$34 Cheap flight deals from Chicago (CHI) to Windsor (DEN)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Windsor

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $34 One Way, $63 Round Trip from Chicago to Windsor

Prices starting at $63 for return flights and $34 for one-way flights to Windsor were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Windsor economy flight packages

Price found within the past 48 hours. Click for updated prices.
Lone Tree Golf Club And Hotel
The Source Hotel
Hilton Garden Inn Denver Union Station, CO
Don't see what you're looking for?
See all available trips from Chicago to Windsor
View all trips

More About Flying To Windsor from Chicago

Route Information for Flights from Chicago to Windsor

Origin Airport IATA Code
CHI
Destination Airport IATA Code
DEN
Distance
886 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Austrian, Aer Lingus, Emirates, Copa Airlines, Swiss, United Airlines, Frontier Airlines, Cathay Pacific, Southwest Airlines, Turkish Airlines, Royal Jordanian, Iberia, Brussels Airlines, Lufthansa, Gulf Air, British Airways
Earliest Flight Arrival
12:42PM UTC
Latest Flight Arrival
3:54AM UTC

Chicago to Windsor

Orbitz On-the-Go is your one-stop shop for discount vacation air travel. Our cutting-edge mobile tools leave you time to pack for the trip. Shop our sales on domestic flights from Chicago to Windsor.

Best Bargains Anywhere

Cheap vacations start at Orbitz On-the-Go. Find the best deals on international flights from Chicago to Windsor.

Complete Travel Planning

Your phone becomes a full-service vacation travel agency with Orbitz mobile phone apps. From reservations to arrivals, every detail is in the palm of your hand. Book budget flights from Chicago to Windsor; add a car and hotel, share your itinerary and keep up with changes. Orbitz apps cover all the bases for you.

Totally Stress-Free

Free Alerts from Orbitz On-the-Go keep your vacation free from worry. Free Alerts updates you the moment any changes occur. You’ll always have the most current flight, gate and baggage claim details. So sit back and enjoy your low fare on Chicago to Windsor flights.

More Miles Faster = Maximum Value

Orbitz On-the-Go securely stores your frequent flier and loyalty program information. Watch your miles add up when you book discount Chicago to Windsor flights with Orbitz. Make your vacation mileage-friendly with low cost air tickets on Chicago to Windsor flights. Orbitz is your destination for vacation value.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.