Ultimate 21-Day Chicago Exploration Itinerary

Spend your morning exploring the Art Institute of Chicago, home to a world-class collection of art.

For lunch, try the innovative cuisine at Alinea. Afterward, visit the Field Museum to learn about natural history and anthropology.

Enjoy a relaxing evening with a gourmet dinner cruise on Lake Michigan with Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise.

Start your day with a visit to Grant Park and take a stroll in the green space.

For lunch, enjoy the vibrant atmosphere at Big Star in Wicker Park. Afterward, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for stunning views.

In the evening, experience the city from a different perspective with the Skydeck Chicago at Willis Tower (Sears Tower) and its famous Ledge. Then, have a delicious dinner at Girl & the Goat.

Spend the morning exploring the unique shops and street art in Wicker Park and Bucktown.

For a late lunch, try the gourmet sandwiches at Xoco by Rick Bayless. Afterward, visit the 606 Trail for a leisurely walk or bike ride.

Enjoy a casual dinner at Big Star and explore the vibrant nightlife of the area.

Start your day with a delightful brunch at Lula Cafe in Logan Square.

Take a food tour of the city, sampling local favorites and hidden gems. For dinner, experience the famous Chicago-style hot dogs at Portillo's Hot Dogs.

Conclude the day with a cocktail at the historic The Violet Hour in Wicker Park.

Explore the unique architecture of Marina City and take a river cruise to learn more about the city's buildings.

For lunch, enjoy the Mediterranean flavors at The Purple Pig. Afterward, visit the Chicago Architecture Center to delve deeper into the city's architectural history.

Have a sophisticated dinner at Au Cheval, known for its upscale diner fare.

Spend a relaxing morning at the Lincoln Park Conservatory and Lincoln Park Zoo.

For a late lunch, enjoy the farm-to-table cuisine at Longman & Eagle in Logan Square. Afterward, take a bike ride along the Lakefront Trail.

Have a casual dinner at Kuma's Corner, famous for its heavy metal-inspired burgers.