Wrigley Field, Magnificent Mile, Millennium Park, Navy Pier, the lake, amazing food, food, food, food, and food. I love the "L". You can get to so many parts of the city and so easily. It is far superior to the trains here in NYC. Chicago itself is a cleaner city when compared to NYC. I love in the spring and summer there. Staying at the Renaissance on Wacker is a given too.
Some fun foodie tips:
- Meli Cafe in Greek town is a healthy, happy breakfast option
- The Bourgeois Pig in Lincoln Park has the best coffee and ambience of the Chicago coffee houses
- Any of the Francesca's restaurants are worthwhile, reasonably priced, and have super yummy food
- Giordano's is the home of the ultimate Chicago deep dish pizza
- The Girl and the Goat is hard to get into, but worth it if you can score a reservation
- The Aviary has the most ridiculous and memorable cocktails in the city
- The Green Mill is the old, jazz-club haunt of Al Capone that brings you back to the 20s!
Chicago is our all-time favorite, big U.S. city! Easy to drive in - although parking in the city is a bit high priced! We've stayed downtown - favorite is Marriott Residence Inn on East Walton, few blocks off North Michigan Avenue; however, we've also stayed west of the city (near O'Hare Airport), and Lombard, Oak Brook area, and driven into the city for visits.
In my opinion, you can't really enjoy all the wonderful sites/spots in Chicago without an auto. For instance, it's an expensive ride to the Museum of Science & Industry, south of the city, or Lincoln Park, north of the city, although there are other museums near South Michigan Ave, (Natural History, Art Museum, Planetarium, Navy Pier, etc.) to which you could walk, if you choose to stay in hotel in this area. It's a step back in history to visit the Conrad Hilton Hotel, South Michigan, the original Hilton hotel. The ballroom in the Drake Hotel is also exquisite, and an after-evening-dinner drink in the hotel lounge is one of our favorite spots.
You can't really go wrong on eating out; however, my favorite restaurants are Tuscany (Little Italy, SW of the city) and Spiaggia (across from the Drake Hotel), and the Water Tower for lunch buffet.
My thoughts in pictures: Chicago ... A Photogenic Town...
Some additional advice, from others, here: Chicago Advice: Blackstone, JW, Rez Inn/Spring Hill Suites Combo, etc?