Ultimate 5-Day Chicago and Milwaukee Adventure Itinerary

Start your day with a breakfast at Lula Cafe, a neighborhood gem known for its farm-to-table dishes. Afterward, immerse yourself in art at the world-renowned Art Institute of Chicago with a fast-pass ticket, allowing you to explore the museum's extensive collection at your own pace.

Grab a quick bite at Xoco, Rick Bayless's casual Mexican eatery, before continuing to the Millennium Park. Take a selfie at the famous Cloud Gate (The Bean) and enjoy the park's other attractions. Then, visit the nearby Chicago Theatre for a guided tour experience.

Dine at Girl & the Goat, an award-winning restaurant offering a bold menu with global flavors. After dinner, experience the city's vibrant nightlife with a Chicago Prohibition Speakeasies Bus Tour or Walking Tour, learning about the city's history of bootlegging and speakeasies.

Enjoy a morning coffee and pastry at Little Goat Diner, a cozy spot with a menu designed by a Top Chef. Then, expand your mind at the Museum of Science and Industry with a ticket and audio guide (available in English), exploring the museum's fascinating exhibits.

Have a fun and interactive lunch at Eataly Chicago, an Italian marketplace with various dining options. Afterward, indulge your sweet tooth at the Museum of Ice Cream with an entry ticket, where you can enjoy whimsical and colorful exhibits.

For a unique and slightly spooky experience, join the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the city's darker history. After the tour, have a comforting dinner at Pequod's Pizza, known for its caramelized crust and hearty pies.

Start your day with a breakfast at Big Star, a vibrant spot serving up delicious tacos and whiskey. Afterward, take a leisurely Chicago Taste of Chinatown Food Walking Tour to sample a variety of flavors and learn about the neighborhood's rich cultural heritage.

Post-tour, continue your culinary journey with a visit to Skydeck Chicago at Willis Tower (Sears Tower), where you can step out onto The Ledge. Then, enjoy a late lunch at Smoque BBQ, a local favorite for its mouthwatering barbecue dishes.

Witness the city's skyline from a different perspective with a Chicago 360 Chicago Observation Deck Sip and View Ticket, allowing you to enjoy a drink while taking in the breathtaking views. For dinner, head to Cafe Ba-Ba-Reeba! for a lively and delicious Spanish meal.

Begin your day in Milwaukee with a hearty breakfast at , followed by a visit to the iconic Harley-Davidson Museum. Explore the history and culture of this legendary American motorcycle brand, and don't miss the chance to see some rare and vintage bikes.

For lunch, enjoy the laid-back atmosphere and delicious tacos at BelAir Cantina, a local favorite. Afterward, take a leisurely stroll through the beautiful Milwaukee Art Museum, known for its stunning architecture and impressive art collection.

Experience the vibrant nightlife of Milwaukee by exploring the city's craft beer scene. Visit some of the best local breweries, such as Lakefront Brewery, Third Space Brewing, and Good City Brewing, and enjoy a variety of unique and flavorful beers. End your evening with a delicious dinner at , where you can savor the flavors of the city.