http://www.explorechicago.org

Explore Chicago is the city's official tourism site and it gets the job done very well. Nicely designed and easy to maneuver through, the site gives you details on anything and everything the city has to offer. They even have a section devoted to President Obama's Chicago Favorites. Fun facts and city history are also included alongside solid coverage of attractions, tours, events, recreation, hotels, restaurants, and more. The handy-dandy Trip Planner really puts them above all the other sites.

http://www.centerstagechicago.com/

Centerstage is billed as “Chicago's original city guide” and it delivers. With listings for food, music, theater, bars/clubs, arts/words, lifestyle, fitness, and travel/tourism, the site is chock full of useful information. In addition to reviews, feature stories are also included to give readers a comprehensive snapshot of the options, though the overall sell is geared more toward locals than tourists. That's not necessarily a negative; a lot of travelers want to get a real experience of a city and Centerstage is a great help in that department.

http://chicago.metromix.com/

Metromix Chicago gives you guides to restaurants, bars and clubs, events, music, theater, movies and television all in one spot. Critics' reviews accompany some of the entries so you don't have to rely solely on peer opinions. The site is fairly straightforward and easy to use, which is always a plus.

http://www.chicagotribune.com/entertainment/

Chicago Tribune's Entertainment section is easy to traverse and hits all the basics – dining, movies, music, theater, events, and TV. Since the paper is a roundly trusted source of news, there's no reason to think that thread wouldn't also run through the entertainment recommendations.

http://www.citypass.com/chicago

City Pass's Chicago site not only provides information on the Second City's top attractions, it gives you discount admission when you purchase a pass to visit five of them during your stay in Chicago. If Shedd Aquarium, The Field Museum, Adler Planetarium, Museum of Science and Industry, Skydeck Chicago, and John Hancock Observatory are on your bucket list, grab a City Pass and get going.

http://www.frommers.com/destinations/chicago/

Frommer's Chicago recommendations are surely worth weighing. Though the site doesn't provide actual calendar listings, it does offer a broad, critical view of restaurants, hotels, attractions, nightlife, and the like. One super feature is the Frommer's Suggested Itineraries for one-, two-, or three-day visits to the city. It maps out the cream of Chicago's crop for you, easy peasy.

http://www.choosechicago.com/Pages/default.aspx

Choose Chicago, for its part, is staking its claim as the “official visitors site for Chicago.” That's a little bit sketchy, and they don't really bring the goods to back it up. Rather than offering calendar-style listings, the site is more a directory of venues, so you have sort of have to know what you want to do beforehand. They do offer a trip planning feature that seems pretty solid, though.

http://www.chicago.com/

Chicago.com has declared itself “The Chicago Experts,” even above the city's own official website. With a simple design packed with informative listings, they can certainly make a case for themselves. The hotel directory is divided by neighborhood, which is helpful if you know where you want to be. One slightly annoying feature is that, when you select a category such as Music or Tickets, you are bounced out to a seemingly separate site.

http://www.chicagotraveler.com/

Chicago Traveler is definitely geared toward visitors rather than locals, as it provides broad information including maps, accommodations, tour, and even visitors' guides. If you're planning a trip to Chicago, this site may be very well worth pouring over.

http://www.chicago-scene.com/

Chicago Scene is, in contrast, the self-proclaimed “premier entertainment guide” for the Windy City. Offering some of the same categories that Centerstage has, Chicago Scene adds in salons and spas, charities, and dating at the expense of arts, theater, and travel. However, the site is very busy, in terms of constantly rotating ads. It's also not anywhere near as user-friendly.