chicago City Tour with Architecture River Cruise Option

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned architecture including the world's first skyscrapers, Museum Campus (for the BEST skyline view in town), Millennium Park (Home of "The Bean"), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical, informational and at times humorous commentary about the area. Four photo stops are a part of each tour. The small-group atmosphere with a maximum of 10 people ensures a more personal experience.  You also have the option to upgrade to include THE most popular Architecture River Cruise in Chicago! For good reason, our partner Shoreline Sightseeing, has been the most booked tour on TripAdvisor for the last 5 years! And yes, there is a bar on the boat.

2 - 4 hours Free cancellation
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$ 47.95

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Private Chicago Scenic Driving Tour

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour will start by meeting our knowledgeable Guide/Driver who will pick you up at your hotel or other location provided and then proceed with the exploration of the beautiful windy city.

2 hours Free cancellation
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$ 315

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Chicago's Ultimate City Bike Tour

Get acquainted with Chicago’s most iconic landmarks on this riotous guided bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. Over the course of a 3-hour bike ride (traversed at a nice leisurely pace), you’ll get up close and personal with Chicago’s legendary Museum Campus, Grant Park, and Millennium Park. You’ll become intimately familiar with Soldier Field, The Adler Planetarium, Buckingham Fountain, The Pritzker Pavilion, and Cloud Gate (the formal name of Chicago’s dearly-beloved “Bean”). This tour is perfect for first time visitors looking to see all of the classic hotspots, and for returning guests looking to understand more about the landmarks they know and love. Hop on two wheels, and come make memories that are sure to last a lifetime!

3 hours Free cancellation
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$ 54.99

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Chicago: Hop-on Hop-off Bus Tour & Architecture River Cruise

Discover Chicago by road and river with our new 48-hour Hop-on Hop-off Ticket and Shoreline Architecture Cruise combo! This ticket includes a 48-hour pass for our hop-on, hop-off Chicago sightseeing bus tour, and a pass for admission to Shoreline Sightseeing's must-do 75-minute Architecture River Cruise! You'll see the city's world-famous architecture from iconic streets like Magnificent Mile, Lake Shore Drive, State Street, Clark Street and Grand Ave, and from all three branches of the Chicago River. Create your own itinerary and explore at your own pace with unlimited bus exit and entry. Over 40 Chicago landmarks await you on the 75-minute Shoreline Architecture Cruise, from hidden architectural treasures to the city’s most famous landmarks. Expert live guides explain how Chicago’s buildings, architecture and engineering made the city famous.

2 hours Free cancellation
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$ 95

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Chicago’s Discounted Tour Bundle with Expert Guides

CHOOSE from our range of discounted tour passes below & save up to $55 per person! Children aged 0-6 are free! Hassle free booking - no referral to third party operators, we own all of the tours! 5 tour pass - SAVE $55 PER PERSON (redeemable March - Oct) -Gangster & Food Walking Tour -Secret Interior Architectural Walking Tour -Gangsters & Ghosts Minibus Tour -Luxury Minibus City Sightseeing Tour -Riverboat Architecture Tour 4 tour pass - SAVE $40 PP (redeemable year-round) -Gangsters Food Walking Tour -Secret Interior Architectural Walking Tour -Gangsters & Ghosts Minibus Tour -Luxury Minibus City Sightseeing Tour 3 tour pass - SAVE $25 PP (redeemable March - Oct) -Riverboat Architecture Tour -Secret Interior Architectural Walking Tour -Gangsters & Ghosts Walking Tour 2 tour pass - 2 TOURS FOR THE PRICE OF 1 (redeemable year-round) -Secret Interior Architectural Walking Tour -Gangsters & Ghosts Walking Tour All tours are led by an expert tour guide. Book now for the best value!

3 - 11 hours Free cancellation
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$ 29

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Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Taste all of Chicago’s classic eats on this 4 1/2 hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike tour company, on this exciting and informative adventure which recently ranked Top 20 in the World by TripAdvisor. The journey is 13 miles (at a leisurely pace) and includes deep dish pizza, a gourmet brownie, a Chicago-style hot dog, and samples of local craft beer! On the daytime version of the tour, you’ll drink in the sights of Chicago’s beautiful northside neighborhoods, including the Lakefront and Wrigleyville, home to our Chicago Cubs baseball team. On the nighttime version, you'll ride through the party districts of downtown and see the lights of Buckingham Fountain, Millennium Park and the glorious skyline. Cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this fun tour! You’ll leave with a profound understanding of our town, even if you only came for the beer.

4 hours Free cancellation
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$ 89

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Chicago Private Tour

Enjoy and appreciate Chicago with your private transportation and guide. Customize your tour and visit the most important sites and landmarks of the Windy City. Be satisfied that you experienced the most important and beautiful sites, taking the most memorable tour of the city.

3 hours Free cancellation
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$ 300

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Chicago Scavenger Hunt and Highlights Self-Guided Tour

Use clues at each attraction to find your next destination and challenge yourself to use logic, imagination, observation, and team spirit to complete the game. Uncover local information and facts about the city as you explore. Discover hidden gems and narrow streets. Without a schedule and at your own pace, pause anytime and continue later or even another day. Work as a team or compete with each other. A unique team-building activity perfect for couples, families, companies, students and groups of friends.

2 hours Free cancellation
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$ 6.8

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2-Hour Chicago Lakefront and Museum Campus Segway Tour

Looking for fun things to do in Chicago? Look no further! Join one of our professional guides on a scenic 6-8 mile Chicago Segway tour. Glide effortlessly through the fragrant garden paths of Grant Park to marvel at the iconic Buckingham Fountain. Enjoy the breeze as you explore the city's top attractions along the Chicago lakefront, including Museum Campus, with stops near Shedd Aquarium, Field Museum, and the historic Soldier Field, home of the Chicago Bears. This guided Segway tour offers a perfect blend of sightseeing and adventure, providing an unforgettable way to experience Chicago's most popular tourist spots that's great for locals and out of towners!

2 hours Free cancellation
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$ 65

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Chicago Self-Guided Audio Tour

Embark on an exhilarating journey through Chicago, the "City of Big Shoulders," with our comprehensive self-guided audio tour. From the bustling Loop to the serene shores of Lake Michigan, uncover the rich tapestry of history, culture, and innovation that defines this iconic American city. Our expert narration brings to life the stories behind Chicago's most famous landmarks and hidden gems, revealing the city's evolution from a frontier outpost to a global metropolis. You'll explore architectural marvels that have shaped the modern skyline, from pioneering skyscrapers to contemporary masterpieces. Delve into the myths and legends that have shaped Chicago's unique character, from the Great Fire to the Prohibition era. Whether you're admiring world-class art, exploring cutting-edge museums, or relaxing in vast urban parks, this tour offers a deep and nuanced understanding of Chicago's past, present, and future.

3 hours
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$ 9

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Chicago Lakefront and Museum Campus Small-Group Segway Tour

Looking for fun things to do in Chicago? Explore the city with one of our professional guides on a scenic 6-7 mile Chicago Segway tour. Begin your adventure by gliding through the fragrant garden paths of Grant Park, where you'll admire the iconic Buckingham Fountain. Feel the breeze as you effortlessly explore the city's most popular attractions along the Chicago lakefront. Visit the renowned Museum Campus, home to the Shedd Aquarium, the Field Museum, and the historic Soldier Field, home of the Chicago Bears. This guided Segway tour offers an unforgettable sightseeing experience, perfect for both tourists and locals. To ensure a personalized experience, we keep our group sizes small, with only 8-10 guests per tour. Join us for an intimate journey through Chicago's top attractions.

2 hours Free cancellation
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$ 65

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5 Day Tour On Lakes Superior Huron and Michigan

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in the United States, Lake Superior, the largest freshwater lake in the world, and Lake Huron. Famous cities along the five great lakes: Chicago, Milwaukee and Traverse City along Lake Michigan, Green Bay along Green Bay, and Sault Ste. Mackinac Island, which was once selected as one of the top ten most beautiful islands in the world. Room Details All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what rooms are availiable at the hotel on the day. The maximum occupancy per room is four travelers. One Room Selection If you are a party of more than four guests or desire to have separate rooms, please create separate bookings. Avoid traveling in a different bus? If you have more than one booking, please provide all confirmation numbers once your bookings are complete.

5 days Free cancellation
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$ 1195

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Best of Chicago Small-Group Tour with Skydeck and River Cruise

Immerse yourself in Chicago’s distinct skyline with bold skyscrapers and incredible views of Lake Michigan .Enjoy the efficiency of having your own local expert and personal guide to share unique and fascinating stories about the surrounding area including exclusive local insights, historic highlights and personalized recommendations. You and your private small group will enjoy complimentary downtown Chicago hotel pick up. To begin your tour your Tripshepherd guide will take you to the Adler Planetarium Pier, a must-stop while in the Windy City. Aboard the Shoreline Architecture Cruise you will enjoy a narrated boat tour where you will see the breathtaking views of over 40 Chicago iconic landmarks, from hidden architectural features to the Windy City's most famous monuments. To finish your exclusive, private tour, you will get to visit two iconic Chicago landmarks - the Buckingham Fountain and the Chicago Bean (Cloud Gate). Enjoy complimentary downtown Chicago drop off.

4 hours Free cancellation
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$ 254

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Lake Michigan and Chicago River Architecture Cruise by Speedboat

Enjoy Chicago’s iconic skyline with an exciting architecture cruise on the Chicago River. Departing from Navy Pier, this 75-minute narrated cruise is the best way to get up-close views of Chicago’s unique architecture and famous landmarks. Seadog offers fun for the whole family (and the dog, too!) with live narration along the city’s shore. Enjoy the speed of Seadog afterward during a short speedboat ride on the lake! Please arrive at the boarding location at least 30 minutes before your scheduled cruise time. The tour will begin promptly.

1 hours
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$ 61.82

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Chicago Mobs and Haunts Walking Tour

Join us along the historic streets and alleys of Chicago as we walk among the spirits of mobsters and ghosts of the condemned. This tour is for lovers of history, true crime, and haunted mysteries. Expect a sultry and gritty cocktail of Chicago's darkest stories hiding in the shadows of the Loop. From Grant Park to the Alley of Death, your expert local guide will shed light on the city’s secrets. Prepare for thrills and just the right amount of chills.

1.5 - 2 hours Free cancellation
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$ 34

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