Experience Chicago's rich culture, stunning architecture, and lively neighborhoods over two packed days. From iconic museums to beautiful parks and renowned attractions, discover what makes the Windy City a must-visit destination.
Wildberry Pancakes & Cafe
Start your day with delicious breakfast options, from fluffy pancakes to hearty omelets.

Art Institute of Chicago
~2 hr 30 minStart with a visit to one of America's greatest art museums, which features an impressive collection of Impressionist icons, modern masterpieces, and the stunning Thorne Rooms.

Millennium Park
~1 hrNext, head to Chicago's signature downtown park, where you can experience Cloud Gate, Crown Fountain, and beautiful gardens set against the skyline.

Chicago Cultural Center
~30 minThen, admire the free public rooms and the stunning Tiffany glass dome at this beloved architectural gem that showcases Chicago's heritage.
Pizzeria Portofino
Enjoy a lunch of fresh pizzas and Italian specialties, located conveniently near your attractions.

Chicago Architecture Center River Cruise
~1 hr 15 minEnjoy a scenic cruise that turns the river into a fascinating classroom showcasing Chicago's iconic skyscrapers and rich architectural history.

Skydeck Chicago at Willis Tower
~1 hrNext, take in breathtaking views of Chicago from the Skydeck, with the thrilling Ledge glass boxes that overlook the city skyline.

Navy Pier
~1 hr 30 minEnd the day at the iconic Navy Pier, where you can enjoy skyline views, family attractions, and even seasonal fireworks on the lakefront.
Gino's East
Savor the famous Chicago deep-dish pizza for dinner at Gino's East, just a short distance from Navy Pier.
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