Things to Do in Chicago, United States of America

Chicago, the 'Windy City,' stands as America's third-largest metropolis and a stunning example of architectural innovation and cultural diversity. Situated on the shores of Lake Michigan, this vibrant city seamlessly blends world-class museums, groundbreaking architecture, and a legendary food scene that extends far beyond its famous deep-dish pizza. From the towering skyscrapers of the Loop to the sprawling lakefront parks, Chicago offers an urban experience that rivals any major city worldwide. The city's rich history of jazz, blues, and architectural pioneering creates a unique cultural landscape where visitors can explore Frank Lloyd Wright's influence, catch a Cubs game at historic Wrigley Field, or stroll through Millennium Park to see the iconic Cloud Gate sculpture. Chicago's neighborhoods each tell their own story, from the trendy boutiques of Wicker Park to the museum campus along the lakefront, making it a destination that rewards both planned itineraries and spontaneous exploration.

Top Things to Do in Chicago

Architecture River Cruise

Glide along the Chicago River while expert guides explain the city's world-renowned architectural history, from the Great Fire's aftermath to modern skyscrapers. This unique perspective showcases buildings by legendary architects like Louis Sullivan, Frank Lloyd Wright, and Mies van der Rohe. The tour provides unparalleled views and photography opportunities of Chicago's stunning skyline.

Booking Tip: Book tours 2-3 days in advance, especially during summer months. Prices range from $35-50 per person, with sunset tours commanding premium rates. Choose operators with certified architectural guides and covered boats for weather protection.

Food Walking Tour

Explore Chicago's incredible culinary landscape beyond deep-dish pizza, sampling everything from Italian beef sandwiches to craft cocktails in historic neighborhoods. These guided tours typically visit 4-6 local establishments while sharing stories about the city's food culture and immigrant influences. You'll discover hidden gems and learn about Chicago's role in American food innovation.

Booking Tip: Tours cost $60-90 per person and last 3-4 hours, so come hungry and wear comfortable shoes. Book weekend tours well in advance, and look for operators that include diverse neighborhoods like Little Italy or Chinatown for authentic experiences.

Millennium Park and Art Institute Visit

Start at Millennium Park to see the famous Cloud Gate sculpture and Crown Fountain, then explore one of America's premier art museums housing works by Monet, Picasso, and Grant Wood. The Art Institute's collection spans thousands of years and includes the world's largest collection of Impressionist paintings. The park itself hosts free concerts and events throughout the year.

Booking Tip: Art Institute admission is $30 for adults, with discounts for students and seniors. Visit weekday mornings for smaller crowds, and consider combination tickets if planning multiple museum visits. The park is always free to explore.

Historic Chicago Neighborhoods Tour

Discover the distinct character of Chicago's diverse neighborhoods, from the Victorian mansions of Old Town to the vibrant murals of Pilsen. These tours showcase local history, architecture, and culture while visiting neighborhood landmarks, local shops, and community gathering spots. Each area tells a unique story of Chicago's immigrant heritage and urban development.

Booking Tip: Walking tours cost $25-40 per person and typically last 2-3 hours. Choose tours that focus on 2-3 neighborhoods maximum for a thorough experience. Some operators offer bike tours as an alternative for covering more ground.

Chicago Sports Experience

Immerse yourself in Chicago's passionate sports culture by catching a Cubs game at historic Wrigley Field, a White Sox game at Guaranteed Rate Field, or touring these iconic stadiums. The experience extends beyond the game itself, with pre-game festivities in surrounding neighborhoods and the chance to understand Chicago's deep sports traditions. Stadium tours offer behind-the-scenes access when games aren't scheduled.

Booking Tip: Game tickets range from $15-200+ depending on seating and opponent. Book stadium tours ($20-30) during off-season for best availability. Consider bleacher seats at Wrigley for the authentic fan experience, and arrive early to explore the surrounding Wrigleyville area.

Getting There

Chicago is easily accessible through two major airports: O'Hare International Airport (ORD), one of the world's busiest airports located 17 miles northwest of downtown, and Midway International Airport (MDW), smaller but often more convenient, situated 10 miles southwest of the city center. Both airports connect to downtown via the efficient CTA 'L' train system - the Blue Line from O'Hare and Orange Line from Midway, each costing just $5 and taking 45-60 minutes. Chicago also serves as a major Amtrak hub at Union Station, with routes connecting to cities across the Midwest and beyond, while several interstate highways (I-90, I-94, I-55) make driving from other Midwest cities straightforward.

Getting Around

Chicago's comprehensive public transportation system, operated by the Chicago Transit Authority (CTA), includes buses and the famous 'L' train system that efficiently connects all major neighborhoods and attractions. A 1-day CTA pass costs $20 and provides unlimited rides on both buses and trains, making it the most economical way to explore the city. The Loop area downtown is highly walkable, and the lakefront trail offers 18 miles of scenic paths for walking or biking. Ride-sharing services like Uber and Lyft are widely available, while traditional taxis can be hailed downtown, though public transit is often faster during rush hours due to dedicated train tracks.

Where to Stay

The Loop

River North

Magnificent Mile

Lincoln Park

Wicker Park

South Loop

Food & Dining

Chicago's food scene extends far beyond its famous deep-dish pizza, encompassing everything from Michelin-starred restaurants to iconic street food. The city is renowned for Italian beef sandwiches, Chicago-style hot dogs (never with ketchup!), and innovative fine dining establishments like Alinea and Girl & Goat. Neighborhoods like Little Italy, Chinatown, and Pilsen offer authentic ethnic cuisines, while the West Loop has emerged as a premier dining destination with celebrity chef restaurants and trendy gastropubs. Don't miss trying a Chicago mix (cheese and caramel popcorn), visiting a classic steakhouse, or exploring the city's thriving craft brewery scene in areas like Logan Square and Ravenswood.

When to Visit

The best time to visit Chicago is during late spring through early fall (May through October), when the weather is most pleasant and outdoor activities are in full swing. Summer months (June-August) offer the warmest weather and numerous festivals like Lollapalooza and the Chicago Air & Water Show, but also bring crowds and higher hotel prices. Fall (September-October) provides ideal conditions with comfortable temperatures, beautiful foliage, and fewer tourists, making it perfect for walking tours and outdoor exploration. Winter can be harsh with temperatures often below freezing and strong winds off Lake Michigan, but the city transforms into a winter wonderland with holiday markets, ice skating, and cozy indoor attractions at reduced prices.

Insider Tips

Take advantage of the Chicago CityPASS for significant savings if visiting multiple major attractions like the Art Institute, Skydeck, and Shedd Aquarium

Many of Chicago's best attractions along the lakefront are free, including Lincoln Park Zoo, beaches, and the 606 elevated trail - perfect for budget-conscious travelers

Avoid driving downtown during rush hours (7-9 AM and 4-7 PM) as traffic can be intense; the 'L' train system is much more reliable and faster during these times

Things to Do in Chicago