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Planning a Trip to Chicago

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Chicago's architecture is elegant and impressive

In general, Chicago's weather is cold and snowy in the winter, mild in the spring, hot and muggy in the summer, and crisp and mild in autumn. The best time to visit is late spring or the early autumn, but anytime you can get to Chicago, well, it’s a treat.

It is thought that Chicago’s “Windy City” nickname was originally coined to refer to its long-winded politicians, although it is now used to describe the weather. A strong wind, known as “the Hawk”, often blows from Lake Michigan, gusting and howling as it is funneled through the city’s gridded streets.  the wind's speed is enhanced as it flows between the city’s ever present skyscrapers.

Although the wind cools the city on hot, humid summer days, it can make walking quite miserable during the frequent spells of cold and, often, inclement weather that occur during Chicago winters.

Public Transportation

The "L" is an iconic image that has long been part of the Chicago transportation sceneChicago has an efficient public transportation system, so it is easy to get around without a car. If you’re staying in the downtown or Near North neighborhoods, you can walk to many attractions.

If you want to go farther afield, there are a variety of public transportation vehicles to get you there, including: buses, the “L” (an elevated train system), subways, commuter trains, and taxi cabs galore. (Note, many Chicagoans call the elevated trains “the El”, but the MTA calls them “L”. ) To access maps, trip planners, schedules and fares for public transportation, go to the official website of the Chicago Transit Authority  or call 1-888-YOUR-CTA.

Navigating Chicago

As in all "big" cities around the world, there are areas of Chicago that  have high crime rates and can be dangerous, especially to visitors.  Ask the staff at your hotel about local safety conditions for areas near your hotel and for other destinations to which you might travel.

To help with your tour around Chicago, take these steps

1.  Be sure to see our map of the best places to visit in Chicago, or any map you prefer, and  use it to familiarize yourself with the geography you intend to visit. 

2.  Study the Chicago Transit Authority's website for details on public transportation and how to use public transportation in Chicago. 

3.  Be sensible about late night transportation and use taxis when: 1) other options can't get you there in time, 2) other options can't get you close to your destination, 3) you are unsure you know how to get to your destination from the public transportation drop-off, or 4) you feel unsafe using public transportation.

4.  Walk whenever you can to experience Chicago's wonderful neighborhoods, but be sensible about walking late at night or in districts in which you feel  apprehensive about your safety.  Always ask a local authority if the area you want to visit is safe.

5.  Parking fees in the Loop and some other sections of Chicago can be sky-high and using a taxi or public transportation is often a good alternative.

Chicago - a Culinary Capital

Although our guides do not provide recommendations on dining, Chicago has a thriving restaurant community featuring food specialties from around the world. Now known as a culinary center, Chicago also has a well deserved reputation for “comfort” food. After all, it was at Chicago’s Billy Goat Tavern that the late John Belushi heard the phrase he made famous on Saturday Night Live of  “Cheeseburger, cheeseburger.” Chicago is, also, the home of the Pizzeria Uno and the deep-dish pizza, not to mention Eli’s, which is famous for its role in popularizing cheesecake in the United States.

If you are in the mood for Greek food, head to Greek Town, or Taylor street for Italian, or.... You get the idea, there are so many kinds of food, styles of restaurants, and pricing tiers available when dining in Chicago that it’s a good idea to ask for recommendations from the desk staff at your hotel or ask a friend who “knows” Chicago .

Now, Just one more food thing – It may sound kind of hokey, but Chicagoans have a thing for hot dogs. In fact, some of the hot dog stands in Chicago have attained an almost gourmet status among residents and visitors.

The Chicago “dog” is not just your everyday, run-of-the-mill hot dog. These delights are served in a poppy seed bun, accompanied by mustard, relish, a pickle spear (sometimes pickle slices), chopped onions, a couple of tomato slices , two or more sports peppers and celery salt.  The wiener is usually Vienna Beef brand and steamed to perfection (plumped, but not soggy and certainly not grilled). Try one - you may just fall in love again.

Chicago's Neighborhoods

Chicago is a city of neighborhoods, each with its own personality, architecture and atmosphere and each offers something unique to the visitor. The Loop or downtown area, for example, offers historic architecture, live theater and entertainment, dining, and art; the Lincoln Park neighborhood is home the zoo, North Avenue Beach, Steppenwolf Theater and a variety of trendy restaurants and bars; and Wrigleyville, named for Wrigley Field, is home to the signature sports bars and pubs….and of course, the Cubs.

We do not cover all of Chicago’s neighborhoods here, as the description would take its own website. Rather, we focus on those central to “tourist” Chicago and the ones that hold the most attraction for travelers. Also, note that many of the areas we mention can be further broken down into smaller neighborhoods. (If you are interested in exploring Chicago's many neighborhoods,, see this real estate website, which has a great introduction to Chicago’s many neighborhoods. Click on North Central on their map to get started.)

The Loop, or Chicago’s downtown area, is bordered by Lake Michigan on the east, The Chicago River on the west and the north, and Harrison Street on the south. In addition to being the business hub of the City, the Loop is also home to Grant Park, The Art Institute of Chicago, Symphony Hall, the Chicago Opera House, theaters, and public art exhibits. Many examples of Chicago’s architectural heritage can also be found here in the Loop’s theaters, public buildings and businesses.


The Near-North Side borders Lake Michigan on the east, the River on the south, Clark Street on the west, and Division on the north. Many of Chicago’s best places to visit lie within this area. The Magnificent Mile, for example, is Chicago’s luxury shopping area with shops like Cartier’s, Gucci, and Louis Vuitton. Then there’s the Gold Coast, thus named because it has been one of the City’s wealthiest areas since 1882 when millionaire Potter Palmer built his 42-room mansion here. The Near-North Side is also home to Oak Street Beach, the Drake Hotel and the John Hancock Center.

Lincoln Park is the name of the neighborhood that encompasses the 1,208 acre park of the same name and the Zoo. In addition to the park and the zoo, Lincoln Park is home to some of Chicago’s trendiest restaurants and bars.

Wrigleyville has one major  claim to fame, and, as you may have guessed, it is Wrigley Field, home to the Chicago Cubs baseball team. The neighborhood is also home to a variety of popular sports bars and restaurants, such as Cubby Bears, Sluggers and Murphy’s Bleachers. An “L” stop is conveniently located on Addison Avenue just east of Sheffield, so getting there is a snap.

 

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Topics  Described On This Page

Weather
Public Transportation
Navigating Chicago
Culinary Capital
Chicago's Neighborhoods


 

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Chicago Lakefront Neighborhoods Bicycle Tour

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