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Top Chicago Travel & Transportation Services

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We’re committed to helping you feel confident as you get back out there. Check out our flexible cancellation policies and learn what steps operators are taking to keep you safe. As conditions evolve, check local regulations for the latest information.

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145 Chicago Travel & Transportation Services | All Chicago Tours

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Chicago Bike RentalBike Rentals

Chicago Bike Rental

star-5
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.
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  • 1 day
  • Free Cancellation
  • Taking safety measures
From
US$25.99
From
US$25.99
Taking safety measures

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

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

star-3.5
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.
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  • 1 hour
  • Free Cancellation
From
US$80.00
per group
From
US$80.00
per group

Transfer to Chicago Premium OutletsDay Trips

Transfer to Chicago Premium Outlets

star-5
Spend a day shopping at the premier name brand shopping destination in the Chicago metro area, Chicago Premium Outlets. Featuring prominent international and American designer brands at discounted prices, you'll find deep discounts at stores like Nike, Armani, Calvin Klein, Kate Spade, 7 for All Mankind, and much more inside the outlet mall. The tour includes pickup and drop-off from Chicago hotels and five hours of on-the-ground shopping time.
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  • 7 hours
  • Free Cancellation
From
US$288.00
per group
From
US$288.00
per group

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

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

star-3.5
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$80.00
per group
From
US$80.00
per group

Hidden History in Chicago's Gold Coast Walking Audio Tour by VoiceMapPrivate Sightseeing Tours

Hidden History in Chicago's Gold Coast Walking Audio Tour by VoiceMap

star-4.5
Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating guided tour of hidden historical spots in Chicago's gilded Gold Coast. Peep behind the gates of the original Playboy Mansion, walk along a wooden block-paved alley, sip a Faster Pussycat in Chicago's oldest piano bar and more as you enjoy a delightful walk through time in this exclusive Chicago neighborhood. The starting point is the Chicago History Museum, located at 1601 N. Clark Street. The tour is ready whenever you are and the audio plays automatically at exactly the right time and place using your smartphone's GPS and the VoiceMap mobile app, which also works offline.
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  • 50 minutes
From
US$5.34
From
US$5.34

A Most Magnificent Mile TourHistorical Tours

A Most Magnificent Mile Tour

star-4.5
Enjoy a walking tour of Chicago’s Magnificent Mile. Located in the heart of downtown, this scenic stretch is beloved by locals and tourists alike for its great shopping and rich history. Visit a Water Tower that survived the Chicago Fire and gave its name to one of the city’s most elegant shopping centers. See a church frequented by Abraham Lincoln and other historic highlights dating back over 344 years.
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  • 2 hours
  • Free Cancellation
From
US$40.00
From
US$40.00

Private Arrival Transfer from Chicago O'Hare Airport to Chicago City Private Transfers

Private Arrival Transfer from Chicago O'Hare Airport to Chicago City

Don't go through all the hassle of waiting in a long taxi or shuttles queues and use our private, door to door airport transfer from Chicago O'Hare International Airport. A professional driver will meet you in the arrivals hall holding a plate with your name and take you directly to a designated place in Chicago. Choose from two comfortable vehicles to suit your group size: sedan up to 3 people and minivan 4-7 passengers. Thanks to the car size variety, it is an ideal choice for individuals, families and bigger groups. Hope you will enjoy your stay in Chicago!
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
US$75.16
Price varies by group size
From
US$75.16
Price varies by group size
Taking safety measures

Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMapPrivate Sightseeing Tours

Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMap

star-1
Take a walk back in time through the history of Chicago's Loop on this app-enabled tour. After downloading the app and tour to you smartphone, you and your party will listen to author Amy Bizzarri, an author and expert in Chicago history, as she leads you through walking tour of the city. The GPS-enabled tour will trigger commentary at just the right times, and you can stop and start whenever you like for a flexible experience that lets you move at your own pace. Highlights include Daley Plaza, the Chicago Theater, Berghoff Restaurant, and the Art Institute of Chicago.
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  • 50 minutes
From
US$5.34
From
US$5.34

Private Airport Round-Trip Transfer: O'Hare Airport to Chicago CityPrivate Transfers

Private Airport Round-Trip Transfer: O'Hare Airport to Chicago City

Don't go through all the hassle of waiting in a long taxi or shuttles queues and use our private, door to door airport transfer to Chicago O'Hare International Airport. A professional driver will meet you in the arrivals hall (arrival transfer) or in the hotel lobby (departure transfer) and take you directly to the point. Choose from two comfortable vehicles to suit your group size: sedan up to 3 people and minivan 4-6 passengers. Thanks to the car size variety, it is an ideal choice for individuals, families and bigger groups. Hope you will enjoy your stay in Chicago!
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
US$150.31
Price varies by group size
From
US$150.31
Price varies by group size
Taking safety measures

Private Departure Transfer from Chicago City to O'Hare International AirportPrivate Transfers

Private Departure Transfer from Chicago City to O'Hare International Airport

Don't go through all the hassle of waiting in a long taxi or shuttles queues and use our private, door to door airport transfer to Chicago O'Hare International Airport. A professional driver will meet you in the hotel lobby and take you directly to the terminal you departing from. Choose from two comfortable vehicles to suit your group size: sedan up to 3 people and minivan 4-6 passengers. Thanks to the car size variety, it is an ideal choice for individuals, families and bigger groups. Hope you will enjoy your stay in Chicago!
More
  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
US$75.16
Price varies by group size
From
US$75.16
Price varies by group size
Taking safety measures

Private Luxury 9-Pax Limo Transfer from or to Chicagoland Airport and SuburbsPrivate Transfers

Private Luxury 9-Pax Limo Transfer from or to Chicagoland Airport and Suburbs

Enjoy convenient private transportation between Midway or O'Hare International Airport and your hotel in the comfort of a private 4 door 9 Passenger Stretch Limousine. Airport transfer Multiple times offered throughout the day.
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  • 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$151.20
per group
From
US$151.20
per group
Taking safety measures

Executive Airport transfer SedanPrivate Transfers

Executive Airport transfer Sedan

For luxury Chicago limo transportation, Ryde Luxury Limousine is the trusted provider for thousands of clients. We provide the best in luxury transportation with affordable rates, professional and friendly chauffeurs, safe and comfortable vehicles, and a focus on customer service. Our limo service in the city of Chicago is the top choice if you need airport transportation, want a special night out, going sightseeing in the beautiful windy city, or need daily business transportation. Our limo services get you to your destination safely, efficiently, and comfortably.
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  • 30 to 45 minutes
  • Free Cancellation
From
US$104.54
per group
From
US$104.54
per group

Chicago O'Hare International Airport One Way Airport TransferPort Transfers

Chicago O'Hare International Airport One Way Airport Transfer

star-2
If you are Traveling Into or Departing from Chicago, Illinois through The Chicago O'Hare International Airport, Get Curbside Pick Up / Drop Off Service. Enjoy The Scenic Ride From and/or The Scenic Ride Back to The Airport. YOU MUST BE IN THE DOWNTOWN Area of Chicago, IL.  The Following Zip Codes are Associated With The Area(s) valid for this offer: 60601, 60602, 60603, 60604, 60605, 60606, 60607, 60616
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
US$100.00
per group
From
US$100.00
per group
Taking safety measures

Chicago Airport Transfers : O'Hare Airport ORD to Chicago City in Luxury SUVPrivate Transfers

SPECIAL OFFER

Chicago Airport Transfers : O'Hare Airport ORD to Chicago City in Luxury SUV

Chicago Airport Transfer Service aims to achieve the very highest possible standards possible for all its passengers. Whether you’re stepping out of or you need to be dropped off at Chicago O'Hare Airport ORD after a holiday, our service will get you there relaxed, recharged and ready with an airport transfer taxi service. Traveling from airports to your hotel with family or colleagues? A  Luxury SUV Car can be shared by to up 6 people together.
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  • 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$113.91
US$119.91
US$6.00 savings
Price varies by group size
From
US$113.91
US$119.91
US$6.00 savings
Price varies by group size
Taking safety measures

Private 14-Pax Mercedes Exec.Sprinter from or to Chicagoland Airport and SuburbsAirport & Hotel Transfers

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

Enjoy convenient private transportation between Midway or O'Hare International Airport and your hotel in the comfort of a private 14 Passenger. Mercedes Sprinter Executive Van. Thank you for choosing us. If you have more than 14 checked bags, we recommend our 24 passenger at an additional cost of $62.50 1 way or $125.00 round trip weekday, or $93.75 1 way or $187.50 round trip weekend. This additional cost can be paid directly to M&M by credit card in advance or cash to driver at time of pick up, prior to leaving location.
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  • 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$228.94
per group
From
US$228.94
per group
Taking safety measures

Chicago Riverwalk Self-Guided Walking TourPrivate Sightseeing Tours

Chicago Riverwalk Self-Guided Walking Tour

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city's 'Second Lakefront', the Riverwalk contains restaurants during the summer months, seating areas to relax, boat rentals, and theater-style seating for various performances. Other attractions along the Riverwalk include the Vietnam Veterans Memorial Plaza, and the McCormick Bridgehouse & Chicago River Museum and if you are lucky enough, see a bridge lift from inside the bridge house. This self-guided audio tour allows you to explore Chicago's wonders with maximum flexibility and value. ----- We’ll email or text you your unique password within 30 minutes after you book the tour. All audios play automatically based on location.
More
  • 1 to 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$6.00
From
US$6.00
Taking safety measures

Private Airport Round-Trip Transfer: Midway Airport to Chicago CityPrivate Transfers

Private Airport Round-Trip Transfer: Midway Airport to Chicago City

Don't go through all the hassle of waiting in a long taxi or shuttles queues and use our private, door to door airport transfer to Chicago Midway International Airport. A professional driver will meet you in the arrivals hall (arrival transfer) or in the hotel lobby (departure transfer) and take you directly to the point. Choose from two comfortable vehicles to suit your group size: sedan up to 3 people and minivan 4-6 passengers. Thanks to the car size variety, it is an ideal choice for individuals, families and bigger groups. Hope you will enjoy your stay in Chicago!
More
  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
US$127.64
Price varies by group size
From
US$127.64
Price varies by group size
Taking safety measures

Arrival Private Transfer Chicago O'Hare Airport ORD to Chicago City by SUVPrivate Transfers

Arrival Private Transfer Chicago O'Hare Airport ORD to Chicago City by 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.
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  • 45 minutes
  • Free Cancellation
From
US$95.83
Price varies by group size
From
US$95.83
Price varies by group size

Private Transportation from Midway Airport (Meet&Greet included)Private Transfers

Private Transportation from Midway Airport (Meet&Greet included)

star-5
We are highly rated premier transportation company , our fleet is no more than 2 years old , all our chauffeurs are trained , screened and insured by commercial insurance $35000.00 to $1,000,000.00 . We are to make sure that your experience will stress free to be transported in a cozy comfortable SUV.
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  • 45 minutes
  • Free Cancellation
From
US$118.00
per group
From
US$118.00
per group

Hire Photographer, Professional Photo shoot - ChicagoPhotography Tours

Hire Photographer, Professional Photo shoot - Chicago

star-5
Glamorous professional photo shoot in unique Chicago locations. The Photo Experience will create amazing photo memories from your holiday. You will be able to see undiscovered locations, and get the best photo story from your Chcicago visit. We can tailor each photo shoot to meet your requirements. Our Photoshoots are ideal for any Tourists - Solo Traveler - Couples - Groups - Hen/Bachelorette & Stag/Bachelor Parties - Families - Secret proposal/Engagement - Honeymoon - Experienced Influencers and Models - New Influencers and Models What's Included: A Private online viewing gallery - 1 hour = 20 professionally edited photos* - 2 hour = 30 professionally edited photos* - 3 hour = 40 professionally edited photos* - 4 hour = 50 professionally edited photos* * same set of images - A unique location professional shoot experience for your holiday - DELIVERY - Up to 14 days after photoshoot. What's Excluded: - Transportation - Entry fees
More
  • 1 hour
  • Free Cancellation
From
US$134.50
Price varies by group size
From
US$134.50
Price varies by group size

Chicago Departure Private Transfers from Chicago to Airport ORD in Luxury SUVPrivate Transfers

Chicago Departure Private Transfers from Chicago to Airport ORD in Luxury SUV

Chicago Airport Transfer Service aims to achieve the very highest possible standards possible for all its passengers. Whether you’re stepping out of or you need to be dropped off at Chicago O'Hare Airport ORD after a holiday, our service will get you there relaxed, recharged and ready with an airport transfer taxi service. Traveling from airports to your hotel with family or colleagues? A  Luxury SUV Car can be shared by up to 6 people together.
More
  • 30 minutes
  • Free Cancellation
From
US$119.91
Price varies by group size
From
US$119.91
Price varies by group size

30 Minute Private Vacation Photography Session with Local Photographer in ChicagoPhotography Tours

30 Minute Private Vacation Photography Session with Local Photographer in Chicago

Go beyond the selfies and smartphone shots—and walk away from your Chicago vacation with professional-quality photos—when you book this private photo shoot experience. Meet your professional photographer guide at a time and place of your choosing and practice your poses: they’ll capture upwards of 15 high-resolution digital photos of you and your party, with Chicago’s majestic scenery as your backdrop. Your guide will also share insider knowledge and tips about the Windy City’s key attractions and eateries.
More
  • 30 minutes
  • Free Cancellation
From
US$272.44
per group
From
US$272.44
per group

Private Arrival or Departure Transfer: Chicago O'Hare AirportPrivate Transfers

Private Arrival or Departure Transfer: Chicago O'Hare Airport

Use a door to door transfer, a comfortable and hassle free service that will allow you to enjoy your journey from the moment you arrive to the beautiful city of Chicago. Your driver will be waiting for you in Chicago O'Hare International Airport arrival hall and will take you straight to your centrally located hotel in Chicago.
More
  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
US$75.16
Price varies by group size
From
US$75.16
Price varies by group size
Taking safety measures

Walking Tour: Chicago's Prairie District - Street of the ElitePrivate Sightseeing Tours

Walking Tour: Chicago's Prairie District - Street of the Elite

Get a sense for how Chicago's wealthiest residents lived around the turn of the century and what remains today. This unique Chicago tour begins at the Cermack-McCormick Green Line Station. The Prairie District is home to many historic sites such as Motor Row, the former Chess Records, the oldest house in the city, the landmark Second Presbyterian Church and the Glessner House. After enjoying some traditional Chicago deep dish pizza, we'll end
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$60.00
From
US$60.00
Taking safety measures


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(888) 651-9785
(888) 651-9785