The essential guide to visiting Chicago

Combining a big-city pedigree with Midwestern congeniality, Chicago often surprises visitors with its wide-ranging yet accessible amenities. Top chef restaurants, world-class museums, historic landmarks, and a verdant natural landscape unfold in a city that stretches into 77 diverse neighborhoods. 

Best times to visit Chicago

Spring:  Surround yourself with every shade of green during Chicago’s legendary Patrick’s Day celebration in March. The Chicago River starts off the festivities with a signature dyeing ceremony in the morning, followed by a weekend of parades downtown (Northwest and Southside), pub crawls, and Irish cultural events. From February to May, soak up the beauty of the season with a visit to the annual spring flower show at the historic Garfield Park Conservatory, one of the world’s largest gardens under glass. Or head to Hyde Park’s Osaka Garden to view cherry blossoms in late April through early May. In mid-April, take in movies from Latin America at the Chicago Latino Film Festival, the longest-running Latino film celebration in North America.

Summer: Chicago explodes with festivals, fairs, and waterside events during this beloved season. The Chicago Blues Festival, the largest free blues festival in the world, kicks things off in early June. On Lake Michigan, the Black Yacht Weekend makes waves with mid-month cruises and parties. The ultimate food fest, Taste of Chicago, serves up the city’s best bites in July, and the Chinatown Summer Fair offers Asian food, music, and dance performances on the last weekend in July. The Chicago Air and Water Show  hosts military jet squadrons and aerial and water performers in mid-August. And later in the month, the House Music Festival & Conference celebrates the percussive genre born in Chicago. 

Fall: Gorge on elevated dishes and wine that reflect the city’s diverse culinary scene at  Chicago Gourmet in late September. Explore over 200 antique vendors, art, décor, and jewelry while sampling food and live music during the last weekend in September at Randolph Street Market Festival, the nation's largest urban antiques market. Discover the back stories of hundreds of Chicago’s iconic skyscrapers and historic sites during Open House Chicago, a free architecture festival in mid-October. Close out the month with Day of the Dead celebrations at the National Museum of Mexican Art, and in early November, the two-day Xempasúchil event in the Little Village neighborhood.

Winter: Layer up for the chilly weather and sample hot mulled wine and roasted nuts at the authentic German Christmas market, Christkindlmarket Chicago, in December. Glide around the McCormick Tribune Ice Rinkwith the famous “The Bean” Cloud Gate sculpture as the backdrop. In January, score some of the best deals to eat at award-winning restaurants during Chicago Restaurant Week. In February, snag discounted tickets to musicals, dramas, and comedies during Chicago Theatre Week and taste the flavors of Black-owned eateries during Chicago Black Restaurant Week.

Key areas to explore in Chicago

Downtown: Many of Chicago’s famous landmarks and cultural sites fill the bustling heart of the city. Climb 105 stories in Willis Tower’s (formerly Sears Tower) Skydeck to gaze at the city’s spectacular skyline, and on a clear day, up to four neighboring states, too. For another angle, try the 360 Observation Deck, offeringpanoramic views and a tilted deck on the 94th floor of the John Hancock building. 

See the translucent beauty of the world’s largest Tiffany Dome at the Chicago Cultural Center and wander through the celebrated Theatre District, which includes the Palace of Versailles-inspired Cadillac Palace Theatre, the mosaic-covered Nederland Theatre, and the Auditorium Theatre, a National Historic Landmark known for its perfect acoustics.

The water: “Chicago is a different waterfront city compared to any other in the world because our waterfront is a public park,” says Geoffrey Baer, TV host and producer of popular PBS shows about Chicago architecture and history. “Other cities have docks and parcels, and it’s not accessible to everyone. Here, we just go to the waterfront and enjoy it.”   

Stroll through any of Chicago’s 24 beaches that cradle the shores of Lake Michigan, including Oak Street Beach, which features downtown skyline views; Montrose Beach, which boasts a bird sanctuary; South Shore Beach, which has a golf course; and the historic South Shore Cultural Center, which hosted the Obama wedding in its grand, stucco-covered walls. Navy Pier runs 3,300 feet along the shoreline and offers attractions like the Centennial Wheel and free concerts. 

The Chicago River has 1.25 miles of aquatic attractions and vistas along the Chicago Riverwalk, and the Chicago Water Taxi floats through downtown and Chinatown.  Both waterways attract visitors and locals who enjoy water sports like kayaking, jet skiing, and stand-up paddleboarding. However, boat cruises are the most popular choice, with the iconic Chicago Architecture Center River Cruise aboard the First Lady to view the city’s standout architecture.

The museums: Globally recognized for its premium museums and cultural institutions, Chicago is home to over 60 museums that cover everything from art to science to money. The Chicago Museum Campus connects the city’s major museums in a 57-acre park along the lake that includes the Field Museum of Natural History, which houses Sue, the most complete T. Rex skeleton ever discovered. 

The campus also includes the saltwater world of sharks, belugas, and sea otters at the Shedd Aquarium and the Adler Planetarium, the first planetarium in the country.  One of the oldest and largest art museums in the U.S., the Art Institute of Chicago houses one of the largest collections of Impressionist art outside of France. A baby chick hatchery, a WWII submarine, and a coal mine are a few highlights at the Griffin Museum of Science and Industry.

The DuSable Black History Museum and Education Center spotlights Black history and culture across the diaspora like the richly detailed "Freedom: Origin and Journey" exhibit, which traces key periods of the African American experience and the Chicago Fed Money Museum focuses on currency and economics, hosting special exhibits like, "A Century of Route 66-Driving Culture and Commerce," which includes displays of early Federal Reserve notes.

The parks: One of Chicago’s nicknames is “city in a garden.” The city is blanketed with 8,800 acres of green space, making it one of the largest urban park systems in the country. Millennium Park is the most famous park, blending the natural allure of Lurie Garden and sprawling lawns with the striking artwork of Cloud Gate and Crown Fountain.

Lincoln Park is Chicago’s largest park, with more than 1,100 acres that include miles of the Lakefront Trail, the Peggy Notebaert Nature Museum, and the Lincoln Park Zoo, one of the last free zoos in the U.S.  A former elevated railway hosts the city’s newest and most unusual green space. The 606 winds seven feet above sidewalks and melds nature with art and innovative architecture. 

Chicago’s first national park covers the historic Pullman neighborhood on the far Southside of the city. Pullman Historical National Park spans 12 acres and preserves the history of one of the first planned communities in the U.S. The park includes the landmark 19th-century buildings of Hotel Florence, the National A. Phillip Randolph Pullman Porter Museum, Historic Pullman Workers Homes, and the Pullman Administration Clock Tower Building. These structures from the 1880s highlight landmark urban planning details, including some of the first buildings with indoor plumbing and steam heating.

“I recommend spending a day in Pullman. Get a tour from a park ranger, walk the neighborhood, and see former tenements,” says Natalie Y. Moore, a journalist and author of “The Southside: A Portrait of Chicago and American Segregation. “Today, Pullman is a vibrant community with an art gallery and tons of history. Stop by Lexington Betty Smokehouse for delicious BBQ.”

 As one of the city’s most expansive parks, Jackson Park includes an 18-hole golf course, the 63rd Street Beach,  and Osaka Japanese Garden. Jackson Park, which touches the Hyde Park and Woodlawn neighborhoods, is the former site of the World’s Columbian Exposition in 1893 , and currently, the location for the Obama Presidential Center. The center’s 19.3-acre campus unfolds within the park with a museum, an athletic center, a public plaza, gardens, a wetland walk, a library, an auditorium, and a playground. Designed to serve as a source of inspiration and connection, the facility has stirred Chicago pride and excitement. 

“Chicago has so many cultural experiences; this is the next jewel,” says Michael Strautmanis, chief corporate affairs officer for the Obama Foundation.  “This is the place that gave us the Obamas; now the world will understand why this is the home for hope.” Although the campus is elaborate, Strautmanis suggests a simple itinerary for first-time visitors. “The first thing they should do is enjoy the park.  Explore the lagoon, the great lawn, and the playground. Go to the Sky Room—it has amazing art and views you can’t get anywhere else. The good thing is that you don’t need a ticket for any of these.”

Where to stay

The Langham Chicago: Perched on the shore of the Chicago River and tucked inside a landmark Mies van der Rohe skyscraper, this elegant property is the essence of Chicago luxury. Floor-to-ceiling windows grant sublime views of the river and lake, and the American contemporary Travelle serves a sophisticated seasonal menu including a flavorful wild mushroom risotto. The hotel is just two blocks away from the Magnificent Mileshopping mecca.

The Gwen: Brimming with style and personality, this boutique hotel is named for pioneering Chicago sculptor Gwen Lux, whose art deco bas-relief sculptures adorn the building.  Noted for a lively rooftop lounge that hosts live music in the summer and a curling rink in the winter, The Gwen exudes vintage chic and provides inventive dining, including a champagne-infused tea party, in the heart of downtown Chicago.

Sophy Hyde Park: A sleek ode to the neighboring University of Chicago and the surrounding community, this boutique property is filled with art, including a life-sized painting of Barack Obama in the lobby and nuclear fission blueprints above the bar as an ode to Chicago Nobel Prize physicist Enrico Fermi. Each room boasts a record player with classic jazz and blues vinyl, and the dynamic Mesler Kitchen buzzes with locals and visitors enjoying hearty food like the 5th Ward prime beef burger, topped with sauteed onions and sharp cheddar. The hotel sits in the middle of Hyde Park’s charming commercial district and is just six minutes away from the Obama Presidential Center.

Taste of Chicago

Restaurants and eateries line the streets of this Midwest metropolis, but the trendy  West Loop Restaurant Row is a timely place to start. Top Chef Stephanie Izard’s hot spot, Girl & The Goat, draws lines for her small-plate menu of bold flavors, like the roasted pig face, while fellow top chef Sarah Gruenberg dishes up Italian delicacies like the colossal ragu alla Napoletana, with stylish vibes at Monteverde. For more casual fare, drop by J.P. Graziano Grocery, an iconic sandwich shop that has been crafting delectable handhelds like the signature Mr. G, bursting with salami, prosciutto, truffles, and artichokes, since 1937. 

Venture to the Chatham neighborhood to taste the sweet and tangy flavor of authentic Southside BBQ at the James Beard-recognized Lem’s Bar-B-Q, and prepare to stand in a line down the block. Try the popular rib tips with fries and a slice of bread to soak up the sauce.  

In Hyde Park, Chef Erick Williams’ award-winning Virtue serves elegant Southern food, such as blackened fish with stone-ground grits and crabmeat étoufée. And when in Chicago, it’s a requirement to try deep-dish pizza, so go to Pizzeria Due for the old-school classic: cheesy deep-dish pizza with a handmade, flaky crust baked in a cast-iron pan.

Getting around Chicago

By public transportation: For easy travel to most places in the city, hop on the CTA, the city’s extensive system of trains and buses. Check out the trip planner to map out how to reach your desired destination.

By car:  Traffic and parking can be challenging downtown and in nearby Northside neighborhoods. The Spothero parking app is a handy resource. Rideshares and taxis are easily accessible.

Here’s what you should know

Crime: Despite the media narrative, Chicago experiences a lower per capita violent crime rate than many other major cities, and it has been declining over the last decade. Chicagoans are friendly and can be helpful when navigating the city. As with any place with you travel, be aware of your surroundings and keep an eye on your belongings.

Weather:  The notorious Chicago winter is harsh indeed, but the key to surviving the city’s temperamental weather is to dress in layers from December to April.

How to visit Chicago sustainably

Transportation: Chicago is a walkable, scenic city. Take public transportation or rent a bike or scooter to lower your carbon footprint.  

Shopping: Bring a reusable shopping bag and visit vintage and second-hand shops like Knee Deep Vintage in Pilsen, Lost Eras in Rogers Park, and The Brown Elephant shops in Lakeview and Andersonville.

Dining: Visit restaurants with sustainable food practices, such as renewable energy, composting, and recyclable containers. Alice and Friends Vegan Kitchen in Edgewater, Lula Cafe in Logan Square, and Antique Taco in Wicker Park are among the top choices.