Visiting Chicago: what are your favorites?

I will be spending a few days in Chicago at the end of August to attend a family wedding. While I probably won’t have very much free time to explore, I do intend to get out for at least and afternoon/evening or two. If you have ever lived there or have spent time in the city, what are your favorite places to eat, drink, and visit?

I’ve never been, except passing through on the highway, but if I ever did visit (and someday I will), I’ve always wanted to see the Shedd Aquarium.

No real recommendations but if you want to do some of your own research this is probably the best resource on the net food wise for Chicago - http://www.lthforum.com/bb/viewforum.php?f=14

I’ve heard nothing but great things about Hot Doug’s. Definitely planning to hit it next time I’m in Chicago.

You’ll have a lot of folks tell you where the best place to get a Chicago-style deep dish pizza is. They’ll tell you Geno’s East, Lou Malnati, or (horrors) Giordano’s. They’re wrong.

Ask any real native who lives near the Clybourn Corridor off North in Lincoln Park and they’ll lay it out for you: the best deep dish pie on the planet is made at Pequod’s. If you’re going to do pizza in Chicago, that’s your place; they’ve got a big neon white whale on the facade of the building, you can’t miss it.

There are approximately 2,000 pizza joints in Chicago, but only about 10 of them are regularly lauded and staunchly defended as the best. Pequod’s, named after the whaling ship from Moby Dick, is one of those 10.

The blue vinyl awning, the lighted whale and neon beer signs belie a typical Chicago dive frequented by blue-collar crowds. When Pequod’s opened in the early 1970s with pool tables, darts and blonde wood, that’s exactly what it was. As the neighborhood gentrified, Pequod’s was infused with hipsters playing Golden Tee attracted by the blue-collar kitsch. In 2005, a kitchen fire temporarily shut down the place, and they cleared out the vintage accoutrement in favor of West Loop loft vibe with a slight Prairie-style accent.

Thankfully, the pizza never changed. Debates rage over whether the crispy thin crust or the deep dish is better. Our money is on the deep dish, baked in cast iron pans blackened by decades of seasoning, the overflowing cheese emerges from the oven as a halo of caramelized crust, lending a crispy nutty counterpoint to the pizza’s gooey interior. Servers bring it tableside and set it on whale-shape cutting boards. If you like encased meats on your pie, the thick hunks of spiced sausage at Pequod’s may be the best in town.

There’s a reason Pequod’s has been lauded by the Trib and Maxim Magazine as the best pizza in Chicago: it is all that and then some.

If you have some sightseeing time, the Chicago Architecture Foundation’s Architecture River Cruise is a great way to see the city. It’s a 90-minute cruise along the Chicago River, focusing unsurprisingly on the city’s architecture. It’s very interesting, and a great way to get a view of the city from a less-common perspective (from the river). You can probably walk up and get tickets on a weekday, but it sells out on weekends, so if you’re interested I’d get them in advance.

From the tour, you can walk north up Michigan Ave to check out the Magnificent Mile shops and such if that’s your thing. You can also see the Hancock Tower, and the Signature Lounge on the 95th floor is a fun (if expensive) place to get a drink and get some great views of the city.

If you walk south, you’ll come to Millenium Park, which I think is worth seeing. The Cloud Gate is probably the biggest draw, and the way it reflects the skyline makes for some fun pictures of the city. South and a bit east of Millenium Park is Grant Park and Buckingham fountain. The Millenium Park/Grant Park area also puts you near a lot of the museums (Art Institute, Shedd Aquarium, Field Museum, Adler Planetarium). The Art Institute recently opened a new modern wing, which I haven’t been to yet, but might be of interest if that’s your thing.

That might be a bit more than would fit in an afternoon/evening, but hopefully gives you a couple of ideas if you want to see some of the sights.

Completely agree. Chicago is really a great town, but the thing that overall speaks to me is the architecture and design of the downtown skyscrapers. Unlike the ones in NYC (and most other cities), which are largely gigantic rectangles…the skyscrapers in Chicago are on the whole, individual and interesting.

Of course, that may just be me; growing up, and now working in DC, I’ve got a serious case of skyscraper envy.

I spent a week in Chicago and loved it, especially the architecture. I went up both the Hancock Center and Sears Tower (is it Willis Tower now?) - Hancock had the best views.

I wrote up my visit here if you are interested.

BTW, I agree with trigger on Geno’s East - I found it distinctly average.

I like that writeup, Tim. Yes, the Sears Tower is now Willis Tower. I think the name change just went officially official this week. I agree with you about the views - Hancock is definitely superior. Though, they did just install some transparent ledges at the Sears Tower, which are worth the trip. You have to get there early, though (it opens at 9) to avoid round-the-block lines on the weekends.

Obviously there is quite a lot to do in chicago. What people have mentioned are good ideas. The archit. boat tour is really good. Pequod’s is pretty good (i tried it over 10 years ago though). Gino’s pizza is not very good but somewhat dependent on the location. Pizzaria Uno (and Due) used to be really good and popular. There are lots of good pizza and food places, you will have to research.

Places i will take visitors after they have done the tourist stuff is a ride on the EL train - take the brown line around the loop and up to Belmont to get a different look at the buildings and neighborhoods. The cultural center can have some interesting stuff. The Tribune building has peices of many famous building on the outside.

I almost always get tickets to Second City. I have never been disappointed. I’m going once, maybe twice, in September, and I plan to visit a bar called Sheffield’s, which was recommended by Esquire. (My main reasons for going up are to see Porcupine Tree and Ani DiFranco in concert. Not together. Wow, that would be a weird and interesting show.)

Definitely hit up the Museum of Holography.

Shedd Aquarium. Do things that excite your curiosity and you will never grow old.

Here is my list:

Museum of Science and Industry. Forget the Shedd, you can see fish anywhere. Where else are you going to see a German U-Boat and a Boeing 707 (hanging from the ceiling, no less)?

Architecture River Cruise.

Go to Wieners Circle for a Chicago style hot dog or go to Mr. Beef’s for an Italian Beef sandwich.

Go to a Cubs game. Show up at Wrigley during the 2nd inning on a weekday day game and buy scalped tickets for face value.

YES! Do this! BUT! Make sure that your tour guide is a man named Kevin L. Burroughs the Mayor of Bucktown. He’s a friend of mine, and does an amazing, amazing job. He is as close to Speed Levitch as Chicago has, and I’d say he’s more cogent and interesting. To top it off, he ends his tour with a blues song about Chicago played on Harmonica.

It’s a great experience. Also I recommend grabbing a Potbellies sandwich, they are tasty and cheap and all over the place.

I will second the notion of the Second City. Their Main Stage shows tend to be spot on. (Bias note: my parents worked there when I was a kid at the ETC. theater)

Finally, this is my favorite Italian Restaurant in the city http://www.trattoriaroma.com/ very close to Second City in Old Town.
A plate will run you at least $14-20 bucks, but the food is well worth. So delicious.

For a special dinner, go to Alinea. It will cost a mortgage payment and take four hours. Well worth it.

In addition to possibly listing cheap airfares (ITA route, fare and availability data are used by most of the US airlines and various major travel websites), matrix2.itasoftware.com will also list festivals and events occurring during your stay (but not tours and permanent attractions). If you use the calendar search mode, the events come up on the first search page, otherwise you can see them in the itinerary after choosing a flight.

I forgot to mention my favorite bar: The Charleston. It’s a special place in Bucktown. Not much I can say except it’s a great bar with a MASSIVE beer selection.

Me and at least half a dozen beer lovers will be in Chicago this Saturday (and some of us Sunday breakfast/lunch, too) and we need a couple places to eat. We’ll be at the 3floyds brewery for DLD but plan on getting out of there as soon as we get our beer. Chicago-style pizza is a must for at least one meal. I was recommended Giordanos by some folks here. Is Pequod’s better?

Do I need any recommendations beyond what’s already in this thread?

Edit: and Downtown Dogs was recommended.

Eating at Giordano’s is like eating at McDonalds. It’s awful.

Is Pequod’s better? That’s like asking if the '27 Yankees are better than your paper boy’s little league team. Go. Eat. Have the pizzagasm of a lifetime!