New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
7 Day Road Trip from Chicago to New York Itinerary
Last updated: 2024 Jun 14Exploring Downtown Chicago
Morning
Start your day with a visit to the iconic Millennium Park, home to the famous Cloud Gate sculpture. This park is a must-see for its beautiful gardens and public art installations. For breakfast, head to Palmer House Hilton [28057] for a classic Chicago experience.
Afternoon
After exploring Millennium Park, take a short walk to the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Enjoy lunch at The Gage, known for its upscale pub fare and proximity to the museum.
Evening
In the evening, enjoy a show at the historic Chicago Theatre. This iconic venue offers a variety of performances from concerts to comedy shows. For dinner, dine at Girl & The Goat, a highly-rated restaurant known for its innovative dishes.
Bedtime
Find amazing hotels in Chicago.
4.69Millennium Park
Book Now
4.69Millennium Park
Book Now
4.61Art Institute of Chicago
Book Now
4.61Art Institute of Chicago
Book Now
Architectural Wonders and Lakeside Views
Morning
Begin your day with a visit to the Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city from one of its tallest buildings. Grab breakfast at Lou Mitchell's, an iconic diner known for its hearty meals.
Afternoon
Head over to the Chicago Riverwalk for a scenic stroll along the river. This area is perfect for people-watching and enjoying some fresh air. Have lunch at Café Bonhomme, which offers riverside dining with Mediterranean-inspired dishes.
Evening
Spend your evening at the lively Navy Pier, where you can enjoy various attractions including rides, shops, and entertainment options. End your day with dinner at Riva Crabhouse on Navy Pier, offering stunning views of Lake Michigan.
Bedtime
Find amazing hotels in Chicago.
4.27Skydeck Chicago at Willis Tower (Sears Tower)
Book Now
4.27Skydeck Chicago at Willis Tower (Sears Tower)
Book Now
4.72Chicago Riverwalk
Book Now
4.72Chicago Riverwalk
Book Now
Cultural Immersion in Chicago
Morning
Visit the fascinating exhibits at the Field Museum, which houses extensive collections related to natural history. Enjoy breakfast nearby at Yolk South Loop, known for its creative breakfast dishes.
Afternoon
Explore more cultural landmarks by visiting the historic Chicago Cultural Center. This building is renowned for its stunning architecture and free public events. Have lunch at The Dearborn, an American tavern offering classic comfort food.
Evening
Conclude your day with some live music at the famous House of Blues. For dinner, try out RPM Steak, an upscale steakhouse that promises an unforgettable dining experience.
Bedtime
Find amazing hotels in Chicago.
4.56Field Museum
Book Now
4.56Field Museum
Book Now
4.71Chicago Cultural Center
Book Now
4.71Chicago Cultural Center
Book Now
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.