The 15 Best Airport Transfers in Chicago
Travelers arriving in Chicago quickly realize that getting from the airport to the city isn’t complicated—if you choose the right transfer. Chicago’s airports, O’Hare International (ORD) and Midway (MDW), are major hubs with excellent transportation options, but navigating the chaos can be daunting. That’s where pre-booked airport transfers come in: they save you time, reduce stress, and often add a touch of comfort after a long flight. Whether you’re traveling solo, with a group, or carrying lots of luggage, there’s an option tailored to your needs.
Chicago’s public transit is extensive, but often impractical for quick arrivals with luggage, especially if you’re pressed for time. Taxis and ride-shares are plentiful, but prices can vary, and wait times are unpredictable during busy hours. Pre-arranged private transfers provide fixed pricing, personalized service, and peace of mind, making your first impression of the city a smooth one. For a city with more than enough skyscrapers and a bustling airport scene, planning ahead pays off.
Quick Overview
This list includes a variety of airport transfer options suited for different needs and budgets. For those who prefer a private, door-to-door experience, options like the One-Way Private Curbside Midway Airport Transfer and Curbside Sedan Transfer from O’Hare to Downtown Chicago stand out for their comfort and simplicity. For travelers seeking luxury and extra safety, the Luxury SUV transfer and Meet and Greet options deliver premium service. Budget-conscious travelers might prefer shared services like the Chicago to Milwaukee bus transfer, while those with flexible schedules can consider multi-stop or round-trip options. Read on to find the best fit for your trip.
1. One-Way Private Curbside Midway Airport Transfer
If you’re arriving at Midway and want to start your trip stress-free, this private curbside transfer is a solid choice. Upon landing, you just text your driver from the arrivals area, meet outside, and enjoy a direct ride to your hotel or destination in Chicago. No shared shuttles, no waiting in line—just a straightforward way to start your visit.
This service is highly rated (5.0/5 from 12 reviews) for its friendly drivers and clean, luxurious vehicles. The typical duration is 30 minutes to an hour, depending on traffic and your destination. The cost is $133 for groups up to three, which balances comfort with affordability. Reviewers mention prompt pickup and a driver who shares good local tips. This is ideal for first-time visitors who want reliability and personal service.
Bottom Line: Excellent for Midway travelers who prioritize convenience and comfort without breaking the bank.
2. Curbside Sedan Transfer from O’Hare Airport to Downtown Chicago
For those landing at O’Hare and heading into the heart of the city, this private curbside sedan transfer offers a hassle-free experience. After collecting your luggage, just call dispatch, and a driver arrives curbside in about 10 minutes. It’s an easy way to avoid the long taxi lines and unpredictable Uber waits.
At $190 for up to two people, this service guarantees a flat fee, so no surprise charges. The ride typically lasts 30 minutes to 1 hour and 30 minutes, depending on traffic. Customers praise the personalized service and prompt communication, making it an excellent choice for business travelers or anyone craving direct, private transportation.
Bottom Line: Perfect for couples or small groups wanting a quick, luxurious ride into Chicago’s city center.
3. One-Way Private Curbside Midway Airport Transfer by SUV
If your group is larger or you simply prefer the space and style of an SUV, this top-rated Chicago service fits the bill. With a 5-star rating (from 4 reviews), the SUV transfer offers comfort for groups of up to six at $155. You’ll meet your driver curbside at Midway and enjoy a direct trip to your destination.
This company boasts over a decade of experience, fully insured vehicles, professional chauffeurs with FBI background checks, and GPS tracking. It’s perfect for families or groups wanting a premium experience with high safety standards. Guests mention the professional staff and clean, luxurious vehicles as key strengths.
Bottom Line: An excellent option for larger groups seeking a reliable, upscale transfer from Midway.
4. Round Trip Private Transfer ORD Airport to Chicago City Oak Brook
This round-trip service simplifies your entire Chicago stay by booking both arrivals and departures in one go. Starting at $91.66 per person, it offers flight tracking, so your driver waits if your flight is delayed, and they’ll meet you either at O’Hare or your hotel. The trip typically takes 20 to 40 minutes, depending on traffic and destination.
Customers appreciate the timely service and the included free waiting time (up to 60 minutes at the airport). This service is flexible, serving destinations from downtown Chicago to Oak Brook or Milwaukee. It’s an excellent choice for travelers wanting peace of mind and a seamless transfer both ways.
Bottom Line: Best suited for visitors planning a full Chicago visit with round-trip convenience and reliable scheduling.
5. Chicago Airport Transfer: Chicago to O’Hare Airport ORD in Luxury SUV
If luxury and safety are your priorities, this premium SUV transfer provides a disinfected vehicle, sanitizer, and a professional chauffeur who assists with luggage. The vehicle is sanitized before each ride, and the driver greets you with a name sign, opening doors and closing them for you—a step above typical transfers.
Priced at $213.94 per person for approximately 30 minutes, this service is ideal for travelers valuing comfort and discretion. While more expensive, reviews highlight the safety precautions and attentive service, making it suitable for VIP arrivals or those with health concerns.
Bottom Line: A top-tier choice for travelers seeking a luxurious, safe, and private ride to O’Hare.
6. One-Way Private MDW Meet and Greet Luxury Airport Transfer
Arriving at Midway? This Meet and Greet service ensures a personalized arrival experience. Your driver will wait inside the baggage claim holding a sign, help with luggage, and escort you to a luxurious vehicle. Priced at $185 for groups up to six, it offers comfort and a personal touch.
Rated 5 stars, reviewers mention the friendly, helpful staff and the convenience of inside airport assistance. It’s perfect for travelers who want a stress-free start, especially after a long flight. The service’s professionalism makes it especially appealing for first-time visitors or those traveling with lots of luggage.
Bottom Line: The ideal choice for a personalized, stress-free arrival at Midway.
7. Curbside Sedan Transportation from O’Hare or Midway Airport to Downtown Chicago
This curbside sedan service prioritizes safety and reliability, with licensed drivers and well-maintained vehicles. At $159 for up to two passengers, it’s a straightforward, no-nonsense option for downtown transfers. The ride lasts roughly 30 to 90 minutes, depending on traffic and destination.
Guests consistently mention the professionalism of drivers and the convenience of meeting curbside, which is especially helpful for travelers with tight schedules. For those seeking a reliable, simple transfer, this service hits the mark.
Bottom Line: A safe, dependable choice for couples or pairs heading into Chicago.
8. Airport transfer between Chicago O’Hare and Milwaukee
For those making an extended trip or connecting between Chicago and Milwaukee, this bus transfer by Couch USA offers a budget-friendly option. With reclining seats, climate control, and a toilet onboard, it makes the 105-minute journey comfortable.
Rated 4.7/5 from 3 reviews, travelers appreciate the frequent schedules and helpful staff. The ticket’s validity of six months adds flexibility for planning. It’s well-suited for travelers who don’t mind a short bus ride and want to save money over private transfers.
Bottom Line: Great for budget-conscious travelers on a flexible schedule between Chicago and Milwaukee.
9. One-Way Private Airport Transfer by Sedan
This luxury sedan transfer offers a high-end experience with personalized service from Chicago airports to your hotel or vice versa. For $179, up to four people can enjoy a comfortable, private ride in a fully insured vehicle.
Reviewers mention efficient communication and clean, spacious cars, making it ideal for business travelers or anyone wanting a premium experience. The service is flexible, with options for pickup at the airport or your Chicago address.
Bottom Line: An excellent pick for those seeking a luxurious, hassle-free transfer.
10. Private Transfer ORD Airport to Chicago / Milwaukee / Oak Brook
This versatile transfer service covers multiple destinations, including Chicago, Milwaukee, and Oak Brook, for $45.83 per person. It’s available 24/7, with professional drivers ensuring on-time pickups and drop-offs.
Reviewers note punctuality and courteous drivers, making it a reliable choice for flexible travel plans. The comfortable, air-conditioned vehicles suit travelers who want a dependable ride without fuss.
Bottom Line: Suitable for travelers needing multi-destination transfers with flexible scheduling.
11. Private Transfer Chicago Airport to Chicago by Luxury Car or SUV
This luxury transfer promises style and comfort for Chicago-bound travelers. While it currently has no reviews, the service offers private vehicles that can be tailored to your needs, with a focus on comfort and discretion.
Ideal for business travelers or special occasions, this service emphasizes a high-end experience with personalized vehicle options. It’s more expensive but worth it if your priority is luxury and privacy.
Bottom Line: Best for travelers who want to arrive in style and comfort, regardless of budget.
12. Private One-Way Airport Transfer from O’Hare Airport to Chicago
For a seamless, private ride, this transfer guarantees reliable service from O’Hare to your Chicago accommodation. Priced at $91.31 for up to four people, it’s an efficient way to avoid lines and enjoy a comfortable trip.
Though reviews are currently unavailable, the focus on professional, private service suggests a dependable experience. It’s well-suited for travelers who value privacy and punctuality.
Bottom Line: An affordable, private option for smooth arrivals into Chicago.
13. Try find your better than us! Airport transfer in Chicago APT-HTL (ORD, MDW)
Offering a range of vehicle options like sedans, MPVs, mini vans, and buses, this service is flexible for groups of different sizes. Priced from $128.38, it emphasizes multilingual support and 24-hour emergency response.
While reviews are not available, the extensive fleet and variety of vehicle choices make this a compelling option for travelers needing customized transportation. It’s best suited for those with specific language needs or larger groups.
Bottom Line: Good for travelers seeking tailored, multilingual service with multiple vehicle options.
14. Private Transfer from Chicago (MDW) Airport to Chicago City
This private transfer service is designed for groups up to 14, offering a comfortable, premium car or minivan. Priced at $152.65, it’s ideal for large families or groups traveling together. The driver will meet you directly at the airport, making arrivals simple.
Reviews are not yet available, but the focus on group capacity and comfort makes it suitable for travelers with lots of luggage or traveling with children.
Bottom Line: Best for larger groups wanting a reliable, spacious transfer from Midway.
15. One-Way Private Meet and Greet Midway Airport Transfer by Sedan
This meet and greet option ensures you’re greeted inside the baggage claim with a sign and assisted with luggage. It costs $154 for groups up to three and is praised for its friendly, attentive staff.
It’s a great choice for travelers who want a personalized arrival experience with minimal stress. The service’s emphasis on inside airport assistance makes it perfect for first-timers or those with lots of luggage.
Bottom Line: Ideal for travelers seeking personalized, inside airport service at Midway.
How to Choose the Best Airport Transfer in Chicago
Picking the right transfer depends on your budget, group size, and comfort preferences. If you’re traveling solo or as a couple, a private sedan like the Curbside Sedan Transfer from O’Hare can be perfect. Larger groups or families should consider SUV transfers or round-trip services.
For those prioritizing luxury and safety, the Luxury SUV or Meet and Greet services are excellent options—especially if health precautions matter. Budget travelers should consider shared options like the bus transfer, which offers comfort without the high price.
Booking early is advisable during peak travel seasons, and always confirm pickup details and timings, especially for services with flight tracking or flexible scheduling.
Final Thoughts
Chicago offers a wide range of airport transfer options that cater to nearly every traveler’s needs—from budget-friendly bus rides to luxurious SUVs. For reliable, door-to-door comfort, the One-Way Private Curbside Midway Airport Transfer and Round Trip private service are top contenders. If you’re traveling in a larger group or want a premium experience, the Luxury SUV or Meet and Greet services make excellent choices.
Planning ahead and choosing the right transfer can turn your first impression of Chicago into a smooth, comfortable experience. Book early, compare your options, and enjoy your stay in the Windy City.