On a Thursday the blue line shouldn't have many service delays, but it might be worth checking to see if any scheduled work will lead to a delay.
http://www.transitchicago.com/travel...s/weekday.aspx

As others have said, plan the round trip to take at least 2 hours. If your flight leaves ORD after 8pm I think you shouldn't have a problem with security.

I used to live in Chicago. What kind of real Chicago dinner are you looking for? I love the stuffed pizza at Giordano's. There are a few locations downtown and you can get downtown and walk around for a while before or after the meal. Definitely allow an hour each way on the L. Someone suggested a cab but it depends on the time of day, a cab can take just as long or longer.

It's actually Halsted and a touch north of Armitage, but it's very good food!!

Dave

Thanks, Dave. My bad.

This. The inbound Kennedy can be a real cluster. Around dinner time (5-ish) on a weekday, forget it... a 40 minute ride on the Blue Line is the way to go.

But I have to disagree about the pizza... if you're going to come to Chicago and eat pizza, it should be Gino's East or Lou Malnati's.

Both are excellent pizzas.

If you land before 4, take a cab to the loop. Between 430 and 7, train. After 7, cab is best but cab lines are long.

If you're there 5 hrs, you probably land before 4. Hop in a cab, head to downtown, and walk around. If youve never been there, have them take you to Michigan and the river and just start walking north. Maybe happy hour in the signature room @hancock before you had back to the airport.

While I like Lou Malnati's and Gino's East...I LOVE Giordano's! Plus, they are in bankruptcy, so might as well eat it up as long as you can. Before long, Gino's East and Lou Malnati's may be all that's left!

I spend a lot of time there, and this sounds like the best and most memorable choices given the time restraints.^

To the OP - if you do decide to go into the city, please do come back to this thread and let us know how it went - (where you went, timings, whether you felt it was worth it, etc).

This question gets asked with some frequency, and a first-hand report would be very helpful to future visitors who are considering a similar layover - thanks!!

Yes, there is Blue Line from ORD to Downtown Chicago. If you get off the train at Clark/Lake station. If you paid $2.25 fare. If you go into the tunnels to pay the fare is at vending machine.

Chicago needs a sampler plate. Half a Jumbo Char-Dog, half an Italian Beef sandwich, and a slice of Deep Dish!

Don't take on cab! It's too extremely expensive! There is very good walking around the street in downtown Chicago. Just try to take a walk or take on the CTA bus. If you get a all-day pass. Ask for the guys who for CTA near vending machine. If you want to talk with him. He will help you to pay the fare. Go to www.transitchicago.com.

Go to DTW.

I live in the Loop (downtown Chicago). Definately can take the Blue Line ("L") downtown. If you're looking for great deep dish pizza, def check out Giordanos.

THe train ride takes 45 minutes from the loop to Clark & Lake (1st stop in the downtown area). Get off at Clark and Lake, walk up the stairs and on the street, walk in the direction the cars are going (East). Keep walking, you'll get to Michigan Avenue in a couple of blocks. Cross Michigan Avenue, and on the right side is a Giordanos. Get yourself a small deep dish, a beer, and enjoy. If you have a few minutes to spare, you could walk south along Michigan Avenue to Millennium Park, its only 2 blocks from there. Walk around, see the Cloud Gate, the fountain faces, and then once you're due back, walk west on Randolph or Washington. There's a blue line stop at Washington & Dearborne, and you can take this back to Ohare.

Enjoy!