Chicago Travel Tips

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Keep in Mind...

  • Winter is no walk in the park Winter temperatures in the teens and 20s are made worse by biting breezes. Come prepared with a warm hat, a reliable pair of gloves and sturdy boots if you're visiting during this season.
  • You don't need wheels Forget the car. Chicago's extensive public transportation system is a much better (and much easier) way to get around.
  • You've got a lot to see So schedule wisely. Group the things you want to do by neighborhood to avoid wasting time in transit.

"It is hopeless for the occasional visitor to try to keep up with Chicago. She outgrows his prophecies faster than he can make them." Although he made up his mind about the Windy City before it even reached its 50th year, Mark Twain's impression of Chicago has proven long-lasting. America's third-largest city has been described in a myriad of ways throughout its lifetime. When Thomas Edison and Nikola Tesla were competing for the right to use their forms of electricity to illuminate the 1893 World's Fair, Chicago was known as a city of industry (a reputation memorialized by the Museum of Science and Industry). When Prohibition set in, notorious mobsters like Al Capone transformed Chicagoland into their own dangerous playground. And intense immigration surges throughout the 20th century brought a host of new identities to the Windy City, including Greek, Polish, Italian and Jewish.

Today, Chicago remains just as diverse, boasting a thriving arts scene, various shopping districts and a cornucopia of eateries. First-time Windy City visitors are sure to have their eyes to the sky for at least a day or two. Chicago's skyscrapers and public art is absolutely worth admiring: Tag along on a Chicago Architecture Tour or pass a few hours in Millennium Park and you'll find yourself spending lots of time looking upward. For a different perspective, head Willis Tower's Skydeck or 360 CHICAGO for the bird's-eye view before diving headfirst into all the city has to offer — from exceptional museums to pizza that takes delicious to whole new depths.

How To Save Money in Chicago

  • Bundle up The weather outside may be frightful, but there are plenty of deals to be found during the winter months. Many hotels slash their rates, and cheap flights are easy to come by.
  • Head north Hotels in the Loop cater to business travelers staying on the company dime. For a more down-to-earth (and more affordable) place to hang your hat, check out the B&Bs in North Side neighborhoods like Lincoln Park and Lakeview.
  • Invest in an all-access pass The Chicago CityPASS and the Go Chicago Card grant access to Chi-town's most popular attractions for one set price. This will help you shave big bucks off your entertainment expenses.

Chicago Culture & Customs

Compared to residents of other large U.S. cities, Chicagoans are generally more approachable, so don't hesitate to ask for directions or to strike up a conversation.

Chicago boasts its fair share of fine restaurants, but don't miss your chance to sample the regional fare. Chicagoans strongly believe that their pizza and hot dogs are better than those in New York City — you may simply want to agree rather than spark a debate. And when you're ordering a beverage, remember that in Chicago soda is called "pop."

Residents of Chicago are also dedicated to their sports teams. You should have no trouble finding a fellow fan of "da Bears" or "da Cubs" (phrases made famous by "Saturday Night Live") at one of the many sports bars scattered throughout Wrigleyville.

If you prefer performing arts to sports, The Reader and Time Out Chicago can point you to musical and theatrical performances taking place around the city.

Chicago Dining

When it comes to Chicago cuisine, most people think pizza, hot dogs and steak. They wouldn't be wrong. The Windy City has an ongoing rivalry with New York City over who can serve up the better slice — while New Yorkers prefer wide and flat, Chicagoans like their pizza with a deep crust that can carry heapings of toppings. And as New Yorkers are keeping their hot dogs simple with potato buns and the ketchup, mustard or relish, Chicagoans prefer their beef franks on a poppy seed bun and garnished with yellow mustard, chopped white onion, tomatoes, dill pickles, pickled peppers and a dash of celery salt.

Chicago is also known for its steak houses The Loop and the North Side are littered with fine dining establishments serving up prime cuts of beef. Some of the most reputed steakhouses include David Burke's Primehouse and Benny's Chop House just off the Magnificent Mile and Bavette's Bar & Boeuf in the River North area. Just be warned: A good steak doesn't come cheap in this town.

If you're looking to save on dining (but don't want to survive on pizza and hot dogs alone), move away from the downtown area into Chicago's more ethnic areas. Head west for the hummus and tzatziki in Greektown, pasta in Little Italy or tacos in the Lower West Side. Or, head south of downtown to Chinatown for Asian specialties. If you're not sure what you're in the mood for, North Side neighborhoods like Streeterville, Lakeview and Lincoln Park boast eclectic restaurant scenes.

You might also like...

  • New York City New York City
    • Another pizza-loving metropolis
    • Lots of high-end shopping and dining
  • Washington D.C. Washington D.C.
    • Plenty of free attractions
    • Very family-friendly
  • San Francisco San Francisco
    • Many vibrant neighborhoods to explore
    • Lots of beautiful architecture
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