5-Day Chicago Adventure Itinerary

Begin your day with a visit to the Art Institute of Chicago. This world-renowned museum houses an impressive collection of art from various periods and regions. Spend your morning exploring its vast galleries.

After the museum, take a walk along the Chicago Riverwalk. This scenic pathway offers beautiful views of the city skyline and the river. Grab lunch at one of the many eateries along the Riverwalk.

In the evening, head to 360 Chicago Observation Deck (Formerly John Hancock Observatory) for stunning panoramic views of the city from above. It's especially beautiful at sunset. Afterward, dine at one of the nearby restaurants in the area.

Start your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views from one of the tallest buildings in North America.

Next, explore some of Chicago's architectural marvels with a visit to Rookery Building followed by Marina City. These iconic structures showcase different styles and eras of architecture in Chicago.

In the evening, experience live music at House of Blues. This vibrant venue hosts various artists and genres. For dinner beforehand or afterward, choose from one of many nearby dining options.

Kick off your day with an educational visit to the Field Museum, where you can explore fascinating exhibits on natural history.

Afterward, head over to Shedd Aquarium located nearby. Spend your afternoon discovering marine life from around the world in this renowned aquarium.

Conclude your day with some relaxation time at Grant Park followed by dinner at one of its surrounding restaurants.

Begin your last day in Chicago with a visit to Adler Planetarium. This historic planetarium offers fascinating exhibits about space and astronomy, and it provides stunning views of the city skyline and Lake Michigan.

After exploring the stars, head over to Navy Pier for some afternoon fun. This iconic pier features various attractions, including rides, shops, and restaurants. For lunch, enjoy a meal at one of the many dining options available on the pier.

Wrap up your trip with a visit to Second City, one of Chicago's most famous comedy clubs. Enjoy an evening of laughter and entertainment. For dinner before or after the show, consider dining at one of the nearby restaurants in the Old Town neighborhood.