Top Chicago Travel & Transportation Services

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.

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.

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!

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.

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).

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.

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.

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.

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.

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.

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.

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.

Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.

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.

Capture the highlights of your Windy City visit—and walk away with a number of professionally taken portraits—on this private photo shoot experience. Meet your guide at a time and place that work best for you; you can also select your preferred duration and number of photos. Then, get ready to strike a pose: your guide will take a number of photos, and chronicle your special moments.

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.

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!

Enjoy an effortless start to your Chicago trip with this private transfer service from O’Hare International Airport. After landing, grab your luggage and meet your driver, who will be waiting for you directly at the terminal. Then, climb aboard your luxurious, air-conditioned vehicle: you can sit back and relax—and take in the Chicago scenery—as your driver whisks you directly to your destination.

Explore Chicago at your own pace on an independent bike tour. With your half-day bike rental, pedal along Lake Michigan and visit top Chicago attractions such as Lincoln Park, Navy Pier, Millennium Park, Wrigley Field and the Shedd Aquarium. This is a fun and active way to experience the city with the whole family, and you can enjoy the flexibility to create your own itinerary with the help of your provided map.

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.

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.

Book a round trip private transfer from/to Airport to your destination, service guaranteed once you make the booking. We will provide all information necessary to meet your driver at hotel or destination. • Meet and greet • Private transfer • 60 minutes waiting time at airport • 24 hours service (all day) • All costs included (taxes, fees, tolls, tips, etc…)

Make your Chicago vacation seamless when you book a private, round-trip airport transfer service from O’Hare International Airport. Begin your trip by meeting your driver at the airport and traveling via clean, comfortable vehicle directly to your local hotel. Later, enjoy a stress-free trip back to the airport, with pickup directly from your local accommodation. As this is a private transfer service, all timings are tailored to your flights and schedule.

Plan a smooth start to your time in Chicago with a private arrival transfer from the Chicago O'Hare International Airport (ORD) to your downtown Chicago hotel or residence. A professional chauffeur picks you up curbside at the airport arrivals deck in a clean, late-model luxury SUV, so there's no waiting for a ride share or a long, crowded shuttle ride.