We are licensed to pick you up at O’Hare.
Which sounds like a technicality until you are standing at a Chicago curb watching your Milwaukee car service explain that it is only allowed to drop off.
Milwaukee to Chicago is a route we run regularly, usually to O'Hare or to a downtown meeting and back the same day. It is priced as a route rather than by the hour.

The permission that matters at the Chicago end
Only City of Chicago authorized public passenger vehicles and transportation network providers may pick up passengers at O'Hare International Airport, Midway International Airport, and McCormick Place Convention Center.City of Chicago Department of Finance, ground transportation registration emblem
We hold that registration on each vehicle, renewed annually, and pay the airport departure tax on every pick-up. It is the reason a return leg from O’Hare is an ordinary booking for us rather than a favor, and it is worth asking any operator quoting you this route whether they have it.
Every permit and registration we hold is listed on the licensing page.
Drive times on the corridor
One way, typical rather than optimistic.
| Leg | Miles | Typical drive |
|---|---|---|
| Downtown Milwaukee to downtown Chicago | 92 | 1 hr 35 min |
| Downtown Milwaukee to O'Hare | 79 | 1 hr 20 min |
| Downtown Milwaukee to Midway | 91 | 2 hr |
| Kenosha to O'Hare | 57 | 1 hr 10 min |
| Downtown Milwaukee to Chicago Executive | 68 | 1 hr 15 min |
Kenosha is on this corridor, which is why O’Hare is a genuine option from there and rarely one from Milwaukee. That page has the comparison.
Rail and the smaller airports
Not every trip on this route is road for its whole length, and the connections people actually use are worth naming:
- Rail
- Harvard Metra station, on the Union Pacific Northwest line; Milwaukee Intermodal Station, downtown; Milwaukee Airport Rail Station, at Mitchell
- General aviation
- Chicago Executive Airport (PWK), Wheeling; Waukegan National Airport (UGN); Kenosha Regional Airport (ENW)
Private arrivals and the FBOs at each are covered on the airport page.
Trips that start down there
We also work with a Chicago operator who covers the runs that start down there, the same way they send us the ones that start up here.
We are a Milwaukee company and we say so. The route is ours; Chicago is not our city, and an operator who tells you otherwise is quoting you on somebody else's ground.
Questions people ask
Can you pick us up at O'Hare, or only drop off?
Pick up as well, which is not the common case for a Milwaukee operator. Only City of Chicago authorized public passenger vehicles and transportation network providers may pick up passengers at O'Hare International Airport, Midway International Airport, and McCormick Place Convention Center. We hold that registration on each vehicle and pay the airport departure tax on every pick-up.
How long is the drive?
About 95 minutes downtown to downtown, and about 80 minutes to O'Hare. Midway runs longer than the mileage suggests because of where it sits. Those are the figures we quote on, rounded up.
Is it cheaper than flying?
Frequently, once two people are traveling and once the airport time at both ends is counted. It is always more predictable, which on a same-day meeting is worth more than the fare.
Do you serve trips that start in Chicago?
We also work with a Chicago operator who covers the runs that start down there, the same way they send us the ones that start up here.
What about the smaller airports on the way?
Chicago Executive, Waukegan National and Kenosha Regional are all on this corridor and all take private aircraft. We coordinate with the FBO at each. The airport page names them.
How is it priced?
Milwaukee to Chicago is a route we run regularly, usually to O'Hare or to a downtown meeting and back the same day. It is priced as a route rather than by the hour. The quote is the number you pay. All fares, fees, taxes, tolls and chauffeur gratuity are in it, and each line is shown rather than buried.
Related
- KenoshaOn this corridor, and the one place O’Hare genuinely competes with Mitchell.
- Airport transfersEvery airport and every FBO, in full.
- Corporate accountsSame-day return meetings, on account.
- Compared with Uber and LyftThe long routes are where a quoted flat rate wins.
Send both legs at once.
A same-day return is one booking and one flat, all-inclusive quote, and the car is there at the Chicago end because we are allowed to be.
rides@luxsuv.com


