Chicago Adventure 5 Days Itinerary

Begin your day with a visit to the renowned Art Institute of Chicago. Spend your morning exploring its vast collection of art from around the world.

Afterward, take a walk along Chicago Riverwalk, where you can enjoy beautiful views of the city's architecture. Stop for lunch at Portillo's Hot Dogs for an authentic Chicago-style hot dog experience.

In the evening, head to Second City for some top-notch comedy. This legendary improv theater has launched many famous comedians' careers. For dinner, savor some deep-dish pizza at Lou Malnati's Pizzeria.

Kick off your day with a visit to the fascinating Field Museum. Explore exhibits on natural history and ancient civilizations.

Next, head over to the nearby Shedd Aquarium to marvel at marine life from around the globe. For lunch, try some BBQ delights at Smoque BBQ.

Spend your evening enjoying live music at House of Blues. This iconic venue offers great performances in an intimate setting. Before that, have dinner at Joe's Seafood, Prime Steak & Stone Crab.

Start your day with an architectural tour focusing on landmarks like Marina City and Wrigley Building. These structures are key examples of Chicago's architectural innovation.

Afterward, explore shopping options along The Magnificent Mile, one of Chicago's premier shopping districts. Enjoy lunch at the highly-rated burger joint Au Cheval.

In the evening, take in stunning city views from the observation deck at 360 Chicago (formerly John Hancock Observatory). End your day with dinner at the upscale steakhouse Gibsons Bar & Steakhouse.

Begin your final day with a visit to Adler Planetarium. This planetarium offers fascinating exhibits on space and astronomy, providing a captivating start to your day.

Afterward, head over to Grant Park for a relaxing afternoon. This expansive park is perfect for a leisurely stroll and offers beautiful views of the city skyline. For lunch, enjoy some delicious Mexican cuisine at Frontera Grill.

Conclude your trip with an evening at Navy Pier. This iconic Chicago landmark offers various attractions, including rides, shops, and dining options. Enjoy dinner at Alinea, one of the finest dining experiences in Chicago.