I have not done a ton of traveling, and have never been out of the United States. But my favorite getaway weekends are to Chicago.

I live in Miwaukee, and for $20 per person one way, Amtrak is the way to go (Oftentimes theres a sale, in fact it was once 2 for 1!). It's an hour and a half ride, fun and affordable. There is no reason to fight the highway traffic- in fact, many of the trains have a snack and beverage cart- I often times will buy a heineken and kick back and look at the scenery from the train window.

Most of the good hotels are a short ride by cab from the train station. In fact, the train station is a block away from the Sears Tower. You can leave your luggage in a locker at the station (a bit expensive quarter-wise) and visit the tower before even checking into your hotel.

Most of the good hotels in the city are located further up the road (Wacker) from the Sears tower or on Michigan Ave by the lakefront. On a nice day, if you don't have a ton of luggage, you could feasibly walk to The House of Blues Hotel or Hotel 71 on Wacker. Michagan Ave is maybe a $5-6 cab ride.

You could spend a whole week doing things up and down Michigan Avenue alone! On the Northern part of Michigan Avenue is Navy Peir and the Miracle Mile for shopping and restaraunts. A bit further south is the world-famous Chicago Art Institute, and a bit further south from there is the Shedd Aquarium, Soldier Field, The Field Museum and the Planetarium. Some really beutiful parks along the lakefront around this area too. A cab ride from one end of Michigan Ave to the other usually runs maybe $8 for 2 people.

The online hotel booking places, Orbitz, Hotwire etc can usually get you a good price on a good room in a 4 star hotel. $99 or so online at one hotel booked online would have cost $160 otherwise!!

And you do NOT have to pay alot for good food! Try the Oak Tree, upstairs at Bloomingdales for example. Or, I have found that my Entertainment card, tho registered in Milwaukee, was good for 50% off at Celio, a top notch italian restaurant in the Omni hotel.