Cheap Flights to Historic Route 66 from CA $186

View CA $186 flight on Fri, May 22, 2026Opens 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 $186 for one-way flights and CA $316 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, May 9 - Tue, May 12
YYC
Calgary
ORD
Chicago
CA $316 Roundtrip, found 1 hour ago
CA $316
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, May 9 from Calgary to Chicago, returning Tue, May 12, priced at CA $316 found 1 hour ago
United
Sun, May 24 - Fri, May 29
YYC
Calgary
ORD
Chicago
CA $324 Roundtrip, found 1 hour ago
CA $324
Roundtrip
found 1 hour ago
Select United flight, departing Sun, May 24 from Calgary to Chicago, returning Fri, May 29, priced at CA $324 found 1 hour ago
American Airlines
Fri, May 22 - Sun, May 31
YYC
Calgary
ORD
Chicago
CA $328 Roundtrip, just found
CA $328
Roundtrip
just found
Select American Airlines flight, departing Fri, May 22 from Calgary to Chicago, returning Sun, May 31, priced at CA $328 just found
WestJet
Fri, May 22 - Sun, May 31
YYC
Calgary
ORD
Chicago
CA $345 Roundtrip, just found
CA $345
Roundtrip
just found
Select WestJet flight, departing Fri, May 22 from Calgary to Chicago, returning Sun, May 31, priced at CA $345 just found
Air Canada
Tue, Oct 6 - Sat, Oct 10
YYC
Calgary
ORD
Chicago
CA $358 Roundtrip, found 17 hours ago
CA $358
Roundtrip
found 17 hours ago
Select Air Canada flight, departing Tue, Oct 6 from Calgary to Chicago, returning Sat, Oct 10, priced at CA $358 found 17 hours ago

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 $316 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 $316 and CA $358 in the last seven days. For one-way journeys departing from Calgary (YYC), the lowest amount paid during this time was just CA $186.
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 $316 and CA $358. 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.

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $316

Trending flights to Historic Route 66

Prices were available within the past 7 days and start at CA $186 for one-way flights and CA $316 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Jul 10 - Fri, Jul 10
YYZ
Toronto
MDW
Chicago
CA $322 Roundtrip, found 1 hour ago
CA $322
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Jul 10 from Toronto to Chicago, returning Fri, Jul 10, priced at CA $322 found 1 hour ago

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