+1 (773) 234-5010
You can request airport round trip car service for a Deer Path Inn stay even when you arrive at O’Hare and depart from Midway: enter two separate reservations with the correct airport on each. Each trip is charged separately on its own scheduled service date. The website has no combined round-trip option or one-way/round-trip selector, so the return is a new trip rather than a duplicate of the arrival.
For Lake Forest airport car service, use Deer Path Inn at 255 East Illinois Road. The hotel’s airport references put O’Hare about 24 miles away with a 30-35 minute drive and Midway about 42 miles away with a 50-60 minute drive. These are published property baselines, not live traffic predictions. A return to Midway needs its own timing calculation even if your arrival from O’Hare felt short.
Two reservations can use two different airports
An itinerary with different arrival and departure airports can suit a household whose preferred flights do not use the same Chicago airport. Private transfers avoid the practical problem of leaving your own vehicle at one airport while flying home from another. What matters for the car request is that both endpoints are written accurately, with separate dates and times.
The arrival reservation runs from O’Hare to the inn. The departure reservation runs from the inn to Midway. Put ORD and MDW in the appropriate requests alongside the full airport names; using only “Chicago airport” leaves a major part of the journey unspecified. The return also starts from the address where you will actually be staying that night, rather than automatically inheriting an earlier address.
Deer Path Inn is a downtown Lake Forest property with an English courtyard garden and Tudor-style architecture. It is a destination for a stay, dining or a celebration, rather than an airport terminal hotel. Its official hotel overview gives that context. A pair of direct transfers can suit guests who want to enjoy the property without keeping a personal vehicle for the whole visit.
Which details belong on each trip?
For the arrival, supply the flight number, scheduled landing date and time, passenger count, luggage and hotel address. Flight details describe the air journey; they do not mean everyone is ready for the car the instant the aircraft touches down. International processing or checked luggage may make the interval before curbside readiness longer.
For the departure, supply the pickup date and time, actual pickup address, departure airport and flight details. List the bags again if the return load changes after shopping or a longer stay. A vehicle request should reflect the luggage traveling on that leg, without assuming every vehicle in a broad category has identical storage space.
An additional household stop is also part of that leg’s itinerary. If you will first collect relatives in Lake Bluff, the Lake Bluff transportation page supports a separate address-specific request. The inn-to-airport baseline will no longer describe the whole journey. Giving the extra stop early makes it possible to discuss both the route and pickup sequence before reserving.
What time should you leave for a Midway flight?
Consider a hypothetical 1:00 p.m. domestic Southwest flight from Midway. Southwest’s airport information lists a suggested 120-minute domestic arrival allowance for MDW. That creates an 11:00 a.m. airport arrival target. The allowance covers time at the airport; it is not the duration of the drive from Lake Forest.
Using the upper end of the inn’s 50-60 minute Midway driving reference, subtract 60 minutes from 11:00 a.m., then add an illustrative 30-minute road contingency by moving the pickup earlier. The result is about 9:30 a.m. at Deer Path Inn for a direct trip. This is a calculated planning example, with a chosen contingency rather than a claimed typical peak-driving time.
Southwest also lists a checked-bag deadline of 45 minutes before departure at Midway. That deadline is later than the suggested arrival target; it is not an alternative airport arrival recommendation. For another airline or an international itinerary, use that carrier’s applicable requirements. An extra residential stop, a different pickup address or unusual road conditions calls for a revised departure discussion rather than reusing the example unchanged.
Arrival help without a combined booking
On the inbound O’Hare trip, standard curbside readiness means leaving the aircraft, retrieving checked bags as applicable and gathering the whole party before calling for the car. Follow airport ground-transportation directions and use the contact number in your reservation email or the company main number when ready to leave. The driver cannot remain parked at an active terminal curb while you are still inside.
If baggage is delayed, wait until it is collected before calling for standard curbside pickup. For a flight change or uncertainty about meeting instructions, contact the reservation number or company main number and explain the situation. Paid Meet & Greet, when purchased for an additional charge, takes place outside security after the applicable arrival and luggage process, never at the aircraft gate.
A return request built around your departure airport
Different-airport round trip transportation works best when the return is treated as its own journey. Keep the departure airport and flight attached to that reservation, along with the pickup location and actual luggage party. A change to the return flight should prompt a change discussion for that trip instead of an assumption that the inbound booking controls it.
Reserve Deer Path Inn airport round trip transportation by entering the outbound and return separately. Identify O’Hare on the arrival and Midway on the departure when those are the airports on your tickets.
