Photo Courtesy of Vincent Desjardins
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. Chicago can be a huge playground with hot, happening nightlife and lush, prestigious hotels.… Travelers also enjoy free access to amazing concerts, public art, and endless late-night fun, like catching a comedy show at the Second City.
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- Take the architectural boat tour. The 90 minutes spent provide a strong foundation for your visit: You'll find out not just about the remarkable buildings and visionary architects, but about Chicago's history and culture.
- Even if you're not traveling with children, the Museum of Science and Industry is endlessly fascinating. The building in which it is housed was built as the Palace of Fine Arts at the famous 1893 World's Colombian Exhibition, so it's a magnificent space, and the exhibits—both the permanent and temporary—include a coal mine experience (the delightfully old-school museum design will transport you back to grade-school field trips), a walk-through of the sleek art deco Pioneer Zephyr passenger train, and lots of ultramodern tech and science.
- A stroll through Millennium Park is great introduction to a friendly and proud city: public art and fountains, the much-photographed Bean, free concerts, gardens, and the beautiful museums.
- Catch a baseball game at Wrigley Field. No kidding. The 1914 brick stadium, the ivy walls surrounding the outfield, the manually updated scoreboard (!), the beloved Cubs, the accents of the fans around you—this is an opportunity to get a strong taste of local flavor. Grab a beer after the game at one of Wrigleyville's many bars and keep your conversation with the locals going. (We like the Guthrie's Tavern, but there are lots of good options in the blocks around the stadium.)
Fly into Chicago’s 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. The Blue Line on the “L” train runs to O’Hare (45 minutes), and the Orange Line runs to Midway (25 minutes).
Chicago is very flat and walkable with “L” trains, buses, and taxis to take you anywhere you want to go. Train rides cost $2.50; bus rides cost $2.25. The buses take cash, but for the trains you’ll need a CTA fare card. The Chicago Transit Authority's website offers a trip planner that can get you from Point A to Point B.
Eat fresh Mexican food in Pilsen, grab a bubble tea in Chinatown, and go to Little Ukraine’s famous bakeries to see why people visit Chicago just to eat. If stuffed pizza and Chicago-style hot dogs are your thing, eat your way across the city in all the restaurants that claim to have originated those Chicago classics. Chicago has some of the best steak houses in the country as well as up-and-coming artisan butcher shops and gastropubs, and if you watched early seasons of Top Chef, you’ll want to eat at Rick Bayless’s XOCO and Stephanie Izard’s Girl and the Goat. To splurge, book 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 artist galleries populate Wicker Park, while formal museums such as the Art Institute of Chicago and the Museum of Contemporary Art, Chicago are found on the shore of Lake Michigan. The Shedd Aquarium, Adler Planetarium, and Lincoln Park Zoo are wonderful places to check out. To fully appreciate Chicago’s architecture, take an architecture 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; Oktoberfest Chicago; the Chicago International Film Festival; and the Chicago Marathon. The year ends with Christkindlmarket Chicago, a Christmas shopping and German food market that’s part of the Magnificent Mile Lights Festival. Celebrate the rest of the year 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 the city's bloviating politicians, but the wind coming off Lake Michigan could convince you otherwise). Bundle up and plan inside activities if you plan to visit anytime December through 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 is not 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. Nicole is also the founder of Doors Open Dishes, an initiative committed to keeping the doors open to the group homes and workshops of individuals with special needs by partnering with chefs and restaurants across the city. Follow her on Twitter or on Instagram.
Kaitlyn Barrett is a freelance writer based in Chicago. She tours with theater shows as a Wardrobe Supervisor and loves food, scuba diving, and unexpected adventures. You can follow her at adventuresofthegypsyqueen.com.