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CityPASS Home  »  City Traveler Blog  »  Chicago City Guide: What, When, Where, Why to Visit

Chicago City Guide: What, When, Where, Why to Visit

Can you name Chicago’s four major nicknames? Answer: Chi-Town, Windy City, Second City and Chicagoland. Just as there are various names for the city, Chicago is also famous for a lot of other things: history, sports, culture, academics, entertainment, and industry. And, what’s really neat, the Twinkie was born in Chicago.

When to visit

The best times to visit Chicago are in the spring or fall, when the temperatures are warm and the city comes alive with festivities. Summer is the most popular time because the weather is temperate enough for sightseeing. But travelers should be prepared for denser crowds and higher prices. If you can brave the Chicago winter, take advantage of promotions offered by both airlines and hotels, as well as buying at Chicago CityPASS which gives you VIP admission to the best 5 attractions in Chicago.

What to do

Skydeck: From 103 floors above the ground, check out the 360-degree views of four states: Michigan, Indiana, Illinois and Wisconsin. One of the highlights of Skydeck is The Ledge. Step outside the tallest building in the western hemisphere and the third tallest in the world. At 1,353 feet in the air, The Ledge’s glass boxes extend out 4.3 feet from Skydeck.

360 Chicago: You can capture 360-degree views and four states from the top of Hancock, too. At 1,000 feet in the air, Hancock has Chicago’s only open-air skywalk and is located just steps from The Magnificent Mile.

Shedd Aquarium: Chicago CityPASS holders love skipping long lines especially in the summer when throngs of people are lined up outside to get in. Admission includes VIP entry to Waters of the World galleries, Amazon Rising, Wild Reef, Abbott Oceanarium, Polar Play Zone, an aquatic show and the Jellies special exhibit through 2013, plus your choice of a 4-D Experience.

MSI: The Museum of Science and Industry, Chicago (MSI), is the largest science center in the Western Hemisphere. Science Storms, the newest permanent exhibit reveals the science behind some of nature’s most powerful phenomena; YOU! The Experience, is an exhibit that lets you explore what it means to live a vital, healthy life in the 21st century; and the U-505 Submarine, the only German U-boat in the United States.

Field Museum: The Field Museum is home to SUE, the largest and most complete T. rex ever found. Descend into an ancient Egyptian tomb featuring 23 mummies or shrink to the size of a bug in Underground Adventure. Now, you can see it all, including special exhibitions and a 3-D film.

Art Institute of Chicago: Voted the #1 Museum in the United States by Trip Advisor in 2013. AIC hosts 1.5 million visitors annually from around the globe. The Art Institute, founded in 1879, now has approximately 300,000 works of art in its permanent collection, stewarded by 11 curatorial departments and nearly 500 employees. This collection is housed in eight buildings—nearly one million square feet—at the heart of Chicago, one block from Lake Michigan and serving as the eastern anchor of the city's downtown.

Adler Planetarium: Take in immersive sky shows in three full-sized theaters including the Definiti Theater, the newly renovated Samuel C. Johnson Family Star Theater, and the Grainger Sky Theater–the most technologically advanced theater in the world.

Navy Pier: There is always something happening at Navy Pier, Chicago's lakefront playground. Offering visitors more than 50 acres of parks, promenades, gardens, shops, restaurants and attractions, Navy Pier is host to an unparalleled array of family-oriented events and entertainment. For additional information about upcoming events, please call (312) 595-PIER or (800) 595-PIER outside the Chicagoland area.

‘The Bean': Cloud Gate, a public sculpture by Indian-born British artist Anish Kapoor, is the centerpiece of the AT&T Plaza in Millennium Park within the Loop community area of Chicago. Constructed between 2004 and 2006, the sculpture is nicknamed "The Bean" because of its bean-like shape. Made up of 168 stainless steel plates welded together, its highly polished exterior has no visible seams.

Where to eat

Chicago is famous for its food. The most famous culinary staples you can get are deep-dish pizza, Chicago-style hot dogs and Italian beef. One great place to go for deep-dish is The Original Gino's East of Chicago, whose interior is almost as beloved as its pie. For a filling frank, put Portillo's on your to-do list. Or, hit up the "Encased Meat Emporium" Hot Doug's, where $2 gets you a Chicago-style hot dog with all the trimmings. And whatever you do, don’t ask for ketchup. Or how about a wet Italian beef sandwich with thin slices of seasoned roast beef? Al's Beef in Little Italy claims to be the inventor of the sandwich and has won countless awards since its founding in 1938.

Where to shop

The Magnificent Mile, of course! The eight block stretch of downtown North Michigan Avenue is Chicago’s premier shopping destination.Chicago’s Magnificent Mile is the great Chicago shopping experience with an abundance and variety of boutiques and stores to spark every interest, meet every need and delight every visitor.

The shops on The Magnificent Mile are as diverse as the goods they sell, with towering shopping centers, chic designer studios, intimate specialty retail shops, iconic department stores, lavish luxury boutiques and trendy favorites all within an easy stroll.

Where to stay

Chicago has many wonderful places to stay and there’s too many to list here. You may start by visiting Choose Chicago’s large list of accommodations.

How to get around

The Chicago Transit Authority (CTA) operates the nation's second largest public transportation system – serving the City of Chicago and 40 neighboring communities by rail and bus. Pay cash for single trip rides or purchase a re-loadable Transit Card or Unlimited Ride Pass for added savings.

For full fare information and maps, visit the Chicago Transit Authority website. Also look to their site for the latest updates to train schedules and routes that may affect your travel plans.

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