AI Travel Planner
5-Day Chicago Highlights and Culinary Delights Itinerary
Chicago, Illinois, USA
Chicago
Iconic Landmarks and River Cruises
Find amazing hotelsMorning
Begin your Chicago adventure with a delightful breakfast at Cindy's Rooftop, offering stunning views of the city skyline. Afterward, take a morning stroll along the Chicago Riverwalk to admire the architecture and the iconic Wrigley Building.
Afternoon
For lunch, head to The Gage, known for its upscale yet approachable cuisine. Post-lunch, enjoy a Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's famous buildings and history. After the cruise, visit the Art Institute of Chicago (skip-the-line ticket) to immerse yourself in world-class art.
Evening
Dine at Untitled Supper Club, an intriguing spot with live music and a speakeasy vibe. Afterward, experience the city from above at the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with a "Sip and View" ticket, savoring the panoramic views with a drink in hand.
Bedtime
Find amazing hotels in Chicago.