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Walking Tours Likely to Sell Out Private and Luxury

Chicago's Hidden Pedway: Underground Walking Adventure

Walking Tour: Underground Chicago via the Pedway is an adventure that explores the city's secret underground tunnel system, called the Pedway, and some special sights above ground. This walking tour is perfect for anyone who wants to see a different side of Chicago and learn about its history and culture.
The tour starts in the Swissotel lobby with a short introduction to the Pedway. Guests will go underground to visit the Cultural Center and see the beautiful Tiffany Dome. The tour continues through the Pedway to Macy's, where visitors can admire the Tiffany ceiling and the famous Walnut Room. Then the tour heads west to see the Picasso sculpture in Daley Plaza and the Chicago Temple with its Sky Chapel.
After a quick train ride, the tour arrives at the start of Route 66, where guests can take photos with the Art Institute's lion statues. Finally, the tour visits Millennium Park to see Cloud Gate (The Bean), Lurie Gardens, and Crown Fountain. The tour includes transit tickets and a local expert guide. Gratuities, food, and drinks are not included.

star Created with Sketch. 5.0 (27 reviews)

Duration In Minutes Duration: 180 minutes

Price from

$65

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Chicago's Hidden Pedway: Underground Walking Adventure

Chicago's Hidden Pedway: Underground Walking Adventure

Discover Chicago's Iconic Loop: Architecture, Art & History Walking Tour

Discover Chicago's Iconic Loop: Architecture, Art & History Walking Tour

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

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

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

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Places in Chicago with No Hidden Costs or Forced Spending

Discover transparent and fair-priced places in Chicago selected using hidden upsell risk scores above 5. These experiences clearly communicate what’s included, avoid forced spending, and offer a stress-free experience without unexpected charges or sales pressure.

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 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 History Tour: Uncover Downtown's Secrets

Location Icon Chicago

$44

Chicago History Tour: Uncover Downtown's Secrets

Small Group Walking Tours Likely to Sell Out

Rating Star 5.0 (216 reviews)

Duration In Minutes Duration: 120 minutes

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour offers a profound walk through downtown Chicago. It uncovers incredible stories and secrets of the city. This walking tour explores “Da Loop,” peeling back the layers of Chicago to reveal its history and beauty.

Participants can expect an engaging and eye-opening experience. The tour goes inside extraordinary buildings and admires amazing art and architecture, uncovering how it all came to be. Key stops include the Chicago Cultural Center, Chicago Board of Trade Building, Federal Plaza, Reliance Building, Chicago Picasso, Chicago Theatre, and Marshall Field's (Macy's on State Street).

This experience includes all fees and taxes. Expert local guides lead small groups through the city's most iconic landmarks, sharing stories and insights along the way. Get ready to walk and discover the heart of Chicago!

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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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Unlock Literary Treasures: Skip the Line at Chicago's American Writers Museum

Location Icon American Writers Museum

$16

Unlock Literary Treasures: Skip the Line at Chicago's American Writers Museum

Excellent Quality Historical Tours Low Supplier Cancellation Rate

Rating Star 4.9 (70 reviews)

Skip the Line: American Writers Museum Admission Ticket grants access to explore American literary history. From Twain to Tupac, immerse yourself in interactive exhibits. Enjoy a free bookmark and optional 3 PM tour. A top-rated attraction in downtown Chicago, offering a unique cultural experience for all ages.

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Milwaukee's Best: City Tour of Sights & History

Location Icon Milwaukee

$45

Milwaukee's Best: City Tour of Sights & History

Small Group Historical Tours Best Conversion

Rating Star 4.9 (807 reviews)

Duration In Minutes Duration: 120 minutes

Milwaukee Tour immerses visitors in the city's rich history and famous attractions, revealing hidden gems along the way. This tour provides an authentic Milwaukee experience, not just a sightseeing trip.

Participants can anticipate a narrated journey through key locations such as Milwaukee City Hall, the Pabst Mansion, and the iconic Bronze Fonz statue. The tour also showcases the vibrant Black Cat Alley Murals, the scenic Lakefront and Lighthouse, and the architectural marvel of the Milwaukee Art Museum. Other highlights include the Historic Third Ward & Milwaukee Public Market, the Harley-Davidson Museum, and the lively Walker's Point neighborhood.

The experience includes a driver/guide offering live commentary throughout the tour. Please note that paid parking is not included, but it is available across Water Street in an underground parking garage. Gratuities and hotel pickup/drop-off services are also not included.

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

Location Icon Chicago

$539

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

Bus Tours City Tours Car Tours

Rating Star 4.9 (201 reviews)

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.

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Chicago Art Institute: Skip-the-Line Private Tour

Location Icon Chicago

$85.5

Chicago Art Institute: Skip-the-Line Private Tour

Historical Tours Museums Low Last Minute Supplier Cancellation Rate

Rating Star 5.0 (271 reviews)

Duration In Minutes Duration: 150 minutes

Private Art Institute of Chicago Skip-the-Line Guided Tour. This is a special walking tour for people who love art and want to see the best pieces at the Art Institute of Chicago without waiting in long lines. The tour is just for the group and a guide, so it feels personal.

What to Expect: The tour visits famous artworks like 'Paris Street, Rainy Day' and 'Sunday on La Grande Jatte'. People will also see 'Nighthawks' and 'The Old Guitarist'. The guide shares stories about the art and artists. The Art Institute of Chicago is a very big museum with lots of famous art. It has art from all over the world and different times in history.

This private tour lasts for 2.5 hours and includes a professional tour guide just for the group. It also includes all entrance fees. The tour is wheelchair friendly. This tour does not include hotel pickup or drop-off, but the guide suggests using UBER or a taxi. Gratuities (tips) are not included in the price.

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Chicago Art Institute: Skip-the-Line Small Group Tour

Location Icon Chicago

$85.5

Chicago Art Institute: Skip-the-Line Small Group Tour

Historical Tours Museums Low Last Minute Supplier Cancellation Rate

Rating Star 5.0 (152 reviews)

Duration In Minutes Duration: 150 minutes

Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max. This tour lets people see amazing art without waiting in long lines. It is a walking tour that is great for people who like art and history.

What to Expect: The Art Institute of Chicago is a very popular museum, just like the Met in New York or the Louvre in Paris. On this 2.5-hour tour, a friendly guide will take a small group (8 people max) to see the most famous artworks. Some of the art you might see includes *Paris Street, Rainy Day*, *Sunday on La Grande Jatte*, and *Nighthawks*. But sometimes, art is not there because it is being fixed or moved.

This tour includes all entrance fees and a guide who knows a lot about art. It does not include tips for the guide or rides to and from your hotel. It's easy to get to the museum by taxi or UBER.

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Soar Above Chicago: A Private Helicopter Skyline Adventure

Experience Chicago like never before with a Private 45-Minute Helicopter Tour. Enjoy breathtaking panoramic views of the city's iconic skyline with family or friends. This exclusive tour offers a thrilling and intimate experience, complete with live commentary and unparalleled photo opportunities. An unforgettable adventure awaits!

star Created with Sketch. 4.8 (126 reviews)

Duration In Minutes Duration: 45 minutes

Price from

$849

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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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