Chicago

Summer is the peak time to visit Chicago. During the warmer months, tourists and locals swarm the city for long days, biking and beaching along Lake Michigan, rooftop-hopping, and a variety of festivals. For milder (if not unpredictable 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. Chicago winters are cold and windy, but this is a city that never sleeps. Dining, cocktailing, and culture continue to thrive throughout the winter, and the city gets especially festive during the holiday season.

Most travelers to Chicago fly into O’Hare or Midway International airports. The city center is a 17-mile, $55 taxi ride from O’Hare and a 12-mile, $45 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 flat and walkable, but “L” trains, buses, and taxis will also get you anywhere you want to go.

Public transportation is also more reliable as of late with taxis in the city sometimes scarce. 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 Ventra fare card to ride the train, but buses also take cash. Fare cards can be purchased at vending machines at all “L” station stops and other retail locations and digitally via the Ventra Card app.

- Spend time along the Chicago River. Start with a 90-minute Chicago Architecture Foundation Center River Cruise with Chicago’s First Lady; it is led by experienced docents who provide a strong foundation for your visit. You’ll discover works by visionary architects like Harry Weese and remarkable new buildings, including the 101-story, Jeanne Gang–designed St. Regis Chicago skyscraper, as well as the city’s fascinating history and culture. River cruises also offer a bird’s-eye view of the buzzy Riverwalk scene and ambient restaurants like Pizzeria Portofino. You’ll wish you had a boat of your own to zip around in and guess what, you can with Chicago Electric Boat Company, which rents everything from easy-to-drive retro electric boats, cycle boats, and pontoon boats to privately chartered yachts.

- Take your pick of incredible museums, including three of the city’s best on the lakefront’s Museum Campus: the Shedd Aquarium, Adler Planetarium, and the Field Museum, the last of which has an exceptional permanent exhibit on ancient Egypt. There are also the little-known gems, like the National Museum of Mexican Art and the American Writers Museum. Families with young children will have an especially good time at the Peggy Notebaert Nature Museum, which has a 2,700-square-foot butterfly haven and is set in the gardens of Lincoln Park, near the free Lincoln Park Zoo. The Museum of Science and Industry is also endlessly fascinating for kids of all ages. Housed in the original Palace of Fine Arts from the 1893 World’s Colombian Exhibition, the museum is a magnificent space with exhibits that include a high-tech Science Storms plus an entire U-505 submarine, the only German submarine in the United States.

- If you’re visiting in summer, get out on Lake Michigan for an entirely different view of the city, one that leaves you gob-smacked with its bright blue, ocean-like vibes. Hit North Avenue Beach for the volleyball scene and a dip in the water, rent a Divvy bike and ride along the lakefront path, or try out any number of boat tour options from Navy Pier.

- Take in Chicago’s rich and varied art scene. Colorful street murals and local galleries populate Wicker Park, while formal museums like the Museum of Contemporary Art Chicago and the extensive Art Institute of Chicago showcase impressive, well-curated collections. Next door to the Art Institute, stroll through Millennium Park for a fine introduction to friendly, proud Chicago. Take in the public art and fountains, the much-photographed Bean, the gardens, and even beyond to explore Grant Park.

- 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—all provide a strong taste of local culture. After the game, grab a beer at one of Wrigleyville’s many iconic bars, like Guthries Tavern, or snag a seat in the chic bar across the street inside the modern Hotel Zachary.

- Chicago has its share of super towers and seeing the view from the top is stunning. The John Hancock’s 360 Chicago Observation Deck on the 94th floor has the wild “Tilt” experience with downward facing views. Go even higher at Skydeck Chicago on the 103rd floor of the Willis Tower, where you can also step out onto the glass-box Ledge.

- Beyond deep-dish pizza and Chicago-style hot dogs, the city is home to some of the best steakhouses in the country, including Steak 48 with its fancy glass-enclosed booths and RPM Steak, as well as gastropubs and up-and-coming artisan butcher shops, like Lardon.

- Zero in on the best neighborhoods for your favorite culinary fare and you’ll understand why many people visit Chicago just to eat. Fill up on fresh Mexican food in Pilsen, try rolled ice cream and bubble tea in Chinatown, and indulge at Little Ukraine’s famous bakeries. Want a little bit of everything? Design your own foodie crawl in Fulton Market, dominated by some of the city’s best restaurants. Find Au Cheval for amazing burgers, the pretty rooftop at Aba, and Time Out Market Chicago, a food hall of stalls representing Chicago’s highest-rated local restaurants.

- Splurge-worthy tasting menu restaurants are all the rage for serious foodies, and you’ll find some of the best in the country in Chicago. Grant Achatz’s famed Alinea, one of the top molecular gastronomy restaurants in the world, and themed Next should be at the top of the list, as should buzzy newcomers that include art-forward Esmé and Filipino-inspired Kasama.

- If you’re a fan of Top Chef, you’ll find several winning chefs and their outposts here, including Joe Flamm’s Italian Croatian Rose Mary, Stephanie Izard’s Girl and the Goat and fun Duck Duck Goat, and Rick Bayless’s Xoco and Topolobampo.

- Cocktailing is an event unto itself in Chicago. When the weather is right, make your way to any number of fabulous rooftop lounges. Favorites include Cindy’s overlooking Millennium Park and the lake, Pendry Chicago’s Château Carbide for French atmosphere, Peninsula Chicago’s Shanghai Terrace (where you can also dine on some of the best Chinese food in the city), Devereaux, and the new Bar Avec decked out in greenery and coastal Spanish flair. If it’s the sultry indoors you’re seeking, don’t miss the scene and complex concoctions at the Violet Hour, artfully made cocktails at José Andrés’s Pigtail, and the playful tiki bar–themed Three Dots and a Dash.

- Chicago hosts some excellent outdoor events and multi-stage summer music festivals, including the Lollapalooza, Riot Fest, and Pitchfork Music Festival. There’s also the Pride Parade, the world’s largest free blues festival, and Taste of Chicago, an event that draws more than 3.5 million people to sample from 70-plus food vendors. Fall brings Chicago Gourmet, hosted by Bon Appétit; 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.

- It may not be New York, but Chicago’s performing arts scene holds court with iconic theater houses, like the Steppenwolf Theatre, Lyric Opera of Chicago, and Goodman Theatre. Broadway-bound plays have made their world premieres here; you may be able to catch one at the Chicago Shakespeare Theater and James M. Nederlander Theatre. You can also check out something funny at the world’s premier comedy club and a first stop for some of the best comedians of all time, Chicago’s Second City.

- Chicago has more than a few intimate concert halls that are definitely worth planning a trip around. Try to nab tickets to a show at the Chicago Theatre, Aragon Ballroom, and Thalia Hall, for starters. You might also be able to time a summer visit with a free outdoor concert at the modern Jay Pritzker Pavilion.

- Though the nickname “Windy City” initially referred to Chicago’s bloviating politicians, winters in the Midwest are no joke and the wind in Chicago is strong. If you plan to visit anytime between December and late March, bundle up and aim for a majority of indoor activities, which can include a Chicago Blackhawks hockey game, a concert at the Chicago Theatre, and dinning on Randolph Street, aka Chicago’s “Restaurant Row.”

- 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. Check out the South Side, where you’ll find Hyde Park with its charming Sophy Hyde Park hotel and chef Erick William’s Virtue Restaurant, the DuSable Museum of African American History, and the future site of the Obama Presidential Center.