3-day itinerary · Chicago
3 Days in Chicago: First-Time Highlights
This plan suits first-time visitors seeking a mix of sightseeing, culture and outdoor experiences. Three days bring together architecture, art, local food and museum discoveries, with skyline views from the water and above.
Customize this with AIDay 1: Architecture and skyline views
Get acquainted with Chicago through an introductory walk, a river architecture cruise and an elevated city panorama.
Morning
Chicago Walking Tour: Must-See Chicago
Walk among famous buildings for an introductory look at the city's architectural highlights.
Afternoon
Chicago Architecture Center River Cruise aboard First Lady
Cruise past riverfront architecture to see the city's buildings from a different perspective.
Evening
Skydeck - Willis Tower Admission
Take in sweeping city views from the Skydeck, rounding out your first day with a sense of Chicago's scale.
Day 2: Art, flavors and city stories
Explore Chicago's cultural side through guided art viewing, a food-focused walk and stories from its crime history.
Morning
Skip-the-line: Art Institute of Chicago Guided Tour
Explore artworks with an art historian guide, adding a cultural centerpiece to your introduction to Chicago.
Afternoon
Chicago Favorites Ultimate Food and Walking Tour
Sample Chicago foods while walking between attractions, combining local flavors with first-time sightseeing.
Evening
Chicago Night Crimes Tour by Bus
Hear stories from Chicago's crime history on a bus tour that adds another layer to the city's past.
Day 3: Museum discoveries and the lakefront
Balance natural history with lakefront cycling before finishing with a sunset cruise.
Morning
Field Museum of Natural History Admission Tickets
Explore natural-history exhibits and artifacts for a museum-focused introduction to the world beyond Chicago's skyline.
Afternoon
Bike Tour of Chicago's Lakefront Neighborhoods
Cycle through lakefront neighborhoods, bringing outdoor exploration and a neighborhood perspective into your highlights itinerary.
Evening
Lake Michigan Sunset Cruise in Chicago
Enjoy a sunset cruise on Lake Michigan for a waterfront finale to your first Chicago visit.
Experiences are supplied by our partner Viator and booked on their site. Check times, prices and availability before you go.