Ideas on things to do/places to stay in Chicago?
June 9, 2011 6:30 AM   Subscribe

I'm a 26-year old guy travelling to Chicago in August with 2 friends. Where should we stay and what areas/neighborhoods/things should we check out to get the full Chicago experience? Details inside...

I'm travelling with 2 friends (all mid-20's) to Chicago on Thursday, August 18th. We're planning on leaving Monday, August 22nd. It's my friends' first trips to Chicago. I've been there many times with my family as a kid but never with 21+ friends.

So far, we're attending the Cubs game on Friday 8/23 and planning on checking out the Air and Water Show on Saturday 8/24. I'm sure Navy Pier will be on the list, as will the Hancock Building or Sears Tower.

Where should we try to find a hotel? Downtown around Michigan Avenue?

We're also going to want to go out at night but we're not sure where the big bar areas are in Chicago. Anyone have any ideas? Are the big nightlife areas downtown or are they outside the downtown area?

Also, recommendations for other things to see/do would be greatly appreciated!

posted by decrescendo to Travel & Transportation around Chicago, IL (19 answers total) 9 users marked this as a favorite
Navy Pier is full of the same sort of tourist attractions you'll find anywhere else, with a slight bit of Chicago branding. Avoid it.

The Chicago Reader is a great source for info on clubs, concerts, food, theater, etc. Also pick up a copy of Time Out Chicago when you get here.

If you stay downtown you are at the hub of the train lines, so it'd be easy to get out to other neighborhoods. There isn't much of a nightlife there besides the big theaters, although the city does some great music programming in Millennium Park.

What kind of nightlife are you looking for? Chicago has lots.
posted by hydrophonic at 7:20 AM on June 9, 2011

Response by poster: What kind of nightlife are you looking for? Chicago has lots.

I think my friends are the pub types as opposed to club / high-end lounge types.
posted by decrescendo at 7:22 AM on June 9, 2011

Not a native, but I'm going in July. I'll be following any hints in here closely. Here's what I've got for my upcoming trip so far:
  • Improv Olympic and/or Second City one night. (based on whim)
  • Not get full value from the "Go Chicago Card" because we walked around trying to re-enact Ferris Bueller moments.
  • Photograph The Bean (I know it's trite. But I'm also going to see U2. Chalk it up to being old and unhip)
  • The cubs aren't in town, which is okay, since I'm a STL Cards fan. Maybe a Whitesox game?
  • Hot Dougs.

posted by DigDoug at 7:28 AM on June 9, 2011

there's also a Best Western walking distance to Wrigley. Good views of the Air and Water Show walking distance from that Best Western, too. There's also the Majestic, near Wrigley Field, but it's a "luxury boutigue" hotel, so I'm not sure how expensive it is. Your itinerary sounds like trying to stay in the Wrigleyville hood will be a good bet. You're walking distance to the red/brown line, which will take you downtown for the Sears Tower or walking distance to the 14x buses, which will take you to the Hancock. There's cheap eats (for example, Joy's Noodles, Five Guys, Clarke's diner) and nicer eats, lots of bars, and during the run-up to the Air and Water show, the jets fly over the neighborhood. You're a reasonable bus ride from Kuma's Corner or Hot Doug's or any of the other Chicago places that get lots of recs in Chicago threads.

As for the big nightlife--there is no single "big nightlife" district in Chicago, unlike a some towns. Right near Wrigleyfield is a strip of busy bars and several live music venues. Down from there and a block or so west of that Best Western is a strip of gay bars. Rush street (the Viagara triangle) still has a lot going on at night. Get south of the loop and there are pockets of great bars, live music and late-night restaurants.

I'd give Navy Pier a pass, too, unless you're going for the stained glass museum (which doesn't sound like your speed) or the Shanghai Circus (ditto). If they're doing the tethered balloon rides, that might be as much fun as going up the tall buildings, but there's not much there at Navy Pier.

Pubs abound in the Wrigleyville/Lakeview/Boy'stown/Uptown neighborhoods I'm talking about. Paddy Long's with the bacon bomb is easy to reach; the Duke of Perth with its scotch list. Sheffield's. Hopleaf.

You will want either to budget for cabs or get comfortable using the bus / walking, if you do end up staying in the Wrigleyville area.
posted by crush-onastick at 7:37 AM on June 9, 2011 [1 favorite]

Rush & Division is ground zero for a lot of nightlife bars, pubs etc.

Or it was 10 years ago.
posted by Bonzai at 8:22 AM on June 9, 2011

Skip Navy Pier. The Air and Water show is the most crowded event of the year in Chicago so prepare for big crowds and allow extra time for any tourist activities, as they will be even more crowded than usual. For instance, it can be a long wait to get to the top of the Sears Tower.

I've watched the Air & Water show from Montrose (the farthest North you can see it) and right on Oak Street beach. It's much more impressive and fun to watch it somewhere closer, like Oak Street, where the planes roar right over your heads. It's really crowded down there, but you can squeeze in somewhere to watch for an hour or two. If you are okay with seeing it from afar you can simply walk East from Wrigley to the lake and you'll have a glimpse of it.

Try to see some comedy or a show. I always recommend Too Much Light Makes the Baby Go Blind, which is an L ride North of Wrigleyville.

The Loop isn't really a going out kind of area except for tourists and maybe some fancy bars that don't sound like your scene. Take the L down there to do tourist things (the architecture and museums are great if you're into that) but spend your nights in the neighborhoods.
posted by Bunglegirl at 8:31 AM on June 9, 2011

I always recommend Too Much Light Makes the Baby Go Blind, which is an L ride North of Wrigleyville.

I came in here to recommend this, with a trip to the Hopleaf preceding it. Given that your friends are "pub types", this sounds like the kind of evening you'd like.
posted by Johnny Assay at 8:42 AM on June 9, 2011

If you find yourself in the Loop (cause you went to the Sears Tower or to the Bean), some casual pubs which might be to your liking include: the Exchequer; Cardozo's Pub (closes early 9ish); Monk's; or Miller's.
posted by crush-onastick at 9:07 AM on June 9, 2011

Stay downtown (North michigan avenue--use priceline), but Chicago is The Neighborhoods.

Nightlife. I've been to at least 200 bars in Chicago so I kind of know this thing.

I'd recommend maybe checking out downtown bars (i.e. rush and division) one night and picking another neighborhood to go out. I'm focusing on places with multiple (i.e. 10 bars a block) areas)

If you are bar type but like the rowdy, collegy, pick up type places to go are Lincoln Park on Lincoln, Wrigleyville (skip it if you're going to game there, but do pregame at a bar up there) and rush and division bars (which are very touristy, but friendly kind of like the NOLA, Vegas bars). Wicker park around Rush and Division is definitely slightly more hipster, but is more or less like Wicker Park. I can't tell you really that much about chill bars.

If you know DC, Rush and Division is like Georgetown, Lincoln Park is more like Dupont/Lower dupont, Wicker Park is like U Street, and Wrigleyville is like Adams Morgan. (But not)

Many Chicago bars are slightly upscale, crazy sports bars with 100 tvs and loud party music. Very friendly people of the opposite sex in most of these.

At night, take cabs. during the day, take public transport. Not for safety or even speed, but you can see alot of the city on the El during the day, but not really save that much money at night taking cabs (they are everywhere!).

Go to Hangge Uppe late night.

(there are about 20 bars in the city that are open between 2-4am (Sun-Friday) and 3am-5am Saturday night. If you and your friends party hard, this is a definite must to go to.

Memail for specific suggestions.
posted by sandmanwv at 11:46 AM on June 9, 2011

Don't go to the Navy Pier. Go on a architectural boat tour.

Oh also, for the Hancock Tower, go to the Signature Room (a cocktail lounge) instead of using the observatory. Sure drinks are not cheap ($7 beer), but its cheaper than taking the elevator the observatory.
posted by sandmanwv at 12:30 PM on June 9, 2011

n'thing to skip navy pier, and i would also advise skipping the air and water show. i've never seen anything spectacularly chicagoan about either. both are filled with just whatever happens to crawl out of the woodwork.

the pub reco's above are good. i would avoid kuma's, because it's usually around an hour wait.

longman and eagle is near kuma's if you want something pubby. gorgeous food there.

a favorite that strikes me as quintessentially chicago is bill kim's belly shack. it's cheap, it's quick, it's well-made and unpretentious. it's basically autobiographical food: bill is asian; his wife is puerto rican. the food's korean/chinese and puerto rican fusion with lots of things from other areas of the city (like sausages made on the south side, iranian breads from the north).

try to check out pilsen. it's a wonderful pan-latin neighborhood on the south side.

pullman, on the southside, is a lovely planned small town, a relic of the industrial age during which moguls would build entire towns to serve their work.

if you're whiskey and punk rock fans, go to delilah's on the northside. if you want a swanky cocktail, go to the violet hour. longman can handle that too. if you want a great dive bar, hit the town hall in boystown near wrigleyville, or the burlington on the west side.

all of thee are decidedly away from tourist spots (excluding town hall and violet hour, whcih are in widely travelled neighborhoods -- but not tourist hangouts) so you'll decidedly see chicago a little more how we see it.
posted by patricking at 12:51 PM on June 9, 2011 [2 favorites]

Rush and Division are in the the Gold Coast. If you want 'hipster' things, you would go to Milwaukee, North and Damen in Wicker Park. I would highly recommend avoiding it at night, as it's terrible and ridiculous on weekends. (I work in the neighborhood, and getting home on Saturdays is a fucking nightmare).

patricking and Johnny Assay have it. Excellent suggestions from both.
posted by bibliogrrl at 6:44 PM on June 9, 2011

In case you decide you want to stay downtown, I wanted to second the recommendation upthread to use Priceline. I've only actually done it once myself, but from what I hear, if you bid $75 a night for a four-star hotel, you basically always wind up in a fairly swanky hotel downtown for that price if that's what you're after (worked for me, anyway).
posted by solipsism at 8:52 PM on June 9, 2011

I just went there for the first time.

Skip Navy Pier! Seriously. Unless you like Bubba Gumps Shrimp Co and shit like that. It's basically a shopping mall overrun with teenagers. We were staying across the street (e Ontario and lake shore drive) so just walked over, I would have been seriously pissed if I had travelled to that shit.
posted by tremspeed at 6:09 AM on June 10, 2011

Oh god please don't go to Hangge Uppe. I'm begging you. That place is terrible. If you are pub people, you probably like decent beer, so let me tell you this story. I work on Michigan Avenue and we had some work people in from out of town and took people there. (Although I tend towards the hipster side of the spectrum, the work people I with are older and more, I dunno, mainstream? so that's where we went. Plus it was close.) I was surprised to find they had Dogfish Head on tap, so I ordered one. Being served in a plastic cup was bad enough, but then I tasted it. It was disgusting. Clearly, their tap lines were really, really dirty. It was so bad I couldn't drink it, so I went back to the bar to talk to the bartender. Her reaction was "Oh, yeah, a lot of people say our beer tastes weird. I think it's the taps," and shrugged. The music is awful, the crowd is weird and creepy, and the bathrooms are disgusting (and not in a charming dive bar kind of way.)

Listen to crush, patricking and Johnny Assay. If you really must do a Chicago Tourist Thing, maybe the Billy Goat Tavern on Lower Michigan Ave? Not Navy Pier. Ugh.
posted by misskaz at 9:22 AM on June 10, 2011

Misskaz, you verified all the great things about Hangge Uppe!

There's two types of people when it comes to Hangge Uppe:

1. You love it if you are single, and 20 beers deep.
2. You hate it you are anything other than that.
posted by sandmanwv at 9:09 AM on June 11, 2011

In what world is public transit not cheaper than a cab? The El is $2.25, while just pulling the flag in a taxi is $3.25 and up. Expect to pay $10-20 per cab ride-- money you could be spending on beer.

Anyway, I'm not a huge fan of the Air and Water show, but if you are, two great places to watch are from the The Terrace at Trump (expensive) or the Navy Pier Park (free).

Well, unless you care about the "Water" part, which to my knowledge doesn't actually exist.
posted by eamondaly at 9:23 AM on June 18, 2011

All right, I'm still waiting on my laundry, so here's my (somewhat drinky-drinky, since you specifically mentioned 21+) itinerary for you:

- Go out for drinks on the top deck of Castaways and enjoy the view
- Rest up

- Have brunch at Pick Me Up Cafe
- Go to the game, eat a couple of hot dogs, and encourage institutional incompetence
- Enjoy the beer garden at the Yard (or continue down to Sheffield's).
- See Blue Man Group at Briar Street Theater
- Have tacos and margaritas at Cesar's
- Visit any or all of Sidetrack (gay), Spin (SUPER gay), Berlin (dance), or Trader Todd's (straight pick-up) for as long as you can possibly stand it
- Close out the night with a shot and a beer (ask for the special) at the L&L Tavern

- Start the day with brunch at South Water Kitchen
- Walk east to Michigan Avenue, then head south to Millennium Park to visit the Bean. Order a vodka neat and a lemonade to go at the Park Grill, then walk a little bit farther south and splash around in Crown Fountain for a bit
- South one more block to the Art Institute of Chicago or continue on to the Field Museum
- Head back north along the lakefront, making a quick detour once you cross the river to Fox and Obel for some picnic food
- Continue east to Navy Pier Park to watch the Air and Water Show headliners
- Head up to the Signature Lounge (not the Signature Room) John Hancock for the view and cocktails
- Window shop around Water Tower Place
- Enjoy any of the (four? five?) rooms of dance music at Excalibur
- Towel off and head west for a steak at Wildfire
- Wrap up your night at Blue Frog for karaoke

- Brunch at Eatt.
- Take any of Wendella Boat's excellent tours
- Head up to the aforementioned Terrace at Trump Tower for mimosas and the end of the Air and Water Show
- Hop on the Red Line at Grand and State and head north (to Howard) and get off at Berwyn.
- Walk west to In Fine Spirits and enjoy some finger food and a glass of wine in the outdoor garden
- Head south and stop in at the Swedish American Museum before it closes at 4pm
- Have the brisket at Hopleaf
- Roll the bones to get into Too Much Light Makes the Baby Go Blind
- Finish your evening at Simon's (laid-back), Hamburger Mary's (a gay Applebee's), or Farragut's (dive)

- Sob into your pillow when you realize you have to leave
posted by eamondaly at 11:31 AM on June 18, 2011 [5 favorites]

Ok, I have to say Pick Me Up cafe was the ONLY thing I did in my recent trip to Chicago that I would have done if I lived there. We went before a Cubs game (OK, guess I'd do that too when finances allowed) and it was great. Probably the only place I didn't have to wait on line to eat at.
posted by tremspeed at 1:19 PM on June 20, 2011

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