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Multi-day & Extended Tours

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267 activities found

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  • Chicago Architecture River Cruise Guided Tour
    3008 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $38.85 USD
    Experience one of the world’s most beautiful cities on a 60-minute cruise on the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building. Take in magnificent city skyline views as you see more than 40 notable buildings, including the John Hancock Center and the Wrigley Building, and learn about their distinctive architecture from your onboard guide, an expert in architecture.
    from
    $38.85 USD
  • Chicago Criminals, Mobsters and Gangsters Bus History Tour
    436 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $45.00 USD
    Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Walking tour paths explore historic crime scenes with great photo opportunities. 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.
    from
    $45.00 USD
  • Chicago Grand Half-Day Bus Tour
    344 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $52.95 USD
    This comprehensive half-day tour of Chicago is the perfect introduction to the Windy City! Discover the highlights of Chicago’s North Side and South Side and enjoy a scenic drive along the Outer Drive. Pass by Chicago's beautiful Washington Park and Grant Park, and make a 20-minute stop at the fascinating Lincoln Park Conservatory. Stop for photo opportunity at the Adler Planetarium, see the impressive Wrigley Building and more. You'll come away with a fantastic overview of the best Chicago has to offer!
    from
    $52.95 USD
  • Chicago CityPASS, with Shedd Aquarium, Skydeck Chicago
    272 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $109.00 USD
    Chicago CityPASS® — Discover Chicago's best attractions at one great price with an easy to use mobile ticket. Spend less, experience more.

    Includes premium admission to 5 must-see attractions:
    • Shedd Aquarium - CLOSED through Jan. 1
    • Skydeck Chicago - TEMPORARILY CLOSED as of Nov. 20
    • Field Museum - CLOSED Nov. 20 through Dec. 3
    • Option Ticket 1: Adler Planetarium - TEMPORARILY CLOSED OR Art Institute of Chicago - TEMPORARILY CLOSED
    • Option Ticket 2: Museum of Science and Industry, Chicago, - TEMPORARILY CLOSED OR 360 CHICAGO Observation Deck - TEMPORARILY CLOSED

    Visit the CityPASS online travel guide for up-to-date attraction information including reservations, entry instructions, hours of operation and helpful tips to plan your visit. https://www.citypass.com/guide/chicago/howto
    from
    $109.00 USD
  • Gangsters and Ghosts Tour in Chicago
    237 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $27.00 USD
    Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago!

    You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Tour departs from 71 E Wacker Drive.
    from
    $27.00 USD
  • 90-min Chicago River Architecture Tour
    194 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $39.00 USD
    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.
    from
    $39.00 USD
  • Skip the Line: Tommy Gun's Garage Dinner and Show Ticket
    173 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $67.00 USD
    Welcome to the only speakeasy dinner show in Chicago Tommy Gun's Garage! Just say the password and you'll be transported back to the roaring twenties. You'll be entertained by gangsters and flappers, dancing the Charleston to the music of Cole Porter and George Gershwin. It's a night out in Chicago you'll never forget!
    from
    $67.00 USD
  • Chicago Explorer Multi-Attraction 30-Day Discount Pass
    172 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $66.00 USD
    Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 45% on ticket prices. This multi-attraction pass, valid for 60 days after your first use, provides admission to your choice of up to five attractions, tours or activities. Select from more than 30 top sites and things to do, including SkyDeck Chicago, Navy Pier and a Shoreline Architecture River Cruise. It's the easiest and most affordable way to explore the Windy City at your own pace. Simply save your pass on your mobile device (available as your 'ticket' after purchase) and go – no voucher redemption required! The pass also provides discounts at restaurants and retailers around the city.
    from
    $66.00 USD
  • Chicago Small-Group Tour With Optional Architecture Cruise
    129 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $39.95 USD
    Enjoy Chicago’s famous sights (now including Wrigley Field) and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, enjoy famout architecture including the world's first skyscrapers, Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its many attractions. The small-group atmosphere with maximum of 10 people ensures a more personal experience. 

    You also have the option to upgrade to include a 75-minute Architecture Cruise down the Chicago River! This popular open-top boat tour offers the perfect vantage point to admire the city’s renowned buildings.
    from
    $39.95 USD
  • Lake Michigan Sightseeing Cruise
    121 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $25.07 USD
    Admire all of Chicago's fabulous lakefront sights and attractions on this 40 minute Lake Michigan boat tour. Cruise along Lake Michigan and take in amazing views of the city’s famous skyscrapers from a great vantage point. Feel free to bring a lunch and enjoy drinks from the onboard bar as you relax on this sightseeing cruise.
    from
    $25.07 USD
  • 360 Chicago Observation Deck Admission Ticket
    121 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $25.00 USD
    The best views of Chicago can be yours at 360 Chicago (John Hancock Observatory)! Perched 94 stories above the Windy City, the 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers, including Willis (Sears) Tower. Located in the heart of downtown on Michigan Avenue, the observatory is steps away from other top Chicago attractions. It will be the high point (literally) of your Chicago trip!

    Upgrade your ticket to include TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. If you want to extend your tour to day and night and observe Chicago at both times of day, upgrade to the Sun & Stars option, good for two visits.

    from
    $25.00 USD
  • Private Arrival Transfer from Chicago Airports (ORD) (MDW)
    121 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $80.00 USD
    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!
    from
    $80.00 USD
  • Chicago Hop-On Hop-Off Big Bus Tour
    119 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $26.10 USD
    The lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful history. Explore the “Windy City” at your own pace, with the choice of a Classic, Premium or Deluxe ticket, all which include a hop-on, hop-off sightseeing bus tour with stops strategically located near the city’s top attractions. Hop on to experience sites like the Adler Planetarium and Navy Pier or hop off along the Magnificent Mile to shop, see the great city at heart-stopping heights from Willis Tower’s Skydeck or visit the Chicago Architecture Center, which is included in the Deluxe ticket.
    from
    $26.10 USD
  • Small-Group Chicago Food Tour: Gold Coast and Old Town
    99 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $74.67 USD
    Discover Chicago's culinary side on this three-hour walking tour to taste the delicious flavors of the Gold Coast and Old Town. Along the way, your guide will show you the history and architecture in these culture-rich neighborhoods, just north of the downtown area. After stops at seven quintessential Chicago restaurants in these two neighborhoods, you'll feel like a real Chicagoan! The tour operates with a maximum of 18 people, ensuring you’ll receive personal attention from your expert guide. Tastings at 7 different locations is included.
    from
    $74.67 USD
  • Spirit of Chicago Sunset Dinner Cruise with Buffet
    93 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $112.74 USD
    Celebrate a night out in Chicago with dinner, 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 listen to fun music!
    from
    $112.74 USD
  • Chicago City Tour and Chicago River Cruise
    92 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $76.95 USD
    Discover Chicago from both land and water on this scenic half-day tour. Take a narrated tour through the city’s South Side and see highlights including Grant Park, the Loop, the Shedd Aquarium and exclusive shopping areas and neighborhoods. Then, experience Chicago from the water! Cruise along the Chicago River in a beautiful streamliner yacht and admire views of the stunning city skyline.
    from
    $76.95 USD
  • Chicago Tour, 360 Chicago Observation Deck Admission Ticket
    82 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $73.95 USD
    Take a tour of Chicago and visit the 360 Chicago (John Hancock Observatory)! This comprehensive half-day tour is the perfect introduction to the Windy City. Visit the highlights of the North Side and South Side and enjoy a scenic drive along the Outer Drive. Explore Chicago’s beautiful parks on this guided tour, including Lincoln Park, Washington Park and Grant Park. Stop at the fascinating Lincoln Park Conservatory and the Museum Campus, and enjoy admission to the skyscraping Hancock Center, one of Chicago's tallest landmarks. Climb to the top for spectacular city views!
    from
    $73.95 USD
  • Chicago Lake and River Architecture Tour
    80 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $39.00 USD
    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!
    from
    $39.00 USD
  • Chicago Food Tour by Bike with Pizza, Beer, Hot Dogs, Cupcakes
    77 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $84.99 USD
    Taste all of Chicago’s classic eats on this four-hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. The journey is 14 miles in total (traversed at a nice leisurely pace) and includes a slice of deep dish pizza, a gourmet brownie (did you know, Chicago invented the brownie), a Chicago-style hot dog, and a few samples of Chicago’s legendary craft beer! Between food and beverage stops, you’ll get to drink in the sights of Chicago’s beautiful north side neighborhoods, including the historic Wrigleyville district, home to our intrepid Chicago Cubs baseball team (and their fiercely loyal fans). Then you’ll get a chance to cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this rip-roaring good time! You’ll leave with a profound understanding of our town, even if you only came for the beer.
    from
    $84.99 USD
  • Chicago Food Tour: Deep Dish Pizza, Beer, Brownies, and More
    70 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $62.99 USD
    Stroll through the beautiful streets of downtown Chicago and taste all of the Windy City’s favorite eats! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, whose walking tours have been recognized nationally by National Geographic, USA Today, and Conde Nast Traveler Magazine. This is Bobby’s quintessential culinary walking tour, complete with a slice of deep dish pizza, a Chicago-style hotdog, Italian beef sandwich, chocolates and pastries, as well as locally crafted beer. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks, including Millennium Park, State Street and Chicago Theatre, Chicago Riverwalk, Michigan Avenue, and the Wrigley Building, all the while regaling you with tales from Chicago’s rich food-centric history. This tour is sure to make memories that will last a lifetime!
    from
    $62.99 USD
  • Chicago Hotel to O'Hare or Midway Airports by Private Transfer
    65 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $80.00 USD
    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.
    from
    $80.00 USD
  • Chicago Odyssey Dinner Cruise
    53 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $108.66 USD
    Expect the exceptional on this 2.5-3 hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop lounge, posh atmosphere and stylish interior. Enjoy a 3-course plated meal with celebrity-chef inspired dishes prepared from fresh ingredients right on board. Dance the night away to DJ entertainment or simply relax in the elegant ambiance and take in the unmatched views of the world-famous Chicago skyline as you sail along the shores of Lake Michigan.
    from
    $108.66 USD
  • Bike Tour of Chicago's Lakefront Neighborhoods
    45 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $49.99 USD
    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 ride is what started it all. Join one of Bobby’s expert guides on this 3-hour romp through Chicago’s beautiful North Side neighborhoods. See the ever-rising skyscrapers of Streeterville, the luxe residential property 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 Lakefront 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! Tour departs from 540 N. Lake Shore Drive, Chicago.
    from
    $49.99 USD
  • Go Chicago Pass with Skip the Line Access
    30 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $118.00 USD
    With the Go Chicago All-Inclusive Pass, get access to more than 30 top Chicago attractions, tours and activities all at one low price! Enjoy fun rides at the Navy Pier; take a hop-on hop-off bus tour; catch amazing views from SkyDeck Chicago and more. Enjoy the flexibility to create your own itinerary and sightsee at your own pace; plus, you’ll save up to 20% on shopping and dining throughout the city. The Go Chicago All-Inclusive Pass offers something for everyone, and is the perfect way to save on your Chicago vacation. Enjoy direct entry to attractions.  Simply save your pass (available as your 'ticket' after purchase) on your mobile device and go – no voucher redemption required!
    from
    $118.00 USD
  • Underground Donut Tour: Chicago's First Donut Tour
    25 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $30.00 USD
    We've always had a passion for donuts, but only recently did we realize just how many others do too. And when looking around, we didn't see anything that truly celebrated donuts in all their glory, hence the Underground Donut Tour was born. This tour is for anyone who truly enjoys donuts. At each location, you'll be able to try a curated sample of one of that location's best donuts. Many locations offer vegan, gluten or nut free options, however, please make sure to let us know ahead of the tour, so we can make sure to highlight those specifically for you. Our tours include such favorites as Do-Rite Donuts, Firecakes, Stans, and Doughnut Vault. Please send us an email if you are looking for a specific location, as tours vary by day.
    from
    $30.00 USD
  • Chicago Odyssey Lake Michigan Lunch Cruise
    21 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $88.26 USD
    Welcome aboard Chicago's largest luxury yacht at Navy Pier! Satisfy your appetite and take in breathtaking views of Chicago's skyline on this 2-hour lunch cruise. While you are on board, not only can you enjoy a freshly prepared three-course meal, but also enjoy live musical entertainment which makes for a truly unforgettable experience.
    from
    $88.26 USD
  • 45-min Chicago River Architecture Tour
    20 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $23.00 USD
    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.
    from
    $23.00 USD
  • Chicago in a Day: Food, History and Architecture Combo Tour
    18 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $102.30 USD
    Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treats and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!

    Marvel at the stunning Chicago skyline and discover why Chicago’s architecture is among the best in the world

    Get around The Loop like a local: at street level, underground, elevated rails or perhaps even on the water

    Enjoy a couple of classic made-in-Chicago snacks like Chicago-style popcorn and homemade chocolate

    Get a taste for Chicago’s most famous food in one of the city’s most historic neighborhoods

    Discover why locals have so much passion for their Chicago-style classics
    from
    $102.30 USD
  • Amazing Lakefront Segway Tour in Chicago
    18 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $75.00 USD
    Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have the experience of a lifetime!
    from
    $75.00 USD
  • 2-Hour Haunted Segway Tour of Chicago
    16 reviews Chicago
    Free Cancellation
    Taking Safety Measures
    from $75.58 USD
    Learn about Chicago’s haunted past and see its mysterious sights as you glide through the city on a segway at night. Venture through the dark with your local guide, and see alleys, hotels, and sites of some of the most gruesome disasters and murders in Chicago’s history. During your spooky adventure through the city, you’ll also see Chicago's famous landmarks lit up in glistening lights.

    Join in the Halloween fun all October long! Costumed guides and ghoulish tales--this haunting good-time is not to be missed!
    from
    $75.58 USD