There are a few questions about Chicago so I thought I'd post some info to help people get started with their trip planning.
The city is very accessible by public transportation: the El or CTA/same thing - it's sometimes above ground and sometimes under so it's not a subway, but that's the idea
Direction: the entire city is on a grid (it was planned that way from the beginning) The center of the grid is at 0-0 or State and Wabash streets in the Loop. The lake is to the East. For accomodations you don't want to go much further than 2800 West in some places (or it gets scary). Close to the lake you can go as far north as you want, south maybe to about 1800 south. There are a few "beaches" on the lake but they are pretty icky by international standards. Many of us don't swim in the lake for fear of growing a third eye (pollution) - or maybe that's just me. the train is like in most cities radiating out from the loop. Busses mostly go back and forth either East-West or North-South (mostly)
The Loop: this is the central business district. The hotels are expensive, not much nightlife except for a few hotel bars like the W, etc, but you'll be w/in walking distance to many museums & millinium park.
River north/Northwestern/Miracle Mile: this is just north of the loop. Famous shopping area, high end, some restaurants, lots of tourists, also close to musuems, etc.
Gold Coast: just north of that, lots of action, pricy, "beautiful people" area, lots of bars, clubs, close to the lake even higher end shopping, very fun if you are into this scene, high prices and stumbling distance bars, clubs, dancing & dining.
South Loop: newly developed area, nice hotels with a bit lower prices, some areas with restaurants & bars, but it's limited. Also very close to museums, etc (walkable)
Beverly: South of that...this is the historic neighborhood with some isolated clubs & restaurants. It's surrounded by unsavory areas so i wouldn't recommend it.
Hyde Park: This is about 5400 south (54th Ave). It's where the excellent Museum of Science and Industry is, also The Smart Museum, University of Chicago and other big institutions. It's near the lake and a beautiful neighborhood but kind of residential and feels far from the action. Better for a visit to the museum than to stay.
Wrigleyville: This is where you can stay to experience the "typical american" in a baseball hat cheering on the baseball team, The Cubs. It's one of the most famous stadiums in the country if you are into sports or Americana. Lots of bars, did i mention there are lot of bars? cheap restaurants, party all the time, but ifyou are here in the summer on a game day - the traffic is horrible. People plan their lives around game days here.
Wicker Park: newish trendy neighborhood, excellent botique restaurants and shopping, mix between super cheapo dollar stores & thrift shops and very high end botiques. It was first put on the map by blue haired, piereced artist types...very diverse ethnically, bars for live bands and cocktails abound, you'll have to take the train/el/cta downtown to get to the museums. the major intersection here is Damen/Milwaukee/North Ave...Northwest of the loop. about 2000 West & 1600 North
Logan Square: mostly residential, not a lot of action, but safe and quite, a few decent restaurants, if you have friends in the city or a car, Wicker Park or Logan Square will get you near some "insider" places to eat. Blue line to downtown. also easy access on Blue line to O'hare Airport. about 2800 West & 2800 North
Old town: Just north west of the loop - about 1200 N & 800 W. some local type shopping (gap, banana republic, victorias secret, home stores, etc. some restaurants, some parts are walkable with great restaurants, also a good movie theater here.
Little Italy - don't stay here, it's a street of fantastic restaurants nestled inbetween public housing projects. Not really dangerous, but definately not tourist friendly. Chez Joel is an excellent restaurant there, french bistro, really good for a special night out. Take a cab or drive. they have a valet.
Boystown - gay friendly but anyone would be comfortable - well, most anyone - funky shops with leather short shorts and bars where they are worn, great neighborhood, but not super easy to get to & from on the train, bus is easy too, though.
Chinatown - south of the loop, great to visit, easy to get to on the train, it's just a little too far and akward to walk to museums, wouldn't stay there but if you find something cheap that looks good it's not dangerous
Devon Ave - this isn't a neighborhood, it's an area where there are a bunch of Indian & Pakistani restaurants and shops. Many people who live here don't even go there, but it's really interesting and whenever my friend from Calcutta comes to visit from Boston, he always wants to go there, it makes him feel like home - lots of excellent and cheap restaurants. Too far out of the way, but great if you are on an ethnic tour of Chicago.
Westtown - this is a newly developed area...if you are on the east side there are lots of hip restaurants on Randolph, not much else, not really accessible by train
Chicago is a fantastic city, excellent architecture, beautiful public parks and world class museums...come on!
Ah, insider restaurants - these are places that you may need to take a cab but the food is excellent and they are places that tourists would never find out about:
1. Think - Italian, BYOB (liquor store across the street), about 2200 North Western Ave just south of Fullerton), you may think you are lost because there isn't much else going on here, but oh, the food is excellent.
2. Tsuki - high end fusion sushi, see & be scene bar, very cool, excellent food & great sake list. It's on Fullerton just west of Racine
3. Roma Cafe - small italian bistro in Old Town. Can't remember the address, delicious
4. Wishbone - "healthy southern cooking" it's funky and delicious and good prices. This is one of my standby, tried and true restaurants, drive or cab. about 1000 W Washington
5. Le Bouchon - in Wicker Park area, Western and North ave i think. Really good small french bistro. not as high end as Chez Joel but food is just as good. both have an excellent wine list.
Ok, that's all I can come up with off the top of my head. If you have some specific questions I'd be happy to try to help. I see it as my way to give back to the world of travellers. feel free to email me directly: -snip-
Happy trails -
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BTW - very good information about Chicago.
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