Okay I'll just dump out some random suggestions
Touristy ****:
- Museum Park where you're going to Field Museum. There's the Planetarium and Aquarium there too.
- Millennium Park: Yeah, it's where the Bean and all that stuff is. Not sure if they have the ice skating rink set up, but who knows.
- Architecture Boat Tour. I am not 100% sure if they do them during the winter, but they are awesome. You learn a lot about the city and the history. 90 minutes, have bars on the boat. Wendella and Chicago Architecture Foundation do both, probably $23-$30 per person.
There is a riverwalk which is cool too (free).
- Michigan Avenue. Yeah, a lot of stores you'll find in a lot of places i.e. Macy's, Nike, Apple, etc but some other cool ones like Tiffany's, Cartier, Armani, Van Cleef & Apels, Chanel, etc. Water Tower is on Michigan and Chicago/Pearson. Cool and all, but nothing to spend a ton of time at IMO. A little less known to tourists is Oak Street (thank god). This is a little more classy on average and you'll find stuff like Prada, Hermes, Moncler, etc on the street (and Gucci is near by). So if your gf/wife is into that, go to Oak Street. Further south on Michigan near the river has some cool architecture, and some good views of buildings, so I recommend going there.
- Chicago Pizza. Everyone always talks about Uno's, Gino's, Giordano's, and Malnati's. Those are the cliche ones and out of those, I like Malnati's the best (a "new" one this summer just opened on State a block or so south of Division). There are other good places besides that, honestly. I am a fan of Chicago Pizza and Oven Grinder Co on Clark personally (be prepared to wait). If you're a history buff, CP&OGC is located right near the St. Valentine's Day massacre site. Edwardo's and Pizano's are good too. Piece Pizza in Wicker Park is good too.
- Signature Room in the John Hancock. It's right off Michigan so that's fine. As I said before, it's better than Sears Tower, but the view is still overrated at night for the most part. Overpriced drinks IMO, but decent. Go more when there's still some light out (i.e. sunset ish time) and the views will be much better.
- Bars on Rush and Division. The bars on division are the ****** college type of bars and totally out of character with the area. The ones on rush are a little nicer in the Viagra Triangle. REALLY fun in the summer for people watching and just being out as everyone is out all night.
- Bulls/Blackhawks. Tickets are expensive, and sometimes hard to come by, but hey if you can get them for a decent price, do it.
- Broadway plays/shows. There's a handful of theatres in the Loop that is "Broadway"
Not as Touristy ****
- Second City. This could qualify as both touristy and not. It's a comedy club doing improv stuff like SNL (heard of SCTV? there you go) with tons of SNL alum who started there. If you can't get tickets there, there's a standup comedy club right near there called Zanie's. They have some good comedians there sometimes. If you're in the area and hungry, if you like Mediterranean/mid eastern food there's a place called Old Jerusalem near there. Good stuff.
- Fan of nice cars? Okay, well there's a Lamborghini, Ferrari, Bentley, Rolls Royce, exotic Mercedes, and sometimes Bugatti dealership on Rush and Pearson. ON the weekends they usually park Lambos and Ferraris on the street and sidewalks. You can walk into the dealership too (many do) and take pics. Just don't touch the cars unless you are going to buy one.
- Goose Island. Brewery...they make some good beer (312, Sofie, etc). *Get a tour there if you can.
- Wrigleyville. *Really just a bunch of overcrowded bars inhabited by everyone from frat guys to older people, but it's worth the experience especially if you're into that. *If you're big into music/movies and crap, there's a good record store on Broadway near Barry called Reckless. They have thousands of vinyl, cds, dvds, etc. *If you're big into that, check it out.
- Wicker Park. *West of downtown, and the Greenwich Village of Chicago. *Tons of bars and places to eat. Also random shops and another Reckless Records, and just random things like ridiculous bookstores where you can find anything from Homer to George Orwell to books on UFOs and the occult. *If you like drunk tacos and stuff, then go to Big Star near the Damen blue line stop.
- Mansions in Gold Coast. If you want to see some impressive houses, go to State and Division and walk north on State for a little bit. You'll come about a bunch of impressive old mansions INCLUDING the original Playboy Mansion (1340 North State). If you walk in all directions from there,it's full of nice places. Some rich/powerful people live there and some others like Billy Corgan and John Cusack own condos in the area.
- If you like MEXICAN food, I recommend going to Xoco, owned by world famous chef Rick Bayless (brother of Skip Bayless). It's mexican street food meaning Caldos and Tortas (baked in a wood fire oven), but they have beer/wine there too as well as amazing churros and amazing hot chocolate and other desserts. Their chocolates are fresh meaning they grind their own chocolate. Busy busy. Very casual, but be prepared to wait in line for awhile if you really want this.
- Purple Pig on Michigan Ave. Named one of the top 10 new restaurants I think in 2010 or 2011. They have tons of crap there, mostly revolving around the pig. Another busy place.
Nightlife
Bars: All over the city. Take your pick really anywhere in River North/Near North, Old Town, Lincoln Park, Wrigleyville, Wicker Park, etc. As far as downtown goes (i.e. River North) there's tons. So some random ones could be anything on Hubbard Street (i.e. Hub 51, Social 25, Rockit (good burgers), Hubbard Inn maybe, Paris Club (I think they have an upstairs nightlife area now), etc. Rush and Division as I said before, bars on Clark Street and Broadway in Lincoln Park, bars near Wrigley Field, and near DePaul in Lincoln Park, etc. Old Town is where Second City is. There's places like Benchmark, Old Town Ale House, Old Town Social, etc. Corcoran's is there too, which is an ISU bar.
Underground Wonderbar near Clark and Superior is also a Brazilian Jazz bar. Meaning they have live brazilian jazz and drinking pretty much every night. Cover is probably $5-$10 there for the music, but it's cool. Near there is a place called Fedora I used to go to all the time (when it was called Shady Lady). Not sure how it is now since it's been a year, but it was decent back then. Zad 451 is near there too...
Lounges: Was my "local" spot for awhile. Seriously, I recommend the upstairs of Le Colonial on Rush and Oak (a little south of Oak, next to Oliver Peoples and Hermes). Fancy restaurant downstairs, but upstairs is a dark lounge with a bar area and couches. Candlelit, tropical trees, etc. Setting is 1920s French Vietnam. Less expensive than Signature Room, but still not 100% cheap. Good food too (I recommend the fried spring roll appetizer (has lobster and pork in it) and the Pho). Can get busy on weekends, but worth it and you don't need a reservation upstairs to sit at the bar or couches. There is talent there (i.e. models) a lot, so you never know who you will run into (I have been next to Tyra Banks and Channing Tatum before). Just don't walk in with sports t-shirt and baseball hat on. Jeans and sweatshirt is totally acceptable though there.
Clubs: If you're into clubs, there's a bunch in River North like Vision, Excalibur, Manor, etc. I like Crescendo but you know, be prepared to pay $20 cover unless you're with someone hot. The Mid is maybe a year old and decent. They get a lot of pretty good acts in there. I also hate Sound Bar, for the record.
Music shows. There are tons of acts playing in town every night. Most aren't huge or anything, but still. I know Wu Tang Clan is playing on Sunday. Funny enough is Radio Moscow is playing next monday here. If you're a fan of blues, go to Buddy Guy's in the south loop, or B.L.U.E.S. on Halsted in Lincoln Park, or a little north of that on the same street.. Kingston Mines. Near the DePaul campus as well.
I'll try and think of other **** in the meantime for you though. Just a random thought dump.
Touristy ****:
- Museum Park where you're going to Field Museum. There's the Planetarium and Aquarium there too.
- Millennium Park: Yeah, it's where the Bean and all that stuff is. Not sure if they have the ice skating rink set up, but who knows.
- Architecture Boat Tour. I am not 100% sure if they do them during the winter, but they are awesome. You learn a lot about the city and the history. 90 minutes, have bars on the boat. Wendella and Chicago Architecture Foundation do both, probably $23-$30 per person.
There is a riverwalk which is cool too (free).
- Michigan Avenue. Yeah, a lot of stores you'll find in a lot of places i.e. Macy's, Nike, Apple, etc but some other cool ones like Tiffany's, Cartier, Armani, Van Cleef & Apels, Chanel, etc. Water Tower is on Michigan and Chicago/Pearson. Cool and all, but nothing to spend a ton of time at IMO. A little less known to tourists is Oak Street (thank god). This is a little more classy on average and you'll find stuff like Prada, Hermes, Moncler, etc on the street (and Gucci is near by). So if your gf/wife is into that, go to Oak Street. Further south on Michigan near the river has some cool architecture, and some good views of buildings, so I recommend going there.
- Chicago Pizza. Everyone always talks about Uno's, Gino's, Giordano's, and Malnati's. Those are the cliche ones and out of those, I like Malnati's the best (a "new" one this summer just opened on State a block or so south of Division). There are other good places besides that, honestly. I am a fan of Chicago Pizza and Oven Grinder Co on Clark personally (be prepared to wait). If you're a history buff, CP&OGC is located right near the St. Valentine's Day massacre site. Edwardo's and Pizano's are good too. Piece Pizza in Wicker Park is good too.
- Signature Room in the John Hancock. It's right off Michigan so that's fine. As I said before, it's better than Sears Tower, but the view is still overrated at night for the most part. Overpriced drinks IMO, but decent. Go more when there's still some light out (i.e. sunset ish time) and the views will be much better.
- Bars on Rush and Division. The bars on division are the ****** college type of bars and totally out of character with the area. The ones on rush are a little nicer in the Viagra Triangle. REALLY fun in the summer for people watching and just being out as everyone is out all night.
- Bulls/Blackhawks. Tickets are expensive, and sometimes hard to come by, but hey if you can get them for a decent price, do it.
- Broadway plays/shows. There's a handful of theatres in the Loop that is "Broadway"
Not as Touristy ****
- Second City. This could qualify as both touristy and not. It's a comedy club doing improv stuff like SNL (heard of SCTV? there you go) with tons of SNL alum who started there. If you can't get tickets there, there's a standup comedy club right near there called Zanie's. They have some good comedians there sometimes. If you're in the area and hungry, if you like Mediterranean/mid eastern food there's a place called Old Jerusalem near there. Good stuff.
- Fan of nice cars? Okay, well there's a Lamborghini, Ferrari, Bentley, Rolls Royce, exotic Mercedes, and sometimes Bugatti dealership on Rush and Pearson. ON the weekends they usually park Lambos and Ferraris on the street and sidewalks. You can walk into the dealership too (many do) and take pics. Just don't touch the cars unless you are going to buy one.
- Goose Island. Brewery...they make some good beer (312, Sofie, etc). *Get a tour there if you can.
- Wrigleyville. *Really just a bunch of overcrowded bars inhabited by everyone from frat guys to older people, but it's worth the experience especially if you're into that. *If you're big into music/movies and crap, there's a good record store on Broadway near Barry called Reckless. They have thousands of vinyl, cds, dvds, etc. *If you're big into that, check it out.
- Wicker Park. *West of downtown, and the Greenwich Village of Chicago. *Tons of bars and places to eat. Also random shops and another Reckless Records, and just random things like ridiculous bookstores where you can find anything from Homer to George Orwell to books on UFOs and the occult. *If you like drunk tacos and stuff, then go to Big Star near the Damen blue line stop.
- Mansions in Gold Coast. If you want to see some impressive houses, go to State and Division and walk north on State for a little bit. You'll come about a bunch of impressive old mansions INCLUDING the original Playboy Mansion (1340 North State). If you walk in all directions from there,it's full of nice places. Some rich/powerful people live there and some others like Billy Corgan and John Cusack own condos in the area.
- If you like MEXICAN food, I recommend going to Xoco, owned by world famous chef Rick Bayless (brother of Skip Bayless). It's mexican street food meaning Caldos and Tortas (baked in a wood fire oven), but they have beer/wine there too as well as amazing churros and amazing hot chocolate and other desserts. Their chocolates are fresh meaning they grind their own chocolate. Busy busy. Very casual, but be prepared to wait in line for awhile if you really want this.
- Purple Pig on Michigan Ave. Named one of the top 10 new restaurants I think in 2010 or 2011. They have tons of crap there, mostly revolving around the pig. Another busy place.
Nightlife
Bars: All over the city. Take your pick really anywhere in River North/Near North, Old Town, Lincoln Park, Wrigleyville, Wicker Park, etc. As far as downtown goes (i.e. River North) there's tons. So some random ones could be anything on Hubbard Street (i.e. Hub 51, Social 25, Rockit (good burgers), Hubbard Inn maybe, Paris Club (I think they have an upstairs nightlife area now), etc. Rush and Division as I said before, bars on Clark Street and Broadway in Lincoln Park, bars near Wrigley Field, and near DePaul in Lincoln Park, etc. Old Town is where Second City is. There's places like Benchmark, Old Town Ale House, Old Town Social, etc. Corcoran's is there too, which is an ISU bar.
Underground Wonderbar near Clark and Superior is also a Brazilian Jazz bar. Meaning they have live brazilian jazz and drinking pretty much every night. Cover is probably $5-$10 there for the music, but it's cool. Near there is a place called Fedora I used to go to all the time (when it was called Shady Lady). Not sure how it is now since it's been a year, but it was decent back then. Zad 451 is near there too...
Lounges: Was my "local" spot for awhile. Seriously, I recommend the upstairs of Le Colonial on Rush and Oak (a little south of Oak, next to Oliver Peoples and Hermes). Fancy restaurant downstairs, but upstairs is a dark lounge with a bar area and couches. Candlelit, tropical trees, etc. Setting is 1920s French Vietnam. Less expensive than Signature Room, but still not 100% cheap. Good food too (I recommend the fried spring roll appetizer (has lobster and pork in it) and the Pho). Can get busy on weekends, but worth it and you don't need a reservation upstairs to sit at the bar or couches. There is talent there (i.e. models) a lot, so you never know who you will run into (I have been next to Tyra Banks and Channing Tatum before). Just don't walk in with sports t-shirt and baseball hat on. Jeans and sweatshirt is totally acceptable though there.
Clubs: If you're into clubs, there's a bunch in River North like Vision, Excalibur, Manor, etc. I like Crescendo but you know, be prepared to pay $20 cover unless you're with someone hot. The Mid is maybe a year old and decent. They get a lot of pretty good acts in there. I also hate Sound Bar, for the record.
Music shows. There are tons of acts playing in town every night. Most aren't huge or anything, but still. I know Wu Tang Clan is playing on Sunday. Funny enough is Radio Moscow is playing next monday here. If you're a fan of blues, go to Buddy Guy's in the south loop, or B.L.U.E.S. on Halsted in Lincoln Park, or a little north of that on the same street.. Kingston Mines. Near the DePaul campus as well.
I'll try and think of other **** in the meantime for you though. Just a random thought dump.
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And the serving is big enough you won't have to stop for lunch.
