Chicago trip planner

Chicago Holiday Planning Guide

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants. Renowned for its distinct architecture that provides countless sightseeing opportunities, the city attracts tourists with its cosmopolitan atmosphere and genuine friendliness, charming visitors with a sense of hospitality rarely found in other urban centers its size. The hub of the Midwest, Chicago features a bold skyline set against the waters of massive Lake Michigan, resembling more an inland sea than a freshwater lake. You have plenty to choose from for a diverse Chicago itinerary, including visits to the city's lakefront, huge parks, public squares, and world-class museums of art and science.

Best Neighborhoods to Visit in Chicago

The Magnificent Mile: Home to some of Chicago's most iconic buildings, this upscale shopping street lures visitors with its high-end stores, luxurious restaurants, and comfortable hotels, located in a vibrant downtown area offering easy access to world-class museums and theaters.

Chicago Chinatown: The cultural and spiritual heart of Chicago's Chinese community, this neighborhood features striking Chinese architecture and a huge selection of Asian-owned businesses, ranging from cozy family-run eateries to hole-in-the-wall souvenir shops.

The Loop: A great place to start your Chicago tour, this downtown financial district contains many of the city's tallest buildings; the neighborhood also draws visitors with its theaters and annual music festivals.

Lincoln Park: A good place to stay if you want to avoid the prices and the crowds of the downtown districts, Lincoln Park sits just north of the center and offers quick access to outstanding parks, the lake, and one of the oldest zoos in America--ranking among the biggest tourist attractions in Chicago.

Greektown: Situated on the west side of the city, Greektown remains one of Chicago's major culinary destinations, packed with tourist-friendly eateries and known for a small-town feel that's rare in a major urban center.

Andersonville: An upscale neighborhood on the city's north side, Andersonville started as a hub of Swedish settlers and now serves as the heart of Chicago's lesbian community, known for its inviting restaurants and innovative theaters.

Boystown: Home to one of America's largest LGBT communities, Boystown remains an ideal destination for visitors looking for some high-energy nightlife; the area also hosts one of the country's biggest annual pride parades.

Wicker Park: In many ways a city within a city, Wicker Park tops lots of Chicago itineraries with its outstanding nightlife and distinct music scene, as well as a huge selection of independent fashion boutiques.

Hyde Park: Home to the renowned University of Chicago, Hyde Park remains a history/architecture buff's paradise, featuring a string of impressive Victorian mansions, Prairie School houses, and independent bookshops.

Pilsen: Boasting an exciting arts scene, this working-class neighborhood is home to large Mexican and Puerto Rican communities, equally proud of their city and their unique ethnic heritage.

Things to Do in Chicago

Popular Chicago Tourist Attractions

The Art Institute of Chicago: Housing a permanent collection of more than 300,000 works of art, this world-famous museum developed from a free art school and now boasts eight buildings filled with masterpieces by Monet, Renoir, Cezanne, van Gogh, Picasso, and more.

Millennium Park: A must-see on your Chicago holiday, this landmark park sits smack in the city center, offering great views of downtown and a giant video sculpture/fountain.

Cloud Gate: Whimsically called "the bean" by locals, this legume-shaped sculpture reflects the city's skyline and provides an ideal backdrop for photographs.

360 CHICAGO: This Chicago attraction provides priceless views across four states from the top of one of the city's highest buildings, accessible by one of the fastest elevators in North America.

Museum of Science and Industry, Chicago: Whether or not you love science, this sprawling museum complex makes it exciting with over 800 interactive exhibits covering subjects like transportation, space, energy, and environment.

The Magnificent Mile: Lined by some of America's top boutiques and department stores, this glitzy avenue draws visitors looking to devote part of their Chicago holiday to upscale shopping and fine dining.

Wrigley Field: Home of the Chicago Cubs for a century, this iconic ivy-covered ballpark--nicknamed the "Friendly Confines"--epitomizes America's love of baseball and draws international visitors with its behind-the-scenes tours of dugouts, press boxes, and the clubhouse.

Shedd Aquarium: This venue houses more than 1,500 different animal species and includes a replica of a Philippines reef ecosystem, a shark exhibit, and a giant oceanarium containing beluga whales, sea otters, seals, and white-sided dolphins.

Skydeck Chicago - Willis Tower: Still called "Sears Tower" by most natives, this Chicago attraction remains one of the tallest buildings in the country, featuring an observation deck on its 103rd floor and offering unobstructed vistas across Lake Michigan and the sprawling plains of Illinois.

Navy Pier: Built in 1916 as a cargo facility for lake freighters, this 1,000 m (3,300 ft) pier long served Chicagoans as an ideal place for cooling off on hot summer days and now features fountains, fast-food eateries, souvenir shops, and a Ferris wheel.

Planning a Chicago Vacation with Kids

Things to do in Chicago with Kids

One of America's most exciting destinations for family holidays, Chicago offers everything from world-class museums and theaters to outstanding zoos and historical ballparks. There's so much you can see and do in the Windy City, the real problem isn't how to fill up one itinerary, but how to avoid doing too much and turning the whole trip into one big blur. Start your Chicago tour at Millennium Park, where you can soak up the city's lively atmosphere and admire its stunning architecture. From there, you can easily get to other popular attractions big on kid appeal, like Shedd Aquarium and Museum of Science and Industry, Chicago. To leave the 21st century behind and visit a time of ferocious dinosaurs and other long-gone creatures, explore exhibits at The Field Museum, home to a collection of about 20 million artifacts from around the world. Be sure to take the kids to the museum's display of an Egyptian burial chamber--complete with 23 real mummies--and don't miss taking a look at "Sue," the best-preserved dinosaur fossil ever unearthed. Other kid-friendly highlights include Chicago Children's Museum and Lincoln Park Zoo. If it's baseball season, round off your Chicago sightseeing experience by attending a game at Wrigley Field, home to the Chicago Cubs and one of America's oldest baseball stadiums still in use. Be sure to check out one of Chicago's independent theater productions; with its thriving, innovative community of companies, there's almost always something on to delight visitors of all ages.

Tips for a Family Vacation in Chicago

A trip to Chicago offers such a diverse selection of activities and attractions suitable for family-oriented holidays, you could easily spend weeks there without getting bored. As you walk around this friendly Midwestern metropolis, make sure the kids look up every once in a while--this city is home to some of the nation's finest architecture as well as some of its tallest skyscrapers. Explore the city's festival scene, known for big music events, world-famous food extravaganzas, and kid-friendly Thanksgiving and Christmas celebrations. Spend time along the shores of Lake Michigan, where you'll have access to beaches, parks, and recreational areas. Tour Chicago on a kid-friendly bicycle trip, or travel across the city's vibrant neighborhoods on "the L," the city's iconic elevated train network. Whatever you do, don't forget that this city lives and breathes sports. Soak up some local atmosphere and root for the home team at a Cubs, Sox, Bears, Blackhawks, or Bulls game.

Dining and Shopping on Holiday in Chicago

Cuisine of Chicago

The city's fantastic restaurant scene generates plenty of gastronomic tourism in Chicago, delighting foodies from around the world. You'll easily find distinctive ethnic cuisine in history-infused neighborhoods like Greektown, Pilsen, and Chicago Chinatown, where you can take a trip around the globe without crossing the city limits. For an upscale dining experience on your Chicago holiday, head to Lincoln Park or Wicker Park, where you can sit down at some the city's finest restaurants. Chicago takes its food as seriously as its sports, and you don't have to go indoors or dress up to try some of its significant contributions to world cuisine. The northwestern sections of town are full of family-operated delis selling Polish sausages, a great barbecue specialty usually accompanied with grilled onions, chili peppers, and mustard. For many people the all-beef Chicago-style hot dog remains the king of all dogs, served invariably on poppy-seed buns and topped with lots of mustard, tomatoes, and pickles. Cap off your culinary adventure with Chicago Pizza Tours, the best way to visit eateries serving both stuffed and deep-dish pizzas, world-famous specialties born in the Windy City.

Shopping in Chicago

If looking to do some shopping on your tour of Chicago, begin by exploring the upscale boutiques of The Magnificent Mile, a busy downtown district that also contains several large malls. The fine establishments lining The Magnificent Mile sparkle and shine with luxurious goodies, but Go Chicago Card at Macy's State Street Visitor Center may provide a slightly more authentic shopping experience. Listed on the National Register of Historic Places, this flagship of one of America's most iconic stores takes up nine floors and features one room known for its lavish vaulted ceiling, designed by Tiffany. For something less burdened by history--and easier on your pocket--consider the eclectic and browser-friendly shops spread across the immigrant communities on the city's far north side. Alternatively, rub elbows with some locals and pick up inexpensive souvenirs for everyone back home at open-air shopping destinations like Randolph Street Market, where you can enjoy a relaxed atmosphere and plenty of opportunities to munch on Chicago-style hot dogs and pizzas.

Know Before You Go on a Trip to Chicago

History of Chicago

Chicago's first inhabitants were the Potawatomi Indians, who gave the area around the Chicago River the name "Checaugou" (or "Shikaakwa"), roughly translated as "wild onions." The area's first non-indigenous settler was Jean Baptiste Point du Sable, known as the founder of Chicago. Other colonists soon followed and quickly established a base at a military fort on the river's southern bank, under today's Michigan Avenue Bridge.

By the 1830s, the growing town of Chicago had a population of approximately 200. The next several decades saw this small settlement turning into one of the world's fastest-growing urban centers. The city's favorable geographic location helped turn the area into a major transportation hub, linking the eastern and western United States. Chicago's first railway opened in 1848, and the same year saw the opening of the Illinois and Michigan Canal, which allowed sailing ships and steamboats traversing the Great Lakes to link up with the Mississippi River. Add Chicago History Museum to your Chicago itinerary to learn more about the city's early development.

A booming economy attracted a growing number of immigrants to Chicago in the second half of the 19th century. Newcomers arrived from Ireland, Germany, Poland, Russia, China, and many other places around the world. This rapid population growth sparked several important projects aimed at improving city infrastructure. In 1856, Chicago became the site of America's first comprehensive sewer system.

The city's swift growth came to a quick halt in 1871, when the Great Chicago Fire destroyed scores of wooden buildings. Modern structures made of steel and stone soon sprang up in the damaged section of the city, setting an important precedent for the worldwide construction boom using sturdy, fire-resistant materials. During this period, Chicago constructed the world's very first skyscraper. Though that building no longer stands, there are plenty of other landmark architectural places to see in Chicago, including Tribune Tower and Chicago Board of Trade Building.

Chicago continued to expand during the 20th century. Thriving industries drew an increasing number of African-Americans from the southern portion of the United States. Adding hundreds of thousands to the city's population, these new arrivals sparked a major cultural movement, called the Chicago Black Renaissance. Stop by DuSable Museum of African-American History for a deeper understanding of the city's diverse cultural heritage.

Today, Chicago represents one of America's biggest and liveliest urban centers as well as one of the world's favorite tourist destinations. A city of outstanding architecture, fine dining, and vibrant festivals, each year Chicago welcomes more than 50 million visitors. See why so many tourists spend their vacations in Chicago by exploring places like The Magnificent Mile and Navy Pier.

Holidays & Festivals in Chicago

Chicago hosts countless special events and street celebrations that can add color and culture to your trip. Grant Park famously hosts Taste of Chicago, a summertime food celebration that remains one of the world's largest outdoor events of its kind. Summer is also a great time for a Chicago trip if you're a fan of practically any genre of music. Top choices include Gospel Fest and Blues Fest in June--both free--and Lollapalooza in August. The latter also features a kid-friendly Kidzapalooza event, offering a range of music-related activities sure to please the youngest festival attendees. Standouts among other notable family-oriented happenings include Chicago Kids and Kites Festival in May and the Magnificent Mile Lights Festival ahead of Thanksgiving--both draw huge crowds and provide a great way to meet the locals and spend some time outdoors. If visiting during the winter holidays, stopping by the open-air Christkindlmarket in downtown is a must: the charming European-style market features crafts, music, and plenty of mulled wine.

Chicago Travel Tips

Climate of Chicago

Chicago features a humid continental climate, which means that it experiences four distinct seasons with extremely hot summers and cold, snowy winters. Summer temperatures often exceed 32 C (90 F), while a typical winter day offers little or no sunshine and a high of just below freezing. The peak tourist season lasts between June and August, a period packed with festivals and extremely hot, humid days. If possible, consider planning your Chicago vacation for spring or autumn, when you can bask in the sunshine and enjoy low humidity.

Transportation in Chicago

One of America's easiest urban centers to get around, Chicago boasts two major airports and features the famous "L," a system of elevated trains providing easy access to the city's many neighborhoods. The train is also the best way to explore the suburbs and visit nearby destinations like Milwaukee, another popular vacation idea on the shores of Lake Michigan. Public buses cover most areas missed by the "L" system, while taxis provide a convenient though rather expensive way for getting around downtown. If you prefer to tour the city and its surrounding area on your own schedule, think about renting a car for the duration of your Chicago holiday. Many Chicago natives get around on two wheels, taking advantage of the wide, flat avenues; for a greener transportation option consider the city's bike-share program, a convenient method for sightseeing, especially if you arrive during the warmer months.