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Top Illinois Private Sightseeing Tours

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76 results | All Illinois Tours

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Chicago Private Tours

Chicago Private Tours

star-5
159
Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.
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  • 3 to 4 hours
  • Free Cancellation
From
$449.00
per group
From
$449.00
per group

Private 45-Minute Chicago Skyline Helicopter Tour
Likely to Sell OutLikely to Sell Out

Private 45-Minute Chicago Skyline Helicopter Tour

star-5
73
Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.
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  • 45 minutes
  • Free Cancellation
From
$849.00
per group
From
$849.00
per group

Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket
Likely to Sell OutLikely to Sell Out

Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket

star-5
58
The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$115.54
Price varies by group size
From
$115.54
Price varies by group size

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
Likely to Sell OutLikely to Sell Out

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

star-5
32
If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.
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  • 2 hours
  • Free Cancellation
From
$427.28
per group
From
$427.28
per group

Private Chicago Highlights Driving Tour

Private Chicago Highlights Driving Tour

star-5
22
Get an insider’s look at the Windy City’s most iconic monuments during this 3-hour private tour. Travel through Chicago aboard a private vehicle as you discover some of the city’s top neighborhoods, including the Loop, River North, the Magnificent Mile (along Michigan Avenue), Streeterville, the Gold Coast and much more. Your private driver-guide and vehicle, bottled water and round-trip hotel transport are all included.
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  • 3 hours
From
$190.00
Price varies by group size
From
$190.00
Price varies by group size

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
8590
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour 15 minutes
  • Free Cancellation
From
$46.87
From
$46.87

90-Minute Chicago River Architecture Tour
Likely to Sell OutLikely to Sell Out

90-Minute Chicago River Architecture Tour

star-4.5
2252
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
$42.00
From
$42.00

Chicago in a Day: Food, History and Architecture Walking Tour
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Chicago in a Day: Food, History and Architecture Walking Tour

star-5
299
An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.
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  • 5 hours
  • Free Cancellation
From
$104.00
From
$104.00

Chicago Lake and River Architecture Tour
Likely to Sell OutLikely to Sell Out

Chicago Lake and River Architecture Tour

star-4.5
880
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
$42.00
From
$42.00

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
2937
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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  • 2 hours
  • Free Cancellation
From
$35.00
From
$35.00

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
1135
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.
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  • 2 hours
  • Free Cancellation
From
$44.99
From
$44.99

Field Museum of Natural History Admission Tickets

Field Museum of Natural History Admission Tickets

star-4.5
196
Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.
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  • 4 hours
  • Free Cancellation
From
$27.00
From
$27.00

Behind-the-Scenes Tour of Historic Chicago Theatre

Behind-the-Scenes Tour of Historic Chicago Theatre

star-4.5
21
Tour the historic Chicago Theater, a must-see city landmark, with a guide providing in-depth commentary. You'll get the most out of your visit by traveling with a guide and get access to some areas of the theater that the public never sees. Learn about its architecture, history, and famous performers throughout the years.
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  • 1 hour
  • Free Cancellation
From
$18.00
From
$18.00

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

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

star-5
388
Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront trail. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
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  • 4 hours
  • Free Cancellation
From
$89.99
From
$89.99

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1529
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
$46.00
From
$46.00

Lake Michigan Sightseeing Cruise
Likely to Sell OutLikely to Sell Out

Lake Michigan Sightseeing Cruise

star-4.5
456
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.
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  • 40 minutes
  • Free Cancellation
From
$28.34
From
$28.34

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

star-4.5
301
Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.
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  • 1 hour 15 minutes
  • Free Cancellation
From
$49.00
From
$49.00

Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

star-5
19
Explore Chicago your way and on your own schedule on a private walking tour that's completely customized based on your interests. Whether you want to learn Windy City history or focus on architecture, street art, or Chicago's food scene, your local guide knows all the best places to see, shop, and dine. Plus, get plenty of personalized recommendations on where to go once the tour ends.
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  • 2 hours
  • Free Cancellation
From
$200.00
per group
From
$200.00
per group

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
Likely to Sell OutLikely to Sell Out

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

star-5
14
Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side.
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  • 2 hours
  • Free Cancellation
From
$427.28
per group
From
$427.28
per group

Eastside Chicago:

Eastside Chicago: "The Art Heist" Exploration Game

star-4
6
Follow a self-guided adventure during this special smartphone-based game in Chicago’s Millennium Park. Learn about the city’s iconic works of art and architecture while enjoying views of Lake Michigan and the Chicago skyline. Play anytime you’d like, seven days a week, with no data or Wi-Fi needed.
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  • 1 hour 35 minutes
  • Free Cancellation
From
$10.32
Price varies by group size
From
$10.32
Price varies by group size

Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

star-4.5
6
Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you’ll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine’s Day Massacre.
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  • 3 hours
  • Free Cancellation
From
$880.00
From
$880.00

Chicago Self-Guided Audio Tour

Chicago Self-Guided Audio Tour

star-4.5
5
Short and highly selective information in the audio commentary for tourist attractions in around Chicago Highlights of this Self-Guided Audio Tour • It allows you to go as per your own convenience of time, pace and location; skip the content that doesn't interest you, and listen longer to content that does interest you. • Not necessary to download any location tracking apps. Audio guide can be listened online (or) offline. •Available in multiple languages, you can choose the one you’re most comfortable with. • It is one of the best options with lowest price when compared to hiring a tour guide. •If you have any questions about any attractions. No worries, we will answer in your language instantly by message.
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  • 1 to 5 hours
From
$5.00
From
$5.00

Chicago Foodie Lovers Tour (Private & All-Inclusive)

Chicago Foodie Lovers Tour (Private & All-Inclusive)

star-5
5
It isn’t a trip to Chicago without tasting deep-dish pizza—and this private tour for food lovers will introduce you to true Chicago-style pizza, plus other Windy City specialties. Meet your guide downtown, and be sure to come hungry: You’ll eat hot dogs, Italian beef sandwiches, pizza, donuts, and more. Along the way, see highlights like the Wrigley Building and Magnificent Mile, and learn more about the city’s history and culture.
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  • 4 hours
  • Free Cancellation
From
$319.00
Price varies by group size
From
$319.00
Price varies by group size

Private Secret Food Tour of Chicago

Private Secret Food Tour of Chicago

star-5
5
Chicago is renowned for its dynamic dining scene—and this private walking tour offers a personalized introduction to its must-eats. Pick a time that works best for you, and head to Gino’s East: one of the city’s classic deep-dish pizzerias. From there, set off on a tour of the Loop, where you’ll taste sweet and savory treats—and learn about the city’s architecture, history, and culture as you go.
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  • 3 hours
From
$186.66
Price varies by group size
From
$186.66
Price varies by group size

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