Chicago, the “Windy City,” is a world-class destination known for its stunning skyline, bold architecture, and vibrant food scene. Whether you are visiting for the world-famous deep-dish pizza or the scenic lakefront, here is your guide for a Chicago vacation in 2025.

🏛️ Top Attractions & Landmarks

• Millennium Park & Cloud Gate: No trip is complete without a photo at “The Bean” (Cloud Gate). In 2025, Millennium Park remains the city’s cultural heart, hosting free concerts and art installations.

• The Architecture River Tour: Highly recommended by almost every traveler, this boat tour offers the best views of Chicago’s historic skyscrapers and explains the city’s unique rebuilding history after the Great Fire.

• Willis Tower (Skydeck) & 360 Chicago: For the best views, head to the Skydeck to step onto “The Ledge” (a glass balcony 103 floors up) or visit 360 Chicago at the 875 N Michigan building for the “Tilt” experience.

• The Art Institute of Chicago: One of the oldest and largest art museums in the world, home to iconic works like Grant Wood’s American Gothic and Georges Seurat’s A Sunday on La Grande Jatte.

• Navy Pier: A classic tourist hub with a giant Ferris wheel, dining, and boat tours. It’s particularly great for families and summer fireworks.

🍕 The Food Scene

Chicago is a serious food town. Make sure to try these staples:

• Deep-Dish Pizza: Iconic spots include Lou Malnati’s, Giordano’s, and Pequod’s (known for its caramelized crust).

• Chicago-Style Hot Dog: Remember—no ketchup! It should be “dragged through the garden” with mustard, onions, relish, pickles, peppers, and celery salt.

• Italian Beef: Made famous globally by the show The Bear, head to Mr. Beef or Al’s #1 Italian Beef for a “dipped” sandwich.

🚶 Neighborhoods to Explore

• The Loop: The central business district, perfect for architecture and the theater district.

• Wicker Park & Bucktown: The “cool” neighborhoods filled with indie boutiques, record stores, and trendy bars.

• Lincoln Park: Home to a free zoo, beautiful gardens, and the scenic Lakefront Trail.

• River North: The go-to spot for high-end dining and a vibrant nightlife scene.

💡 Travel Tips for 2025

• Transportation: Chicago has an excellent public transit system (the “L” trains). You don’t need a car if you’re staying near the city center. Use the Ventra app for easy fare payment.

• Timing: Summer (June–August) is beautiful but crowded and humid. Fall (September–October) is arguably the best time to visit for mild weather and changing leaves.

• Lakefront Trail: If the weather is nice, rent a Divvy bike and ride along Lake Michigan. It offers incredible skyline views without the downtown crowds.