The Windy City: 48 hours in Chicago

Welcome to a new Tour Travel & More adventure, where we explore one of the most fascinating and vibrant cities in the United States: Chicago. This metropolis, located on the shores of majestic Lake Michigan, is known for its iconic architecture, cultural heritage and famous Midwestern hospitality. On this 48-hour itinerary, we’ll take you on a tour of the highlights of the Windy City, allowing you to make the most of your time in this exciting city. Check out our private tours here! 

Day 1: Discovering Chicago’s Architecture and Culture


Start your first day in Chicago with breakfast at one of the cosy cafes in the Wicker Park neighbourhood. This quaint neighbourhood is full of bohemian charm and will give you a taste of local life. Once you’ve recharged your batteries, head into the heart of the city to explore its iconic architecture.

Our first stop is the famous Skydeck at the Willis Tower, formerly known as the Sears Tower. Take the high-speed lift up and enjoy panoramic views of Chicago from 103 stories up – photos from the “Ledge” are a must!


After touching the clouds on the Skydeck, walk to Millennium Park, where you’ll find the sculpture “Cloud Gate”, also known as “The Bean”. This piece of public art is a true emblem of the city and a great place to take pictures. Also, in summer, you can enjoy free concerts at the Jay Pritzker Pavilion.

For lunch, head to one of the local restaurants and try the famous Chicago-style pizza – you won’t regret it!


In the afternoon, we recommend an architectural boat tour on the Chicago River. This experience will allow you to admire the city’s iconic skyscrapers up close while learning about its architectural history. Expert tour guides will take you through the evolution of the city, from historic to modern Chicago.

After the boat tour, visit the Art Institute of Chicago, which houses an impressive collection of masterpieces from around the world. From the paintings of Grant Wood to the sculptures of Pablo Picasso, this museum has something for every art lover.

Day 2: Immerse yourself in Culture and Cuisine


Start your second day in Chicago with a visit to the Field Museum of Natural History. This museum is a treasure trove of science and natural history and offers an educational and entertaining experience for all ages – don’t miss the skeleton of Sue, the world’s largest and most complete Tyrannosaurus rex!

After the museum, take a stroll through the famous Chinatown neighbourhood, where you can enjoy authentic Asian cuisine and explore the local shops. Be sure to visit the Chinatown Gateway, an architectural masterpiece in itself.


For lunch, we suggest trying one of Chicago’s most iconic dishes: the Chicago-style hot dog. You can find them at food carts all over the city. Accompany it with some fries and a soft drink.


In the afternoon, explore the Logan Square neighbourhood, known for its arts scene and vibrant food scene. You can visit the Logan Square Cultural Center or simply stroll the streets and enjoy the murals and unique shops.

To end your visit to Chicago, catch a live show at one of the city’s renowned theatres, such as the Steppenwolf Theatre or the Goodman Theatre. Chicago is famous for its theatre scene and you don’t want to miss out on the opportunity to enjoy a quality production.

In just 48 hours, you’ve had the chance to experience the rich culture, stunning architecture and delicious food that Chicago has to offer. This city, with its mix of tradition and modernity, never ceases to amaze visitors. We hope you enjoyed your time in the Windy City and take away unforgettable memories of your trip with Tour Travel & More – until the next adventure!

Posted in North America, United States of America.