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.
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 $2.25; bus rides cost $2. The buses take cash, but for the trains you’ll need a CTA fare card.
Take a train to Ashland and Foster at 10 p.m. on Friday or Saturday night to see the Neo-Futurists’s longest-running show, Too Much Light Makes the Baby Go Blind. Roll a six-sided dice to determine your entry fee, and watch as the troupe attempts to perform 30 plays in 60 minutes in a tiny theater space seating only 150 people. They write new material every week, and this show is one of the best in Chicago—definitely the cheapest.
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 follow the reality cooking show 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 visitors are quickly introduced to the concept of “wind chill”: The temperature may be above zero, but the wind makes it feel much colder. Bundle up and stay inside if you plan to visit anytime December through February. 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 suburbs all around Chicago.
Kaitlyn Barrett is a freelance writer based in Chicago. She tours with theatre shows as a Wardrobe Supervisor and loves food, scuba diving, and unexpected adventures. You can follow her at adventuresofthegypsyqueen.com.