O’Hare vs Midway From Milwaukee: Distance, Drive Time and Which Airport to Pick
The two Chicago airports compared for Wisconsin travelers, with the distance between them and the cost of the ride to each
Written by the Pharaoh’s Transportation dispatch team, Milwaukee
Last updated: November 10, 2026
Quick answer: From Milwaukee, O’Hare is about 80 miles and 1 hour 30 minutes to 2 hours; Midway is about 95 miles and 1 hour 45 minutes to 2 hours 15 minutes, because you cross through or around Chicago to reach it. The two airports are about 27 miles apart, 45 to 75 minutes by car depending on traffic. Pick O’Hare for international flights and the most nonstops; pick Midway for Southwest and shorter security lines. Pharaoh’s Transportation drives both, flat rate: O’Hare from $199, Midway from $209 by sedan, tolls included, flight tracked. Call or text (414) 322-3751 or book online.
Key takeaways
- O’Hare is closer to Milwaukee and faster to reach; Midway is on the south side of Chicago, so every Wisconsin trip to Midway passes O’Hare’s latitude first.
- The gap between the two airports is 27 miles, but 45 to 75 minutes, because the route runs through the city.
- Fare savings of $100 or more per ticket usually justify Midway; otherwise O’Hare wins on drive time.
- The ride price difference is small: $199 vs $209 by sedan, $234 vs $259 by SUV.
- Never book a connection that requires moving between the two airports in under three hours.
Either airport, one flat price. Text your flight and address to (414) 322-3751: O’Hare from $199, Midway from $209, chauffeur tracks the flight both ways.
Milwaukee to O’Hare and Milwaukee to Midway: Miles, Minutes and Rates
| O’Hare (ORD) | Midway (MDW) | |
|---|---|---|
| Distance from downtown Milwaukee | About 80 miles | About 95 miles |
| Drive time, normal traffic | 1 hr 30 min to 2 hr | 1 hr 45 min to 2 hr 15 min |
| Drive time, rush hour or snow | 2 hr to 2 hr 30 min | 2 hr 15 min to 3 hr |
| Route | I-94 South, I-294 Tri-State | I-94 South, I-294, then I-55 or the Stevenson into the south side |
| Airlines | All majors; international via Terminal 5 | Southwest hub, plus Delta, Frontier and a few others |
| Nonstop destinations | The most of any Midwest airport | Fewer, but strong on domestic leisure routes |
| Security lines | Longer; TSA PreCheck helps | Shorter on average |
| Pharaoh’s sedan, one way | From $199, tolls included | From $209, tolls included |
| Pharaoh’s SUV, one way | From $234 | From $259 |
| Best for | International, nonstop long-haul, business travel | Southwest fares, short domestic trips, south-side destinations |
Prices are flat and confirmed in writing when you book; see limo prices. The O’Hare service page is Milwaukee to O’Hare limo service; the Midway page is Milwaukee to Midway limo service.
O’Hare to Midway: 27 Miles, 45 to 75 Minutes
About 27 miles by road. O’Hare sits on the northwest edge of Chicago; Midway sits on the southwest side. Between them is the city, so the drive is 45 minutes on a clear Sunday and 75 minutes or more on a weekday afternoon. There is no direct train; the CTA Blue Line serves O’Hare and the Orange Line serves Midway, with a transfer in the Loop, about 90 minutes door to door. If an itinerary lands at one and departs from the other, allow at least three hours between flights and book a car for the transfer; we run it as a flat-rate ride and the chauffeur tracks the inbound flight. See O’Hare pickup guide for where we meet you at O’Hare.
Airlines and Routes: International and Nonstops Favor O’Hare
International flights. Terminal 5 handles nearly all international departures from Chicago; Midway has almost none. Nonstops. If your destination is served nonstop only from O’Hare, the shorter flight beats a Midway connection every time. Business travel. The widest schedule, the most same-day rebooking options when weather hits. Drive time. O’Hare is the closer airport from everywhere in Wisconsin, by 15 to 30 minutes. For the terminal layout and drop-off doors, see O’Hare terminal guide for Wisconsin travelers; for how long the drive takes from your part of town, see how long Milwaukee to O’Hare takes.
Southwest, Shorter Security Lines and the South Side Favor Midway
Southwest fares. Midway is a Southwest hub; when the fare is $100 or more cheaper per ticket, the extra 20 minutes of driving is easy to justify, especially for a family of four. Shorter security. Midway’s checkpoints are consistently faster, which matters for early flights. South-side destinations. If you are also visiting the south suburbs, Indiana or the Loop’s south end, Midway is on the way. See Milwaukee to Midway limo service, Milwaukee to Midway limousine guide and Midway to Milwaukee car service guide for the Midway rides in both directions.
A Cheaper Ticket at Midway: Does the Longer Drive Pay?
| Scenario | O’Hare | Midway | Pick |
|---|---|---|---|
| Solo, domestic, fares equal | $199 ride, shorter drive | $209 ride, longer drive | O’Hare |
| Family of 4, Southwest fare $120/ticket cheaper at Midway | $234 SUV | $259 SUV, $480 saved on fares | Midway |
| International | Only option | Not available | O’Hare |
| 6 AM departure, want the shortest security line | Longer lines; leave 4 AM | Shorter lines; leave 3:45 AM | Midway, if the fare is close |
| Snow day | Closer; fewer miles of I-94 in weather | Longer; more city driving | O’Hare |
If you are weighing Milwaukee’s own airport against both, the three-way comparison is in MKE vs O’Hare vs Midway: which airport to use; this page is only about the two Chicago airports.
Flying Southwest out of Midway? Flat $209 by sedan from Milwaukee, tolls included, 24/7. Milwaukee to Midway limo service or call (414) 322-3751.
Split Itineraries: Arriving at O’Hare, Leaving From Midway
Some itineraries arrive at O’Hare and leave from Midway, or the reverse, usually because two different airlines priced the legs. It is workable with a reserved car and a three-hour gap, and risky with anything less: the transfer is 45 to 75 minutes of city driving plus check-in at the second airport. We run it as a flat-rate transfer with the inbound flight tracked, and the chauffeur meets you at the arrivals door; see O’Hare pickup guide for the O’Hare meeting points and Midway to Milwaukee car service guide for Midway. For the leave-time math from Milwaukee to either airport, use how long Milwaukee to O’Hare takes; for the day a flight cancels, flight cancelled backup plan; for winter, Milwaukee winter travel guide.
Booking the Ride to Either Airport From Milwaukee
Flat rate by pickup address, tolls included, confirmed in writing. Flight tracked on the return with no charge for waiting on a delay. Chauffeur at the terminal door or inside at baggage claim with your name. Sedans, SUVs with car seats on request (airport limos with car seats), and Sprinter shuttle for groups; corporate limousine service accounts for business travelers. Chauffeurs are background-checked, licensed and insured; meet our chauffeurs and read customer reviews. Pharaoh’s is based at 5151 S Howell Ave, two minutes from MKE, and runs both Chicago airports around the clock (4 a.m. airport car service guide).
Quick facts
- Milwaukee to O’Hare: about 80 miles, 1.5 to 2 hours, sedan from $199
- Milwaukee to Midway: about 95 miles, 1.75 to 2.25 hours, sedan from $209
- O’Hare to Midway: about 27 miles, 45 to 75 minutes
- Company: Pharaoh’s Transportation, 5151 S Howell Ave, Suite D1 & D2, Milwaukee, WI 53207
- Phone / text: (414) 322-3751, 24/7
- Reviews: 4.9 stars on Google, 300+ reviews
Frequently Asked Questions
Is Midway or O’Hare closer to Milwaukee?
O’Hare, by about 15 miles and 15 to 30 minutes. O’Hare is on Chicago’s northwest edge; Midway is on the southwest side.
How far is it between Midway and O’Hare airports?
About 27 miles by road, 45 to 75 minutes by car depending on traffic. By CTA train with a Loop transfer, about 90 minutes.
Which is cheaper to reach from Milwaukee by car service?
O’Hare: $199 by sedan vs $209 to Midway; $234 vs $259 by SUV. Tolls included in both; see limo prices.
Which airport has shorter security lines?
Midway, on average. O’Hare is larger and busier; TSA PreCheck narrows the gap.
Can I fly internationally from Midway?
Almost never. International flights from Chicago use O’Hare’s Terminal 5.
Which airport does Southwest use?
Midway is Southwest’s Chicago hub. Southwest also has a smaller operation at O’Hare.
Can you drive me from O’Hare to Midway if my flights use both?
Yes, as a flat-rate transfer with the inbound flight tracked. Allow at least three hours between flights; see O’Hare pickup guide.
Is it worth driving to Midway to save on a Southwest fare?
Usually yes when the saving is $100 or more per ticket, and especially for families. For one traveler and a small saving, O’Hare’s shorter drive wins.
How long is the drive from Milwaukee to Midway?
About 1 hour 45 minutes to 2 hours 15 minutes in normal traffic, longer at rush hour because the route passes through the Chicago area.
What time should I leave Milwaukee for a Midway flight?
About 4 hours 15 minutes before a domestic departure with checked bags; add 45 minutes on holiday weeks or snow days.
Do you serve both airports 24 hours?
Yes, pickups and drop-offs at O’Hare and Midway any hour; see 24-hour limo service.
Should I fly from Milwaukee’s own airport instead?
Often, if the fare and schedule are close; MKE is 15 minutes from downtown. The three-way comparison is in MKE vs O’Hare vs Midway: which airport to use.
Are tolls included to both airports?
Yes. Illinois tolls are inside the flat price for O’Hare and Midway.
Do you pick up at Midway for the ride back to Wisconsin?
Yes. The chauffeur tracks your flight and meets you at the Midway terminal, same flat rate; see Midway to Milwaukee car service guide.
