Jump To:
About this guide
Chicago, Illinois, has been the birthplace of iconic cultural movements, influential music genres like jazz and blues, and groundbreaking social and political change. Iconic neighborhoods like Bronzeville and Hyde Park highlight Chicago's history, heritage, and historic landmarks. The vibrant arts district celebrates Black culture while the culinary scene has become home to world-renowned cuisine. The streets flow with jazz and blues as museums stand on nearly every corner to celebrate the arts, sciences, and legacy of Chicago. From Black-owned businesses to community-beloved festivals, The Windy City shares all it has to offer with every kind of traveler.
- Best time to travel: June to August (peak season), November to March (off season), April to May and September to October (shoulder season)
- Time zone: Central Standard Time (CST)
- Currency: USD ($)
- Language: English
- Noteworthy: Expo Chicago (April), Sueños Music Festival (May), Corn Fest August), Taste of Chicago (September), Christkindlmarket Holiday Market (November-December)
- Best for: American History Buffs, Foodie Lovers, Art and Culture Festivals, Sports Fans
Get Away: Getting To And Around Chicago, Illinois
By Air
Chicago has one of the busiest airports in the world, O'Hare International Airport, which offers extensive domestic and international flights. Midway International Airport is another convenient option, primarily serving domestic routes. Both airports are well-connected to downtown Chicago via public transportation for a seamless itinerary.
By Car
Getting around Chicago by car can be more convenient, especially when planning excursions outside of the city center. While downtown traffic can be heavy, the city's well-marked streets and numerous parking options make driving manageable. Consider using a GPS or a rideshare app for more convenience and be extra mindful of parking fees in busy areas.
By Public Transit
Chicago’s public transit system, the CTA, offers efficient and affordable travel options. The extensive network of buses and trains, known as the "L," connects major attractions, neighborhoods, and both airports. Consider using a GPS or rideshare app for more convenience and be extra mindful of parking fees in busy areas.
Explore Chicago, Illinois On Foot
Neighborhoods like the Loop, River North, and the Magnificent Mile deserve to be explored on foot. The Windy City’s pedestrian-friendly streets and scenic lakefront paths make walking a memorable way to learn about the local culture. From iconic architecture to beloved parks to public art, Chicago’s atmosphere is worth experiencing in nearly every way possible.
Quick facts
Central Standard Time (CST)
USD ($)
English
Good For
American History Buffs
Foodie Lovers
Music, Arts, and Culture Festivals
Sports Fans
Keep in mind
- Expo Chicago (April)
- Sueños Music Festival (May)
- Corn Fest August)
- Taste of Chicago (September)
- Christkindlmarket Holiday Market (November-December)
Gourmet
Gourmet: Places To Eat In Chicago, Illinois
As the only James Beard award-winning spot in Chicago, Lula Cafe serves a farm-to-table menu full of seasonal dishes. This spot offers evolving brunch to dinner menus including breakfast sandwiches, pasta, and tagine dishes.
Known for creative cocktails and non-alcoholic mocktails, the queer- and Black-owned cocktail bar Nobody’s Darling brings the vibes, too. This James Beard-nominated bar serves drinks named after iconic Black figures and high-end spirits for every patron.
Tucked away in a greystone building in Little Village, Osito’s Tap offers inventive cocktails and mocktails like the coffee-mezcal slushy. This Latino neighborhood gem serves late-night bites like the Mexican Street Burger and Burnt Basque Cheesecake.
In Bridgeport, the Black-owned Koto Hibachi serves heaping portions of buttery fried rice topped with perfectly cooked shrimp, chicken, or lobster. Their maki rolls, like the shrimp tempura, make this a perfect casual dining spot for a quick lunch or dinner.
The Black and woman-owned speakeatery, 1308 Chicago, serves amazing drinks and Southern-inspired dishes. Tucked in a small courtyard on Goose Island, the menu includes blueberry butter cornbread and miso glazed roasted chicken.
Awarded World’s Best in Chicago, Bronzeville’s Black woman-owned Shawn Michelle's Homemade Ice Cream serves world-class ice cream and desserts. Flavors include honey-cinnamon graham cracker, Jamaican rum raisin, Barack Supreme, and more.
Play
Play: Things To Do In Chicago, Illinois
Take laughing seriously at Chicago’s Second City Comedy Show, renowned for the rise of beloved comedians and iconic improv theaters. As the cultural epicenter of live comedy, guests experience top-notch humor with a new generation of comedy legends.
Perched just off the shores of Lake Michigan, the Shedd Aquarium shares educational aquatic wonderland experiences that teach about protecting our blue planet. Visitors see beluga whales, otters, stingrays, and other marine life.
For an ultimate foodie adventure in historic River North, this Chicago Food Tour shares the city’s culinary roots. The delicious food samples include a Chicago-style hot dog, deep-dish pizza slice, and Italian beef sandwich.
Chicago has an amazing creative atmosphere and the Street Art and Aerosol Workshop dives into urban art guided by local artists. Guests unleash their creative side with spray paint techniques on a 50-foot wall and even take home a keepsake piece of the mural.
A fifth-generation South Side guide takes guests on a tour of Black History on the South Side of Chicago. Visit landmarks like Barack Obama’s and Muhammad Ali’s homes, local cultural murals, and other historical sites.
Escape the city for a relaxing afternoon or evening Chicago Skyline Tall Ship Sightseeing Cruise. Aboard the historic Windy, guests sail around Lake Michigan, take in the world-famous skyline, and experience a unique maritime perspective.
Learn the secrets to crafting the perfect Neapolitan pizza from an expert chef at this intimate pizza making class. Guests enjoy complimentary beer, wine, and appetizers at the Napolita Pizzeria and Wine Bar while connecting with other guests.
Housed in a beautifully restored 1902 River West factory, AIRE Ancient Baths Chicago offers the ultimate in luxury rejuvenation. This highly acclaimed spa features seven distinct thermal baths—paying homage to timeless Roman, Greek, and Ottoman rituals.
