Wiener's Circle
Man, ya'll hit it up hard fast!
Take your car north up Sheridan Rd for some beautiful scenic views up through and past Evanston. Totally worth driving 30mph (um don't do it during rush, it's an alternative commuter road).
I'm really biased when it comes to architecture, but hot damn the architecture tour is great. Anything by Sullivan is fantastic. Check out Graceland Cemetery for some really cool cenotaphs and other tombs (a lot of them famous Chicagoans - Ludwig Mies Van Der Rohe is buried there as well).
This is also a great chance to visit Milwaukee (as previously mentioned) and visit the Milwaukee Museum (well, the exterior sure is fun and makes for great photo-ops). If you use the Metra at all, be sure to buy a Weekend Pass (it only works on Sat/Sun though) which is basically unlimited rides for $7.
Also, Six Flags Great America is still running really solid and clean. They tore down most of their dilapidated pieces of shit (except American Eagle, but by god if they tear that down people will be bitter).
There are also some pretty cool neighborhoods for bars. Logan Square has some decent spots (Whistler and the Boiler Room were pretty fantastic). It's kinda the poor-hipster neighborhood, whereas Wicker Park is for the upscale hipsters. Both really nice neighborhoods to visit and all accessible via the El.
I know that someone said the Museum campus (I hope), but definitely visit ALL the museums. Or try. I spent a good 3hrs at the Art Institute of Chicago and hardly explored 3/4ths of the building. The new Renzo Piano addition is pretty cool, but I don't know what their special exhibits are right now in the Modern wing. Used to have Goldberg studio stuff which was really friggen awesome (architect of Marina City Towers and the soon-to-be-demolished Matron's Hospital). So good luck with Museum of Science and Industry or the Field Museum. The Adler Planetarium and Shedd Aquarium are pretty easy-going places, though.
the picasso exhibit going on right now at the art institute is unreal, it seriously takes like an hour to go through. its expensive as far as museums go but a great way to kill an afternoon
the architecture tour is the best thing ever. if you are there on a saturday take the 3:15 wendella boat river and lake tour. the tour guide, Andrew, is amazing. Had him the last two years. http://www.wendellaboats.com/experie...rivertour.aspx
drinks on top of the hancock is pretty awesome but expensive as hell, love going there just before sundown because you can actually take good pictures, have a few $15 drinks and then go to dinner somewhere downtown.
since i dont live there idk the neighborhoods as well as the locals but i've always had good times in wicker park/bucktown and lakeview. n clarke st is a bar every 10 feet.
also there are two theaters that run nerd themed (super mario, doctor who, indiana jones, star wars) burlesque shows that are a fucking blast gorilla tango and plan 9
I work across the street from one, I went for lunch every day for like two months then realized I had gained 15 pounds and had to cut it out lol
go to kumas and have the best burger in the fucking world, and what rhino and callisto said. they are correct, and the things they've said have basically made me fall in love with the city. i don't want to move out lol
I've been to Chicago twice now, done a lot of the touristy stuff. The things I thought were the best were definitely the Field Museum and the Shedd Aquarium. Those two are definite musts if you like museums/aquariums. If you go to the Field museum though, it will take all day to see everything in it.
I was less impressed with the art musuem, planetarium and the random tall towers. They were still cool but I just love animals and history and stuff so much that the aforementioned activities really wowed me. Navy Pier is also extremely excellent, lots of stuff to do there in the summer. There's a glass museum around there somewhere too that was kinda spiffy...
Drivers there are crazy though. I got a lot of great use out of my train pass :D
Maybe you should also try to order some chicago style pizza. I'm sure you can get it other places but...y'know, Chicago pizza in Chicago...fuck yeah.
Deep dish pizza is pretty amazing. If you can't find a non-chain that looks good, there are Giordano's and Uno's scattered everywhere. I get up to Chicago about once a year and always have to have my deep dish!
Acceptable options are Lou's, Gino's East, or Giordano's. Uno's is garbage.
This is a lot of food to eat.
I'll have to start widdling this list down.
Or just suck it up and eat 5 times a day
Echoing a few things.
Get a 3 day pass for CTA, don't try to drive around.
Portillo's is a must
Giordano's is most boss.
Unos is complete garbage.
The Maggiano's in Chicago is the best Maggiano's Ive been to (I've been to 3 nation wide)
My favorite restaraunt? And if your going to get me to buy a drink for you? Elephant and Castle. Seriously awesome pub and theres 3 downtown. One in the financial district, one north of the river and one on the north end of Wabash. The one on the end of Wabash is the best. Its never too busy and the bartenders and waiters are great. They are not expensive at all, and have the 2nd best Bangers and Mash I've ever had.
(Best Bangers and Mash are in a small place called brocach's in Milwaukee)
If you want to be adventurous, you can take the #6 bus to my part of town, Hyde Park. You can eat at "Ribs N Bibs" (You can throw a rock at my apartment window from here) see the Museum of Science and Industry, walk by the President's house and get frisked by Secret service and check out a Frank Lolyd Wright house. Also, the UIC campus is a great place to walk around.
Also Valois... This place will make me fat someday, I know it. Its a cafateria type food place, and that might turn you off, but even the President says its his favorite place to eat in Chicago. For good reason too. Love me some Valois
Little less mainstream food places I love:
http://www.millerspub.com/
http://www.warehouseliquors.com/ is one of the coolest liqour stores you can check out if your near the downtown area.
If you want to go a further east a few blocks of that, Binny's Liquor has a "Toys R Us" of liquor that will blow your mind.
Shed Aquarium is worth it for the sharks alone.
Museum of Science and Industry is a nice half day thing.
Field Museum is great, but I would spend an entire day there.
The art museum is meh (Thanks Europe for spoiling me). Just seems so small...
Millennium Park is a must, as a matter of fact just about anything on the Lake Front is awesome. I run from Hyde Park to Millennium Park and its gorgeous this time of the year.
I hate Navy Pier. unless they have fireworks. Even then, you can watch them anywhere on the Lakefront. Its just such a huge tourist trap, and the food is god awful expensive. Harry's is probably one of the most expensive and overrated restaurants on that peninsula.
If you go to Navy pier, walk around, and maybe check out the small shops and get on the Ferris wheel. But don't spend the day there.
Movie places: On Roosevelt there is a theatre tucked away called ShowPlace ICON at Roosevelt Collection. We've tried countless places in the city and keep going back to this one. They have a bar upstairs, and you can get food there. Overall, for the price, they are just the best.
Milwaukee is a great place to visit if you want to take a quick train up there. If I had a day there I would go to brocach's, go watch beer get made, and hit the lake front's art museum/war memorial. My fiance' and I go there about 4-5 times a month and are getting married at the War Memorial in a month.
Uno's is like the Appblebee's of Chicago pizza lol
Gene sikel I think is the name of an independent theatre, downtown. Iirc its on state. I went there last year to see a miazaki movie. Comfy, serves beer, plays independent films year round. Cheap too
Ya most icons are the same, there are a few in the city too. The difference I think is the location. Its tucked away in a cool aparement complex, so its never insanely busy. Its always super clean and the staff is awesome.
Compared to the one just north of the river downtown or the theatre on navy pier, they are always insanely busy. Makes for a lot of people coming in so late, that they are still seating people in the first 5 min of the movie.
Yeah we just had a work party last night where we went to the Icon here (Central West End) and rented out a theater to see Star Trek. Free drinks and food too! Was pretty fun.