Private Transfer from Chicago City to Chicago (MDW) Airport
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Location: Chicago, USA
Price: $152.80 per group (up to 3)
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SimilarExperiences: Chicago River Architecture Tour, Chicago River Experience, Chicago Architecture River Cruise, 360 Chicago Observatory, Chicago Sunset Cruise
A Comfortable, Hassle-Free Way to Reach Midway Airport

If you’re leaving Chicago and want to avoid the chaos of hailing a cab or navigating public transit with luggage, this private transfer service might be just what you need. For $152.80 per group (up to three people), you get a door-to-door service that takes you from your hotel or private residence directly to Chicago’s Midway International Airport. The ride lasts roughly 35 minutes, depending on traffic, which isn’t much longer than waiting in line for a taxi — but it’s a lot more relaxing.
What we love about this experience is the personalized meet-and-greet service, meaning your driver will come right to your hotel lobby or your home, helping you start your journey with less stress. Plus, you get your own chauffeured sedan or minivan, ensuring your group travels comfortably and privately. And because it’s a private transfer, only your group will be in the vehicle, making it ideal for groups of up to 14 people for larger parties.
One potential consideration is the price — while $152.80 might seem steep compared to a taxi or ride-share, it’s often comparable to the total cost for multiple ride-shares and can be worth it for the convenience. However, note that excess luggage charges could apply if you bring oversized bags, so packing smartly is advisable.
This service is best suited for travellers who value ease over cost and prefer a smooth, private experience especially at the end of a trip. Whether you’re on a family vacation, a small group of friends, or traveling with colleagues, it simplifies your departure and ensures you arrive at Midway on time and relaxed.
Key Points

- Convenient door-to-door service from hotel or private address to Midway Airport.
- Private ride for groups up to 14, offering comfort and exclusivity.
- Meet-and-greet service simplifies the start of your journey.
- Approximate 35-minute transfer depending on traffic, making it a quick, reliable option.
- All taxes, tolls, and gratuities included, so no hidden costs.
- Booking in advance usually 17 days ahead ensures availability and peace of mind.
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A Closer Look at What to Expect

When you book this private transfer, you’re paying for comfort, convenience, and the peace of mind that everything’s organized ahead of time. The process is straightforward: just confirm your pickup point, whether it’s your hotel lobby or a private residence, and your driver will be ready to meet you.
The ride itself is in a premium vehicle — either a sedan or a van — based on your group size. This means plenty of space for your luggage and a smooth, climate-controlled environment. While the transfer is nonstop, your driver will navigate Chicago’s roads efficiently, aiming to get you to Midway within about half an hour.
The meet-and-greet service adds a personal touch; you’ll be welcomed by your driver, making the departure stress-free. This is especially helpful if you’re unfamiliar with the city or have tight schedules.
Traffic can influence your travel time, so it’s wise to plan accordingly, especially during rush hours. The service’s 60-minute waiting window after your flight lands offers some flexibility, but if your flight is delayed, a quick call to their assistance can keep things running smoothly.
Why This Transfer Is a Good Value

At first glance, $152.80 might seem like a hefty price. But when you break down what you’re getting — door-to-door service, a private vehicle, all taxes and tips, and a reliable, professional chauffeur — it becomes clear this is a good deal for peace of mind, especially if you’re traveling with luggage or in a group. You avoid the uncertainty of hailing a taxi, or the hassle of coordinating multiple ride shares, and you start your airport journey relaxed and prepared.
For travelers with tight schedules or those arriving late or early, this service guarantees a predictable, comfortable transfer without waiting in line or worrying about public transportation delays.
Who Should Consider This Service?
This private transfer is perfect for busy travelers, families, or small groups who want a seamless travel experience. It’s especially suited for those who value privacy and comfort at the end of their stay or before an early flight. If you’re traveling with large luggage or simply dislike the hassle of navigating Chicago’s busy streets with bags, this service offers a calm, organized exit.
However, if you’re traveling solo or on a very tight budget, you might prefer a cheaper ride-share option, keeping in mind that you’d sacrifice some of the personalized service and convenience.
The Sum Up
For those heading to Midway Airport from Chicago’s city center, this private transfer offers a reliable, comfortable alternative to taxis or shared rides. It’s well-suited for travelers who appreciate personalized service, door-to-door convenience, and a stress-free start or end to their journey. While the price might seem high for some, the value of predictability, comfort, and time savings makes it worthwhile, especially for groups or travelers with lots of luggage.
If you want peace of mind and a smooth, private ride that minimizes stress and maximizes comfort, this service is deserving of serious consideration. It’s a practical choice for those who prioritize their time and comfort over a few extra dollars.
Prefer personalized experiences? Here are other private options we've covered in Chicago
- Chicago: Private Architecture Tour – 3 or 6 Hours
- Chicago Downtown Highlights Private Walking Tour
- Chicago: Private Guided Tour of Chicago Suburbs Movie Sites
- Chicago Highlights Private Walking Tour With A Guide
- Echoes of Elegance: Chicago Private Architecture Tour
- Chicago: Private custom tour with a local guide
FAQ
Is this transfer suitable for large groups?
Yes, the service can accommodate groups of up to 14 people, making it a flexible option for small to medium-sized parties.
How far in advance should I book?
It’s recommended to book about 17 days in advance, but you can make arrangements earlier or closer to your departure date, subject to availability.
What if my flight is delayed?
The driver will wait up to 60 minutes after your plane lands. If you’re delayed longer, contact the assistance center to inform them.
Are tips included in the price?
Tips and gratuities are included in the booking price, ensuring no surprises when paying.
What types of vehicles are used?
Depending on your group size, you’ll travel in either a premium sedan or a premium van, both offering comfort and space.
Are there any extra charges I should be aware of?
Extra charges might apply if you bring oversized or additional luggage, as only one standard suitcase per passenger is included in the price.
This private transfer service offers a straightforward, comfortable way to conclude your Chicago trip, especially if you value ease, privacy, and reliability. Whether you’re flying out after a city stay or just want a stress-free way to reach Midway, it’s an experience that can make your journey smoother and more enjoyable.
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