I recommend that people check airport vs off airport rates to see if they can save money,
but in many instances extra transportation costs and inconvenience factors can outweigh the savings. If someone is flying into an airport, for example, to visit relatives, and someone can pick them up at the airport and then take them to a local rental place the next day and go with them to return the car and then drive them back to the airport, there's a possibility of some savings, ut when you have to pay transportation to and from the airport, in can cancel out any savings.
I did some research and couldn't find any hotels in Chicago that had on-site car rental so I did some checking with airportexpress.com which provides shuttle service to and from Chicago Hotels and the Airports.
Trips avg about $50 each way for two people airport to hotel and back.
So then, I decided to check car rental rates with a Costco discount (I can't access the Boeing Corporate discount number without being an employee) -- Costco members get discounts with Alamo, Enterprise, Avis, Budget and Hertz.
Here's what I found for both O'Hare Airport and Midway Airport based on your dates, times and car size and a Costco discount. While I don't give specific rate quotes (they change too frequently to be accurate) here are the approximate results that I found:(car rental company links open in a new window)
ORD Cost around $360
all off airport locations are closed
on June 10th (Sundays)
MDW Cost around $440
203 North Lasalle
Chicago , IL 60601
Cost around $310
Based on these 4 locations, while
North Lasalle is the cheapest, by
the time you add in $100 for
transportation to and from the
airport you're only saving about $10.
MDW Cost around $380
So, not a big difference here, but
ORD is the cheaper airport location to rent from.
ORD Cost around $420
1160 E Ogden Ave
Naperville , IL 60563
Cost around $385 (closed at 730pm on the 1st- pickup would have to be 9am on the 2nd)
For convenience sake.... I would call ORD price the cheapest for Alamo, but Enterprise at ORD is still the cheapest.
ORD Cost around $650
Chicago 214 North Clark St
Cost around $350
MDW Cost around $480
3721 North Broadway Street,
Chicago, (closed Friday evening, pickup would have to be 9am on the 2nd)
Cost around $345
6501 West 95th Street
Sears Auto Center, Chicago Ridge IL
(closed Friday evening, pickup would have to be 9am on the 2nd)
Cost around $350
So, out of these locations, North Broadway Street is the cheapest, but with $100 for transportation to and from the airport, Enterprise at ORD is still the cheapest.
Based on the research I've done, getting a rental car not from the airport in Chicago would not be cheaper... go for the airport pickup!
I would also suggest that your husband contact someone from his HR department to find out which car rental companies they offer discount codes for... and check rates with that as well. You may not find anything cheaper than with the Costco discount for Enterprise, but it never hurts to check!