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Lake Michigan Sunset Cruise in Chicago
4.5
(1,211)

Lake Michigan Sunset Cruise in Chicago

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel in the heart of the Magnificent Mile, and cruise along the Chicago River, where your guide will point out architectural highlights. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$45
Likely to Sell Out
Chicago River 45-Minute Architecture Tour from Magnificent Mile
4.7
(1,948)

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.
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  • 45 minutes
  • Free Cancellation
from
$28
Likely to Sell Out
Chicago River 90-Minute Architecture Tour
4.7
(7,197)

Chicago River 90-Minute Architecture Tour

Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$45
Likely to Sell Out
Chicago River Architecture Tour with Small Boat Upgrade Option
4.8
(817)

Chicago River Architecture Tour with Small Boat Upgrade Option

Chicago is known internationally for its architectural diversity and dynamism—and this in-depth tour will introduce you to many of the city’s best-known and most influential landmarks. Meet at the pier right off Lake Shore Drive, hop aboard your boat, and set off. You’ll spy highlights ranging from Chicago’s skyscrapers and bustling Navy Pier to the famous “Bean” sculpture—and will learn about the different architectural movements that shaped the city. Upgrade your experience to a small boat with a maximum of 60 people, or choose the combo tour option which includes a 90-minute sightseeing tour of Chicago's architecture by minibus.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$49
Chicago's Delicious Donut Adventure with Underground Donut Tour
4.9
(1,196)

Chicago's Delicious Donut Adventure with Underground Donut Tour

Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
from
$65
Likely to Sell Out
Chicago River Cocktail Cruise
4.5
(85)

Chicago River Cocktail Cruise

See Chicago from its best side and marvel at its top architectural gems with this one-of-a-kind Chicago River cocktail cruise. Sip the cocktail of your choice—or glass of wine or beer—as you glide down the river past landmarks like the Wrigley Building and Michigan Avenue Bridge. Learn about the history and design of 50 of Chicago’s most significant skyscrapers with on-board commentary and snap spectacular photos while cruising through the heart of the city.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$59
Chicago Lincoln Park Indoor Skydiving with Two Flights
4.6
(63)

Chicago Lincoln Park Indoor Skydiving with Two Flights

Feel the rush of skydiving without going anywhere near a plane, with this indoor skydiving experience in Chicago. Start off with thorough training so you feel confident and know what to expect. Then, enjoy two 60-second ‘free fall’ experiences in a technologically advanced vertical wind tunnel, which feels much like real skydiving. No experience is necessary, and your instructor will give you hands-on assistance when you need.
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  • 1 hour 15 minutes
  • Free Cancellation
from
$102
Likely to Sell Out
Chicago Lake and River Architecture Tour
4.7
(2,012)

Chicago Lake and River Architecture Tour

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$45
Lake Michigan Fireworks Cruise in Chicago
4.1
(89)

Lake Michigan Fireworks Cruise in Chicago

Enjoy an only-in-Chicago night out—and admire views of the city's skyline (and its evening fireworks shows) that most visitors miss—on this Lake Michigan cruise. Make your own way to the departure point at Navy Pier, hop aboard your well-appointed vessel, and set sail. In between marveling at the views, you can also purchase drinks and snacks from the on-board cash bar, if you wish.
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  • 2 to 3 hours
from
$50
Chicago Craft Brewery Barrel Bus Tour
4.9
(278)

Chicago Craft Brewery Barrel Bus Tour

Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
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  • 3 hours 45 minutes
  • Free Cancellation
from
$100
Haunted Chicago Booze and Boos Ghost Walking Tour
4.9
(135)

Haunted Chicago Booze and Boos Ghost Walking Tour

Enjoy a memorable Chicago experience on this haunted pub tour. Your costumed guide, dressed as a Flapper or 1920s Gangster, will lead you on a mile-long journey while telling spooky stories of forgotten cemeteries, lingering spirits, and more. Stop at three different bars for drinks (at own expense) as you learn the secret tales behind Chicago’s haunted past.
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  • 2 hours 30 minutes
  • Free Cancellation
from
$36
Chicago Pizza Tour
4.9
(403)

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.
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  • 3 hours 30 minutes
  • Free Cancellation
from
$89
Chicago's Ultimate City Bike Tour
4.9
(171)

Chicago's Ultimate City Bike Tour

Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
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  • 3 hours
  • Free Cancellation
from
$55
Likely to Sell Out
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
4.9
(186)

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Discover a side of the Windy City that many visitors overlook—and immerse yourself in its vibrant street art scene—on this urban walking tour. With your art-expert guide in the lead, you can focus on soaking up the city's ambiance, and spotting artworks and murals you may not have discovered on your own. As you go, listen to in-depth commentary about the artists and artworks, and explore some of the city's hippest neighborhoods.
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  • 2 hours
  • Free Cancellation
from
$40
Likely to Sell Out
Chicago: Culture and Architecture of the Prohibition Era
4.8
(79)

Chicago: Culture and Architecture of the Prohibition Era

Walk Chicago to see the legacy left behind by the Prohibition Era. See the gorgeous Chicago skyline and discover why this city's architecture is among the best in the world. Take in famous landmarks like the Chicago Riverwalk, Wrigley Building, Tribune Tower, Magnificent Mile, and many more, all while your guide shares insider tips and stories you'd miss on your own. Then, taste surprise local treats along the way.
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  • 2 hours 30 minutes
  • Free Cancellation
from
$50
Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour
5.0
(97)

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about the city’s past. See the stunning interiors and exteriors of noteworthy buildings and leave with a comprehensive understanding of the city’s downtown.
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  • 2 hours
  • Free Cancellation
from
$44
Likely to Sell Out
Bike Tour of Chicago's Lakefront Neighborhoods
4.9
(217)

Bike Tour of Chicago's Lakefront Neighborhoods

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.
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  • 3 hours
  • Free Cancellation
from
$55
Likely to Sell Out
Historic Homes and Cottages of Wicker Park Walking Tour
5.0
(34)

Historic Homes and Cottages of Wicker Park Walking Tour

Discover one of Chicago’s most picturesque, historic neighborhoods—and learn all about the buildings that make it an architectural standout—on this small-group walking tour of Wicker Park. Meet your guide in the morning, and set off on foot: you’ll discover the 19th-century workers’ cottages that fill the neighborhood, will admire local landmarks like mansions and historic baths, and will learn all about the city’s architectural history.
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  • 2 hours
from
$45
Likely to Sell Out
Chicago River Architectural Lunch Cruise
4.2
(30)

Chicago River Architectural Lunch Cruise

Travel down the Chicago River on an architecture cruise aboard the "Odyssey." As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch with salad, a main course such as chicken, salmon, pasta, or short ribs, and a dessert such as cheesecake or sorbet. Listen to onboard narration about the city's architecture along the way.
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  • 2 hours
from
$105
Chicago Buffet Lunch Cruise on Lake Michigan
3.9
(315)

Chicago Buffet Lunch Cruise on Lake Michigan

Perfect for families, groups, and corporate outings, the Spirit of Chicago lunch cruise lets you kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.
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  • 2 hours
from
$66
Chicago Buffet Dinner Cruise on Lake Michigan
3.8
(347)

Chicago Buffet Dinner Cruise on Lake Michigan

Make your evening in Chicago one to remember with this sunset cruise featuring dinner, sightseeing, and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain, and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ who will mix up a selection of dance favorites.
... More
  • 2 to 3 hours
from
$122
Likely to Sell Out
Chicago's Luxury Minibus City Sightseeing Tour
3.7
(3)

Chicago's Luxury Minibus City Sightseeing Tour

Experience the best of Chicago on our top rated City Sightseeing & Architecture Minibus Tour, featuring stops at the city's most iconic landmarks. Our knowledgeable guides, comfortable buses, and thoughtfully selected stops ensure you don’t just see Chicago—you truly experience it.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$65
Likely to Sell Out
Chicago Ghosts & Haunted History Walking Tour
5.0
(6)

Chicago Ghosts & Haunted History Walking Tour

The Windy City is known for its food, architecture, and haunting history! Walk with us as the sun sets through downtown Chicago, hearing some of the most gruesome and creepy Chicago stories. The first stop is the Congress Hotel, the most haunted hotel in Chicago. Walk along the streets that H. H. Holmes, Chicago's first serial killer, wandered as he stalked his prey, get a glimpse of Chicago’s sordid past through stories of the Everleigh Club and the 1900s Red Light district, and learn about downtown prison breaks.
... More
  • 2 hours
  • Free Cancellation
from
$39
Likely to Sell Out
Chicago Luxury Minibus City Tour and Architecture River Cruise
4.4
(7)

Chicago Luxury Minibus City Tour and Architecture River Cruise

Experience the best of Chicago by land and water on our exclusive Luxury City Minibus Tour & Riverboat Architecture Cruise! Start with a 90-minute guided luxury minibus sightseeing tour through downtown, and seamlessly transition to the Chicago Architecture Riverboat. Here you will glide along the Chicago River and learn about the city's rich history and iconic architecture from a knowledgeable guide.
... More
  • 3 hours 30 minutes
  • Free Cancellation
from
$99
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