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Top Chicago Travel & Transportation Services

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100 results | All Chicago Tours

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Private Arrival Transfer from Chicago Airports (ORD) (MDW)

Private Arrival Transfer from Chicago Airports (ORD) (MDW)

star-3.5
145
Ensure a hassle-free arrival at Chicago O'Hare International Airport (ORD) or Midway Airport (MDW) with this private transfer service to your downtown Chicago hotel. Take the stress out of finding a taxi at Chicago's busy airports and book a private vehicle in advance. You'll travel in style by luxury sedan or SUV that can accommodate up to five passengers.
More
  • 1 hour
  • Free Cancellation
From
US$89.60
per group
From
US$89.60
per group

Private Arrival Transfer from Chicago Airports ORD Or MDW

Private Arrival Transfer from Chicago Airports ORD Or MDW

star-3.5
48
Worried about navigating public transportation, or finding your own way to your hotel upon arriving in Chicago? Leave all the logistics to your driver instead—and enjoy a stress-free experience—when you book a private transfer service from either O’Hare or Midway International Airports. Meet your driver after grabbing your bags, hop aboard your air-conditioned vehicle, and relax as you’re whisked straight to your destination.
More
  • 45 minutes to 1 hour
  • Free Cancellation
From
US$45.00
Price varies by group size
From
US$45.00
Price varies by group size

Private Departure Transfer to Chicago Airports (ORD)(MDW)

Private Departure Transfer to Chicago Airports (ORD)(MDW)

star-3.5
72
Arrange for a stress-free ride to O'Hare International Airport (ORD) or Midway Airport (MDW) with this private transfer service. Meet your professional chauffeur at your downtown hotel and relax on the journey to the airport in a private sedan or minivan (depending on the size of your group). Reach the airport relaxed and in time for your flight!
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  • 1 hour
  • Free Cancellation
From
US$89.60
per group
From
US$89.60
per group

Private 14-Pax Mercedes Exec.Sprinter from or to Chicagoland Airport and Suburbs

Private 14-Pax Mercedes Exec.Sprinter from or to Chicagoland Airport and Suburbs

star-5
3
Don't worry about navigating public transit or long taxi lines—and take the stress out of your Chicago arrival and departure—with this private airport transfer service. Depending on your needs and group size, you can book a limousine or Mercedes Executive Sprinter, and can choose between one-way and round-trip packages to either O'Hare International Airport or Midway International Airport. Whichever you pick, enjoy a seamless, worry-free way to travel.
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  • 30 minutes
  • Free Cancellation
From
US$228.94
per group
From
US$228.94
per group

O'Hare Airport (Curbside) To Chicago, Luxury Private Sedan, All Inclusive

O'Hare Airport (Curbside) To Chicago, Luxury Private Sedan, All Inclusive

star-4.5
28
Skip the hassle of long taxi lines or crowded airport shuttles and treat yourself to a VIP arrival in Chicago. During this one-way, private car service, you’ll travel comfortably in climate-controlled, newer model sedan with driver to your downtown hotel accommodation. One-way rides include curbside pickup outside the arrivals hall.
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  • 30 minutes to 1 hour
  • Free Cancellation
From
US$133.00
per group
From
US$133.00
per group

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
9672
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
  • Free Cancellation
From
US$46.87
From
US$46.87

Executive Airport transfer Sedan

Executive Airport transfer Sedan

star-5
2
Don't worry about finding your own way to or from the airport: with a private airport transfer service, you can navigate Chicago without worry. Choose between various luxury vehicle options, including an executive sedan, first-class sedan, and SUV, and meet your driver directly at your Chicago address or at your arrival gate. Then, enjoy a stress-free ride through the Windy City directly to your destination.
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  • 30 to 45 minutes
  • Free Cancellation
From
US$140.54
per group
From
US$140.54
per group

Private Transfer from Chicago (ORD) Airport to Chicago City

Private Transfer from Chicago (ORD) Airport to Chicago City

Take the worry out of your arrival to Chicago (ORD) Airport and pre-book a private transfer to suit your group size (up to 14 people). Avoid the long lines for taxis on arrival, and travel in the comfort of a Premium car or minivan.
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  • 35 minutes
  • Free Cancellation
From
US$99.86
per group
From
US$99.86
per group

360 CHICAGO Observation Deck Admission (Hancock Center)

360 CHICAGO Observation Deck Admission (Hancock Center)

star-4
419
Tower above the Windy City’s world-famous skyline with admission to 360 Chicago (John Hancock Observatory). Ascend 94 stories to the observation deck of one of the tallest buildings in North America aboard its lightning-fast elevator. Then check out bird’s-eye views of landmarks like the famous Willis (Sears) Tower and the lakefront shoreline, and enjoy a variety of educational exhibits on site. Upgrade your ticket to include TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. Or, choose the Sun and Stars package for two visits to the observation deck within 48 hours. With mobile tickets, simply scan your phone for direct entry into 360 Chicago.
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  • 1 to 4 hours
  • Free Cancellation
From
US$30.00
From
US$30.00

Chicago Crime and Mob Bus Tour
Likely to Sell OutLikely to Sell Out

Chicago Crime and Mob Bus Tour

star-4.5
1700
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.
More
  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
US$46.00
From
US$46.00

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
1313
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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  • 1 hour
  • Free Cancellation
From
US$44.99
From
US$44.99

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
3538
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.
More
  • 2 hours
  • Free Cancellation
From
US$35.00
From
US$35.00

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
2816
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
US$42.00
From
US$42.00

Chicago CityPASS

Chicago CityPASS

star-4.5
380
Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Shedd Aquarium, Skydeck Chicago, and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers. Attractions may be required to verify proof of full COVID-19 vaccination (14 days past final vaccine dose) before allowing entry. Please review attraction requirements before visiting Chicago.
More
  • 9 days
From
US$114.00
From
US$114.00

Lake Michigan Sightseeing Cruise
Likely to Sell OutLikely to Sell Out

Lake Michigan Sightseeing Cruise

star-4.5
530
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.
More
  • 40 minutes
  • Free Cancellation
From
US$28.34
From
US$28.34

Chicago Full Day Bike Rental

Chicago Full Day Bike Rental

star-5
43
Discover Chicago's many delights from the comfort of two wheels. Simply pick up your full-day bike rental with lock, map and helmet and start exploring, either solo or with friends. Make your way through Millennium Park and to historic Wrigley Field, stop for a visit at Navy Pier or spend a couple hours watching sea turtles, penguins and even a piranha at Shedd Aquarium. You get to tour Chicago independently at your own pace and leisure without having to deal with parking or public transit.
More
  • 1 day
  • Free Cancellation
From
US$29.99
From
US$29.99

Chicago City to Chicago Midway Airport (MDW) - Departure Private Transfer

Chicago City to Chicago Midway Airport (MDW) - Departure Private Transfer

Book your Private Departure Transfer from Chicago hotel or address to Chicago Midway Airport (MDW). Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door airport transfer. Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination. • Meeting with a Nameplate • We track your Flight • Door-to-door Service • No Hidden Charges • Clean cars & Professional drivers
More
  • 30 minutes
  • Free Cancellation
From
US$43.89
From
US$43.89

Chicago Midway Airport (MDW) Airport Hotel Shuttle

Chicago Midway Airport (MDW) Airport Hotel Shuttle

star-3
1
If Your Flying Into or Out Of The City, Allow The Chiefton Group To Meet You There or Get You There… Get Curbside Pick Up / Drop Off Service. Enjoy The Scenic Ride From and/or The Scenic Ride Back to The Airport.
More
  • 1 hour
  • Free Cancellation
From
US$94.00
per group
From
US$94.00
per group

Private Transfer from Chicago City to Chicago Airport ORD by luxury car or SUV

Private Transfer from Chicago City to Chicago Airport ORD by luxury car or SUV

Why spend your precious time waiting in long shuttle or taxi lines. Avoid the language barrier and currency exchange. Travel in style from your Hotel in Chicago City Center to O'Hare Airport ORD by private vehicle and reach your final destination relaxed and refreshed.
More
  • 45 minutes
  • Free Cancellation
From
US$85.94
Price varies by group size
From
US$85.94
Price varies by group size

From/to Chicago O´Hare International Airport: Private Round Trip Transfer

From/to Chicago O´Hare International Airport: Private Round Trip Transfer

star-5
3
Ensure hassle-free O'Hare International Airport pickup with this Private Round trip transfer. Book your drop off or pick up from your hotel in Downtown Chicago or surroundings. * Our drivers can track your flight, so they can be on time for your airport pick -up. Free waiting for any flight delay issues. * 24/7 Help Center for any changes/updates to your ride * Meet & Greet at arrival hall *Cancel at least 24 hours prior to your service and get a full refund *Wide array of vehicles according to your needs *All-inclusive fare
More
  • 30 minutes to 1 hour 30 minutes
  • Free Cancellation
From
US$189.00
per group
From
US$189.00
per group

Private Transfer from Chicago O'Hare Airport ORD to Chicago City by car or SUV

Private Transfer from Chicago O'Hare Airport ORD to Chicago City by car or SUV

Why spend your precious time waiting in long shuttle or taxi lines. Avoid the language barrier and currency exchange. Travel in style from Chicago Airport ORD to your Hotel in Downtown Chicago by private vehicle and reach your final destination relaxed and refreshed.
More
  • 45 minutes
  • Free Cancellation
From
US$85.94
Price varies by group size
From
US$85.94
Price varies by group size

Private Vacation Photography Session with Local Photographer in Chicago

Private Vacation Photography Session with Local Photographer in Chicago

star-5
1
Flytographer Private Vacation Photo Shoot Connect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot. Get insider tips on the best things to do in Chicago, including where to eat & what to see from your vacation photographer. Return from your trip with beautiful, high-quality vacation photos — the best souvenir ever. We specialize in: - honeymoons - family trips - engagements - anniversaries - romantic getaways - multi-generational trips - babymoons - solo travellers - and just because! With over 10,000 5-star reviews, Flytographer is the global leader in vacation photography and has captured over 3 million memories for travellers across six continents. We’ve been featured across A-list media, including Conde Nast Traveler, Oprah, Forbes, Travel + Leisure, New York Times, BRIDES, Martha Stewart Weddings, InStyle Magazine, Elle, Buzzfeed, Refinery29, Huffington Post, & many more.
More
  • 1 hour
  • Free Cancellation
From
US$299.00
per group
From
US$299.00
per group

Private Sedan Transfer from Chicago Downtown to O`Hare airport

Private Sedan Transfer from Chicago Downtown to O`Hare airport

star-5
8
Don’t worry about the hassle of getting to and from Chicago’s O’Hare International Airport: start or end your trip on a relaxed note with this private transfer service. Avoid navigating public transit or long taxi lines, and instead meet your driver at your hotel or at the airport, and hop aboard your luxury vehicle. Door-to-door service will whisk you directly to where you want to go with no added stress.
More
  • 30 minutes to 1 hour 30 minutes
  • Free Cancellation
From
US$160.00
per group
From
US$160.00
per group

Transfer in private vehicle from Chicago City - Chicago Airport (ORD)

Transfer in private vehicle from Chicago City - Chicago Airport (ORD)

Don’t worry about nabbing a taxi or timing a rideshare to get to Chicago O’Hare (ORD). With this professional driving service, your personal driver will meet you right at your preferred location, assist with your luggage, and get you to the airport safely, comfortably, privately, and right on time. You and your crew—up to 3 people—will arrive refreshed and in exclusive, VIP style.
More
  • 1 hour
  • Free Cancellation
From
US$60.67
Price varies by group size
From
US$60.67
Price varies by group size

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These hidden gems in Chicago may have limited interaction with crowds:

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