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Top Chicago Sightseeing Tours - page 3

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122 results | All Chicago Tours

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Private 45-Minute Chicago Skyline Helicopter Tour

Private 45-Minute Chicago Skyline Helicopter Tour

star-5
38
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

Chicago Walking Tour: A Walk Through Time

Chicago Walking Tour: A Walk Through Time

star-5
35
Travel through architectural history on this walking tour that covers Chicago's most famous buildings in chronological order. With a guide in the lead, there's no need to fuss over maps or worry about directions. Simply stroll along and listen to the in-depth guided commentary on Chicago's architectural history; you'll learn about each building and its importance in the architectural canon.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$30.00
From
$30.00

Go City: Chicago All-Inclusive Pass with 25+ Attractions

Go City: Chicago All-Inclusive Pass with 25+ Attractions

star-2
29
Enjoy admission to more than 25 of Chicago's most popular attractions with Go City's All-Inclusive Pass. Enjoy the freedom to create your own itinerary and save far more than if you were to purchase individual attraction tickets. Take a hop-on hop-off bus tour of the Windy City, admire the stunning views from SkyDeck Chicago, discover fascinating creatures at Shedd Aquarium, and much more. You can visit as many attractions as you like over the course of 1, 2, 3 or 5 days. Save your pass, available as your 'ticket' after purchase, on your mobile device; don't waste time redeeming vouchers. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for the number of remaining consecutive days purchased.
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  • 1 to 5 days
From
$95.00
From
$95.00

2-Hour Haunted Segway Tour of Chicago

2-Hour Haunted Segway Tour of Chicago

star-4.5
27
Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.
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  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

Chicago Fireworks Dinner Cruise with Buffet

Chicago Fireworks Dinner Cruise with Buffet

star-4
27
Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan. Glimpse top Chicago attractions like Navy Pier, Soldier Field and more while you dine on a lavish, all-you-can-eat buffet! See spectacular views of the Chicago skyline and a live DJ spinning your favorite songs. In the summer months, enjoy a breathtaking fireworks display.
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  • 3 hours
From
$158.98
From
$158.98

1920s Chicago Walking Tour: Art Deco Architecture, Gangsters, and More

1920s Chicago Walking Tour: Art Deco Architecture, Gangsters, and More

star-5
25
Discover Chicago of the Roaring '20s thru its Art Deco architecture! We all LOVE the elegance, glam, and glitz of the 1920s. This 2-hour walking tour explores the interiors and exteriors of gorgeous buildings from this surprisingly brief architectural period in Chicago, with some interesting details and stories about life in that era. Flappers, gangsters, jazz, speakeasies — we'll pepper those throughout our larger exploration of Chicago's magnificent Art Deco buildings in order to truly set the context for you! You’ll walk in the footsteps of those high on the potential of the future, before the infamous Crash of ‘29. In addition to experiencing magnificent Art Deco architectural interiors, you’ll also learn about Chicago’s notorious gangster history — even ending the tour inside an old gangster headquarters surrounded by real photographs, newspapers, and an old uncovered vault!
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  • 2 hours
  • Free Cancellation
From
$33.00
From
$33.00

2-Hour Chicago Fireworks Segway Tour

2-Hour Chicago Fireworks Segway Tour

star-5
24
Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see Buckingham Fountain’s breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, then witness Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
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  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

Chicago Premier Fireworks Dinner Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Premier Fireworks Dinner Cruise on Lake Michigan

star-2.5
23
Set sail on Lake Michigan aboard a luxury yacht for a gourmet dinner cruise with views of the Chicago fireworks display. During the 3-hour cruise, the crew serves a 3-course plated meal with dishes prepared by your onboard chef. You can enjoy the stylish interior of the rooftop lounge, dance to DJ entertainment, or relax and soak in the views of the Chicago skyline.
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  • 3 hours
From
$179.38
From
$179.38

2-Hour History of Chicago Architecture and Art Segway Tour

2-Hour History of Chicago Architecture and Art Segway Tour

star-5
20
Explore the art and architectural highlights of Chicago on a Segway during this guided tour. This family-friendly tour takes visitors by the outdoor sculptures, landmark buildings, and iconic skyline of the city. Accompanied by educational and informative commentary, this city tour saves you from hours of walking and lets you see all of Chicago's top art and architectural attractions in one tour.
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  • 2 hours
  • Free Cancellation
From
$75.10
From
$75.10

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
18
Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English, French, or Dutch. Focus can be on public or street art, architecture, food, and much more!
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  • 2 hours
  • Free Cancellation
From
$200.00
per group
From
$200.00
per group

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

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

star-5
20
The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2 to 2.5 hour private guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. Highlights Generally Include: (if artwork is not on loan or being restored etc.) Paris Street, Rainy Day by Gustave Caillebotte Sunday on La Grande Jatte - Georges Seurat Sky Above Clouds - Georgia O'Keefe Nighthawks - Edward Hopper A Picture of Dorian Gray - Ivan Albright America Windows - Marc Chagall The Old Guitarist - Pablo Picasso Inventions of Monsters - Salvador Dali Four Mona Lisas - Andy Warhol
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  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
From
$153.70
Price varies by group size
From
$153.70
Price varies by group size

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

star-5
17
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

Half-Day Small-Group Chicago Highlights Tour with Pick Up

Half-Day Small-Group Chicago Highlights Tour with Pick Up

star-4.5
15
This Tour is the quickest, best way to explore a place that you are visiting for the first time, we take you to all the hot spots in the city in less than a day. We take care of everything for you, from picking you up at your hotel, to making reservations, parking, helping you with photos, all the way to dropping you off back where you started. zero worries and 100 percent enjoyment.
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  • 4 hours 30 minutes
  • Free Cancellation
From
$198.00
From
$198.00

Chicago's Wicker Park Food Tour

Chicago's Wicker Park Food Tour

star-5
14
Explore Chicago’s Wicker Park neighborhood on a three-hour guided food tour. Stop at five different culinary destinations for an incremental meal as you walk through the neighborhood. Try fried chicken from President Obama’s favorite spot, meatball sliders, tacos, and other tasty treats. Get to know the city’s history, as your guide points out significant architecture and cultural landmarks, and see how the food you sample is made with behind the scenes peeks at some of the area’s most love eating establishments. Be sure to wear comfortable shoes to enjoy the walk.
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  • 3 hours
  • Free Cancellation
From
$75.00
From
$75.00

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

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.
More
  • 2 hours
  • Free Cancellation
From
$427.28
per group
From
$427.28
per group

2-Hour Chicago City Lights Evening Segway Tour

2-Hour Chicago City Lights Evening Segway Tour

star-4.5
14
Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see famous Buckingham Fountain’s breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, taking in views of the Field Museum of Natural History, Shedd Aquarium, Soldier Field and Michigan Avenue. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
More
  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

Premier Chicago River Dinner Cruise
Likely to Sell OutLikely to Sell Out

Premier Chicago River Dinner Cruise

star-3.5
14
Cruise down the Chicago River in style during this 3-hour dinner cruise aboard the Odyssey. Watch the beautiful city and its architecture pass by through the ship’s panoramic windows. Then sit down to delicious 3-course meal accompanied by DJ entertainment to set the mood for your journey. A full-service bar complete with microbrews, creative cocktails, and a wine list is also available for purchase.
More
  • 3 hours
From
$172.58
From
$172.58

Lonely Planet Experiences: River North Historical Food Tour

Lonely Planet Experiences: River North Historical Food Tour

star-5
14
Get to know the food offerings in River North on this small-group walking tour. As you explore, listen to in-depth commentary from your guide on the culinary history of Chicago and the culture of the River North neighborhood. With a small group of just 12 fellow food-lovers, you'll enjoy personalized attention and the chance to chat about your favorite tastings. Samples include the classic Italian beef, a Chicago-style hot dog, and the famous deep dish pizza.
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  • 2 hours
  • Free Cancellation
From
$60.96
From
$60.96

Private Chicago Highlights Driving Tour
Likely to Sell OutLikely to Sell Out

Private Chicago Highlights Driving Tour

star-5
14
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
  • Free Cancellation
From
$190.00
Price varies by group size
From
$190.00
Price varies by group size

Holiday Hike Chicago-Style: Festive Food & Walking tour

Holiday Hike Chicago-Style: Festive Food & Walking tour

star-5
13
Stroll through Chicago's winter streets, lit up for the holidays, on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.
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  • 3 hours
  • Free Cancellation
From
$69.99
From
$69.99

Chicago Premier Lake Michigan Brunch Cruise

Chicago Premier Lake Michigan Brunch Cruise

star-4.5
11
Enjoy waterfront views of downtown Chicago on a 2-hour brunch cruise through the heart of the city. Board a luxurious yacht at Navy Pier then relax on deck with a complementary mimosa. Find a comfortable spot on the three climate-controlled observation decks, and enjoy a sumptuous buffet while the onboard DJ spins a leisurely afternoon playlist. Capture unforgettable images of downtown skyscrapers and architectural landmarks as you navigate along the historic shoreline, then loop back and finish your outing at the bustling Navy Pier.
More
  • 2 hours
  • Free Cancellation
From
$111.38
From
$111.38

2-Hour Chicago Holiday Lights Segway Tour

2-Hour Chicago Holiday Lights Segway Tour

star-4.5
10
Soak up the Windy City’s festive holiday feel and explore local landmarks with ease on this Segway tour in Chicago. Hop onto your Segway and spin through Chicago’s Millennium Park to the Loop. With your guide, you'll watch skaters enjoying the ice rink, explore Michigan Avenue and admire festive department store displays. See the German Christmas market stalls at Daley Plaza, where locals sip hot chocolate and munch 'bratwurst,' and enjoy the atmosphere beneath the city’s Christmas tree. Get the personalized feel of a small-group experience.
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  • 2 hours to 2 hours 15 minutes
  • Free Cancellation
From
$75.10
From
$75.10

Chicago Walking Tour: Modern Architecture

Chicago Walking Tour: Modern Architecture

star-4.5
10
Embark on a walking tour of Chicago's more-recent architecture heritage with a 2-hour stroll highlighting the city's modern, postmodern, and international structures. Especially known for its architectural originality, Chi-town boasts everything from the elegant metal and glass tower of One South Dearborn to the Harold Washington Library, with its Beaux-Arts inspired exterior. Your guide will highlight these and other unique buildings, relaying background on their individual histories and construction en route.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$30.00
From
$30.00

Downtown Chicago Walking Pizza Tour

Downtown Chicago Walking Pizza Tour

star-5
10
Immerse yourself in the taste and culture of pizza on this Chicago walking tour that focuses on the food Chicago does best. You'll be with a group of 16, which gives you lots of access to your guide and time to ask questions. Sink your teeth into different styles—deep dish, grandma-style, Neapolitan, Roman, and pan style—then decide which one you like best.
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  • 2 to 3 hours
  • Free Cancellation
From
$49.00
From
$49.00

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