I am planning a weekend in Chicago with my sister and mother as it's between my Ontario home and my sister's St. Louis. We are in our late 20s and my mom is very youthful and fun-loving. Suggestions on the best things to do and see much appreciated!

What type of things do you want to do in Chicago? There are lots of great museums
but one things for sure you have to go up the Sears Tower.
E-mail me and let me know your taste.
[email protected]
p.s I'm a canadian, from Winnipeg

Wow! There is so much to do in Chicago. One thing no one should miss is a boat tour out onto Lake Michigan. If you search the Internet you can find several operators with different kinds of tours. My favorite is the Architectural Boat Tour. You can go to Navy Pier's website (http://www.navypier.com/nav.html) and find a listing of operators. Navy Pier also has a lot of fireworks show throughout the summmer, I think Wed and Sat nights.

You didn't mention when you were coming, but every weekend there are different neighborhood festivals which are always a great time. I think the best place to find out information about what's happening in Chicago for any given weekend is chicago.sidewalk.com. Being a Chicagoan, I was kind of skeptical when Microsoft came out with this "all about Chicago" website (they have one for most major cities) but I have found it an invaluable guide for what's going on.

Please feel free to e-mail me if you have any questions.

Message: Ditto on the neighborhood festivals and Navy Pier (see Erika's response). Definitely go to Navy Pier where you can shop, eat, ride the huge ferris wheel and take a one hour lake cruise. There's food and entertainment on the Pier. There are many neighborhood festivals going on throughout the summer. Check the Friday newspapers when you get here. There's a weekend section that lists all the festivals. They're alot of fun. Most usually have bands and food tents setup so you can sample some of the great foods served by local restaurants.

If you like blues music, Chicago has some great blues bars with live bands. Be sure to go to one.

There are cruises on Lake Michigan you can take. From lunch cruises to midnite dinner cruises. Some can be $$ but they're nice.

Try an outdoor concert at Ravinia. That's always a nice time.

If you feel like driving away from the city, you can go up to the Chain of Lakes area, rent a boat and spend the day boating on the Fox River or through the many connected lakes northwest of Chicago.

Or you can got to a White Sox or Cubs baseball game. You may like a Cubs game better. The ballpark is nicer. Kindof the old time baseball park feeling.

Don't miss sunset/dusk at top of the sevens--top of the john hancock building. If not for dinner, for a drink at least. Beautiful view of the city--pricey, but worth it.
If you like museums and such--Shedd's Aquarium.

The Art Institute is one of the best art museums in the world. I agree, the architectural boat tour is the best. If you come in the summer you can rent bikes at Oak Street beach and ride along Lake Michigan up to Evanston, a beautiful suburb with huge old homes with lots of character.

There's an open air double decker bus tour that is inexpensive and you can get on/off at several locations throughout the downtown area all day -- it provides a good overall look-see and works great for avoiding costly cabs. It used to board across the street from Water Tower Place or someplace close there on Michigan Ave.

In no particular order I recommend the Art Institute, Architecture Foundation Boat Tour, Navy Pier, an evening blues show (there are upscale blues clubs right in nice parts of downtown e.g. Buddy Guy's Legends), a walking tour of the park areas on the lakefront and if going to Ravinia for music make reservations at The Bistro (it might be called the French Bistro or the Country Bistro). It's a great little country French cafe in a small storefront. They have excellent food at reasonable prices and an atmosphere that is best describes as casual elegant. I do NOT recommend the Sears Tower - instead make reservations for lunch at the restaurant on the 85th (or 86th) floor of the Hancock Tower. It's got floor to ceiling windows on three sides wiht an incredible view of both the lake and the city and an excellent lunch for $10-15 per person (the Sears Tower costs about $7 each and the view, although higher up, is not as good).

I always think about food when it comes to questions like these. If you love the stuff, I highly recommend a place called Uno's. The best I've ever eaten!

Uno's is the original Chicago deep-dish pizza and it's excellent...as is that from it's sister (block away) restaurant, Due. Another fun, reasonably priced restaurant is Heaven On Seven, in a shopping complex at Ontario and Rush -- cajun food....something nice and different for you Ontario folk, perhaps.
As noted, skip the Sears Tower; go to the 95th restaurant at the top of the Hancock, -- actually, the cocktail lounge one floor above -- around dusk. Have a cocktail and enjoy a spectacular view from a comfortable chair, and at no more cost than the price of you drink, etc.