Is there somewhere you could catch AMTRAK? It is exhausting to go into and out of big cities for sightseeing and shopping. Much more relaxing to be there, where you can go back to your hotel for a rest. And the points of interest, both cultural and shopping, in Chicago are in a very small area.

I would also note that midweek hotel rates are much more expensive than on weekends, and of course weekend traffic is much less than on a weekend.

Guess what I am suggesting!

We took Amtrak out of Indy a few years ago. The schedule is the pits. That's why I would prefer to drive to the outskirts of Chicago and take public transportation into the city. I don't know how crazy shopping is during the week. We were there for a day a few years ago on a Saturday and it was insane.

Midway is about 45 minutes from The Loop via the Orange Line L. To that, you'd need to add the time for a shuttle between your hotel and the airport. So, if you get tired while shopping and want to drop packages at your room or rest a few minutes, you'd have a long haul to do so.

You also realize that reaching MDW from Indiana will involve around 7-10 miles of driving through the city once you exit the highway. If you take I-90/94 to I-57 and head up Lake Shore Drive or I-90/94 to Ohio Street to one of the hotels in river north, you'd be driving less than 5 miles in the city.

Your other options to avoid the city would be to stay in NW Indiana and take the South Shore line into the city. However, as with Amtrak, their scheule isn't great and trains only operate every 60 minutes outside rush hours. For South Shore schedules and info, check www.nictd.com.

You could also take I-294 west of the city to Oakbrook. In addition to several hotels, there's also Oakbrook Center, a large shopping center anchored by Macy's, Nordstrom, Lord & Taylor, Neiman Marcus and Sears.

To reach the city from there, you could drive south to Hinsdale or Western Springs and catch the BNSF Metra (commuter) Line or north to Berkeley and catch the Union Pacific West line into Union Station. Again, the problem is that the trip takes about 45-minutes and outside rush periods, trains only operate about once per hour. For Metra schedules and station info, check www.metrarail.com.

Lots at the Metra stations fill early with commuters so parking may be difficult to find after 9:00 or 9:30 and nearby streets are strictly regulated.

When I had a nephew graduating form Great Lakes (Navy) we stayed in Lake Forest. http://metrarail.com/metra/en/home/maps_schedules/metra_system_map/up-n/station.LKFOREST.html
I did ride the Metra into the city of Chicago once.

Why not just drive in and park the car until it is time to leave? Mid week, non rush hour traffic will not be bad at all.

Staying so far out would be a logistical PIA for shopping and sight seeing downtown.

Two thoughts: do as others have suggested, drive in mid-day to avoid traffic, OR park your car at Midway in long-term parking, then take the Orange line to a downtown hotel.

Parking in downtown is expensive but it's only about $10/day at Midway. You'd just have to deal with the hassle of taking the Orange Line back and forth twice with luggage and all your shopping bags. But that might be worth it if you'd save a significant amount of money on parking. Then again, for just a couple days the savings might not be worth the extra hassle, just depends on what your hotel charges or if you can find public parking that is cheaper.

I'd definitely look into a downtown hotel, use Priceline or look for deals for your dates. I just would not want to take the El back and forth for a couple days. I've stayed just a bit north of downtown and even that gets a bit old going back and forth, and that was only about 15-20 minutes on the train.

Thanks for all of the ideas. The problem is, I don't have a definite date. We are thinking of a spur of the moment trip, depending on the weather. We have been to Chicago on a bus trip a couple of times prior to Christmas and both times the weather was horrible. We are planning to watch the weather forecast starting after Thanksgiving and making a quick reservation. When we decide I will definitely see if there are any downtown specials. Maybe driving in around noon wouldn't be to bad. I'm sure we could stay near Midway if we can't find anything else. Also,Oakbrook is an idea. My friends went to the mall there last year and were impressed. They traveled back and forth from downtown.

Thanks again for all of your help!