The Chicago Tourism Board has included information on its website (choosechicago.com) about the favorite haunts of President-Elect Barack Obama and his family.  For example: 

The Obama Family's Favorite Restaurants:

Topolobampo
445 North Clark Street
Chicago, IL

Described as "elegant regional Mexican cuisine," owned by chef Rick Bayless. 
 

R.J. Grunts
2056 N Lincoln Park W
Chicago, IL

Described as a place to go for a casual bite. 

Sepia
123 N Jefferson St
Chicago, IL

Described as "inventive American cuisine; said to be Michelle Obama's favorites.

MacArthur's
5412 W Madison St
Chicago, IL

Serving fine Southern Cuisine; said to be one of Barack Obama's favorite Chicago restaurants. 

Favorite Shopping Spots of the Obama Family:

57th Street Books
1301 E 57th St
Chicago, IL

Maria Pinto Boutique
2211 N Elston Ave
Chicago, IL

Sells dresses by Chicago designer Maria Pinto, a favorite designer of Michelle Obama.

So, on your next getaway to Chicago, you might want to check these places out. And, what better way to experience Chicago, the home of future president Barack Obama than a stay at one of the Presidential Suites the city has to offer?  Just know they're not cheap.  Most of the times you can't even find the rates of the presidential suites on the websites.  You know, if you have to ask, you can't afford it anyway.  Oh, well, here are a select few:

Four Season's Hotel Chicago
120 East Delaware Place
Chicago, Ill

The 2,315 square-foot Presidential Suite at the Four Season's Hotel Chicago occupies a corner position on the 46th floor, with a sweeping view of Lake Michigan.  The suite also has two private bars.

Also included:   two king beds, and two rollaway beds (by request).  And, two full marble bathrooms, with a guest powder room.  Is it me, or does a "rollaway bed" in a presidential suite seem weird? 

Sheraton Chicago
301 East North Water Street
Chicago, IL

The Presidential Suites of the Sheraton Chicago include a Contemporary, Oriental and Southwestern Presidential Suites which all feature themed decor and fabulous views of the city skyline and Lake Michigan.  You also get a full pantry and a complete entertainment center. 

Conrad Chicago
521 North Rush Street
Chicago, IL

The Conrad Chicago is located on the Magnificent Mile, just off Michigan Avenue.  Its 2,000 square-feet Presidential Suite features a 336-square-foot secluded terrace space overlooking the Magnificent Mile. The bathroom features a deep-soaking bathtub and separate shower.

Hyatt Regency Chicago
151 East Wacker Drive
Chicago, IL

I've read the Obama's were celebrating their victory Election night at a Presidential Suite in the Hyatt Regency Chicago.  Don't know if this is true, but if you're looking for an awesome Presidential Suite, this one's a winner.  1,045-square-foot of luxury, with views of the city, river, lake and Navy Pier. You get an extra large parlor with a large plasma screen TV, cable and in-room pay movies, a surround sound system and an iHome Alarm Clock. You can also welcome your guests in the separate living area, then entertain them in the dining area, which can accommodate up to 75 people for a party.