1

If you are looking to go out at night, Lincoln Park area near DePaul University might be fun.

Museums, stay along the lake shore.

Shopping-stay along the Magnificent Mile and your head will explode with shopping.

Navy Pier is overrated, but there are cool boat tours that start near there, either on the lake itself, or Chicago River tours that highlight the history/architecture. I teach and we take our students on these every year. Actually, scratch that idea...it will be February.

You can do a food tour of the different ethnic neighborhood.

What types of things are you looking to do?

2

Lincoln Park is mainly a collegiate and residential area that is not exactly trendy, hip or cool, its more sports bars, most young people in Chicago go out downtown and Bucktown, or west loop.

It will be pretty cold and wintery in Chicago, and there is great public transport for most your cultural/tourist must do/see areas, then you can also taxi at night to bars/clubs.

Chicago has two area for hotels, the downtown "Loop", this area is closer to the lakefront and museums, but mainly served the businesses in the loop as the its the main financial area, can be a tad desolate at night and not lot of retail or shopping besides one street, State Street. But there are some nice places to stay and can be cheap on weekends, like the Hilton, Palmar House and W hotel.

Then there is the Michigan Avenue and River North area, this is the main retail shopping and hotel/nightlife district for the city, as well as residential condos and apartments. There are many hotels spanning this area from the Chicago river to the Goldcoast which is a old and affluent area before you get to Lincoln Park. The Mag mile as its known, has a of hotels and is pretty much ground zero for tourist.

As for areas to party and go out, this city is pretty diverse and is spreads in all directions but east (Lake), but the hippest area would be the Bucktown area near North Ave and Milwaukee Ave, this is area mainly bars and hipsters living there as it gentrifies from run down to small shops and places to eat and drinks. It runs from Chicago Avenue on the south, to Armitage Avenue on the north, along Milwaukee, Damen and the streets mentioned. This would be a $10-$12 taxi from most hotels on the Mag Mile.

As for cultural highlights, and considering it dead of winter (bring hats/gloves/boots and sweaters and good winter coats) you have the main Millenium Park area, which is where the Art Institute is located, a huge museum with excellent art, and a new modern wing as well. Nearby to the south on the Museum Campus is the Field Museum, the Shedd Aquarium, and the Adler Planetarium. MOMA is located off Michigan Ave at Chicago Ave. The Museum of Natural History is also great, as is the Chicago History Museum.

The live music scene is pretty diverse and always good, on Thursdays The Reader paper comes out with all the bars/bands and shows in the city that weekend. Also check out TimeOut Chicago for good places to eat/drink, events, the arts from dance to plays to recitals and concerts. Metro Mix is also good for events and happenings.

http://timeoutchicago.com/

http://chicago.metromix.com/events

http://www.chicagoreader.com/

You might want to keep a eye on Segway tours of the city, a easier way to get around in the cold than walking if conditions permits, check LivingSocial and Groupon for specials, as well as walking tours, bike tours, food tours, mafia tours, and architecture tours if possible, which normally are boat on the Chicago river and lake but not in Feb...

There is also ice skating near the Art Institute at the Bean, and for sports you have the Bulls and Blackhawks.

Bundle Up, downtown is cold and windy.

Check Priceline and Expedia for hotel deals.

3

I'm going to disagree with #2 on the Loop, upper State, Wabash, and Randolph Streets are anything but desolate at night. No, its not River North or MagMile but the big theatres are in that area. Speaking of which, Kinky Boots and Book of Mormon may still be playing. Hotels there are not much cheaper than north. Avoid Congress Hotel and Essex House as they are utter dumps.

Bucktown is more like a $20 cab ride nowadays. Cheaper to get there on the Blue Line. I will agree its mostly hipsters and trendies. Amusing to watch them burning up their parents money, though.