Cheap Flights to Historic Route 66 from HK$695

View HK$695 flight on Sat, 28 Feb 2026Opens in a new window

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Cheap round-trip flights to Historic Route 66

Prices were available within the past 7 days and start at HK$695 for one-way flights and HK$1,465 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 21 Feb - Mon, 2 Mar
EWR
New York
MDW
Chicago
HK$1,465 Return, found 23 hours ago
HK$1,465
Return
found 23 hours ago
Select Delta flight, departing Sat, 21 Feb from New York to Chicago, returning Mon, 2 Mar, priced at HK$1,465 found 23 hours ago
United
Sat, 25 Apr - Mon, 27 Apr
EWR
New York
ORD
Chicago
HK$1,620 Return, found 3 days ago
HK$1,620
Return
found 3 days ago
Select United flight, departing Sat, 25 Apr from New York to Chicago, returning Mon, 27 Apr, priced at HK$1,620 found 3 days ago
American Airlines
Mon, 23 Mar - Mon, 30 Mar
EWR
New York
ORD
Chicago
HK$1,706 Return, found 2 days ago
HK$1,706
Return
found 2 days ago
Select American Airlines flight, departing Mon, 23 Mar from New York to Chicago, returning Mon, 30 Mar, priced at HK$1,706 found 2 days ago
Air Canada
Wed, 24 Jun - Tue, 21 Jul
HKG
Hong Kong SAR
ORD
Chicago
HK$6,000 Return, found 9 hours ago
HK$6,000
Return
found 9 hours ago
Select Air Canada flight, departing Wed, 24 Jun from Hong Kong SAR to Chicago, returning Tue, 21 Jul, priced at HK$6,000 found 9 hours ago
China Airlines
Mon, 5 Oct - Tue, 6 Oct
HKG
Hong Kong SAR
STL
St. Louis
HK$6,680 Return, found 20 hours ago
HK$6,680
Return
found 20 hours ago
Select China Airlines flight, departing Mon, 5 Oct from Hong Kong SAR to St. Louis, returning Tue, 6 Oct, priced at HK$6,680 found 20 hours ago

Frequently asked questions

How do I find cheap flights to Historic Route 66 that have flexible change policies?
At Expedia, we've been channeling our inner contortionist to get you the most flexible fares in town. Simply tick the "No change fee" box right under the "Flexible change policies" filter to find your dream flight to Historic Route 66.
How can I find cheap tickets to Historic Route 66?
To get your hands on a great deal to Historic Route 66, book ahead of time. Also take advantage of Expedia's handy "flexible dates" link at the top of your search results. This will display prices for similar time frames. In the last seven days, HK$1,465 was the lowest price for a flight to Historic Route 66.
How much is a flight to Historic Route 66?
In the last seven days, round-trip flights to Historic Route 66 sold from just HK$1,465 and peaked at HK$6,680. For one-way journeys departing from New York (EWR), the cheapest seat during this same period was just HK$695.
When is the cheapest time to fly to Historic Route 66?
Consider jetting off early in the week to secure a bargain airfare to Historic Route 66. Tuesday is generally the cheapest day to depart, with Monday right behind it. Saturday typically has the most expensive fares. This is because many people choose to kick off their trip on a weekend.
How much is a plane ticket to Historic Route 66?
In the last seven days, plane tickets to Historic Route 66 ranged between HK$1,465 and HK$6,680. The early bird catches the worm, so pick up a terrific deal today.
What months are the cheapest to book a flight to Historic Route 66?
A good month to purchase cheap flights to Historic Route 66 is February. Bear in mind that in the United States, the most expensive time to secure a seat is the festive month of December.
Flights to Historic Route 66 information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Return price
HK$1,465

Trending flights to Historic Route 66

Prices were available within the past 7 days and start at HK$695 for one-way flights and HK$1,465 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Wed, 24 Jun - Tue, 21 Jul
HKG
Hong Kong SAR
ORD
Chicago
HK$6,000 Return, found 9 hours ago
HK$6,000
Return
found 9 hours ago
Select Air Canada flight, departing Wed, 24 Jun from Hong Kong SAR to Chicago, returning Tue, 21 Jul, priced at HK$6,000 found 9 hours ago
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