Limo Service from Toronto to Chicago Midway Airport (MDW)
About This Route
The Toronto to Chicago Midway International Airport (MDW) limousine transfer is the cross-border service for Ontario travellers flying Southwest Airlines or other domestic carriers from Midway. At 845 kilometres, the journey takes approximately 9 hours including a typical border crossing -- and your chauffeur handles every kilometre, every border, every toll.
The route follows Highway 401 west across southern Ontario, crosses the Canada-US border at the Ambassador Bridge (Windsor-Detroit) or Blue Water Bridge (Sarnia-Port Huron), continues on I-94 West through Michigan and Indiana, then transitions to I-55 (Stevenson Expressway) for the final approach to MDW on Chicago's southwest side. Our chauffeurs check real-time border wait times and choose the fastest crossing.
Many Toronto-area travellers choose Midway over O'Hare for Southwest's no-bag-fee, no-change-fee fare structure and competitive pricing on US domestic routes -- particularly Florida, Texas, Las Vegas, and the West Coast. With a professional chauffeur, leather-appointed cabin, complimentary Wi-Fi, and climate control, the cross-border drive becomes a productive workspace or restful lounge. All bridge tolls and applicable highway fees are included in the flat quote.
Pricing
Custom Quote
Call for Booking
This route is priced on request. Reach our 24/7 dispatch for a flat, all-inclusive rate — you'll have a written quote within 15 minutes.
What's Included
Route Details
Primary Route
Highway 401 West to Ambassador Bridge / Blue Water Bridge to I-94 West to I-55
Toronto to Chicago Midway Airport (MDW) FAQ
How long is the drive from Toronto to Chicago Midway?
Approximately 9 hours including a typical border crossing. We recommend leaving Toronto at least 12 hours before scheduled departure to allow for traffic, the border, and US airport check-in.
Why use Midway instead of O'Hare?
Midway is the hub for Southwest Airlines, which often offers more affordable fares on US domestic routes (especially Florida, Texas, Las Vegas, the West Coast) and includes free checked bags. The compact single-terminal layout also means faster check-in, security, and baggage claim than O'Hare.
Do I need a passport?
Yes. All passengers must carry a valid passport. NEXUS cards expedite border crossings significantly. Children require their own passport regardless of age.
Which border crossing do you use?
We typically use the Ambassador Bridge (Windsor-Detroit) or the Blue Water Bridge (Sarnia-Port Huron) based on real-time wait times. Both routes lead to I-94 West, then I-55, for the approach to MDW.
Are bridge tolls included?
Yes. All Ambassador Bridge and Blue Water Bridge tolls are included in your flat-rate quote.
What about meals and rest stops?
On a 9-hour trip, we plan a meal break and one or two short rest stops at clean, well-maintained service plazas. Tell us your preferences and dietary requirements at booking.
Do you offer round-trip service?
Yes. Round-trip bookings are discounted and include monitoring your return flight at MDW with meet & greet on arrival.
Book Your Toronto to Chicago Midway Airport (MDW) Limo
Professional chauffeurs, door-to-door service, request a custom quote in minutes.
Same number — 1-855-552-5559 — for both calls and WhatsApp · North America.