Choose Chicago (tel. 877/CHICAGO [244-2246]; www.choosechicago.com) produces a Chicago Visitors Guide, available online and at Visitor Information Centers. The City’s Department of Cultural Affairs and Special Events is also a good resource to learn about cultural events and festivals (tel. 312/744-3316; www.cityofchicago.org/specialevents).  

January

The latest boats and recreational vehicles are put on display at the Chicago Boat, RV & Sail Show (tel. 312/946-6200; www.chicagoboatshow.com), which also features trout fishing, a sailing simulator, boating safety seminars, and big-time entertainment. The action takes place in early-January. 

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Grab a prix-fixe meal for a steal during Chicago Restaurant Week, sponsored by Choose Chicago (tel. 312/567-8500; www.choosechicago.com). Lunch and dinner is priced at $22, $33, or $44 at participating restaurants around town. Make a reservation—the most popular spots fill quickly during the 2-week event.  

February

True, many attendees will get to the Chicago Auto Show (tel. 630/495-2282; www.chicagoautoshow.com) via public transportation. Irony aside, it’s the largest auto show in North America and winter is a great time to peruse 1,000 shiny new vehicles on display at McCormick Place. You can get inside them for a closer look, and some you can even drive around an obstacle course.

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March

The Chicago River is dyed green for the St. Patrick’s Day Parade (www.choosechicago.com), a Chicago tradition since the 1840s that’s held on the Saturday before March 17. The parade route is Columbus Drive from Balbo Drive to Monroe Street. The South Side Irish Parade (www.southsideirishparade.org), which is more community oriented, happens the day after the downtown parade, on Western Avenue from 103rd to 115th streets.  

April

Join the enthusiastic fans of the Cubs (tel. 773/404-CUBS [2827]; www.cubs.mlb.com) or the White Sox (tel. 312/674-1000; www.whitesox.mlb.com) on Opening Day. Be sure to get your tickets early for this eagerly awaited day, and go prepared with warm gear, because it’s usually freezing cold in early April.

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May

On the third Saturday in May, you can take the annual Wright Plus Housewalk (tel. 312/994-4000; www.flwright.org/wrightplus), a rare look at the interiors of notable buildings in Oak Park. Tickets go on sale January 1 and can sell out within a few weeks. 

Lakeshore Drive (aka LSD) shuts down to cars and opens to bikes one morning a year for the annual Bike the Drive (tel. 312/427-3325; www.bikethedrive.org). Cyclists can ride for a few miles or opt for a 30-mile loop with unbeatable views of Lake Michigan and the downtown skyline. Sunday morning, Memorial Day weekend.   

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Highland Park’s Ravinia Festival (tel. 847/266-5100; www.ravinia.org) is the open-air summer home of the Chicago Symphony Orchestra and many first-rate visiting orchestras, chamber ensembles, pop artists, dance companies and so forth. It runs from late May to September. 

June

The largest free literary fest in the midwest, Printers Row Lit Fest (http://printersrowlitfest.org) features more than 200 booksellers displaying new, used, and antiquarian books for sale. Add in readings and signings by big-name authors and panel discussions on how to pen your first novel, and you’ve got a full day of entertainment. It takes place the second weekend in June. 

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Dozens of acts perform over 3 days at Chicago Blues Festival (tel. 312/744-3370; www.chicagobluesfestival.us) in Millennium Park. Many of Chicago’s legendary musicians show off their stuff at Chicago’s largest music festival. All shows are free, so get there early to nab a good spot on the lawn, along with hundreds of thousands of other fans. Second weekend in June. 

The Grant Park Music Festival (tel. 312/742-7638; www.grantparkmusicfestival.com) at Pritzker Pavilion in Millennium Park offers free outdoor musical concerts from June to August. One of the city’s best bargains, the concerts feature musicians from the Grant Park Orchestra and Chorus. Bring a picnic and enjoy dinner beforehand with a view of the Chicago skyline.

The floats and marching units at the LGBTQ Pride Parade (tel. 773/348-8243; www.chicagopridecalendar.org) are the definition of over-the-top. Halsted Street is always mobbed; Grab a spot on Broadway to be on the outskirts. The parade runs between Addison and Diversey, mostly along Halsted, the last Sunday in June. A 2-day Pride Fest takes place the weekend prior in the Boystown neighborhood.  

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The annual Old St. Patrick’s World’s Largest Block Party (tel. 312/648-1021; www.worldslargestblockparty.com) is a beloved blowout at the city’s oldest church, an Irish Catholic landmark in the West Loop area, in late June. Beer flows and rock bands perform over 2 nights. Bonus: Proceeds benefit social justice causes. 

Late June through late August, the city’s Department of Cultural Affairs hosts Chicago Summerdance (tel. 312/742-4007; www.chicagosummerdance.org). A 4,900-square-foot outdoor dance floor is the venue for 1-hour lessons followed by open dancing, from ballroom to samba. Thursday, Friday, and Saturday from 6 to 9:30pm and Sunday 4 to 7pm. Free admission. 

July

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Enticing smells waft through downtown during Taste of Chicago (tel. 312/744-3316; www.tasteofchicago.us), the gigantic outdoor festival that draws more than 1 million to nosh on top city offerings—well beyond pizza and ribs—served al fresco and priced ala carte (admission is free). An A-list of headliners makes for a rollicking nightly soundtrack (admission required) throughout the 5-day event. 

More than 80 homeowners open their backyards to visitors at the annual Sheffield Garden Walk (www.sheffieldgardenwalk.com) in the Lincoln Park neighborhood near DePaul University. Intersplice your self-guided garden tour with guided architectural tours and breaks for food, drinks, kid’s activities, and live music at the street festival held in tandem with the walk. Third weekend in July. 

August

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Grab your fedora and festival gear for Lollapalooza (tel. 888/512-SHOW [7469]; www.lollapalooza.com), which brings 3 days of big-name bands to Grant Park. Beyond the music (more than 150 bands on 8 stages), there are after-shows, artisans, and incredible food offerings from local chefs. Early August.   

The U.S. Air Force Thunderbirds and U.S. Navy Leap Frogs usually put in an appearance at the Chicago Air & Water Show (tel. 312/744-3316; www.chicagoairandwatershow.us), which is held the third weekend in August. Admission is free to this hugely popular aquatic and aerial spectacular at North Avenue Beach. 

Northalsted Market Days (tel. 773/883-0500; www.northalsted.com) is the city’s largest street festival, drawing nearly 200,000 to the heart of this gay neighborhood. Centered on Halsted Street between Belmont Avenue and Addison Street, the 2-day extravaganza includes food, crafts, DJs, dancing, and plenty of pride.  

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September

National headliners are always on hand at the Chicago Jazz Festival (tel. 312/744-3316; www.chicagojazzfestival.us). The free event, which includes an art fair, takes place in Millennium Park Labor Day weekend.

October

The oldest U.S. festival of its kind, the Chicago International Film Festival (tel. 312/683-0121; www.chicagofilmfestival.org) screens films from around the world—including shorts, documentaries, indies, noir, local films, and more—at various theaters over 2 weeks in October. 

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The Chicago Marathon (tel. 312/904-9800; www.chicagomarathon.com) has become a major event on the international long-distance running circuit. Held Columbus Day weekend, the marathon begins and ends in Grant Park, but can be viewed along any of the many vantage points along the route (Lincoln Park provides some of the best).  

November

Magnificent Mile Lights Festival (tel. 312/409-5560; https://www.themagnificentmile.com/lights-festival) kicks off the holiday season by lighting up Michigan Avenue at dusk the Saturday before Thanksgiving. But it’s more than just lights. There’s also a parade of Disney characters, carolers, elves, minstrels, Santa, and family-friendly activities Friday evening and all day Saturday.  

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December

The esteemed Joffrey Ballet of Chicago performs The Nutcracker (tel. 312/386-8905; www.joffrey.com) with a twist: the plot revolves around Chicago’s 1893 World’s Fair. A family holiday tradition, performances begin after Thanksgiving and continue through the end of December.  

Christkindlmarket, Daley Plaza, in the Loop (tel. 312/494-2175; www.christkindlmarket.com), is an annual holiday event inspired by traditional German Christmas festivals, with vendors flying in from Germany to sell handcrafted ornaments and decorations. Don’t miss the hot spiced wine, beer, and sausages. Open Thanksgiving Day through Christmas Eve. For a smaller, less crowded version—complete with ice skating—head to Gallagher Way at Wrigley Field.  

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Goodman Theatre’s A Christmas Carol (tel. 312/443-3800; https://www.goodmantheatre.org) is a seasonal favorite, performed from Thanksgiving through December.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.