Cheap Flights to Historic Route 66 from CA $157

View CA $157 flight on Sat, Nov. 15, 2025Opens in a new window

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How much is the cheapest flight to Historic Route 66?

Prices were available within the past 7 days and start at CA $157 for one-way flights and CA $244 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Fri, Nov. 14 - Mon, Nov. 17
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 18 hours ago
CA $244
Roundtrip
found 18 hours ago
Select Air Canada flight, departing Fri, Nov. 14 from Toronto to Chicago, returning Mon, Nov. 17, priced at CA $244 found 18 hours ago
United
Sat, Nov. 8 - Wed, Nov. 12
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 15 hours ago
CA $244
Roundtrip
found 15 hours ago
Select United flight, departing Sat, Nov. 8 from Toronto to Chicago, returning Wed, Nov. 12, priced at CA $244 found 15 hours ago
American Airlines
Sat, Nov. 1 - Tue, Nov. 4
YYZ
Toronto
ORD
Chicago
CA $261 Roundtrip, just found
CA $261
Roundtrip
just found
Select American Airlines flight, departing Sat, Nov. 1 from Toronto to Chicago, returning Tue, Nov. 4, priced at CA $261 just found
Delta
Tue, Oct. 28 - Fri, Nov. 7
YYZ
Toronto
ORD
Chicago
CA $286 Roundtrip, found 17 hours ago
CA $286
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Oct. 28 from Toronto to Chicago, returning Fri, Nov. 7, priced at CA $286 found 17 hours ago
Alaska Airlines
Tue, Nov. 11 - Tue, Nov. 18
YYZ
Toronto
ABQ
Albuquerque
CA $628 Roundtrip, found 2 days ago
CA $628
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Nov. 11 from Toronto to Albuquerque, returning Tue, Nov. 18, priced at CA $628 found 2 days ago

Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD)

June is typically the cheapest month to fly

From CA $106 - CA $344 per traveller.

Graph displaying average flight prices per month

Expedia.ca gives you the best tools to secure great deals on flights to Historic Route 66. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Historic Route 66. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Historic Route 66.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Historic Route 66 flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Historic Route 66.

Looking to save even more? Get additional savings by bundling your Historic Route 66 flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Historic Route 66 trip!

Frequently asked questions

How do I find cheap flights to Historic Route 66 that have flexible change policies?
By using our convenient "No change fee" filter, that's how. Just type in your origin, destination and dates, click the "Search" button, then tick the box directly underneath the "Flexible change policies" subheading (left-hand side of your screen). Expedia makes it a cinch to find cheap, flexible tickets to Historic Route 66.
How can I find cheap tickets to Historic Route 66?
You'll always pick up an amazing deal with Expedia, but our "flexible dates" search function makes it that much easier. Enter your preferred flight date, then tick the flexible dates box above to compare the cheapest prices for nearby days. CA $244 was the lowest price for a flight to Historic Route 168 kg the last seven days.
How much is a flight to Historic Route 66?
You could have snapped up a return ticket to Historic Route 66 from anywhere between CA $244 and CA $628 in the last seven days. For one-way journeys departing from Toronto (YYZ), the lowest amount paid during this time was just CA $157.
When is the cheapest time to fly to Historic Route 66?
If you'd prefer to spend your vacation cash enjoying the best of Historic Route 66 rather than on your trip there, depart earlier in the week. The cheapest day to fly is usually Tuesday, with Monday running a close second. With many people travelling over the weekend, Saturday typically has the most expensive airfares.
How much is a plane ticket to Historic Route 66?
In the last seven days, seats to Historic Route 66 ranged between CA $244 and CA $628. Prices depend on multiple things, particularly the time of departure, cabin class, airline and how early you make your booking.
What is the best time to go to Historic Route 66?
If you live for the crowds and excitement of a major city, head to Virden during the months of March, April and July. This is the busiest time for one of Historic Route 66's main destinations. Summer kicks off June 20 and brings average temperatures of between 18ºC and 28ºC. Time your trip then and you can look forward to glorious sunny days.
What months are the cheapest to book a flight to Historic Route 66?
The ideal month to purchase affordable airfares to Historic Route 66 is February. Remember that in the U.S, the most expensive time to purchase a ticket is during the month of December.
Flights to Historic Route 66 information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $244

Trending flights to Historic Route 66

Prices were available within the past 7 days and start at CA $157 for one-way flights and CA $244 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Fri, Nov. 14 - Mon, Nov. 17
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 18 hours ago
CA $244
Roundtrip
found 18 hours ago
Select Air Canada flight, departing Fri, Nov. 14 from Toronto to Chicago, returning Mon, Nov. 17, priced at CA $244 found 18 hours ago
*Available to Expedia members.