I am traveling to Ireland in May, but i have a layover in Chicago. I will arrive around 8:30 p.m. and need to return to O'Hare the following day at 2:30 p.m. I will have a rental car, & I will be staying at the Ambassador East. Restaurant and a couple of attraction suggestions will be greatly appreciated. I know we will be having an early breakfast at Orange.
Thanks in advance,
Trae

It seems to me that the only thing that you need is dinner suggestions for after you land in Chicago. Arrive, pick up bags at luggage claim, rent car, check into hotel, have dinner. Go back to hotel. It is now midnight or 12:30am. Go to sleep. Wake up in the morning. Check out of hotel at 10:00-11:00am. Have breakfast at Orange. Return rental car. Check in for flight. Go to Ireland.
8-)

Not sure what sort of rate you're getting on the rental car, but parking will probably run about $35-40 in addition to your rental.

The shuttle from O'Hare will cost about $45 round trip. With your flight times, you shouldn't have to worry about traffic either coming from or going to the airport.

If you decide to do some early sightseeing before your flight, you'd still be able to leave your bags and check out at 11:00 or so.

Check www.airportexpress.com for full information and reservations.

Hi kerouackid,

Since your flight is getting in so late, you may have already had something on the plane to tide you over food-wise. If so, instead of dinner, I suggest going to the John Hancock lounge (a floor under the Signature Room dining area) to have a drink and view the city from these regal vantage point. Drinks are pricey, but you're paying for the view. (You'll probably want to opt for something else if it's raining, though, because you won't be able to see a thing with the clouds.)
In the morning, enjoy Chicago's beautiful downtown. For walking, Michigan Avenue can't be beat. The Art Institute of Chicago, which opens at 10 or 10:30, is fabulous. If it's pouring rain, that's where you want to go after breakfast (Just hail a cab from Orange to get there.).
If you don't plan on sightseeing by car, then I would forego having a rental car and just take a cab to/from the hotel. It will save you time not having to pick up the car, park it, and return it; and it will most likely save you money as well.
However, if you really want a car, then if the weather is nice (again, no rain), then take the scenic route back to O'Hare--a drive along Lake Shore Drive, starting south from the Museum of Science and Industry, or farther north at Buckingham Fountain, and go north to where the Drive turns into Sheridan Road. (From here, continue on Sheridan to Loyola campus, which is where Sheridan turns west and becomes Devon. Head straight west on Devon until you reach I-90, which you'll take west to O'Hare. Another, faster, option is to turn west earlier off Lake Shore Drive at Foster. You'll catch I-90 much more quickly. Ask your hotel concierge or the car rental company to provide you with a map. Tip: Give yourself plenty of driving time. Devon can get backed up.)
Have a fabulous trip!

Sorry--I meant EAST on I-90 if you take Devon all the way over. You hit Rosemont first and the airport is just south of there. If you're not familiar with the area, it's probably best to take Foster. You don't want to miss your plane to Ireland!

This is just a suggestion, but if I were you I would do the following:

1. Cancel Ambassador and the rental car.

2. Book the O'Hare Hilton - a short walk from the terminals through a connected tunnels.

3. Book a late dinner at Gibson's Rosemont, not my usual recommendation, but it is a sister restaurant of a Chicago institution, Gibson's on Rush. Taxi - ~$10-15 each way. Get back to the hotel and sleep.

4. Ask the hotel for late check-out. If not possible, pack and checkout very early. Leave the bags with the bell captain.

5. Take the train into the city. Do the breakfast, walk around some and take the train back to O'Hare. If you did not get a late checkout, ask for shower possibility at the spa/gym. If you did get a late checkout, take a shower, get your bags and walk over to the terminal.

The way I see it, you won't be at Ambassadors and "maybe" ready to hit the streets until ~10:30p if not later. What's the point?

Parking is very expensive and the traffic can be really bad.

Unfortunately, I cannot change my reservations. The rental car is $22 and the hotel is $100 + taxes. That is not too bad. I found 24 hour parking 2 blocks from the hotel for $18. We are going to try the John Hancock Bldg. Lounge. Next, we are going to try and grab a pizza. Most of the more famous places are open until 11. Then to bed. The next morning we will have breakfast at Orange. Then we will try and see a few exibits at TAIOC. Then off to the airport. We are going to try and make the most of our brief stay. Thanks for all of your help and suggestions.
KK

Kerouackid-that is a great plan. There are plenty of great pizza places within an nice walk from the hotel-Ginos East,Pizzaria Unos or Dues. Walk back to the hotel if it's a nice night down State Street for good people watching.