Chicago , General info:
7/10

Two airports -Midway or OHare (ORD).OHare is major airport; both convenient to downtown (called The Loop)

Chicago , Different stuff:
6/10

flee market - great fun!

Chicago , Don't miss:
5/10

sambucca

Chicago , Food:
9/10

Food in Chicago is excellent! There is so much variety. There are many places for steak (Carmine's, Wildfire). There is also great Italian (Sappori Trattoria). Many ethnic restaurants if you want tasty affordable alternatives. My advice - go to a BYOB with a bottle or two of wine and you'll save.

Chicago , Hotels:
7/10

Hotels along Michigan Avenue are fun yet expensive. For a cheaper place in a great location, try Congress Plaza hotel.

Chicago , Safety:
6/10

OK for the most part. Just plan out your route in advance. Take cabs, buses, or trains.

Ulaanbaatar , Cheap stuff:
6/10

Local "black" markets have much to offer. Language barrier is an issue, so bartering can be problematic. Best to have a local as a guide and don't be surprised at the practice of Mongols being charged far less than tourist.

Cashmire is a reasonable purchase. A cashmire or camelhair blanket will be a purchase you will enjoy for decades.

Ulaanbaatar , Don't miss:
10/10

Milk Vodka...

Ulaanbaatar , Food:
5/10

International cuisine can be found. No McDonalds yet. Traditional Mongol food can be found and if you like mutton you will be in heaven.

Ulaanbaatar , Hotels:
2/10

There are only really 2 to chose from.

Ulaanbaatar , Safety:
5/10

Be very careful of traffic. Pickpockets. Being out at night might be a problem, yet doesn't seem to bother residents, but much of the city's once operational street lighting doesn't work.