I second
@Gonzo with the plan to just park your car and use Uber/Lyft if you’re staying downtown. Hotel parking rates can be insane - I recommend using an app like SpotHero to reserve a space near your hotel, it’ll save you money.
There are lots of places to stay downtown, although a lot of times they can be really pricey depending on what’s going on. We like River North/Streeterville; we’ve stayed at the Courtyard Magnificent Mile on Ontario Street, the Marriott on Michigan, the Embassy Suites on State Street, the Residence Inn or Springhill Suites River North (they share a lobby in the same building), among several other hotels.
- I can’t recommend the Architecture Institute boat tour highly enough. They cruise up and down the Chicago River and give you neat information about the history and designs of the buildings
- There are also scenic boat tours along the lakefront if you’d prefer that
- The Art Institute has the original American Gothic painting, plus the Seurat painting from Ferris Bueller (and a ton of other stuff)
- If you like the view from tall buildings, I prefer the 360 Chicago (formerly the Hancock building) over Willis Tower (formerly Sears Tower). Willis Tower is taller, but the Hancock is closer to the lake and I just think it’s better
- The Museum of Science and Industry is incredible (its south of the Loop a ways near Hyde Park)
- Shedd Aquarium and the Field Museum are also fantastic (near Soldier Field at the south end of Grant Park)
- Don’t Miss Grant Park/Millenium Park, just to walk around and see the skyline from there. Buckingham Fountain (featured in the opening credits of Married With Children), Cloud Gate (or “The Bean”), it’s a neat park right in the middle of the city
- Second City comedy club is a good time, in Old Town between downtown and Wrigleyville
- There are so many good restaurants, whether you’re looking for high-end fine dining or a dive bar with good pub food. Pizza is, of course, big in Chicago … our favorites include Pizanos (the north State location) or Lou Malnatis … we get the thin crust at Malnati’s and have them overbake it to get it really crisp