Things to do in Chicago, IL

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Discover the Best Activities in Chicago, IL

Students in Hyde Park can ponder philosophy, and floor traders at the Board of Exchange can make millions, but at the end of the day Chicago places its trust in the tangible. Its heroes are builders and magnates; its version of the American dream raises a glass to anyone who can get ahead in this clamorous boomtown. Long a city of immigrants and underdogs, Chicago knows how to rub elbows with sophistication and then hop on the wheezing, clanking L for the long ride home.

Top Things to Do in Chicago, IL

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Get to Know Chicago, IL

Your one stop resource for where to go, what to see, and how to make the most of your stay.
Produced in partnership with Let's Go! Travel Guides.

Get Oriented

Chicago dominates the entire northeastern corner of Illinois, running north-south along 29 mi. of the southwest Lake Michigan shoreline. The city sits at the center of a web of interstates, rail lines, and airplane routes. Chicago is the origin or terminus, depending on the direction in which you travel, of Old Route 66. The flat and sprawling city grid usually makes sense to drivers. At the city’s center is the Loop, Chicago’s downtown business district and the public-transportation hub. The block numbering system starts from the intersection of State and Madison St. The Loop is bounded loosely by the Chicago River to the north and west, Wabash Avenue to the east, and Congress Parkway to the south. A good map is essential for navigating; pick one up for free at the tourist office or any Chicago Transit Authority (CTA) station if you don’t want to reply on your phone or GPS.

North of the Loop, LaSalle St. loosely defines the west edge of the posh Near North area; most of its activity is centered along the Magnificent Mile of Michigan Avenue, between the Chicago River and Oak St. A trendy restaurant and nightlife district, River North lines N. Clark St. just north of the Loop and west of Michigan Ave. The Bucktown/Wicker Park area, at the intersection of North, Damen, and Milwaukee Ave., is home to many artsy cafes and to the city’s wildest/hippest nightlife venues. Lincoln Park revolves around the junction of N. Clark St., Lincoln Ave., and Halsted St. To the north, near the 3000 block of N. Clark St. and N. Halsted St., sits Lakeview, a gay-friendly area teeming with food and nightlife that becomes Wrigleyville in the 4000 block. Andersonville, 5 mi. farther up N. Clark St. north of Foster Ave., is the center of the Swedish-American community, though immigrants from Asia and the Middle East have recently settled here. It is a good idea to stay within the more active and populated areas as evening sets in; especially avoid the South Side neighborhood.

See & Do

What to do in Chicago

Tourist brochures, bus tours, and strolls through the downtown area reveal only a fraction of Chicago’s eclectic attractions. Chicago’s sights range from well-publicized museums to undiscovered back streets, from towering skyscrapers to sunny beaches and beaches and parks. Seeing it all requires some off-the-beaten-path exploration. Fortunately, Chicago is one of a growing number of cities worldwide to have a Greeter program, whose volunteer staff of knowledgeable Chicagoans will show you around.

Top Attractions in Chicago

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Eat & Drink

Chicago’s many culinary delights, from pizza to po’ boy sandwiches, are among its main attractions. One of the best guides to city dining is the monthly Chicago magazine, which includes an extensive restaurant section indexed by price, cuisine, and quality. It can be found at tourist offices and newsstands throughout the city.

Arts & Culture

Who drives route 66?

Route 66 holds most meaning for those who lived on its path and for the people whose lives were shaped and sustained by the steady stream of voyagers who passed along it. But there is also a strong interest in Route 66 from beyond the communities situated directly along the road: from elsewhere in America, from Europe, and beyond.

Indeed, many of those driving the route today are foreigners who come to the US to explore a lifelong interest in the legendary highway. Exposed to the ethos of classic American road trip culture in Europe, they come to get a taste of it for themselves. The custom is to fly into Chicago or LA, buy a Harley Davidson, drive the route, and then get the bike shipped back to one’s home country.

There are also many non-American Route 66 support groups and fan clubs. The first website dedicated to Route 66 was set up by a man from Belgium. And in February 2008 the first Czech Route 66 Association Convention was held, with more than 150 Route 66 aficionados from the Czech Republic and Slovakia gathering to celebrate the Mother Road. Roadtripping USA raises a glass to all voyagers of this legendary route; may you find every diner open.


Comedy & Theatre

One of the foremost theater centers of North America, Chicago boasts more than 150 theaters featuring everything from blockbuster musicals to off-color parodies. Downtown, the Theater District centers on State and Randolph St. and includes the larger venues in the city. Smaller theaters are scattered throughout Chicago. Half-price tickets are sold on the day of performances at Hot Tix booths and at the Water Works Visitor Center. The “Off-Loop” theaters on the North Side put on original productions, with tickets usually under $18.


Chicago is proud of the innumerable blues performers who have played here. Jazz, folk, reggae, and punk clubs groove, step, jam, and pogo all over the North Side. The Bucktown/Wicker Park area stays open late with bars and clubs. Some of the best dancing in town is at Rush Street and Division Street. Full of bars, cafes, and bistros, Lincoln Park is frequented by singles and young couples, both gay and straight. The center of gay culture is between 3000 and 4500 North Halsted Street. For more upscale raving and discoing, there are plenty of clubs near River North, in Riverwest, and on Fullerton Street.


The city celebrates summer on a grand scale. During the first week in June, the Blues Festival celebrates the city’s soulful music. The Chicago Gospel Festival takes place in late May or early June, and Nashville moves north for the Country Music Festival (date varies). In late June or early July, the Taste of Chicago festival cooks for eight days. Seventy-plus restaurants set up booths with endless samples in Grant Park, while crowds chow down to the blast of big-name bands. The Taste’s fireworks are the city’s biggest. The ¡Viva Chicago! Latin music festival steams up in late August, while the Chicago Jazz Festival scats over Labor Day weekend. All festivals center on Grant Park‘s Petrillo Music Shell and Millennium Center. The Ravinia Festival, in the Highland Park area, is the oldest outdoor music festival in the country. During the festival’s 14-week season (June-Sept.), the Chicago Symphony Orchestra, ballet troupes, folk and jazz musicians, and comedians perform. On certain nights, the Orchestra allows free lawn admission with student ID. 

Customs & Etiquette

Table manners

In the US, good table manners means quiet eating. Loud chewing, talking with food in your mouth, or slurping are seen as rude, and burping or flatulence is not seen as complementary to the chef. Servers at sitdown restaurants usually expect to be tipped 15-20%.

Public behavior

Dress in the US tends to be more modest than in Europe. Toplessness, particularly in women, should be avoided. Many establishments will require a customer to wear a shirt and shoes. The most acceptable forms of public affection are hugging and holding hands; kissing in public will usually draw some glances. Although most cities are tolerant of homosexuality, gay or lesbian couples should be aware that they may receive unwanted attention for public displays of affection, especially in rural areas. Also, note that many American will say “see you later” without really intending to make future plans.


One of the most offensive gestures in the US is extending your middle finger at someone. Known as “giving someone the finger,” this gesture is considered not only rude, but obscene. On the other hand, a “thumbs up” gesture is a sign of approval and a widely recognized signal for hitchhiking, which Let’s Go does not recommend.

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