Chicago (Seamless Experience)

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Chicago Private City Tour: Discover the Windy City in Style & Comfort!

Chicago Private Custom City Tour offers a personalized exploration of Chicago with hotel pick-up. Enjoy a 3-4 hour chauffeured tour, led by knowledgeable guides. Stops include Millennium Park and Museum Campus. Interactive and entertaining, this tour covers Chicago's history, architecture, and culture. Concludes with drop-off at your preferred downtown location.

star Created with Sketch. 4.9 (201 reviews)

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$539

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Chicago Private City Tour: Discover the Windy City in Style & Comfort!

Chicago Private City Tour: Discover the Windy City in Style & Comfort!

Discover Labor's Art: Skip the Line at Milwaukee's Grohmann Museum!

Discover Labor's Art: Skip the Line at Milwaukee's Grohmann Museum!

Chicago's Hidden Pedway: Underground Walking Adventure

Chicago's Hidden Pedway: Underground Walking Adventure

Relive 'Ferris Bueller's Day Off' Through Art: An Iconic Chicago Museum Tour

Relive 'Ferris Bueller's Day Off' Through Art: An Iconic Chicago Museum Tour

Chicago's Hidden Gems: Unearthing the Pedway & Loop Secrets

Chicago's Hidden Gems: Unearthing the Pedway & Loop Secrets

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Smooth & Well-Organized Places to Visit in Chicago

Discover smooth and well-organized places in Chicago selected using logistics friction scores above 5. These experiences are known for clear planning, timely execution, and minimal waiting, ensuring a hassle-free and reliable visit from start to finish.

Wicker Park's Architectural Gems: A Historic Homes Walking Tour

Location Icon Chicago

$45

Wicker Park's Architectural Gems: A Historic Homes Walking Tour

Historical Tours Architecture Tours Walking Tours

Rating Star 5.0 (44 reviews)

Duration In Minutes Duration: 90 minutes

Explore Wicker Park's architectural evolution on this walking tour. Discover hidden historical insights as you journey through diverse streetscapes, from gritty realism to magnificent beauty. Enjoy historical photos via a free app, enriching your understanding of this vibrant Chicago neighborhood. A small group experience.

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Chicago Shoreline Adventure: High-Speed History & Thrilling Spins!

Location Icon Chicago

$90

Chicago Shoreline Adventure: High-Speed History & Thrilling Spins!

Adventure Tours Speed Boat Rentals Small Group

Rating Star 5.0 (38 reviews)

Duration In Minutes Duration: 90 minutes

The Chicago Shoreline Adventure Boat Tour offers an exhilarating and educational experience. Aboard a former military vessel, enjoy high-speed runs and spins while learning about Chicago's history. This unique tour combines adrenaline-pumping thrills with historical insights, perfect for adventure seekers.

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Chicago's Best Bites: A Delicious Bike & Brews Tour

Location Icon Chicago

$89

Chicago's Best Bites: A Delicious Bike & Brews Tour

Culinary Tours Short term availability Best Conversion

Rating Star 4.9 (731 reviews)

Duration In Minutes Duration: 270 minutes

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour lets people taste all the best Chicago foods on two wheels! This 4 1/2-hour guided bike tour, led by the experts at Bobby’s Bike Hike, takes riders on a fun and yummy adventure. It was even ranked in the Top 20 tours in the world by TripAdvisor!

The easy 13-mile ride explores Chicago's famous eats, including deep-dish pizza and a Chicago-style hot dog. Sample local craft beers while seeing cool spots like the Gold Coast, Lincoln Park, and Wrigleyville, home of the Chicago Cubs. Night tours light up with Buckingham Fountain, Millennium Park, and downtown sights. Pedal along the Lakefront Trail, a top bike path, and discover the heart of Chicago.

This experience includes an expert local guide, a water bottle to stay hydrated, a bicycle, a helmet for safety, and delicious food and beer samples. The tour does not include the suggested $15 guide gratuity per person, payable via cash, Venmo, or PayPal. Get ready to roll, taste, and learn on this unforgettable Chicago adventure!

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Chicago Sightseeing Boat Tour: City Views & Skyline

Location Icon Chicago

$89

Chicago Sightseeing Boat Tour: City Views & Skyline

City Tours Sightseeing Cruises Low Supplier Cancellation Rate

Rating Star 5.0 (95 reviews)

Duration In Minutes Duration: 90 minutes

Small-Group Sightseeing Boat Tour in Chicago is the ultimate way to see the city! This custom experience gives folks amazing views and photo opportunities of Chicago's famous skyline.
The boat zips around local waterways, passing sights like Navy Pier and Soldier Field. See Fort Dearborn, the Vietnam Memorial, Wolf Point, and the Shedd Aquarium. This tour gives a unique and personal look at the City!
Folks will ride in a safe and strong Rigid Inflatable Boat (RIB), originally built for the US NAVY. Life jackets are provided. The boat tour focuses on the Chicago skyline, including views of the Adler Planetarium. Please bring your own bottled water and sunscreen.

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Chicago Insta-Walk: Capture Stunning Photos with a Pro!

Location Icon Chicago

$169

Chicago Insta-Walk: Capture Stunning Photos with a Pro!

Low Last Minute Supplier Cancellation Rate Small Group Excellent Quality

Rating Star 5.0 (31 reviews)

Duration In Minutes Duration: 60 minutes

The Chicago Insta Walk offers a fun, relaxed exploration of the city, capturing stylish photos with digital and Polaroid cameras. Receive 100 digital photos (10 color-corrected) and 5 Polaroid prints for unique souvenirs. A friendly tour guide helps you discover Chicago from a fresh perspective.

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Chicago Art Institute: Expert-Led Private Tour

Location Icon Chicago

$215

Chicago Art Institute: Expert-Led Private Tour

Low Supplier Cancellation Rate Walking Tours Historical Tours

Rating Star 5.0 (83 reviews)

Duration In Minutes Duration: 120 minutes

Art Institute of Chicago Private Expert Guided Tour. Explore one of the world's finest art museums with a local expert! This private 2-hour tour is perfect for art lovers of all levels.

Visitors can expect to see famous artworks from different times and places. The expert guides will tell the stories behind the art, making it fun and easy to understand. You'll see amazing paintings, sculptures, and more!

This tour includes early admission on morning tours, skip-the-line access, and all entrance fees. It's wheelchair-friendly, so everyone can join. Gratuities and transportation to and from the museum are not included. Discover the Art Institute of Chicago with someone who knows and loves art!

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Private Sail: Chicago Skyline Views from Navy Pier!

Location Icon Chicago

$507.96

Private Sail: Chicago Skyline Views from Navy Pier!

Private Sightseeing Tours Likely to Sell Out Day Cruises

Rating Star 5.0 (70 reviews)

Duration In Minutes Duration: 120 minutes

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago, offers a memorable two-hour private sailing adventure for up to six people. Guests can relax and enjoy stunning views of the Chicago skyline with a US Coast Guard licensed captain.

The flexibility of a private charter allows guests to customize their experience. From music selection to sailing route, the trip can be tailored to individual preferences. Key sights include the Navy Pier Marina, the iconic Navy Pier itself, the breathtaking Chicago Skyline, Adler Planetarium, Soldier Field, and Buckingham Fountain.

This experience includes the use of Bluetooth speakers, the Navy Pier facility fee, all taxes, and a professional US Coast Guard licensed captain. Food, drinks, gratuities, and parking are not included.

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Chicago Sunset Sailing: Private Lake Michigan Cruise Awaits!

Location Icon Chicago

$507.96

Chicago Sunset Sailing: Private Lake Michigan Cruise Awaits!

Low Last Minute Supplier Cancellation Rate Likely to Sell Out Day Cruises

Rating Star 5.0 (27 reviews)

Duration In Minutes Duration: 120 minutes

Come Sailing at Navy Pier Marina for a stunning sunset sail on Lake Michigan! Enjoy a two-hour private charter for up to six guests, customizable with your choice of music and route. Relax as a licensed captain guides you, offering historical anecdotes and unforgettable skyline views. A perfect, serene escape on the water.

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Milwaukee E-Bike Adventure: Unveiling History & Hidden Gems!

Location Icon Milwaukee

$79

Milwaukee E-Bike Adventure: Unveiling History & Hidden Gems!

Low Supplier Cancellation Rate Top Product E-Bike Tours

Rating Star 5.0 (48 reviews)

Duration In Minutes Duration: 180 minutes

Old Milwaukee Guided E-Bike Tour: Explore 17½ miles of Milwaukee's best spots with ease. Discover historic neighborhoods, iconic architecture like the 8 million brick city hall, and scenic parks. Enjoy lake and river views while understanding Milwaukee's rich past and bright future on this ride through the whole city.

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Chicago Crime & Architecture Walking Tour

Location Icon Chicago

$35

Chicago Crime & Architecture Walking Tour

Architecture Tours Low Supplier Cancellation Rate Low Last Minute Supplier Cancellation Rate

Rating Star 5.0 (326 reviews)

Chicago Architecture and True Crime History Tour offers a thrilling exploration of Chicago's iconic skyline intertwined with its intriguing, sometimes dark, past. Inspired by 'Devil in the White City,' this guided walking tour unveils secrets hidden within architectural marvels and overlooked landmarks that are typically missed by boat tours.

Participants can anticipate venturing to significant sites, including the Marshall Field's Building (Macy's on State Street), a testament to architectural grandeur, and the modern Chase Tower, learning about their historical and cultural impact on Chicago. Along the way, the tour guide will share true crime stories that will transport participants to another time.

This experience includes the expertise of a local guide, and excludes gratuity. This tour is perfect for those seeking a unique perspective on Chicago's history and architecture.

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Kayak Milwaukee River: Rentals & Brews!

Milwaukee Kayak Rental offers a fun way to see the city from the water. Brew City Kayaks lets people explore the Milwaukee River at their own speed. It's a great way to see Milwaukee's skyline and stop at riverside spots.

Rent a single kayak for up to 4 hours. People can paddle by the city and even get out to visit places along the river. Many people like to stop at the local beer places or restaurants. The kayaks are made so they are easy to use and safe. They also have room for a cooler! Life jackets and help on how to kayak are given to everyone.

Paddle past the Hoan Bridge and Bronze Fonz, seeing city highlights. The kayaks launch from the "Paddle Shack" at 820 S. Water St. People can take their time and enjoy the city views. Remember to leave enough time to paddle back to the launch. This kayak rental provides a unique way to experience Milwaukee's blend of urban beauty and riverside attractions.

star Created with Sketch. 5.0 (28 reviews)

Price from

$55

Explore More Tours by Real Experience Factors In Chicago

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Chicago Best Things to Do: Concerts, Helicopter & Food Tours

The Chicago skyline is hiding a secret- a ton of them, actually. It’s more than a view: it’s got adventures you're meant to explore. Breathe in the winds and excitement of a helicopter tour, party at top concerts, or dive into food and pizza tours. Walk beside history on a gangster mob tour, take a fireboat or bus tour. Looking to get wild tonight? Find events going on sooner than tomorrow, from EDM to country concerts. Check all your bucket list boxes, and live stories you’ll remember forever.

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