First: DO NOT DRIVE AND PARK DOWNTOWN. Drive to Harvard, IL and take the Metra in; you'll get off on the opposite side of the river from the Civic Opera House.

If you are okay with a hotel downtown, go to the Wit. Looks like rates start around $229, which is steep but not terrible. It's a division of Doubletree, but it's some kind of newer concept that has more upscale amenities and is only about a year old. A friend of mine manages the spa there (her name is Elie and she rocks). They have specials, which I imagine you can probably take advantage of if you're going during the week.

This recent comment suggests the Days Inn in Lincoln Park. Another couple of people recommended the Ruby Room in Wicker Park, which might be a nice alternative to the Loop.

Also, another plug for Lookingglass Theatre -- haven't actually been there myself, but a friend is their marketing director.

I am in Madison, too, and I am telling you right now: DO NOT TAKE HIGHWAY 12.

And go to the Art Institute, and do not under any circumstances miss the Bean.

Agreed, do not take Highway 12 unless you have some sort of strip mall traffic jam fetish. Train FTW.

When are you planning this getaway? Perhaps we could have a mini-meetup?

Living in Chicago, I always wish I could offer more advice for visitors. But I don't stay in hotels here, so I'm not much help. A quick peek at Expedia says the Hotel Sax, Palmer House Hilton, and Hotel Felix are less than or around $160 per night. The Palmer House is in the loop - very close to all the L lines, Millennium Park, and the Art Institute. The Hotel Sax has a very cushy bar, the Crimson Lounge, attached to it and is right near the river. I'd say you could walk from there to the Art Institute, etc. I've never been to the Hotel Felix, but it seems to get good reviews and is in the River North neighborhood - a lively place, but probably a cab or train ride to the loop.

Yelp has a pretty big presence in Chicago, and I find I can usually trust the reviews there.

If you want to know about hole in the wall bars, especially those with pool tables or dart boards, I'm your gal.

I have enjoyed staying at the Palmer House Hilton in the past. It's a neat old fashioned looking place, right on the subway, a little bit of a hike from like dinner and hangout places, but I think that's fine.

Oh, you are all so wonderful. Thank you!

I definitely do NOT have a crawling traffic fetish, so I'll stay away from 12.

The visit is going to be, uh, tomorrow (oh how I love last minute things... wait, no, I don't) and Sunday, and it looks like we'll have our plates pretty full - I've been meaning to get down to Chicago for a meet-up (mini or otherwise) for a while now, but the drive and traffic intimidate me, to be honest. We need to do one in Madison sometime, seriously!

The Art Institute is definitely on our to-do list. I'm excited! I'm just not a good last-minute planner person. This is all helping enormously, though. Thank you. :)

I'm going to be in Milwaukee tomorrow for a wedding, but will be back in the city on Sunday, which just so happens to be my birthday. I think we're going to the Sox game, a 1.05pm start. I just emailed you my cell number just in case you'd like to grab a quick drink or something. Yay August birthdays!!!!

Happy early birthday! I'll definitely get in touch if we have some time, but right now it looks kind of like a whirlwind weekend. Wheeee!

Ohh - and brunch suggestions:

Dunlay's on the Square - BEST HASH BROWNS EVAR! From the loop, take the Blue Line toward O'Hare and get off at the Logan Square stop.

LOKal - $7 bottomless mimosas or $9 bottomless bloody marys every Saturday and Sunday from 9.00am to 3.30pm. From the loop, take the Blue Line toward O'Hare and get off at the Damen stop.

Moonshine - Great food, excellent mojitos, and a bloody mary bar for brunch. From the loop, take the Blue Line toward O'Hare and get off at the Division stop.

You know, I'd actually avoid the Field Museum unless he has some deep need to see one of the things there. I went a couple years ago, and we paid something like 27 bucks to get in (and 25 for parking!), including 18ish for regular admission and another 9 for the special exhibit of giant bugs underground. That exhibit wasn't thrilling, and overall my partner and I* ended up hanging out in the McDonalds while our other friends tromped around. I KNOW! Isn't that stupid? We are totally not that kind of people, usually, but I think between the drive down the aforementioned Hwy 12 and the complete lack of parking (and the assorted maneuvers used in trying to discern this fact), we had HAD IT.

(Also, I got my ass stuck in a concrete ant.)

*It was a very special weekend for us, as that was when we got to spend our first solid time together as boyfriend and girlfriend, and the thought of cheap milkshakes and Mold-a-Ramas makes me feel fuzzy inside. If you go, make sure to use the photo booth!

If you like sitting on your butt for about 2 hours on top of a bus and learning about Chicago, then by all means take the signature double-decker bus tour. On my recent trip, my sister signed up me and my mom (and my two young nieces) for it and the girls made it through one of the two hours. HOWEVER, my mom and I could have totally done the entire loop and then some.

I also went to the Museum of Science and Industry by myself from about 3 pm to closing and it was pretty cool. My favorite exhibits were in the Science Storms hall, but I took more picutres on my phone from the1 transportation center. Other favorites were the chick hatchery and the conveyor belt assembly line (haven't opened up my toy yet).

Yeah, I think we can give the Field Museum a miss this time - the Shedd and the Art Institute should keep us busy.

Also, argh, the mister is now saying he doesn't want to ride the train - he wants to "just drive in and park somewhere convenient, maybe at whatever hotel we stay at".... I am now breathing in and out slowly and reminding myself that it's his special day, dammit. I offered this as an option.

Also also, the cheap milkshake pictures are adorable. Just sayin'.

If you do drive in, park under Grant Park south of the Art Institute -- at least it used to be cheaper there than Millennium Park/Monroe. It's more competitive with private Loop garages, now, but I think that's one of your cheaper all-day bets, and it's convenient enough to both museums and Loop/Upper Michigan shopping. Otherwise, official parking for the Shedd is next to Soldier Field, although if you really want to you can tool out toward Adler and see if you can find a metered spot along Balbo.

Personally, I'd rather spend my time looking at the Loop than driving through its traffic, but YMMV.