Chicago · Airports
Airport transfers in Chicago
Two airports on opposite sides of the city, and the wrong one turns a twenty-minute run into an hour across town.
| Route | Off-peak | Allow in peak | Sedan all-in | SUV all-in |
|---|---|---|---|---|
| ORD to the Loop | 30–40 min | 55–80 min | $149.00 | $189.00 |
| Midway to the Loop | 20–30 min | 35–55 min | Quoted | Quoted |
| ORD to the Magnificent Mile | 35–45 min | 60–85 min | Quoted | Quoted |
Weekday afternoon examples from our quote engine, as of Oct 2026. Includes 20% chauffeur gratuity, tolls, parking, airport fees, surcharges and taxes. Your quote is confirmed in writing and held for 72 hours. Routes marked Quoted are priced for your exact addresses.
- Gratuity and airport fees included
- Rate agreed in writing, no surge pricing
- Free cancellation up to 2 hours before pickup
- 60 minutes free waiting after landing, flight tracked
The two Chicago airports
O’Hare is one of the largest airports in the world and behaves like it; Midway is small, close and considerably easier. Which is right for you depends entirely on where you are staying, because they sit on opposite sides of the city and the journey between them is a genuine cross-town run. We confirm the terminal against the flight number on the day, meet inside arrivals by default, and hold through customs rather than starting a clock against a queue we can see.
O’Hare International (ORD)
Four terminals, with international arrivals at Terminal 5 sitting apart from the domestic three and connected by a transit system rather than a walk. Terminal 5 is a different pickup entirely and the most common thing people get wrong here. The run into the Loop uses the Kennedy, which has a reversible express lane that helps enormously in one direction and not at all in the other.
Midway (MDW)
South-west of the city, small, and from kerb to car a fraction of the walk that O’Hare demands. For anyone staying in the Loop or the South Loop it is frequently quicker end to end despite thinner flight options. The arrivals level is simple enough that a kerb pickup genuinely works, which is not true at O’Hare.
Winter in Chicago, and how we plan around it
Snow is a scheduling problem, not a driving one
Chicago clears its roads well and the vehicles are equipped for the season, so the driving is rarely the issue. The issue is that everything takes longer at once — de-icing queues, gate holds, slower surface streets. From December we build a real allowance into every airport booking rather than quoting the summer number and apologising in January.
Delays, diversions and early landings
We track the tail number, so an arrival that lands early is met early and a diversion is re-planned before you are off the aircraft. Chicago weather sends diverted traffic to Milwaukee, Indianapolis and occasionally further; those are long ground runs and we quote them honestly rather than pretending otherwise.
From the Chicago airports into the city
Door to kerb, ordinary conditions. The peak column is a working weekday in reasonable weather; a snow event is planned separately rather than absorbed by a margin.
The Kennedy carries almost everything heading to O’Hare and it does not fail gracefully, so an airport run timed off the off-peak figure is a gamble rather than a plan. Winter adds its own margin, which we build in rather than hoping against.
| Route | Approx. distance | Off-peak | Allow in peak |
|---|---|---|---|
| O’Hare to the Loop | 18 miles | 30–40 min | 55–80 min |
| O’Hare to the Magnificent Mile | 19 miles | 35–45 min | 60–85 min |
| O’Hare to Schaumburg | 13 miles | 20–25 min | 35–50 min |
| Midway to the Loop | 11 miles | 20–30 min | 35–55 min |
| Midway to Hyde Park | 12 miles | 20–30 min | 35–50 min |
| O’Hare to Midway | 26 miles | 35–50 min | 60–90 min |
How Chicago airport transfers are priced
Every airport route is quoted per route and confirmed in writing before you travel, with no surge pricing at any hour. Both airports levy access fees that we show you rather than fold into a round number. Rates are set per market, so a Chicago quote reflects Chicago.
If you are staying in the Loop and the flight options work, Midway will usually get you to your hotel sooner than O’Hare will. We will say so before you book rather than after you have landed.
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Loop days, suburban corridors and consolidated billing
Private aviation
Chicago Executive, DuPage, Midway and ORD private terminals
Hotel transfers
The Magnificent Mile, River North and the Loop
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McCormick Place, the United Center, Wrigley and the theatres
Universities & campuses
UChicago, Northwestern, Booth and the medical district
All Chicago services
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