$110
Taxi from Winnetka to Midway Airport
Schedule private airport car service from Winnetka to Midway Airport. Flat-rate pricing, scheduled pickups, sedan, SUV and minivan options — same price both ways.
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Scheduled pickup — driver confirmed before your travel day
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Flat fare locked at booking — no surge, no meters
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Return pickup available from Midway directly to Winnetka
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Flight tracking included for Midway arrivals
Vehicle Options — Winnetka to Midway
Midway to Winnetka Taxi Rates
| Vehicle | Passengers | Midway (MDW) | O'Hare (ORD) |
|---|---|---|---|
| Sedan | Up to 3 | $110 | $73 |
| SUV | Up to 4 | $115 | $78 |
| Minivan | Up to 6 | $125 | $88 |
Car seats are $15 each and must be requested when booking. Same-day and last-minute rides are welcome, subject to driver availability. Tipping is not enforced but is highly appreciated.
Arriving at Midway? Here’s Where to Meet Your Driver
Midway has one terminal. After baggage claim, go to the lower-level arrivals curb, Door 2. Your driver's name and vehicle are texted to you the day before your ride.
Midway at a Glance: One terminal · Concourses A, B, C · Southwest's Chicago hub · Usually shorter walks and faster baggage claim than O'Hare.
Explore Winnetka
Winnetka to Midway International Airport runs about 28 miles south via I-94 and the Stevenson Expressway — a historic North Shore village to southwest side MDW run for Southwest Airlines travelers. Your driver handles the complete expressway approach from your lakefront neighborhood to 55th Street.
Winnetka is a North Shore village where the residential architecture is part of the experience — historic homes on tree-lined streets running down to Lake Michigan bluffs, Hubbard Woods as a traditional downtown anchor and lakefront beaches that define the community's summer. It is a small village that has held onto its character deliberately, and the result is one of the Chicago area's most consistently admired suburban addresses. The I-94 south and I-55 Stevenson Expressway corridor connects Winnetka toward Midway Airport.
Learn more about Winnetka on the official municipal website.
Plan Your Winnetka to Midway Trip
Leave time to spare. Aim to reach Midway about 2 hours before a domestic flight. The drive from Winnetka is usually around 55 minutes, but rush-hour traffic, winter weather, and holiday travel can add time.
Check with your airline. Confirm your flight status, bag-drop deadline, and recommended arrival time before your pickup. Current screening information is available on the Midway TSA page .
Safety first. Your driver follows all traffic laws and cannot make up time lost because of a late start, so select a pickup time that includes a reasonable buffer.
Missed or canceled flight? Call dispatch immediately. Transportation back to Winnetka is booked as a new trip and remains subject to driver availability. Full delay and missed-flight policy →
Book Your Ride from Winnetka to Midway
Need a ride to or from O'Hare? Winnetka to O'Hare O'Hare to Winnetka