Chicago for a weekend in Octoboer

Despite the cost, you'd probably be better off spending a night or two right in the city. If you look at Google Maps, it takes 45 minutes to drive, and 2+ hours by public transportation to get from Lemont to the Shedd Aquarium (for example). And the 45 minute drive is very optimistic, because there's always traffic. Public transportation is city bus, which is also at the mercy of traffic. Add to that: time it would take to find parking, etc. You're looking at over an hour just to get where you want to go. Closer suburbs aren't much better.
Honestly, Chicago traffic is horrible. If you want to see downtown sights, stay downtown. That's what I'd do, anyway.

I don't know how the marathon will affect your plans, except it would definitely make traffic even worse. Maybe find out the route, and choose attractions that are not right next to it!

I agree you don't want to stay in the outskirts and drive in every day. Chicago traffic is awful. Get a hotel downtown. I like the theater district or near there. There is a suburban train called the Metra if you really don't want to stay downtown. Take a look at where it goes. I have cousins in Arlington Heights and have taken the Metra out to see them several times. There is a station near Amtrak's Union Station downtown, but I think there are other downtown stations, too.

Thank you very much for your input! We ended up finding a more affordable airbnb in Mayfair area which looks likes its only a single train ride to downtown and not as far out as some of the other suburbs.

Looking forward to my trip!

We spent a long weekend in Chicago in early December and despite the weather we had a wonderful time. Definitely loved the Art Museum, and the architecture boat tour is very cool indeed. Actually it was freezing, but it won't be for you - ha. I recommend you follow it with a nice big ice cream sundae at the chocolate shop near the boat launch. We stayed at the Royal Sonesta Downtown, right in the thick of things, and loved the location. If you like comedy at ALL, consider taking a ride share to Second City to enjoy an improv show. Finally, we indulged in old school deep dish pizza at Lou Malnati's. Have a great trip!

Make sure you go on the Chicago Architectural boat cruise on the First Lady, not a copy cat tour of which there are many!
Go to www. architecture.org to book tickets!
Mayfair is pretty far out. You may want to keep trying to find a closer location to the city.

You gotta plan on the culinary aspect of this trip. That means Chicago hot dogs and Italian beef (sort of a french dip - sliced beef on a hoagie roll with au juic and peppers and onions). Wife and I love the Portillo's chain in Chicago. There's usually lines. There's also Johnnie's Beef.

If you want upscale, there's Topolabampa - Rick Bayles' fancy Mexican restaurant downtown on Canal St. For German food downtown, try the Berghoff Cafe - very old-school, male waiters. For dim sum, go to Chinatown and hit the Imperial.

Oh man thank you ALL for the wonderful recommendations- we are SUPER excited for everything!!! We decided that there was just so much to see and do we extended our trip 1 night LOL