not at all.
what do you want to know?
shopping- Michigan Ave. good shopping but i'm more of a boutique shopper. if you want to stay downtown and want a change from michigan ave. i suggest going to state street. it's downtown, but a long walk, short cab, or cheap el (train) ride from downtown. it has a better filene's basement, the "real" marshall field's, nordstrom rack, plus a bunch of other stores.
food- i really like bandera (on michigan ave.) for their amazing chicken salad. they kinda have everything so it's a good place for lunch or dinner. chicago is also supposedly known for their popcorn (garrett's on michigan ave.) so you might want to check that out. i would not eat at navy pier (over-priced), but rather walk down the street (grand) to eat at fox and orbel's for lunch. it's a gourmet grocery store that has a nice cafe attatched. i don't really have any recommendations for pizza because i've had it once and that's enough (i don't like the way i feel after i eat it). due's and uno's is same company, so good choices downtown. chicago hotdogs are also a hit (maybe at a game?) i would suggest if you like meat you can do a brazillian steakhouse (not my thing because it's pricey and filling, but the salad bar is AMAZING!). you can also do it for lunch, it's the same concept, but half price. my absolute favorite recommendation for dining is tapas. there's a restaurant downtown called iberico! it's so good and the sangria is delish (not expensive either....but get there early (6pmish), they don't take reservations and it gets CROWDED).
attractions- the aquarium is my favorite (great photo ops there), the planetarium is not worth it. the art museum, and the museum and science and industry is good too. i'm a huge baseball fan, so it might be fun to check out the cubs (not the sox). but to be fair, you will be able to get sox tickets game day, cub tickets you can check craigslist, or get them the day of the game from a scalper (in chicago EVERYONE does it right in front of cops, it's just the way it is). you can also wait till the game starts to get better prices outside the park. plus, it's a cool area of the city (some great boutique shopping in that area). also, my absolute favorite thing to do with tourists is the architectural boat tour. it's nice to be on the water, and you learn a ton! they are usually about an hour to 90 minutes, but sooo nice (it does get chilly on the lake so bring a light jacket or sweater).
transportation- don't be scared of the el! it's cheap ($1.75-$2.00 one way), it takes you everywhere (i don't have a car....don't need it), so check it out. you can get day passes and people are definitely willing to help you out. i would even suggest taking it from the airport to your hotel. if you want to go from michigan ave. to the state street shopping, you can take the el. from michigan ave. to the cubs game or sox (boo) game, you can take the el.
i hope that helps. if you have a certain type of cuisine you like (there's a greektown part of the city that's really good too) or if you like a different type of shopping you can message me.
have fun, i hope i helped out a bit!
Anyone familiar with Chicago?
to be going to Chicago! 
