Welcome to Chicago

Chicago, Illinois, known as the Windy City, is a bustling metropolis on the shores of Lake Michigan. Famous for its bold architecture, Chicago is home to iconic skyscrapers like the Willis Tower and the neo-Gothic Tribune Tower. The city is a cultural hub, offering world-class museums, vibrant neighborhoods, and a thriving arts scene. Whether you're a foodie, history buff, or architecture enthusiast, Chicago has something for everyone.

Before you embark on your journey, consider booking your flights through Trip.com for the best deals. Once you arrive, you'll find that Chicago's public transportation system, the 'L' train, is an efficient way to explore the city.

For accommodations, Chicago offers a range of options from luxury hotels to cozy vacation rentals. Check out VRBO or Hotels.com to find the perfect place to stay.

Day 1: Arrival and Evening Exploration

Arrive in Chicago in the afternoon and settle into your accommodation. After freshening up, head to the Magnificent Mile, a bustling shopping district with a mix of high-end boutiques and popular retailers. Stroll along the avenue and soak in the vibrant atmosphere.

For dinner, indulge in Chicago's famous deep-dish pizza at Lou Malnati's or Giordano's. Both offer a quintessential Chicago dining experience with their rich, cheesy pies.

After dinner, take a leisurely walk to Millennium Park to see the iconic Cloud Gate sculpture, affectionately known as "The Bean." The park is beautifully lit at night, providing a serene backdrop for an evening stroll.

Day 2: Architecture and Culture

Start your morning with a visit to the Art Institute of Chicago, home to an impressive collection of artworks from around the world. Consider booking the Art Institute of Chicago Skip-the-Line Exclusive Guided Tour for an in-depth experience.

In the afternoon, embark on a Chicago River 90-Minute Architecture Tour to admire the city's stunning skyline from the water. This tour offers a unique perspective on Chicago's architectural marvels.

For dinner, head to the West Loop, known for its vibrant dining scene. Try Girl & the Goat for innovative dishes or Au Cheval for one of the best burgers in the city.

End your day with a visit to the 360 CHICAGO Observation Deck for breathtaking views of the city skyline and Lake Michigan. You can book your 360 CHICAGO Observation Deck Admission in advance to skip the lines.

Day 3: History and Departure

On your final morning, explore the historic neighborhoods of Chicago. Consider joining the Chicago Crime and Mob Bus Tour to delve into the city's notorious past and learn about its infamous gangsters.

For lunch, try Portillo's for a classic Chicago-style hot dog or Italian beef sandwich. It's a local favorite and a must-try for any visitor.

Before heading to the airport, take a leisurely walk along the Chicago Riverwalk, a scenic promenade offering beautiful views of the city. It's the perfect way to end your Chicago adventure.

As you prepare to depart, consider booking your return flight through Trip.com for a seamless travel experience.

Summary

In just three days, you've experienced the best of Chicago, from its iconic architecture and rich history to its diverse culinary scene. Whether you're admiring the skyline from a river cruise or savoring a deep-dish pizza, the Windy City offers unforgettable experiences at every turn. We hope this itinerary has inspired you to explore all that Chicago has to offer.