Places to Go

For food, Portillo's Italian beef and hotdogs are a must. Also, Giordono's pizza.
The Hancock building downtown has a great view of the lake and you won't have to wait as long as going to the observation deck at the Sears tower. Just be prepared to pay a lot for parking downtown.
Jen D.-Frisco

Navy Pier
Shopping on the Magnificent Mile
The Excaliber night club was fun when we were there 2 yrs ago.
We went to a baseball game
We did a lot of walking and while doing so stopped into some great spots along the way but I forget all the names. Mostly local bars or restaurants with bars. Higher end steak houses, etc.
Enjoy!

If you are traveling alone...just remember as in all big cities or little cities to be careful. My hubby is from that area and he recommends staying in downtown so hope it works for you to stay in downtown. The last time we were there it was over the 4th of July and won't do that again...it was too crazy at the Pier.

We had a great time at the musuem. Even if you do not go to the museums take a drive to them. It is so pretty!!
The Navy Pier was fun the other couple of times we were there. We did the drive by Sears Tower, but did not go in.

You will have fun just be careful. The first time I went ...I asked my hubby why do the police have police dogs with them?? This was in the parking garage at the Navy Pier. That was a first for me, and seeing the transit system the "L" I had not really been to another big city other than Dallas was cool to see the difference yet some of the same.

Have fun!!

My husband spent a summer in Chicago. He said you've got to try Giordono's. They've got great pizza and he's been threatening to pay to have it shipped down.

He also said to go to any ethnic borough and eat at their restaurants (Chinese & German/Polish). He said there's a great Thai place called the Star of Siam.

Have fun!

ask the person at the hotel front desk.

I haven't been to Chicago in several years, But I always tried to get to the Art Institute when I was there. If you like German food, go to the Berghoff Restaurant.

If you want to go shopping, obviously Michigan Ave...but you HAVE to go to H&M! There are only a few of these stores in the US (NY, Chicago & DC, I think). They always talk about the store in fashion magazines as the place to get "high" fashion on a budget!! It's great (and huge!). Also, Gino's East has the BEST Chicago deep dish pizza...yum! Have fun!

Food Musts:
Gino's Pizza
Navy Pier

Sites:
Field Museum of Natural History
Shedd Aquarium
The Art Institute of Chicago
Sear's Tower

Have fun!!!

The Sears Tower and the Navy Pier are a must. You don't sound like you are interested in museums, but I think you will be astounded by the Art Institute. I highly recommend it.
I wish I were with you! Have fun and see a much as you can.

We moved here from Chicago just last year. To address the safety issue, yes you need to be careful wherever you go, but Chicago is a pretty safe city. Also, the "hot" places are not easy to get into, even for people who live there, so you should plan ahead.
For restaurants-Frontera Grill/Topolobampo (mexican, if you can't get reservations, it's usually an hour wait or more, but good for drinks)
Cafe Spiagga-Italian
Hot Chocolate-chocolate desserts
Trump hotel restaurant-nice bar, good views
Japonais
Table 52-Oprah's chef's restaurant
Sushi Samba
China Grill
Those are some...
Chicago magazine usually has some good listings as well
For clubs I would check Citysearch.com (I didn't go dancing much)