Visiting Chicago ... any suggestions?

[Chicago60614]

When you figure out what days you'll be here, check out the festival guide to see what neighborhood fesivals are going on. I actually like those a lot better than the "mega festivals" that they have in Grant Park.

Chicago Festival Guide 2011 | Metromix Chicago

Other suggestions:

1) I agree go to the signature lounge on the 96th floor of the Hancock.
2) Do a boat cruise on the river or the lake. I like the Wendella Architectural tours, they're around $20 to $25. Not sure what your budget is....

Chicago Lake & Chicago River Boat Tour Cruise Comparison Chart - Review

3) Take the train up to Wrigley Field (especially if it's game day) and walk around. I'd venture down Clark Street to Belmont or Diversey.
4) On that same note, check out a bar with an outdoor patio and do some people watching. Terasca's on Wrightwood and Clark is good for margaritas, Mickey's on Clark and Arlington is good for people watching, as is Wilde on Broadway and Barry. There are a ton though, and some nice laid back beer gardens too like Kirkwoods on Sheffield and George.
5) Do the Lincoln Park Zoo and Conservatory - both free on the north lakefront.
6) Check out a comedy show - they're normally fairly cheap and a good "Chicago" thing to do.
7) I would check out Navy Pier if you've never been here before. Good views.
8) Walk Michigan Ave from the Art Institute up through Millenium Park, the Mich. Ave bridge and up to Hancock (then you get your drink at the Signature Lounge).
9) Walk through the upper floors of the Cultural Center. Takes 15 minutes, but it's an amazing building and free.
10) See if there's anything going on at Daley Plaza. There are lots of little farmers markets and ethnic fests that go on there, and if anything it will let you wander deeper into the Loop and check out the buildings and swarms of people - especially on a weekday during the afternoon.

[stephei2000]

Originally Posted by Vlajos

This is a great reco! Awesome views for the price of an expensive drink!

I never understood why people always mention a drink. My sister came to visit me in 2008 and I did not buy any drinks since I do not drink and I just sat down and enjoyed the view. You can just get a water and chill a bar or a table

[ForYourLungsOnly]

Originally Posted by stephei2000

You can just get a water and chill a bar or a table

Sure...you CAN... but why not enjoy the view with a Windy City Martini?

[jdiddy]

Originally Posted by stephei2000

I never understood why people always mention a drink. My sister came to visit me in 2008 and I did not buy any drinks since I do not drink and I just sat down and enjoyed the view. You can just get a water and chill a bar or a table

Depends when you go and who serves you - at certain times they mandate everyone at the lounge orders one alcoholic drink.

[tonythetuna]

Originally Posted by karevin

I know we can get suggestions from all sorts of travel websites, but we don't want to be typical tourists. Instead, we want to integrate more with residents and experience authentic Chicago, not the commercialized version.

You basically need to go to a part of the city that is not on many tourist maps.

[It'sAutomatic]

There really is nothing of interest at Navy Pier.

If you want to check out inner city places that actual Chicagoans hang out at, I can think of a few areas offhand. Go down sidestreets in these areas, too:

SW side: 18th Street from Canal to Damen, Loomis and Taylor (one of Chicago's little Italys)

NW side: Erie and Noble, Chicago Ave and Ashland, Division and Damen, North/Milwaukee/Damen, Milwaukee/Kedzie/Logan Blvd,

N side: Astor from Division to North (if you like vintage mansions), North and Wells, Lincoln and Wells, Clark St. from downtown to Irving Park, Lawrence and Broadway, etc.

[karevin]

These are all great, great suggestions! Thank you, everyone! I'm keeping a mental checklist and will certainly come back to read more as the time nears. Reading all of these ideas makes me even more anxious to get on the road and just get there already. I can't wait to see Chicago. It certainly seems as though we'll have to stay as long as we can just to take everything in.

Thanks again, I really appreciate it!