I recently put a list of things to do in Chicago together for a friend and thought it might be useful to others so I'm sharing it here.
Chicago Weekend Notes:
I try to denote touristy and not touristy not as a bad thing or anything but more so you can know what to expect and for your adventure level. Also, any of the addresses that I list, a cab driver will know if you just say the address or cross streets. For example, you can tell any cab driver 958 W Wrightwood and they will know what you mean.
Touristy
Millenium Park
Millenium Park, Cloud Gate (aka the Bean). This is one of the top tourist spots because of the large open spaces and view of the city from the east. Lots of people to watch, and artwork is scattered throughout. There are restaurants and shops all over, mostly touristy, but plenty of snacks and small eats as well as some nicer restaurants if they so choose. (*This is where Tavern on the Park is, a restaurant that you and I have been to.) Free to walk around of course. Take the bus or red line to get there. See note about Google maps at the bottom for directions.
Michigan Ave
Of course Michigan Avenue is known for it's shops but it's also nice to just walk down to see the artwork and flowers (if they're out) and of course window shop and people watch. The Apple store is one of the larger ones in the country though not as large as the Manhattan store.
Navy Pier
This is of course the tourist destination. Lots to look at, tons of shops of course and lots of people. There's always something going that's seasonal: ice sculpting and dog races in the winter, demonstrations and shows in the summer and all kinds of things.
Museums: Lots of them, all good. (see link below)
National Geographic put together a list of "free things to do in Chicago":
http://travel.nationalgeographic.com/travel/city-guides/free-chicago-traveler/
Not Touristy
Wrigleyville
After a Cubs game, go hit up the batting cages upstairs at Sluggers, right near the stadium. It will be an "interesting" crowd because of the number of Cubs Fans that pile into the surrounding bars but it's always a fun time to be in the action, especially after a win.
Downtown
Grab a drink at the Roof. The Wit hotel has a fantastic roof top bar. It's a little trendy with low slung chairs and the drinks are more of the martini style but it's a great view of the city and it's fun to people watch. They also have a few open air areas which are great for sipping martini's. Free to enter, the only cost would be drinks (if any)
http://www.thewithotel.com/
Grab a bite to eat at the Purple Pig. While this restaurant is on Mich Ave, it's considered one of the top new restaurants. http://www.thepurplepigchicago.com/
If you're into walking and architecture, there's a lot of hidden gems in the city, one of them right behind Wrigley Field. Alta Vista Terrace is a tiny little street where every house is considered a replica of London. Not very big but fun to look at: http://home.xnet.com/~jkelley/VirtualTours.fldr/VirtualChicago.fldr/AltaVista.fldr/AltaVista.html
Deep Dish Pizza (this is a whole email in and of itself but this is a good overview)
The number one touristy spot: Uno's on State and Ontario (49 East Ontario) This is the one that made Chicago famous for it's deep dish and they now deliver all over the country. Touristy
http://www.unos.com/
My favorite is Lou Malnotti's on Sheffield and Lincoln (958 W Wrightwood). Supposedly Lou Malnoti actually made the first Uno's pizza and then went out on his own. Very good. Not touristy at all.
If you're downtown (e.g. near Navy Pier or Millenium Park) there's Pizano's pizza on State and Madison (61 E Madison) http://www.pizanoschicago.com/loop.html This is another one that was started by the same Uno's/Lou's crew. Also very good.
Last but not least, Gino's East is like Uno's in that they've made a name for Chicago Deep Dish. Plenty of locations and their schtick is that you can write on the walls. http://www.ginoseast.com/ If you go to the Superior location or the Wells location, they're pretty touristy. The others aren't as much.
True Chicagoan
If you really want to get out of the touristy scene altogether, head over to wicker park. One of my favorite spots is Violet Hour. It's hard to find (there's no sign) and the drinks are made very meticulously. It's modeled after an old 1920's speak easy with very high backed chairs, very private and dark. http://www.theviolethour.com/
Also in Wicker Park/Bucktown area is Jerry's Sandwich Shop. Amazing food, a huge beer selection and it's nestled in between a bunch of great little bars. http://www.jerryssandwiches.com/ (Address on bottom right of page)
Hop Leaf
"Up north" in Andersonville this little spot has a fantastic beer selection and is often full because of it. http://www.hopleaf.com/dining_menu.html Very casual beer spot but great.
There are a lot of other, more casual places like this that serve good food and have great beer. If you're interested I can expand on this section.
Mercadito
Great food, located in River North neighborhood, good lively atmosphere and is often a place to see and be seen. http://www.mercaditorestaurants.com/chicago/index.php
Uber Exclusive:
Sunda and Underground. Owned by the same guy, these two places, the first a restaurant that serves high end philipino food is often frequented by celebrities whenever they're in town, the second a dance club that is frequented by the same celebrities. The club can be hard to get into.
http://www.sundachicago.com/
http://chicago.metromix.com/bars-and-clubs/lounge/the-underground-river-north/146714/content
Other Links for More Info:
http://www.explorechicago.org/city/en.html
http://www.chicagotraveler.com/things-to-do.htm
http://www.chicago.com/things_to_do/
For Getting Around:
Google Maps does a great job of listing both walking diretions and public transit directions. It's even smart enough to know if you type "wrigley field" as your stating point and "millenium park" as your destination.
Example: http://www.google.com/maps?ie=UTF8&f=d&sll=41.812267,-87.837067&sspn=0.732868,1.450195&saddr=&daddr=&ttype=dep&date=4/14/2011&time=11:44%20AM&dirflg=r
This is the main site for all things public trans. You don't need to use it really just know that it costs $2.25 to ride the CTA per person, one way. So two people riding the train or bus "there and back" would be $9. Weekend unlimited passes are a good deal and the site lists where you can get them.
http://www.transitchicago.com/
