New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Chicago Adventure 2 Days

Chicago Adventure 2 Days Itinerary

Last updated: 2024 Jun 14

Exploring the Heart of Chicago

Morning
Start your day with a visit to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture (often referred to as 'The Bean'), which offers great photo opportunities. Enjoy a morning stroll through the park's beautiful gardens and take in the serene atmosphere.
Afternoon
Head over to Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend a few hours exploring its vast collection of artworks from around the world. For lunch, make your way to The Purple Pig, known for its delicious Mediterranean-inspired dishes and vibrant atmosphere.
Evening
In the evening, enjoy a live music performance at House of Blues. This iconic venue offers a fantastic lineup of artists and bands across various genres. For dinner, indulge in some classic Chicago-style deep-dish pizza at Lou Malnati's Pizzeria.
Bedtime
Find amazing hotels in Chicago, Illinois.

Cultural Gems and Scenic Views

Morning
Begin your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views of the city from one of the tallest buildings in the Western Hemisphere. Afterward, grab breakfast at Au Cheval, famous for its mouthwatering burgers.
Afternoon
Spend your afternoon exploring Navy Pier, a popular destination featuring shops, restaurants, and entertainment options. Take a ride on the Ferris wheel for stunning views of Lake Michigan. For lunch, head to Girl & The Goat, known for its innovative dishes and lively ambiance.
Evening
Conclude your trip with an evening visit to Chicago Riverwalk. Stroll along this scenic waterfront path and enjoy beautiful views of the city skyline. For dinner, treat yourself to an unforgettable dining experience at Alinea, one of Chicago's most acclaimed restaurants.
Bedtime
Find amazing hotels in Chicago, Illinois.
kayakFind the right stay during your trip.
Got a question about your trip?