Ultimate 12-Day Chicago Adventure Itinerary

Immerse yourself in art at the world-renowned Art Institute of Chicago. Before your visit, grab a quick bite at About Last Knife.

After the museum, enjoy a relaxing lunch cruise on the Chicago River with entertainment and stunning skyline views. Dine at Adamus Lounge for a sophisticated atmosphere.

Spend your evening at the vibrant Millennium Park, where you can witness the famous Cloud Gate sculpture, also known as "The Bean." For dinner, head to Venteux Brasserie, Cafe & Oyster Bar for a taste of Paris in Chicago.

Begin your day with a visit to the charming Lincoln Park & Zoo. Enjoy breakfast at New Line Tavern before exploring the exhibits.

Have a picnic lunch in the picturesque Grant Park, then take a guided tour of the historic Wrigley Field, home of the Chicago Cubs. After the tour, grab a drink at First Draft.

Dine at City Social and enjoy panoramic views of the city. End the night with a relaxing walk around the serene Wrigley Building and Tribune Tower.

Start your day with a visit to the interactive Museum of Science and Industry. Grab a quick breakfast at Doc B's Restaurant (River North) before diving into the exhibits.

After the museum, head to the nearby Shedd Aquarium for a fascinating underwater journey. Enjoy a seafood lunch at 320 River Bar with views of the Chicago River.

Relax and unwind at Reviver with a cocktail before heading to Adler Planetarium for an evening of stargazing and celestial exploration. For dinner, indulge in the flavors of Spectrum Bar & Grill.

Explore the architectural wonders of the Marina City and the Rookery Building. For breakfast, enjoy the ambiance at O'Callaghan's.

Have a hearty lunch at 312 Chicago, then take a guided tour of the United Center, home to the Chicago Bulls and Blackhawks, to learn about the city's sports history.

Dine at Staytion Market & Bar and savor their diverse menu. End the night with a visit to the Palmer House Hilton, one of the city's most iconic hotels, for a drink at their historic bar.

Spend your morning exploring the upscale shops and boutiques along The Magnificent Mile. Fuel up with a delicious breakfast at Elephant & Castle.

Enjoy a leisurely lunch at Mother Hubbard's Sports Pub and then continue your shopping spree. Take a break at the Water Tower Place and admire the historic Chicago Water Tower.

For dinner, indulge in the flavors of Cherry Circle Room and then catch a live performance at a nearby jazz club or blues bar to experience the soul of Chicago's music scene.

Start your day with a visit to the serene Chicago Cultural Center, where you can admire the stunning architecture and art exhibitions. Enjoy a light breakfast at Long Room Chicago.

Afterward, pamper yourself with a spa treatment at a luxury hotel like the Palmer House Hilton. For lunch, head to Shamrock Club for a casual Irish dining experience.

Spend your evening at a comedy club or catch a Broadway show at one of Chicago's renowned theaters. Dine at About Last Knife for a memorable meal to cap off the day.

Embark on a day trip to Milwaukee, just a short drive from Chicago. Explore the city's breweries, visit the Harley-Davidson Museum, and enjoy a traditional Wisconsin lunch at a local favorite spot.

Take a stroll along the scenic Lake Michigan waterfront and visit the Milwaukee Art Museum. Before heading back to Chicago, indulge in some cheese and beer tastings to experience the best of Wisconsin.

Return to Chicago and relax with a dinner at Staytion Market & Bar, reminiscing about your day trip and planning for the remaining days of your Chicago adventure.

Begin with a guided architectural tour of the city, exploring famous landmarks and hidden gems. Grab a quick breakfast at Adamus Lounge before the tour.

After the tour, enjoy a sumptuous lunch at Venteux Brasserie, Cafe & Oyster Bar. Then, take a relaxing river cruise to admire the city's skyline from a different perspective.

Dine at Staytion Market & Bar and enjoy their diverse menu. End the night with a visit to the Frederick C. Robie House, a masterpiece of the Prairie School architectural style.

Start your day with a visit to the Field Museum, where you can explore natural history and cultural exhibits. Enjoy breakfast at First Draft before your museum visit.

After the museum, have a casual lunch at Timothy O'Toole's Pub Chicago. Then, head to the Soldier Field for a guided tour and learn about the stadium's rich history.

For dinner, try the innovative cuisine at Reviver. Cap off the night with a live game or event at the United Center, immersing yourself in the excitement of Chicago sports and entertainment.

Enjoy a morning run or walk in Grant Park, taking in the fresh air and greenery. Refuel with a healthy breakfast at Doc B's Restaurant (River North).

Spend your afternoon at the Maggie Daley Park, where you can engage in various recreational activities. For lunch, visit 320 River Bar and enjoy their riverfront dining.

As the sun sets, head to the Skydeck Chicago at Willis Tower (Sears Tower) to witness the breathtaking panoramic views of the city. Dine at City Social and reminisce about your Chicago journey.

Enjoy a final breakfast at Staytion Market & Bar, savoring the flavors of Chicago one last time. Take a morning walk along the Chicago River to bid farewell to the city's iconic waterway.

Spend your last hours in Chicago at Navy Pier, exploring the attractions, shops, and entertainment. Have a memorable lunch at 312 Chicago with views of the pier and the lake.

Reflect on your Chicago journey over a farewell dinner at Staytion Market & Bar, where you can enjoy a variety of cuisines. As the night falls, take a final stroll through the city, cherishing the memories you've made.