So i’m going to Chicago this weekend. I’m working in St. Louis and will be driving up Friday 9/5 and driving back down to St. Louis on Sunday 9/7.
I can get a hotel (marriott), but I don’t know where would be good.
I plan to…
Any recommendations on where to stay or what to do?
I was in Chicago a couple of weeks ago. A weekend is not nearly long enough to do it justice. I stayed at the Days Inn Chicago, on Diversey. They had a wonderful little directory there that had all sorts of things to do and eat in the area.
I imagine it would be hard to NOT have a good time in Chicago, unless you’re sick. It seemed that everywhere I looked, I saw something that needed investigation.
The traffic is fierce, and the water is rather sulfurous. Other than that, be on the lookout for the various cow artworks. Some years ago, the city of Chicago gave a cow statue to each of several local artists, and they all put their spin on the cows.
It’s been awhile, but last I knew:
Pizza Uno is very good: http://www.unos.com/
Giordano’s is also excellent: http://www.giordanos.com/main.php
Italian Village is also great: http://www.italianvillage-chicago.com/
Field Museum is worth seeing: http://www.fieldmuseum.org/
You can buy tickets to the Sears Tower Skydeck on line: http://www.theskydeck.com/
I think the art-type displays change yearly or so, though I suspect some places may have them yet. The last time I was on/around Michigan Avenue, they had fashion designs on display. (I might have overlooked some cows but if so, they just blended in to the background, to my eyes.)
Michigan Avenue is the big shopping and architecture street, aka “The Magnificent Mile”. It runs right past Millennium Park, which has wonderful statue and architectural features, like the Crown Fountain and the Cloud Gate. This is also known as “the Bean” - it looks silly at first, but when you get there you can see the whole skyline reflected in the outside of the sculpture, and if you walk underneath, you look up and up as the reflections of everyone under it stretch far up and away. Meanwhile, the Crown Fountain has photos of many everyday Chicagoans ‘projected’ onto the fountain columns. Right before the picture changes to the next person, the lips of the image purse around a small water spout, and water jets forth onto the granite floor.
For “Chicago-style” pizza, I like Lou Malnati’s, though to be honest I only ever eat that with tourists. 
I’m a fan of thin crust, myself. I’d tell you to be quiet about that but really, I don’t think the preference is that uncommon.
What kind of spoken-word performance did you have in mind? If you’re more theater-leaning, I’m having a hard time thinking of anything that’s more classic Chicago than the Neo-Futurists’ “Too Much Light Makes the Baby Go Blind.” Plus the cost is only $7 plus the result on a 6-sided die’s roll (so, $8-13), and that’s hard to beat.
I dunno if Sears gets crowded, but I went to the Hancock when I was there. Good views, plus you get to actually see the Sears Tower.
I’ll second Millennium Park & the nearby Museum Campus. It’s a great walk.
Giordano’s, Lou Malnati, and Gino’s East are, as I understand then, the go-to places for deep dish pizza (I certainly enjoyed all three).
What else are you in to? Beer, sports, theater, etc…?
I dunno if Sears gets crowded, but I went to the Hancock when I was there. Good views, plus you get to actually see the Sears Tower.
I’ll second Millennium Park & the nearby Museum Campus. It’s a great walk.
Giordano’s, Lou Malnati, and Gino’s East are, as I understand then, the go-to places for deep dish pizza (I certainly enjoyed all three).
What else are you in to? Beer, sports, theater, etc…?
You mention stopping by the Threadless store while you’re here. Too bad you’re not here during the week because their head office/ warehouse (on Ravenswood, just north of Irving Park on the north side) is open to the public and you can actually go there to buy your shirts directly. It’s as awesome and as fun as you’d expect it to be.
They have computers set up and you place your order on them as if you are shopping online. Once you submit your order, you put “warehouse” as your shipping option (only available if you’re doing this there), and the receptionist runs back into the warehouse to grab your order. Speaking of the receptionist, you’ll likely recognize her from the website as a t-shirt “model” as are most of the other employees there.
The store is nice too, but only usually has 12 shirts or so available at any one time - and I think they change their inventory weekly. If I were you, I’d definitely check to see if the warehouse is open on Saturdays - it’s worth a visit.
Oh, and I second the Hancock building over the Sears Tower. In fact, don’t go to the observatory - go to the Signature Room restaurant which is near the top floor as well. For the same price of admission to the deck, you can have some drinks and still enjoy the same view.
Don’t try to drive. We drove to Chicago early this summer, and that is one thing we won’t be doing again. I do wish we had taken an Architectural Tour - the amount of amazing buildings we saw was astounding.
Sometimes - I’m not sure of the frequency - there are free walking tours from the Chicago Cultural Center. We stumbled on that when we were there in May and had a great time on the tour. They take you in to some of the cool buildings and point out the mosaics in the ceilings and such. It was really interesting, and we saw stuff that we never would have found on our own.
The Lincoln Park Zoo is a bit further north than most of the tourist attractions, but it’s free and only a bus ride away. We found it to be quite a nice zoo (and we’re nearly zoo experts), smaller than some, but well designed with decent habitats.
Don’t forget the Museum of Science and Industry. It’s on the south side and is also a bus ride away. Plan lots of time to spend there!
I haven’t been to the Art Institutein years, but I remember enjoying it the last time I was there.
If you’re into trying different restaurants, Rick Bayless’ Frontera Grill is amazing. It’s within walking distance of the Loop. We also really liked Custom House, which is in the Loop. They’re both a bit upscale, and if you’re looking to do this on a budget, they might not be the best choices. But we tend to plan one fancy meal out - usually lunch when it’s cheaper - and really like trying places like these.
Chicago’s a great city! Have fun!
I agree with Ferret Herder, Too Much Light is a Chicago classic, but get there early because it does get crowded and will sell out.
I can vouch for the architecture boat tour given by the Chicago Architecture Foundation. They have other tours as well, including by bus and on foot.
Grumph. If you were staying Sunday night, I’d tell you to go to the Uptown Poetry Slam (the original one that started all the others) at the Green Mill.
Actually, just stay Sunday night and do it. You can go back Monday morning! 
I will add my voice to the recommendations for Gino’s East. I went there twice the last time I was in Chicago. Best freaking deep dish pizza I’ve ever had. Thick golden crust, a thick layer of gooey cheese, and the toppings swimming in a veritable ocean of delicious sauce. Man, I’m starting to wish I was back there right now.
As for the Hancock tower: it’s interesting, but kind of a touristy thing. If you’re into that, go for it. The view is definitely nice, but not, in my opinion, worth the $12 or so it costs to see it. Just think: with that money, you could buy almost half a pizza at Gino’s East! Think of the pizza, man!
What route are you taking home Sunday? If you’re planning on I-55 you might want to be aware that the Indy car race is running at Chicagoland Speedway, near Joliet, that afternoon. Might be better to take I-57 to I-70 and avoid the traffic. I’m probably telling you what you already know, but maybe better safe than sorry.
If you happen to be on I-55 driving home, near Springfield, some of the best Thai food you’ll ever have:
http://www.illinoistimes.com/gyrobase/Content?oid=oid%3A6483
Agreed. I was actually going to recommend this show, as well. Show up about an hour early (usually 10:15-10:30 works) for this one to make sure you can get in.
i was there back in april–don’t miss the art institute or the museum of science and industry. we had some great meals at les nomades, gibson’s, and le colonial. if you’re into molecular gastronomy and have unlimited funds, try alinea. not for the faint of heart, but a once in a lifetime experience!
Or, at the end of the day, go to the Signature Lounge on the 96th floor of the Hancock Bldg. Great views - just amazing after dark - and you can relax and enjoy a cocktail! There’s no charge to go up to the bar.
I’d also consider Edwardo’s Stuffed Crust pizza. Nothing beats it.
Not sure if you’ll be far up north, but Thai Spice is just about the best northern Thai cuisine outside of Thailand…