Chicago Bike Lane Map

If you’re planning to explore Chicago on two wheels, you’re in for a treat. The city’s bike-friendly infrastructure is second to none, with more than 200 miles of on-street protected bike lanes and off-street trails. But Chicago is more than just a cyclist’s paradise. It’s a city of contrasts, where towering skyscrapers rub shoulders with serene parks, and ethnic enclaves coexist with hipster neighborhoods. In this comprehensive travel guide, we’ll show you the best of what Chicago has to offer, from top attractions to hidden gems, food scene to outdoor adventures, historical landmarks to family-friendly activities, off-the-beaten-path experiences to natural wonders, vibrant nightlife to local markets, beaches and mountains to cultural immersion, art and music scene to walking tours, architectural marvels to historical sites, biking routes to wellness retreats, and adventure sports.

Top Attractions

Chicago is home to some of the most iconic landmarks in the world, such as the Willis Tower (formerly known as Sears Tower), the John Hancock Center, and the Navy Pier. But the city also boasts a wealth of cultural and artistic attractions, such as the Art Institute of Chicago, the Museum of Contemporary Art, and the Chicago Symphony Orchestra. If you’re a sports fan, don’t miss the chance to catch a game at Wrigley Field (home of the Chicago Cubs) or the United Center (home of the Chicago Bulls and Blackhawks).

Hidden Gems

Despite its fame, Chicago still has some secrets up its sleeve. For example, have you heard of the Garfield Park Conservatory, a stunning botanical garden that spans six acres and features more than 2,000 species of plants? Or how about the Money Museum, where you can see millions of dollars in cash and learn about the history of money? And if you’re a fan of literature, don’t miss the chance to visit the American Writers Museum, which celebrates the legacy of American writers from all genres and periods.

Food Scene

Chicago is a foodie’s paradise, with a diverse and dynamic culinary scene that reflects the city’s ethnic and cultural diversity. From deep-dish pizza to hot dogs, from Italian beef sandwiches to Polish sausages, from Korean barbecue to Mexican street food, from Michelin-starred restaurants to hole-in-the-wall joints, Chicago has something to satisfy every taste and budget. Be sure to try the local specialties, such as the Chicago-style pizza (with a thick crust, lots of cheese, and toppings under the sauce), the Chicago-style hot dog (with mustard, relish, onions, tomatoes, pickles, and celery salt), and the Italian beef sandwich (with thinly sliced roast beef, gravy, and giardiniera).

Budget-Friendly Tips

Chicago can be an expensive city, but there are ways to save money without sacrificing fun. For example, many of the museums have free admission days (usually on Tuesdays or Thursdays), and some have suggested donations instead of fixed prices. You can also take advantage of the city’s public transportation system, which is affordable and efficient. And if you’re looking for cheap eats, check out the food trucks, the farmers’ markets, and the neighborhood delis and bakeries.

Outdoor Adventures

Chicago may be a big city, but it also has plenty of green spaces and outdoor activities. For example, you can bike along the Lakefront Trail, which offers stunning views of Lake Michigan and the skyline. You can also paddle along the Chicago River, which meanders through the heart of the city and offers a unique perspective on the architecture. And if you’re in the mood for some beach time, head to Oak Street Beach or North Avenue Beach, which are both popular spots for swimming, sunbathing, and people-watching.

Historical Landmarks

Chicago has a rich history that spans centuries, from the Native American tribes that first inhabited the area to the immigrants who built the city to the modern-day innovators who continue to shape the future. Some of the most significant historical landmarks include the Chicago Water Tower (one of the few buildings that survived the Great Chicago Fire of 1871), the Pullman National Monument (a tribute to the company town that was once a model for industrial communities), and the Robie House (a masterpiece of Frank Lloyd Wright’s Prairie School of Architecture).

Family-Friendly Activities

Chicago is a great destination for families, with plenty of kid-friendly attractions and activities. Some of the most popular options include the Lincoln Park Zoo (which is free and open year-round), the Shedd Aquarium (which has more than 32,000 animals and 1,500 species), and the Museum of Science and Industry (which features interactive exhibits and live demonstrations). You can also take a family bike tour, go on a riverboat cruise, or attend a children’s theater performance.

Off-the-Beaten-Path Experiences

If you’re looking for something a little more unusual, Chicago has plenty of off-the-beaten-path experiences to offer. For example, you can take a tour of the Pedway, an underground network of tunnels and corridors that connects many of the downtown buildings. You can also visit the International Museum of Surgical Science, which showcases the history of medicine and surgery through artifacts, exhibits, and interactive displays. And if you’re feeling adventurous, you can try the Escape Game Chicago, a real-life puzzle game where you have to solve clues and escape from a themed room.

Natural Wonders

Chicago may be a city, but it also has some natural wonders that are worth exploring. For example, you can visit the Morton Arboretum, which has more than 4,000 kinds of trees and shrubs on 1,700 acres of land. You can also take a trip to the Indiana Dunes National Park, which has 15 miles of beaches and more than 350 species of birds. And if you’re up for a longer drive, you can visit the Starved Rock State Park, which has 18 canyons and 13 miles of trails.

Vibrant Nightlife

Chicago is a city that never sleeps, with a vibrant nightlife that caters to all tastes and moods. Whether you’re in the mood for a cozy jazz club, a trendy rooftop bar, a divey dive bar, or a pulsing dance club, Chicago has it all. Some of the most popular nightlife destinations include the Green Mill Cocktail Lounge (which has been around since 1907 and was a favorite of Al Capone), the Signature Lounge at the 96th (which offers panoramic views of the city), the Hideout (which features live music and local beers), and the Smart Bar (which is known for its techno and house music).

Local Markets

If you’re a fan of shopping and local products, Chicago has plenty of markets and fairs to explore. Some of the most popular options include the Maxwell Street Market (which has been around since 1912 and features street food, antiques, and clothing), the Chicago French Market (which offers gourmet food and artisanal products), and the Randolph Street Market (which has vintage and handmade items, as well as food and drinks). You can also check out the farmers’ markets, which are held in various neighborhoods throughout the city.

Beaches and Mountains

Chicago may not have mountains, but it does have some impressive sand dunes and bluffs along the shore of Lake Michigan. Some of the best beaches include the aforementioned Oak Street Beach and North Avenue Beach, as well as Montrose Beach and 12th Street Beach. You can also visit the Indiana Dunes, which are about an hour’s drive from the city and offer hiking, biking, and swimming opportunities. And if you’re willing to travel a little farther, you can explore the rolling hills and lush forests of the Shawnee National Forest, which is about six hours’ drive from Chicago.

Cultural Immersion

Chicago is a melting pot of cultures and traditions, and there are many ways to immerse yourself in this diversity. For example, you can visit the National Museum of Mexican Art, which showcases the art and culture of Mexico and the Mexican-American community. You can also attend the Chinatown Summer Fair, which celebrates Chinese culture with food, music, and dance. And if you’re interested in African-American history and culture, you can visit the DuSable Museum of African American History, which has exhibits and programs that explore the contributions of African Americans to the arts, sciences, and society.

Art and Music Scene

Chicago has a vibrant art and music scene that is constantly evolving and expanding. Some of the most notable venues and events include the Art on theMART (which projects large-scale art installations on the façade of the Merchandise Mart), the Chicago Blues Festival (which showcases the best blues musicians from around the world), the Pitchfork Music Festival (which features indie and alternative bands), and the Lollapalooza Music Festival (which is one of the biggest music festivals in the country). You can also visit the Museum of Contemporary Photography, the Chicago Cultural Center, and the Music Box Theatre, which are all dedicated to showcasing the best in contemporary art and music.