Chicago Adventure 5-Day Trip Itinerary

Begin your morning with a visit to Skydeck Chicago at Willis Tower (Sears Tower), where you can enjoy breathtaking views of the city from one of the tallest buildings in the world. Afterward, grab a coffee at a nearby café before heading to your next destination.

Spend your afternoon exploring The Magnificent Mile, Chicago's premier commercial district filled with shops, restaurants, and attractions. For lunch, dine at The Purple Pig, known for its Mediterranean-inspired small plates.

In the evening, catch a show at Chicago Theatre, an iconic venue that hosts a variety of performances. Before the show, have dinner at Au Cheval, famous for its gourmet burgers.

Start your day with a visit to the renowned Art Institute of Chicago, home to an extensive collection of art from around the world. Enjoy breakfast or brunch at their on-site café before exploring the museum.

Afterward, head over to Field Museum for an afternoon filled with natural history exhibits and fascinating displays. For lunch, try some deep-dish pizza at Lou Malnati's Pizzeria, a Chicago classic.

In the evening, take a leisurely walk through Grant Park and enjoy dinner at The Publican, which offers hearty meals in a rustic setting.

Begin your day with breakfast at Eataly Chicago, where you can enjoy Italian pastries and coffee. Then make your way to Navy Pier for some fun by Lake Michigan – ride the Ferris wheel or explore other attractions on-site.

Spend your afternoon visiting the fascinating marine life exhibits at Shedd Aquarium. For lunch nearby, dine at Shaw's Crab House for some fresh seafood delights.

Conclude your day with dinner at Gibsons Bar & Steakhouse, renowned for its prime steaks and classic ambiance.

Start your final day in Chicago with a hearty breakfast at Maple & Ash, where you can enjoy a luxurious morning meal in an elegant setting. After breakfast, visit Museum of Science and Industry, one of the largest science museums in the world, offering interactive exhibits and fascinating displays.

In the afternoon, take a trip to Lincoln Park & Zoo, a beautiful urban park that includes a free zoo with a wide variety of animals. For lunch, head to Pequot's Pizza to savor some of Chicago's best deep-dish pizza.

End your day with a visit to 360 Chicago Observation Deck (Formerly John Hancock Observatory) for stunning panoramic views of the city skyline and Lake Michigan. For your farewell dinner, dine at Alinea, one of the most acclaimed restaurants in the world, known for its innovative and artistic cuisine.