12 Hour Layover in Chicago....

By all means take the train downtown. Take the Blue Line from O'Hare (ORD) Airport to the city and get off at the Clark street stop. The journey time is about 45 minutes and cost $1.75 each way at the time of this writing. The train runs 24 hours.
The Airport CTA station is located on the lowest level of the main parking garage at Terminals 1, 2 and 3. Walk over to Wacker Drive and into the beautiful Hyatt Hotel and get some literature about the city. There are wonderful brunches ($$) in most of the hotels. Then cross the Michigan Ave/Wacker bridge and discover the Magnificant Mile. You can go into the Marriott and sit in the lobby of any it or any of the nice hotels, waiting for the stores to open. Walk the mile on down to Water Tower Place, which is a huge vertical shopping mall that probably doesn't open until 12 a.m However, the Ritz Carlton is connected to it in the rear and you can ride up to the Ritz, sit in their nice lobby, use the swanky restrooms, etc. You could also ride the elevator to the top of the Hancock Building which is right next door if heights are your thing. Then once the mall and stores open you can shop to your hearts content. You can then take the train back. I would leave downtown by 4 pm. just to be on the safe side.

Or, check out the world famous Art Institue of Chicago, open at 10 a.m. on Sunday. It is $12 but well worth it. It is on Michigan Ave. but in the opposite direction of the Water Tower. It is just a couple of blocks from the Clark Street Station as well. Get on line and check out the great city. I lived there for 25 years and it is beautiful, except in February and March..too cold!!

Things to see and do in the airport are:

Visit the Brachiosaurus Dinosaur in the B concourse of Terminal 1. Our Brachiosaurus is one of the largest mounted dinosaurs in the world. The four-story high, 72-foot long skeleton model is on loan from the Chicago Field Museum.

The Butch O’Hare WWII Fighter Airplane Exhibit is located in Terminal 2. The exhibit is a replica of the WWII F3F-4 fighter plane flown by airport namesake and US Congressional Medal of Honor recipient Lt. Comdr. Edward "Butch" O’Hare.

Also in Terminal 2 is the Kids on the Fly Children’s Exhibit. Kids on the Fly is an interactive play area that educates and entertains children up to twelve years of age and their families. The exhibit's displays include an air traffic control tower, a fantasy helicopter, a cargo plane, a luggage station, and more.

The pedestrian tunnel between concourses B and C in Terminal 1 is the location of a 744 foot long kinetic neon sculpture of light and sound titled "The Sky’s the Limit", designed by Michael Hayden.

Of course, over 100 food and retail options are available throughout the airport terminals. Have a great time.

RJames - When will you be in Chicago (date), and what would like to see about the city?

If the weather is nice, you might enjoy an architecture cruise or strolling around Millennium Park. My personal preference would be to not waste time shopping on Michigan Ave. It's just not that exciting. I do think the State Street Marshall Fields store is worth a visit though - see the Tiffany ceiling by going up to the 5th floor, then to the center of the store.

If you'll be there after November 19, it's fun to wander around looking at the Christmas displays in the store windows.

I'd probably start my day off with a fun breakfast. You could take the blue line all the way to the Clinton stop, then walk 2 blocks north to have breakfast at Lou Mitchell's. It's divine! After that you can take a quick cab ride, or walk, or el depending on weather and your energy level to do some of the other things suggested. I'd probably then finish the day with a late lunch somewhere before heading back to the airport.

Geckolips and jlm_mi, thank you for the feedback. I will be in Chicago on November 6. Hopefully, I'll be able to explore a little bit of the city when I'm there.

You may want to wonder Navy Pier which is not too far from the magnificent mile (Michigan Ave). The John Hancock on the 90th floor has a fabulous all you can eat brunch. It is a bit pricy 5 years ago it was $35. But well worth the once in a lifetime experience and the views of the lake are to die for. Oh and a piece of Chicago trivia the condos at the John Hancock that have an iron beam cutting through their windows and impeading there view a bit cost more than those that have no obstruction. Why you ask? It's a stasus symbol due to the unique archtecture of the building. Who new?

You might want to browse the fodor's miniguide to Chicago for ideas - you can find it by clicking "destinations" at the top. We all have different tastes, so that will help you narrow down the ideas that appeal to you.

I'm not a fan of Navy Pier (and it will be cold!), but others are. And you can definitely go up Hancock without the brunch - either to the observatory (something like $11), or pay for a drink in the lounge (probably also around $11) and go to the lounge level for free. I do love views, so this is something I always enjoy.

Holiday decorations will mostly not be up yet, but there's still plenty to love about Chicago. You'd have time for a couple hours in one museum if you're a museum buff - Natural History, Adler Planetarium, Aquarium and Art Institute are all right in the heart of the city.

If you want to list some particular interests, I'm sure you can get more help. And exiledprincess always knows what's going on when, so if she sees this, she may have some really fun specific ideas for that date.

Just my 2 cents, but sending someone who is totally unfamiliar with the city over to Lou Mitchells...well, I just don't think that's a real sensible suggestion.

You will have a nice long day to 'get a feel' for Chicago, though, RJames. And even if you don't do any shopping, a stroll down Michigan Avenue, north from the River, will be very enjoyable. About a 15-minute walk will take you to Chicago Avenue, site of the landmark Water Tower - the Water Tower Place shopping mecca and John Hancock building are just another 2-3 blocks ahead. Keep walking all the way to the north side of the Drake Hotel and turn east. You'll have Chicago's legendary lakefront on one side of you and some of the highest priced real estate coops on the other. Follow the lakefront east for a block where you'll have to turn right (in essence, go around the block) and end up back at The Drake, another excellent choice for a place to rest your feet.

Hope you get good weather and are able to get a taste of a terrific city.

Actually, my reasoning for Lou Mitchell's is that RJames will likely arrive in the city before 7am, and there isn't much else to do then but eat breakfast. Lou Mitchell's is great, open that early, and easy to find coming in on the blue line. It's easy to get back on the blue line to get back into the loop also.

Unless RJames is very unfamiliar with cities in general, and with map-reading and public transportation, I don't see the problem. Some people are indeed very intimidated by getting around in the city, so the suggestion would not be a good one in that case.

Just curious, though - why do you think it's a bad idea?

jlm, I liked your idea of Lou Mitchell's - it's a Chicago institution, and open very early! From there, RJames can wander east past the Sears Tower, LaSalle Street canyon, the Federal Plaza, and north on Dearborn to see the Chagall mosaic and Picasso statue before heading east on Washington to Millennium Park. He'll have seen a lot, and have many hotels and shops to choose from for rest stops.

RJames, the train from the airport to downtown takes about 45 minutes, but allow more time because Sunday trains are not frequent. You could wait up to a half hour for a train. Also, O'Hare can be busy on Sunday nights. If the main security line is long, check out the smaller security stations. For both terminals 1 and 3, the extra station can be found at the end of the airline counters, before the connecting corridor to terminal 2. They're not always open, but if they are it can save a long wait. You'll see a lot of airline staff using them.

Totally agree with patg about the route. Nothing wrong with Michigan Ave and just going North of the River but for a one time taste and that short a stay- I agree LOOP/history/dowtown- the icons.