Photo by Svetlana Ageeva
Internationally recognized chefs, lovely old architecture, open green parks, world-renowned artwork, and a friendly Midwestern attitude all combine to make Chicago one of the best of the nation’s big cities. Here, travelers find a huge playground with happening nightlife and lavish hotels, as well a…s free access to amazing concerts, public art, and endless fun, like catching a comedy show at The Second City.
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Chicago winters are brutally cold and windy, so summer is the peak time to visit. During the warmer months, tourists swarm the city for long days, outdoor activities, and a variety of festivals, though temperatures can sometimes be stifling. For more mild weather, fewer crowds, and better deals, visit during the shoulder seasons of April through May and September through October, when temps hover between 50 and 70 degrees.
Most travelers to Chicago fly into O’Hare or Midway International airports. The city center is a 17-mile, $50 taxi ride from O’Hare and a 12-mile, $40 taxi ride from Midway. Alternatively, Chicago’s rapid transit system, the “L,” runs from both airports. To get downtown, take the Blue Line from O’Hare (45 minutes) or the Orange Line from Midway (25 minutes).
Chicago is very flat and walkable, but “L” trains, buses, and taxis will also get you anywhere you want to go. Use the trip planner on the Chicago Transit Authority website to figure out how to get from point A to point B. Train rides cost $2.50; bus rides cost $2.25. You’ll need a CTA fare card to ride the train, but buses take cash.
- It may be touristy but take First Lady’s Center River architecture tour. The 90 minutes spent on the water will provide a strong foundation for your visit—you’ll learn not just about remarkable buildings and visionary architects, but also Chicago’s fascinating history and culture.
- Even if you’re not traveling with children, the Museum of Science and Industry is endlessly fascinating. The museum is housed in the original Palace of Fine Arts from the 1893 World’s Colombian Exhibition, so it’s a magnificent space, and exhibits include a coal mine experience (the delightfully old-school design will transport you back to grade-school field trips), an actual car from the art deco Pioneer Zephyr passenger train, and lots of ultramodern tech and science.
- A stroll through Millennium Park offers a great introduction to friendly, proud Chicago. Make several stops to take in the public art and fountains, the much-photographed Bean, the gardens, and the beautiful museums. If you’re lucky, there may even be a free concert going on during your visit.
- Catch a baseball game at Wrigley Field, a brick stadium built in 1914 that serves as home base for the beloved Cubs. The ivy walls surrounding the outfield, the manually updated scoreboard, the accents of fans around you—everything here provides a strong taste of local culture. After the game, grab a beer at one of Wrigleyville’s many bars. We like Guthrie’s Tavern, but there are several good options in the blocks around the stadium.
- Fill up on fresh Mexican food in Pilsen, grab a bubble tea in Chinatown, and indulge at Little Ukraine’s famous bakeries to see why people visit Chicago just to eat. Beyond deep-dish pizza and Chicago-style hot dogs, the city is home to some of the best steakhouses in the country as well as up-and-coming artisan butcher shops and gastropubs.
- If you watched early seasons of Top Chef, you’ll want to check out Rick Bayless’s Xoco and Stephanie Izard’s Girl and the Goat.
- For a real splurge, make a reservation at Alinea, one of the top molecular gastronomy restaurants in the world.
Chicago has a rich and varied art scene. Colorful street murals and local galleries populate Wicker Park, while formal museums like the Art Institute of Chicago and the Museum of Contemporary Art, Chicago line the shores of Lake Michigan. The Shedd Aquarium, Adler Planetarium, and Lincoln Park Zoo are also wonderful places to explore. To fully appreciate Chicago’s architecture, take a cruise up the Chicago River.
The world’s largest free blues festival happens in Chicago over three days in June, followed immediately by the Gay Pride Parade. July brings Taste of Chicago, an event that draws more than 3.5 million people to sample from 70-plus food vendors. September’s festivals include Chicago Gourmet, hosted by Bon Appétit; St. Al’s Oktoberfest; the Chicago International Film Festival; and the Chicago Marathon. The year ends with Christkindlmarket, a Christmas shopping and German food market that’s part of the Magnificent Mile Lights Festival. Celebrate the rest of the time with a myriad of local ethnic festivals, neighborhood parties, and holiday events.
- Winters in the Midwest are no joke and the wind is strong in Chicago (you’ll hear that the nickname “Windy City” initially referred to Chicago’s bloviating politicians, but the wind coming off Lake Michigan could convince you otherwise). Bundle up and plan inside activities if you’re visiting anytime between December and late March.
- Getting out of the city for a day trip can be easily accomplished on the Metra rail trains or with a car rental, and there are great restaurants, museums, and parks in the neighborhoods beyond the Loop and Magnificent Mile, as well as in the suburbs all around Chicago.
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Nicole Schnitzler is a freelance writer who covers food, drink, travel, entertainment, and lifestyle. When she isn’t planning her next adventure, she can be found commuting between bakeries, yoga classes, live music shows, and libraries in her hometown of Chicago. She is most comfortable with a pen in one hand and a fork in the other. Follow her on Twitter or on Instagram.