There aren't really "outlets" in the city of Chicago.  For "department store" shopping go to Michigan Avenue where you will find bloomingdales, nordstroms, neimans, macys, lord and taylor, and just about any other store you can think of in 900 N Michigan Ave and Water Tower Place.  

If you want more "cute boutique" type shops I'd go to Armitage and Halstead.  There are great stores around there as well.  

Check out the shops at 900 N Michigan Ave and Water Tower Place for moderate to high end shopping on Michigan Ave.

It depends on how much you are planning to spend. Most high end stores line Michigan Avenue. There is a new outlet mall near Chicago, it's in Rosemont, IL. Maybe about 20 minutes away. I personally haven't been to it because I hear it's filled to the brim with people, but you're required to pay for parking either hourly or a flat fee (the parking garage next to the mall or across the street, respectively). But there's a great outlet mall I go to in Chicago Premium Outlets in Aurora, IL. It's about 30ish minutes from Chicago. If you sign up for their website, you can score some discounts. And depending on what time you go, some stores have deals during the week before a holiday so you can beat the crowds and get what you want. Sign up at their website and it has coupons and more if you pick up the free booklet (if you sign up) the information center inside the food court. http://www.premiumoutlets.com/chicago. And make sure to go to Garrett's popcorn, http://www.garrettpopcorn.com/chicago-locations/

Water Tower Place is a cool mall - check it out! There are also a ton of stores on State Street and Michigan Avenue :) idk of any outlet malls very close... Gurnee Mills Mall is a popular outlet mall but it's not in the city, it's like an hour away. 

Water Tower Place would be nice. It has eight levels, it's pretty much what you expect out of a mall downtown in Chicago.

Water Tower Place is nice with about 7 floors  

Navy Pier is nice lot of eating places