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.

Woodstock , General info:
10/10

A unique village in New England largely dominated by the Rockefeller family fortune. It is full of historic buildings, small independent businesses and restaurants. It is the only village in the US that you can walk from the village centre straight into a National Park.

Woodstock , Cheap stuff:
10/10

The village is not known for offering anything cheap!

Woodstock , Different stuff:
10/10

Marsh Billings Rockefeller mansion

Woodstock , Food:
10/10

Pane e Salute - 2007 Vermont Hospitality Council restaurant of the year.

Woodstock , Hotels:
10/10

Woodstocker Organic Boutique Inn -

2006 Award - Vermont Hospitality Council - Innkeepers of the year

2006 Award - Vermont Governor's award - Green hotel in Green Mountain State

2007 Award - Top 10 B & B in all US - B&B.com

2007 Award - Guest Favourite BnBFinder.com

Trip Advisor - #1 in Village #2 in entire State

Woodstock , Safety:
10/10

Very safe

Virtually no crime as the population has 11 police for 3000 people.