On Belmont, there are loads of thrift shops you can stop in. Just don’t try to take photos in any of them, they’ll yell at you!

I live in Dallas and the weather is really mild, so I hate having to buy expensive heavy coats that I will only wear once or twice a season. You should try Burlington Coat Factory, if you will be buying once you arrive. They have a huge selection of heavy coats at very reasonable prices. Here is the website: http://www.burlingtoncoatfactory.com/

Strange Cargo is a great thrift shop. I think that’s in the Belmont area.

In terms of things to do, the Art Institute is great. It will be a little chillier down by the lake but it’s worth going down there. Also, the aquarium. At night, Second City, Blue Man Group, or Improv Olympic are all really fun.

I would check out the Family Village Thrift resale shops. There is one on Milwaukee, one on Kedzie, one on Elston, one on Laurence (there’s even more than I am listing). They have the cheapest gnelty-used clothing in town, but you must be willing to go through rack after rack of clothing items. I have found some really nice clothing there. Also, the Salvation Army on Clybourne is fabulous! If you are ever in the western suburbs, check out Aspire on Broadway in Melrose Park. A nonprofit resale shop, they offer nice clothing for the entire family, housewares, jewelry, shoes, and more.

Filene’s Basement and H&M are my two top pics. The other would be the store that is Silver Spoon, or right next to it. I can’t remember what it’s called, but it was good a year ago. Filene’s in Boston is much better than the one in Chicago, actually most Filene’s are better than the one in Chicago. All of them have good deals on jeans though.

Look me up when you get there, we’ll hit the town.

There a several outlet malls in the suburbs – though they can be a little high end for outlets, they still have good deals. Huntley Prime Outlets is far NW suburbs and Chicago Prime Outlets is actually in Aurora in the far west suburbs. Last I was there, the best prices were at Gurnee Outlet Mall in the far north suburbs.
As for stuff to do, winter is pretty bitter and windy, but there’s tons of stuff to do. Millenium Park and the lakefront are worth checking out if you can brave the weather. For indoor stuff, check out any of the clubs or theaters for music/theater/dance of almost any kind. Rush Street and Clark Street both have restaurants/bars. If it’s around Christmas time, most of the major departments stores on Michigan Ave. (“The Magnificant Mile”) decorate and everybody comes to town to check it out. For the best cheap eats, check out Reza’s (Persian/Middle Eastern food). Chinatown on the Southside also has good deals on food and some clothes. Have fun!

TJ MAXX! The best place to buy a discount coat. They have designer coats at very low prices. A big one is located downtown on State Street. The best one is in Countryside, IL. It is about twenty minutes west of Chicago. I shop everywhere to find the best fashions, then I go to TJ Maxx to buy them. Sometimes the same designs that are in the department stores are at TJ Maxx for a fraction of the cost. Imagine a DKNY wool coat for $50! In February, all of the winter stuff will be dirt cheap. Yes, TJ Maxx!