8 Days Exploring Chicago Itinerary

Begin your day at the renowned Art Institute of Chicago, home to an extensive collection of art from around the world. Enjoy breakfast at a nearby cafe before heading in.

Take a leisurely stroll through Grant Park, often referred to as 'Chicago's front yard.' For lunch, dine at RPM Italian, offering modern Italian dishes in an elegant setting.

Visit the historic Chicago Theatre for an evening show or tour. Afterward, enjoy dinner at Smyth and The Loyalist, known for its innovative cuisine.

Discover the architectural marvels of Chicago with a visit to Marina City. Start your morning with breakfast at a local coffee shop nearby.

Spend your afternoon shopping along The Magnificent Mile, one of the most famous shopping districts in the world. Have lunch at one of the many eateries along this stretch.

Head over to Navy Pier for an evening filled with entertainment options including rides, games, and dining. Enjoy dinner at one of Navy Pier's waterfront restaurants.

Visit the historic Field Museum where you can explore fascinating exhibits on natural history. Grab breakfast at their on-site cafe before diving into exploration.

Make your way to Millennium Park where you can see iconic landmarks like 'The Bean.' Have lunch nearby at one of Millennium Park's cafes or restaurants.

Enjoy an evening cruise along the beautiful Chicago Riverwalk. Dine along this scenic route with plenty of riverside restaurant options.

Start your day exploring space and science at the impressive Adler Planetarium. Have breakfast overlooking Lake Michigan from their cafe.

Head over to explore more scientific wonders at the famous Museum of Science and Industry. Enjoy lunch within their food court offering various options.

Conclude your day by visiting another observation deck - this time it's 360-degree views from atop 875 North Michigan Avenue (formerly John Hancock Center) via 360 Chicago Observation Deck (Formerly John Hancock Observatory)