
The most-booked Chicago tours and tickets right now

If you’re in Chicago for a short stay and want to tick off the city’s must‑see sights, the All‑Inclusive Pass has you covered.
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Book your architecture river cruise and gaze at the most iconic buildings along the Chicago River!
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See the Windy City from the very best vantage point: 103 floors above the ground!
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Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building. Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including: John Hancock Center: An iconic skyscraper that defines the Chicago skyline. Wrigley Building: Known for its distinctive white facade and clock tower. As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities. Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.
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Chicago opens up effortlessly with the Go City Chicago Explorer Pass.
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Enjoy a 90-minute comprehensive boat cruise of Chicago's legendary architectural wonders from the best seat in the house, the river.
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Home to some of the world's most recognizable artworks, the Art Institute of Chicago is America's second-largest art museum.
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Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today. The Chicago River Architecture Tour is the most authentic and encompassing Chicago experience the city has to offer.
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Major attractions with reserved entry - skip the queue, walk straight in

If you’re in Chicago for a short stay and want to tick off the city’s must‑see sights, the All‑Inclusive Pass has you covered.
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See the Windy City from the very best vantage point: 103 floors above the ground!
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Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.
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Experience thrilling roller coasters at Six Flags Great America in Gurnee, featuring Maxx Force, Wrath of Rakshasa and spectacular shows.
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Chicago opens up effortlessly with the Go City Chicago Explorer Pass.
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Visit 360 Chicago Observation Deck, located 1,000 ft above Michigan Avenue on the 94th floor of 875 N. Michigan (formerly known as the John Hancock Center). It offers views of the Chicago skyline and Lake Michigan.
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Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping views and is full of interactive exhibits. To complete your exciting Chicago experience, head to the Ledge, a glass balcony showcasing unbeatable views of Chicago’s top attractions like Wrigley Field and the Navy Pier. We added a brand new Chicago Experience that you start with by the box office prior taking the elevator trip to the 103rd floor. It is a 45,000 sq ft. museum of today. The New Experience is part Chicago History, part Architecural tour, part Selfie Museum and part Children's Museum. This is fun and interactive for all ages. Ride our "L" Train, see our infinity pizza bed, take pictures ontop of Willis Tower and so much more! This is the best way to see Chicago in one setting. With mobile tickets, simply scan your phone for direct entry into the SkyDeck
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Enjoy the atmosphere of an NHL game and cheer for the Chicago Blackhawks at United Center.
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Small-group + private walking tours with a local guide
Book your architecture river cruise and gaze at the most iconic buildings along the Chicago River!
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UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's exclusively offered interiors-themed tours in Chicago for more than a decade, and that's INSIDE CHICAGO WALKING TOURS. Our "World Within: Dazzling Interiors of the Loop" tour is Chicago's first and best architecture interiors tour. Accept no imitations! Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t shown them by a seasoned, in-the-know tour guide. Ranging from stained glass mosaics from the turn of the century to soaring Art Deco spaces from the Roaring 20s, these spaces are some of the most beautiful in the city -- and open to us to explore!
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Explore Chicago at your own pace with a hop-on hop-off bus tour.
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• This all-in-one ticket covers round-trip hotel transportation, admission to all attractions, skip-the-line access, and a narrated architecture cruise.
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See amazing animals, incredible views, fascinating science, world-class art, and more with Chicago CityPASS tickets.
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Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging in delectable local cuisine. From deep-dish pizza to hidden gems, savor the flavors of Chicago as a knowledgeable guide unveils the city's culinary secrets and fascinating history.
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Home to over 300,000 works of art, the Art Institute of Chicago showcases a wide range of artistic innovation, from European masters to American icons.
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Guided, behind‑the‑scenes tour of The Chicago Theatre, covering 60–75 minutes of history, design, and star stories.
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Food tours, market walks, wine tastings, cocktail experiences

The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the beautiful streets of downtown & taste the Windy City’s favorite eats on this iconic Chicago Food Tour! Bobby’s Bike Hike & Food Tours, whose food tours rank Top 20 worldwide on Tripadvisor, offers this ultimate walking & food experience featuring the hard-working, salt-of-the-earth classics Chicago made famous: a slice of deep dish pizza, a Chicago-style hot dog, Italian beef, popcorn & dessert. Expert guides lead you through downtown’s most iconic landmarks on our Day tours—Millennium Park, Chicago Theatre, Riverwalk, Michigan Ave—Night tours go a different route, please check itinerary for details-we share Chicago’s rich, food-loving history. It’s one of the tastiest Things to Do in Chicago! Enjoy your tour & get a BONUS 2-hour FREE bike or kayak rental gift per ticket. Cruise the Lakefront Bike Trail or paddle Lake Michigan for extra fun!
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The Underground Donut Tour is the only food tour dedicated specifically to donuts! Enjoy a charming a sweet, sweet experience in Chicago.
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Travel between breweries on the unique Barrel Bus for a Chicago brewery tour.
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Recently voted one of TripAdvisor's top food tours in the US. Discover the sweet side of the Windy City on the Underground Donut Tour, Chicago’s Delicious Donut Adventure. We’ll kick things off at the legendary Doughnut Vault, tucked beside the historic Merchandise Mart, where you’ll enjoy one of Chicago’s most beloved treats. From there, we’ll stroll across the Chicago River, taking in picture-perfect skyline views before heading to a local artisan donut shop crafting fresh, handmade creations daily. As we wind our way through downtown, we’ll make our way toward Michigan Avenue, home to two iconic stops. First, indulge in a California-style donut shop bursting with flavors and flair, followed by a visit to Do-Rite Donuts, famous for their creative combinations, seasonal specials, and perfectly glazed classics. Equal parts tasty and scenic, this walking tour is the ultimate way to explore Chicago’s flavors, views, and charm. We hope you can join us!
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Go on a real foodie adventure as you eat our way through the River North and Wicker Park and uncover the off-the-beaten-path food spots of Chicago!
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Join a food tour through Chicago’s Loop district and the River North neighborhood with a local guide who knows where to find the city’s most popular eats.
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Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked Top 10 in America by USA Today & Top 20 in the world by Tripadvisor, for a day of interesting stories and scrumptious eats on this delicious Food Tour in Chinatown. This 3-hour Walking and Chintown Food Tour, you’ll see the bustling Chinatown Square, then get to sampling some of the richest cuisine around; including Cantonese dim sum, Portuguese-Chinese bakery treats, Szechuan style, and even Xi'an cuisine, all while learning about the history of how these foods & culture arrived in Chicago. This is a totally unique culinary tour experience, and not to be missed! Upon arrival to the tour, you can add a VIP Drink option for alcoholic and ethnic drink pairings! Chinatown can be challenging to navigate on your own, so let our expert local guides show you the way & discover 5 of our all-time favorite dishes.
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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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River cruises, sailing, sunset boats, harbour tours

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building. Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including: John Hancock Center: An iconic skyscraper that defines the Chicago skyline. Wrigley Building: Known for its distinctive white facade and clock tower. As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities. Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.
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Book your architecture river cruise in Spanish and pass the most iconic buildings along the Chicago River!
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After the Great Chicago Fire in 1871 the city had to rebuild, and they made sure to rebuild big. Chicago became a pioneering destination for skyscrapers, taking advantage of new architectural practices, and hasn't looked back since.
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Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today. The Chicago River Architecture Tour is the most authentic and encompassing Chicago experience the city has to offer.
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Learn about Chicago's history and enjoy the city's world-famous skyline as you cruise across Lake Michigan.
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All aboard for the most popular river cruise in the States!
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Museums, ruins, art collections, religious sites with expert guides
Enjoy a 90-minute comprehensive boat cruise of Chicago's legendary architectural wonders from the best seat in the house, the river.
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Home to some of the world's most recognizable artworks, the Art Institute of Chicago is America's second-largest art museum.
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The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. As a certified nonprofit, all ticket purchases directly support education efforts and community engagement projects. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.
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A spectacular journey above the windy city
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Admire Chicago from the 94th floor. Learn about Chicago's history and architecture and discover the CloudWalk and the 3D mural by Nate Baranowski.
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The world-famous ice cream attraction is now sprinkling its yummy joy in Chicago! Step into an ice cream wonderland designed to ignite your senses through a theatrical experience, hosted by a truly talented ice-cream team.
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Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities. Hear true crime stories about Chicago Gangster Al Capone, The Untouchables, The Chicago Mob, Prohibition, John Dillinger, Frank “The Enforcer” Nitti, Cap George Streeter, Leopold & Loeb, H.H. Holmes and more. Visit historic landmark buildings like: The Biograph Theater, Holy Name Cathedral, Cook County Criminal Court House, Harry Caray’s Italian Steakhouse, etc. Tour famous Chicago neighborhoods: Streeterville, River North, Gold Coast, Lincoln Park, Old Town, Loop and Magnificent Mile. Locals and tourists agree that this educational and entertaining thing to do in Chicago is a unique cultural experience.
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• Trace Chicago’s architectural evolution on a guided 90-minute walking tour, from 1870s reconstruction to today’s glass-and-steel marvels.
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Bike tours, e-bikes, kayaking, rafting, anything outside
Book a Chicago lakefront neighborhood bike tour today and enjoy a three-hour, guided tour on two wheels around the Windy City!
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Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s first city bike tour company, on this exciting & informative adventure which recently ranked Top 20 Food Tours in the World by TripAdvisor. The journey is a leisurely paced 13mi & includes deep dish pizza, Chicago-style hot dog, Italian Beef, & dessert. Upgrade to sample local craft beer! On the DAY version of bike tour, you’ll drink in the sights of Chicago’s beautiful northside neighborhoods, including the Lakefront and Wrigleyville, home to our Chicago Cubs baseball team. On the NIGHT bike tour, you'll ride through the major downtown attractions & see the lights of Buckingham Fountain, Millennium Park and the glorious skyline. Cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this fun tour! You’ll leave with a profound understanding of Chicago, even if you only came for the food.
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Speed around Lake Michigan in a blaze of orange glory on the _Seadog_ and scan Chicago's world-famous skyline at high speed.
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Rent a bike in Chicago, America's number one city for biking and follow the famous Chicago's Lakefront Bike Path
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The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll explore in motion with scenes captured by an award-winning creative team using custom-made drones and helicopter-mounted cameras, while scents, sounds and music deepen the immersion. It’ll take your breath away (we promise you’ll get it back).
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Explore Chicago on a guided adventure featuring top attractions, food, and highlights. Start at the historic Water Tower on North Michigan Avenue, a survivor of the Great Chicago Fire of 1871.
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Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. Over the course of a 3-hour bike ride (traversed at a nice leisurely pace), you’ll get up close and personal with Chicago’s legendary Museum Campus, Grant Park, Chicago Riverwalk, Lakefront and Millennium Park. You’ll become intimately familiar with Soldier Field, The Adler Planetarium, Buckingham Fountain, The Pritzker Pavilion, and Cloud Gate (the formal name of Chicago’s dearly-beloved “Bean”). This tour is perfect for first time visitors looking to see all of the classic hotspots, and for returning guests looking to understand more about the landmarks they know and love. Hop on two wheels, and come make memories that are sure to last a lifetime! All equipment included on this Bicycle Tour of Chicago.
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This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence by National Geographic, USA Today, The Associated Press, Conde Nast Traveler, and more! Bobby’s now offers over a dozen specialized tours, but The Lakefront Neighborhoods Chicago Bike Tour is what started it all. Join one of Bobby’s expert guides on this 3-hour bicycle tour through Chicago’s beautiful North Side Lakefront neighborhoods. See the ever-rising skyscrapers of Streeterville, the deluxe residential mansions of the Gold Coast, the cozy artists’ village of Old Town, and the rolling greenery of Lincoln Park. You’ll finish off with a cruise down the world-famous Lakefront Bike Trail, one of the most popular waterfront bike paths in the nation. This leisure-paced journey is sure to make memories that’ll last a lifetime! This Bicycle Tour of Chicago is kid-friendly and all equipment (bikes, helmets) is included.
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Vespa, golf cart, hot-air balloon, vintage car - unique ways to see the city

The iconic Centennial Wheel on Chicago's Navy Pier offers some of the best views of _The City of the Big Shoulders_.
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• Plan your Chicago itinerary without worrying about arranging travel with this 24/48/72-hour hop-on hop-off bus tour, hopping off unlimited times.
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Experience the best views of Chicago from the comfort of the double-decker bus, explore the city at your own pace, and learn from the audio commentary.
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Some of the world's most famous criminals and gangsters bamboozled their way through Chicago, and now you can follow in their shady, calculating footsteps!
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Skip the heat of the day (and the crowded streets) while in Chicago and opt for tickets for a bus tour of the Windy City at night.
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Offering stunning views of The Windy City, the Centennial Wheel at Chicago's Navy Pier is a 200-foot-high ride set in a modern capsule, complete with air conditioning, plush seating and a glass bottom.
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John Dillinger once escaped from jail using only a phoney wooden gun, and Al Capone was never convicted of murder, despite his brutally violent rule over Chicago in the 1920s.
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Visit Chicago and learn about its history during the 1920s and 1930s.
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Half-day to full-day trips out of the city - Pompeii, Tivoli, Tuscany, you name it
Get your Go City Explorer Pass, pick 2, 3, 4, 5, 6 or 7 attractions of your choice in Chicago, scan your pass at the entrance and you're in. It's easy and convenient!
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This tour visits the homes of Louis Farrakhan, the former home of Elijah Muhammad and the former home of Muhammad Ali. We will pass by and take pictures at the home the 44th President of the Unites States, Barack Obama. Visitors will see the home of Reverend Jessie Jackson and Ida B. Wells along with Thomas Dorsey and Mahalia Jackson. Visitors have the option to stop at the new Obama Presidential Library for 3 hours. We give a chronological history of blacks coming to Chicago after the civil war to today. We provide facts, figure and insight. The tour guide was part of the Great Migration; it is like listening to his story firsthand. You will get well thought-out analysis on why Chicago is like it is today. This is a dialogue driven tour where you are given information and asked questions. You will be a part of this tour. Most importantly, you will laugh. After the tour, if wanted, we will stop at a soul food restaurant to dine for an hour. Come tour with us!
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Get your Go City's All-Inclusive Pass and take advantage of unlimited access to 25+ top attractions in Chicago and a downloadable guide to help you plan your itinerary.
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Kickstart your adventure in Chicago with the tour that started it all. Explore the grandeur of the city and soak up all the vibes it has to offer.
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Learn what tragic story is covered by Chicago River's waters, explore the most haunted sites and buildings, hear about rise and fall of the most infamous gangsters.
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Discover Chicago's iconic landmarks on foot. Skydeck, Millennium Park, Navy Pier, and river cruise await. Embark on your urban adventure today!
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Explore one of the largest science museums in the world at your own pace with this in-app audio tour of the Museum of Science and Industry in Chicago.
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Hop on the majestic Odyssey for a special lunch cruise in Chicago and start your weekend off with a splash of finesse.
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Tours and activities chosen for kids, teens, and multi-generational groups

Get your ticket to this colossal playground of scientific discovery, and prepare to be blown away.
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An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century of groundbreaking architecture. The journey begins with an up-close perspective of Chicago's internationally-known architecture as seen from the Chicago River. Then venture through the Chicago Lock on to the calm, cool waters of Lake Michigan for expansive views of Chicago's extraordinary 26-mile skyline. Take the selfie of a lifetime on this inspirational experience!
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Arrive at Six Flags Great America and head to the main entrance.
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Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire.
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On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through some of the city's world renowned architecture and public art in the famed Chicago Loop District. Experience our famous deep dish pizza, taste the amazing Italian beef sandwich, enjoy gourmet popcorn, and lots of other treats. Plus, there is our mouth-watering secret dish that you can only find out about on the day of the tour!
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Visit Six Flags Great America with flexible good any day tickets and optional all day dining and drinks add-ons.
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There’s no shortage of things to see in Chicago, and the C3® CityPASS® is your ticket to three of the best.
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They’re BACK! #MOIChicago is bigger and better than ever, unveiling a completely NEW experience with an addition of +20 never-before-seen illusions and almost double the space!
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Airport pickups, point-to-point transfers, and city transport

Travel between Chicago O’Hare Airport and Milwaukee on a comfortable coach and relax with onboard amenities like reclining seats and more.
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Why stress about finding a taxi at Chicago's busy airports when you can book a private car in advance? Ensure a smooth ride from Chicago O'Hare International Airport (ORD) or Midway Airport (MDW) to downtown Chicago and complete your journey in style!
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Why stress waiting for unreliable taxis or bus transfers to Chicago's busy airport? Ensure peace of mind with a private transfer from your downtown Chicago accommodation to O'Hare International Airport (ORD) or Midway Airport (MDW). Reach the airport relaxed and in good time for your flight! Transfer services are available 24 hours a day, 7 days a week. Choose from a luxury sedan transfer for 3 people or an SUV transfer that carries up to 5 passengers. All vehicles feature stylish and spacious interiors and you will be met and escorted by a professional chauffeur.
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Private guides, VIP access, after-hours tours, premium small-group

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour exclusive 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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PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago. Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more. The tour will be interactive and entertaining, covering history, architecture and culture. We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.
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This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is the total for all 3 passengers (saving you money compared to other operators who charge per person.)
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Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse the hallowed halls, you’ll discover an extraordinary collection spanning centuries and cultures, from classical masterpieces to cutting-edge contemporary works. Our expert guides will illuminate the stories behind each brushstroke, sculpture, and masterpiece, providing a rich narrative that breathes life into the art.
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Common questions about booking Chicago experiences through SimilarTours
Summer and early fall dominate - Lake Michigan sailing and Great Lakes cruises are most popular June through September. If you're planning a multi-day tour like the Mackinac Island trip or Great Lakes voyage, book 2-4 weeks ahead during peak season. Winter's quieter but some operators still run, so check before you go.
For sunset sailing or fishing charters on Lake Michigan, 1-2 weeks usually works, though peak summer weekends fill faster. If you want a specific captain or larger private yacht, aim for 3-4 weeks. Multi-day yacht charters need more notice - check availability early.
Absolutely, if water access or customization matters to you. Private sedan transfers save hassle if you're flying in and heading elsewhere. Group sailing or fishing charters split costs while keeping the experience personalized - you're not stuck on a crowded boat.
Most water tours pick up from downtown marinas or lakefront hotels, so rideshare or public transit gets you there easily. For day trips beyond the city - Lake Geneva, Mackinac Island - booking a private tour or charter typically includes transportation from Chicago, which saves you the drive.
Fishing charters and scenic boat tours work well with kids if you pick calmer water days - check age restrictions with operators before booking. Multi-day Great Lakes tours appeal more to experienced sailors or adventurous families. Most private sedan services handle families without issue.
Transportation from Chicago, guided exploration, and accommodation are typically included on 4-6 day tours, but meals and specific amenities vary. Check the full itinerary before you go - some tours are more hands-on sailing experiences, others more relaxed cruises with sightseeing.
Private yacht charters often come with a captain, so no experience needed - you just relax. Sailing charters vary - some teach beginners, others expect basic skills. Always confirm experience requirements when booking.
Browse every tour and activity across United States, with Chicago as your starting point
See all experiences in United StatesBrowse Chicago by category - skip-the-line tickets, walking tours, day trips, food experiences & more
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Chicago's a natural hub for water lovers and road-trippers. You'll find serious sailors chartering private yachts on Lake Michigan at sunset, families booking fishing charters, and adventure seekers heading north to Mackinac Island or the Great Lakes for multi-day explorations. Day trips to Lake Geneva and Japanese gardens pull people inland, while those passing through often arrange private sedan transfers to Indianapolis. It's a city where most of the memorable experiences seem to happen on the water or heading somewhere else.