Two nights in Chicago. What to do?

I fly in Chicago on 9/30, and fly out on 10/2. I’ll be taking the train to a downtown hotel, within walking distance of a training class. So, while the trip is paid for, I don’t have to be especially alert in the mornings, not that I’m much of a night owl.

I’m looking for suggestions. What should I do in downtown Chicago those two nights?

Do you like blues? There are some pretty good clubs which should be easy to locate.

Chicago is not much of a tourist town like, say, Washington or New York or San Francisco but it has plenty to offer a visitor (it is a major metropolis after all). Since you didn’t say where your interests lie I’ll just offer some broad ideas.

  • Shopping: The Magnificent Mile runs along Michigan Avenue from the lake to the river (about a mile long…go figure). I think it was the President of Dayton-Hudson who opined some years back that he felt it was the best shopping strip in America beating out the likes of Rodeo Drive and 5th Avenue. Enough there to spend hours on.

  • Food: Chicago has some outstanding restaurants. Dining is a real treat in this city. Too many to list. Provide some cuisine you prefer and perhaps we can help point you to some good ones.

  • Museums: The museums in Chicago are world class. Most are rather close together (good walk or short cab ride). The Field Museum, Art Institute, Shedd Aquarium, Adler Planetarium, Museum of Science and Industry and Museum of Modern Art come to mind. Plenty of others as well but those are the biggies.

  • Theater: Short of New York perhaps one of the better theater scenes in the country. From big productions to small (seat less than 50 and you bring your own beer) theaters and everything in between. The smaller productions can be very entertaining and I personally prefer them to the big productions but whatever suits you. Plenty to choose from.

  • Music: As noted above Chicago has a great Blues scene. Generally though they tend to be expensive ($10 cover charges, expensive drinks) but worth a go if you like the music. Everything else too…Opera to Metal in a variety of venues. I HIGHLY recommend you pick yourself up a Chicago Reader (the people who operate this website in fact) for a good listing of what is going on in the city art-wise (music/theater mostly). The paper is free and can be found in most convenience stores. Ask someone if you cannot find one.

  • Tours: Been awhile since I looked in to these but in particular I would recommend an architectural tour of downtown. I think there are several to choose from. Chicago is known for some of its architecture so this is a very worthwhile tour to take.

  • Parks: Chicago has some great parks. Millennium Park, Grant Park and Lincoln Park in particular. Lincoln Park has the Lincoln Park Zoo in it as well which is smallish for a zoo but fun and convenient. Just off the lake so you can wander along that.

  • Tourist Traps: Sears Tower (which I still think of as the tallest building in the world…Petronas Towers and Taipei 101 cheat). Navy Pier. 95/96th floor of the John Hancock (95th is an overpriced restaurant…96th is a bar…you are there for the view which is great).
    Hope that helps.

Improv! If you enjoy live comedy, Chicago is a great place to be!

Metromix says Improv Rebellion is playing on 10/1 at IO (Improv Olympic, right next to Wrigley Field) at 10:30 on 10/1, cover is $5. It’s rated a “Good Pick”. Bar Louie is right by there, they have excellent burgers (plus there are about a million other choices further down the street).

Go to the corner of Belmont and Broadway. You will see a Chipotle. A few doors down there is a tiny bar. Above the door it says “reflections” however this is not the actual name of the bar. You will see one whole wall lined with fish tanks. You may also notice that someone has drawn a sign that says “SQWIDGE” on a napkin in sharpie that is taped to the wall. That was the work of one lobster mobster. You will find an older man sitting at the end of the bar. This is the owner.

You won’t find a better place in all of chicago

I hear there’s some message board hosted there.

Well, that is one reason I asked here. And, thanks for the posts.

Let me see, I’m not a shopper. The only shopping I enjoy I can do from here - bookstores, outdoor stuff, and that’s about it.

Since I’m assuming it will be dark when I’m free, the only way to use a park will be to take a morning run. I’m not afraid of the dark, so assuming the criminal element is under control, I should have no problem.

Now, eating is something I like and am good at. Same with drinking beer. Best yet is both together. I like to eat at places I can’t at home, so chains are out. I’m sure I can get fresher sea food when I go to HI, or some place on a coast, so let’s exclude that. I can get Thai and Vietnamese here. Seems to me I ought to have some actual Chicago pizza, instead of Chicago style Colorado pizza, while I’m in Chicago. I know of Uno’s, but I can believe there are other good places to go. Otherwise, what’s in walking distance/train ride of Club Quarters Centra, or the Monroe trainstop? Italian might be nice, but so would Polish, German, reasonably priced French, American, etc.

I am assuming that by the time I get out this training, and eat dinner/supper, that museums and planetariums would be closing on Monday, and Sunday evening is more problematic. It thinking it would be fun to go to the planetarium and an art museum, since Mrs. Slow isn’t much for those I don’t get to go much.

I will check out the Chicago Reader. Comedy sounds good, since Mrs. Slow won’t do that, either, but I suspect it is too smoky for me. I don’t mind a bit of smoke in the air, but many comedy shops and bars are too thick for me. I don’t feel right for days afterwards. (I’m an outdoor kind of guy. Give me a mountain to run up, or and island to swim around, and I’m happy.) Smoking is banned in pretty much all buildings here. Is it in Chicago? Otherwise, I’d take advantage of the music scene. I enjoy music more with company, but that can’t be helped.

I guess I’m talking myself into theater. I’m sure the major theaters are on line. What about the byob sized places?

You’re sure the napkin is still there? And, how do you know this owner is older than me?

You are absolutley correct on that. There used to be a nice scale drawing on the web that showed the world’s tallest buildings side by side on it is painfully obvious that the Sears Tower dwarfs the Petronas Towers and Taipei 101 in almost every way including usable height. I always wondered why the designers didn’t build buildings that really are taller than the Sears Tower? That was obviously one of their goals since they stuck misc. crap on to have something a bird could land on at a height just barely taller than the Sears Tower. Based on that logic, I think I will make a hat for myself with a three foot antenna on top so that I can claim the title as the world’s tallest person.

Blue Man Group is right near Wrigley field too. Comedy, and not smokey at all.

Well, maybe some dry ice fumes.

Unfortunately, my flight arrives at 4:40 on Sunday, and the show starts at 4. There is no show on Monday.

Are you male or female? Either way, no real problem with the “criminal element” for running. My running buddy is from Detroit, and he regularly comments “You wouldn’t see women running alone like this even in the middle of the day in Detroit.”

What hotel will you be in? If it is anywhere downtown, head east until just before you get wet in that big puddle. There’s a running trail that goes about 18 miles N and S from Evanston down to way on the S. Side. One day take it N, the next go S. You’ll treat yourself to some of the nicest views in Chicago.

Male, and yes, I’ll be downtown, so I’ll find that trail. (For the record, I’ve never had a problem running anywhere, not that I frequent Detroit. It’s just that when running at 5:30 am in the dark, it pays to be careful. Out here, mountain lions and coyotes are a bit of concern at that time of morning.)

I hear ya but it really is a nice shopping strip and has something for everyone. It is also a busy part of the city with a lot of foot traffic and some few historical landmarks (ok…just the old waterworks that was the only thing in the area to survive the Chicago fire).

Not to mention you might find something nice for the missus.

If you go running I would suggest going north more than south from the Loop (where it sounds like you will be). Especially once you get towards Lincoln Park it is quite beautiful and lots of activity along the water front (people running, volley ball, walking dogs, cycling, etc.). If you make it north far enough as I mentioned there is the zoo (it’s just off the lake).

Unfortunately there will be no Cubs games in Chicago when you are here but looks like you will be here for the end of the season. The Cubs are currently in a hunt for a playoff spot so depending on where they stand hitting a bar around Wrigley Field during a game could be quite fun even if you don’t care about the Cubs or baseball at all. If they actually clinched a playoff spot while you were there you’d be treated to a special kind of pandemonium that could be a ball.

If you don’t mind taking a (still statistically tiny!) risk with yourself, you gotta go to 57th and Ashland. There’s a bar there called the Williams’ Inn. The bar is nothing special–but you’re not there to drink, or even to stay. What you want to do is call in an order for a sausage pizza. That’s all. No fancy toppings needed. Pick up your pizza, head out to Grant Park or North Avenue Beach… should still be warmish I think, though with this town ya never know… and chow down.

You will thank me. Your arteries won’t, but hey, ya buys ya ticket…

Yep. I believe the new building in Dubai is actually legitimately the tallest building in the world no. No tricks. However it is still under construction so while it has surpassed everything else it won’t count till the building is fully open.

The deal with Petronas is its spire is considered part of the “structure” of the building while the antennas on the Sears Tower are not. That technically make Petronas taller but it is obvious crap when you look at a scale model or drawing. Taipei 101 gets closer but the Sears Tower still beats it in scale drawing I have seen and again the Taipei 101 gets away with a fudge.

I never understood why someone would build a building to within a few meters of “tallest” status and not go the extra bit to claim the record. If you are only a few floors off why not? You’re already in for the cost…may as well nudge it that bit further.

Here’s a link to maps of the lakefront path. If you go N, coming back S is the money view of downtown that you see in so many movies. There are markers every 1/2 mile.

I’m a big fan of the S part, mainly because it is so much less crowded - but you shouldn’t have a problem early in the a.m. Takes you right past Buckingham Fountain, the museum campus, Soldier Field, and McCormick Place. Like I said, I’d strongly recommend that you go one direction one day, and the other the next. Probably the best and quickest way for a visitor to get a quick overview of a bunch of the downtown/lakefront area.

Let me know if your schedule allows you to squeeze in a lunchtime run on a weekday. Or even just lunch.

I was partially to Giordano’s when I was at U of C, and they have a downtown location – 730 N Rush Street.

Holy shit. They mail-order pizza.

You said you aren’t much of a night owl, but I pulled these up. Any of them catch your fancy?

Sun 09/30/07 Hanson House Of Blues Chicago,IL
Sun 09/30/07 Charlie Hunter Old Town School Of Folk Music Chicago,IL
Sun 09/30/07 Suzanne Vega Park West Chicago,IL
Sun 09/30/07 Golem Schubas Tavern Chicago,IL
Mon 10/01/07 BobaFlex Elbo Room Chicago,IL
Mon 10/01/07 Egypt Central Elbo Room Chicago,IL
Mon 10/01/07 Fixer Elbo Room Chicago,IL
Mon 10/01/07 Hydrovibe Elbo Room Chicago,IL
Mon 10/01/07 The Blow Empty Bottle Chicago,IL
Mon 10/01/07 Stephen And Other Dummies TBA Sycamore,IL

I see Metro has the Hives on the 30th, but they are sold out. You might check out Double Door, The Green Mill, or Buddy Guy’s Legends (right downtown), depending on your preferred style.

If you like theater, there are several theaters big and small on the N side of the Loop. Like Q says, Blue Man is a hoot. And these guys are really - uh - different, and just a mile or 2 W of downtown. An easy bus/cab ride.

And there are many worldclass museums right downtown - not sure which, if any, have evening hours on a Monday.

Let us know what you like - in terms of entertainment, food, etc., and we’ll set you up! (Giordano’s pizza is great, but IME many visitors prefer the Uno’s or Due’s experience.)

Many years ago I used to live in Chicago, and there were two really cool haunts I remember. One was the Annoyance Theater which is great for performances; it may be all or mostly comedy. The sketch comedy I saw there was great, and (I can’t guarantee if this is still true) they had these great couches to sit on instead of regular chairs.

The second is the Vic Theater which has a “brew and view” which means during special shows you can buy alcoholic beverages as you watch the movie.

For Chicago style pizza (at least for the 15 years I used to live there) the best place was Gino’s East. I loved that place. I hope that they are still there.

During the day, of course there is Lake Michigan, and Grant Park is very nice. If you have access to a car, driving down Lake Shore Drive is really scenic because you have the Lake Michigan on one side and a great view of the city skyline on the other. Chicago has some sweet architecture and lay out.

The Museum of the Art Institute is known for a large Impressionist collection.

The Field Museum has the two stuffed maneating lions from the movie “Ghost of the Darkness”. The Shedd Aquarium is cool. The museums are worth seeing.

When I used to live in Chicago, there were two neighborhoods which were the arty ones, Wicker Park (home of Smashing Pumpkins, I’ve actually met James Iha once) and Bucktown. I have to say that the art scene there is very cool. It has a very different vibe from New York. If you like art, I would check it out. As another poster suggested look in the Chicago Reader for galleries. There were a few galleries I could recommend. I-Space (the Uof I Champaign-Urbana gallery), the gallery in the School of the Art Institute, and Randolph Street Art Gallery (experimental stuff very cool). If you are into contemporary art, you might like the Museum of Contemporary Art. It reminds me of a smaller, cuter version of the MOMA in NY. Art can be very hit or miss, but I’ve seen some great stuff there. It may be just my view, but I remember the art in Chicago being quite playful and cute. It’s a very creative city if you know where to look. Some great cartoonists have come from that city (ie. Lynda Barry, Chris Ware, Daniel Clowes).

I also have to mention Lake Michigan again. Great for relaxing. It’s very beautiful on a clear moon-lit night. If you stand by the edge of the lake, there is an optical illusion that the moon’s light will create line of light that comes from the horizon directly to you and will follow you. This may happen by all or most lakes, but I have very fond memories of it.

There is also a small Chinatown there where I had some good meals.

I believe that Chicago may also be know for their hotdogs with lots of stuff on them. I can’t recommend a place because I’m not that into hotdogs.

In terms of the blues and jazz, (I know others may disagree with me) but I didn’t think it was all that great there. I think in the past, it was much better I’ve heard. New York is better for jazz and blues. But I could be wrong on this.

I know you said that you’re not into shopping, but the shopping there is great. Good selection and good prices. You can get some really funky awesome clothes for not too much. I could recommend some places.

I could recommend some cool bars and clubs, but after so many years, I don’t even know if they are still around. They are small and cute as hell and have a really comfortable vibe (compared to New York where I moved later).

Chicagoans are really friendly and nice. Have fun.