Many of the city's most popular tourist attractions are located in downtown Chicago, between Michigan Avenue and Lake Michigan. The Art Institute of Chicago and The Museum of Contemporary Art have fantastic permanent collections and exciting traveling exhibits. The Art Institute is located between Millenium Park (at the north end of Grant Park with the famous Gehry bandshell, sculptures, and ice-skating rink) and Buckingham Fountain (located in the middle of Grant Park). At the south end of Grant Park are a famous trio of museums: The Field Museum, The Shedd Aquarium, and The Adler Planetarium.
To the northeast of Grant Park is Navy Pier, home to the Chicago Children's Museum, shopping, and a giant ferris wheel. For more shopping and people watching, head north up Mighigan Avenue to walk the The Magnificent Mile. Take a break from walking with a fabulous 360 degree view of the city from the top of Chicago's third tallest building at The John Hancock Observatory. Watch out, though, as the wait to the top can get long on the weekends.
If you have time to venture away from the heart of downtown, I recommend the Lincoln Park Zoo and Conservatory. The animals are housed both inside and out, and the indoor greenhouse is beautiful year round. If the weather is good, you might like to see what's blooming at The Chicago Botanic Gardens in the northern suburbs near the Hotel Moraine. And for fascinating architectural tours, visit one of the Frank Lloyd Wright Homes in various locations around the city.
There are tons of fun things to do at night in the city, especially on the weekends. Check out a unique theatre experience put on by the The Neo-Futurarists such as T.M.L.M.T.B.G.B. (30 plays in 60 minutes) on Friday, Saturday, and Sunday. For comedy sketches at Chicago's most famous venue, go to a show at Second City. If you're interested in serious theatre with amazing actors, see what's playing at Steppenwolf. And if you still want more theatre, Blue Man Group is an amazing musical and visual treat. If you've never seen the show, please go. Great for all ages.
Chicago is home to lots of great music locales too. Classical music fans might try to score tix to the Chicago Symphony Orchestra. There are also many great jazz and blues clubs around the city. Some personal favorites are The Green Mill, Kingston Mines, and Blue Chicago. Cover charges can run $5-$15 which may or may not include drinks. Pete Miller's in Evanston has music every night with no cover, and has a full dinner and dessert menu.
If you're in the mood for the cinema, there are a few theatres which show limited release and artsy films. The Art Institute of Chicago Film Center often has unusual features, and The Music Box and Pipers Alley have a mix of popular and more obscure movies. And for something more active, any time day or night, there's bowling at Waveland Bowl.
Of all foods, Chicago is probably most renowned for it's pizza. You may have heard of the Pizzeria Uno chain, but it's nothing compared to the original. Go downtown for some authentic Uno's and Due's pies. Chicagoans are also quite fond of burgers and hot dogs. Dine in a 50's style diner at Ed Debevic's and don't forget to order a milkshake!
For a change of flavor, try some cajun food at the delectible Heaven on Seven downtown. I recommend ordering the Feed Me, Jimmy - seven surprise courses prepared and delivered specially to you by the chef. For sushi, go to Kamahachi. There's great Mexican food all over the city, but a personal favorite is El Tipico up north in Skokie. Get a pitcher of strawberry margaritas. For Indian food, adventure to Devon Ave and pick any restaurant. I've tried many and all have been great.
For breakfast all day long, try Ann Sather's Swedish menu. Vegetarians can find delicious meals at The Blind Faith Cafe in Evanston, or The Chicago Diner in the city. And for coffee, tea, and yummy light meals and desserts, go to Kopi Cafe, the Traveler's Cafe.