Chicago in 5 days
Explore Chicago's rich culture, diverse cuisine, and stunning views over five exciting days. From must-visit museums to vibrant parks, this itinerary offers a balanced pace for comfortable exploration.
Different dates, a different pace or a bigger group? Build the same trip for yours. Or see everything vetted in Chicago.
Tickets & tours
Skip-the-line tickets and guided tours for the marquee stops on your route.
Art Institute of Chicago
Skydeck Chicago at Willis Tower
Wrigley Field
Museum of Science and Industry
Field Museum
Chicago Architecture Center River Cruise
360 CHICAGO Observation Deck
Tour links open Viator / GetYourGuide. Itnify may earn a commission, at no extra cost to you.
Passes & transport
Passes worth buying before you arrive, plus how to get around.
Transit
Taxis
- Yellow Cab Chicago312-829-4222
Useful info & numbers
Emergency numbers, money, connectivity and official links.
- Emergency
- 911 for police, fire, and ambulance
- Money
- United States Dollar (USD). Cards accepted everywhere; tipping 15-20% at restaurants.
- Connectivity
- Prepaid eSIMs are available from local carriers, and many cafes and public areas offer free Wi-Fi.
Chicago Transit Authority (CTA) operates trains and buses; use a Ventra card for seamless payment.