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Historic Route 66

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Historic Route 66 Flights as Low as $75

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Tue, Aug 26 - Sat, Aug 30
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$75 Roundtrip, found 2 hours ago
$75
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Aug 26 from George Bush Intercontinental to O'Hare Intl., returning Sat, Aug 30, priced at $75 found 2 hours ago
Frontier Airlines
Mon, Sep 8 - Fri, Sep 12
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 8 from George Bush Intercontinental to O'Hare Intl., returning Fri, Sep 12, priced at $98 found 2 days ago
Frontier Airlines
Mon, Sep 22 - Thu, Sep 25
IAH
George Bush Intercontinental
MDW
Midway Intl.
$168 Roundtrip, found 3 days ago
$168
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Sep 22 from George Bush Intercontinental to Midway Intl., returning Thu, Sep 25, priced at $168 found 3 days ago
American Airlines
Wed, Aug 20 - Sat, Aug 23
IAH
George Bush Intercontinental
TUL
Tulsa Intl.
$177 Roundtrip, found 3 hours ago
$177
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Aug 20 from George Bush Intercontinental to Tulsa Intl., returning Sat, Aug 23, priced at $177 found 3 hours ago
United
Mon, Oct 27 - Sat, Nov 1
IAH
George Bush Intercontinental
OKC
Will Rogers World
$177 Roundtrip, just found
$177
Roundtrip
just found
Select United flight, departing Mon, Oct 27 from George Bush Intercontinental to Will Rogers World, returning Sat, Nov 1, priced at $177 just found
United
Thu, Sep 25 - Thu, Oct 2
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$183 Roundtrip, found 10 hours ago
$183
Roundtrip
found 10 hours ago
Select United flight, departing Thu, Sep 25 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Thu, Oct 2, priced at $183 found 10 hours ago
Spirit Airlines
Wed, Aug 27 - Thu, Sep 4
IAH
George Bush Intercontinental
ABQ
Albuquerque Intl. Sunport
$187 Roundtrip, found 9 hours ago
$187
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Wed, Aug 27 from George Bush Intercontinental to Albuquerque Intl. Sunport, returning Thu, Sep 4, priced at $187 found 9 hours ago
American Airlines
Tue, Oct 28 - Sat, Nov 1
IAH
George Bush Intercontinental
SGF
Springfield-Branson National
$189 Roundtrip, found 10 hours ago
$189
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Oct 28 from George Bush Intercontinental to Springfield-Branson National, returning Sat, Nov 1, priced at $189 found 10 hours ago
Delta
Sat, Sep 6 - Sat, Sep 6
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 4 days ago
$191
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Sep 6 from Love Field to O'Hare Intl., returning Sat, Sep 6, priced at $191 found 4 days ago
Delta
Tue, Oct 14 - Tue, Oct 21
DAL
Love Field
STL
Lambert-St. Louis Intl.
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 14 from Love Field to Lambert-St. Louis Intl., returning Tue, Oct 21, priced at $197 found 5 days ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 2 days ago
Delta
Tue, Sep 2 - Wed, Sep 3
DAL
Love Field
ABQ
Albuquerque Intl. Sunport
$237 Roundtrip, found 10 hours ago
$237
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Sep 2 from Love Field to Albuquerque Intl. Sunport, returning Wed, Sep 3, priced at $237 found 10 hours ago
American Airlines
Sun, Aug 24 - Tue, Aug 26
IAH
George Bush Intercontinental
FLG
Flagstaff Pulliam Field
$348 Roundtrip, found 4 days ago
$348
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Aug 24 from George Bush Intercontinental to Flagstaff Pulliam Field, returning Tue, Aug 26, priced at $348 found 4 days ago
Delta
Thu, Sep 18 - Tue, Sep 23
DAL
Love Field
SGF
Springfield-Branson National
$485 Roundtrip, found 4 days ago
$485
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Sep 18 from Love Field to Springfield-Branson National, returning Tue, Sep 23, priced at $485 found 4 days ago
Delta
Sun, Aug 10 - Sat, Aug 30
DAL
Love Field
OKC
Will Rogers World
$758 Roundtrip, found 5 days ago
$758
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Aug 10 from Love Field to Will Rogers World, returning Sat, Aug 30, priced at $758 found 5 days ago
Delta
Fri, Aug 1 - Sun, Aug 3
DAL
Love Field
TUL
Tulsa Intl.
$1,149 Roundtrip, found 3 days ago
$1,149
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Aug 1 from Love Field to Tulsa Intl., returning Sun, Aug 3, priced at $1,149 found 3 days ago

Cheap Flights to Historic Route 66

Fall in love at first flight with your vacation to Historic Route 66 by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Historic Route 66 on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Historic Route 66, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Historic Route 66

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Historic Route 66 with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Historic Route 66?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Historic Route 66 are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Historic Route 66?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Historic Route 66.

What airport is best to fly into Historic Route 66?

When you’re planning your trip to Historic Route 66, convenience is the name of the game. Luckily, Historic Route 66 Enid Woodring Municipal Airport is nearby so you can deplane and get going on checking off everything on your Historic Route 66 must-do list.

How much are flights to Historic Route 66?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Historic Route 66 on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $75, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Historic Route 66?

The trick to saving a stack of cash on your flight to Historic Route 66? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $75 right now, why wait?

Historic Route 66 Flight Information
Destination airport
Will Rogers World
Destination airport IATA code
OKC
Roundtrip price
$58

Last Minute Hotel Deals in Historic Route 66

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.6/10 Excellent! (3,354 reviews)
"Nice room. Great nespresso coffee maker. Perfect location."

Reviewed on Jul 21, 2025

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Club Quarters Hotel, Central Loop, Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,939 reviews)
Historic Charmer
"GORGEOUS view of downtown and Lake Michigan! Light filled room. Comfortable bed. Bathtub to welcome zen. Restful sleep nightly to embrace the day ahead. All staff were welcoming and helpful. Gym more than sufficient for maintaining my fitness goals while traveling. I appreciate renovated spaces that ..."

Reviewed on Jul 22, 2025

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Congress Plaza Hotel
The Aquarius Casino Resort, BW Premier Collection

The Aquarius Casino Resort, BW Premier Collection

3.5 out of 5
1900 S Casino Dr, Laughlin, NV
Stay at this 3.5-star business-friendly resort in Laughlin. Enjoy free WiFi, 4 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (6,660 reviews)
"Convenient food locations"

Reviewed on Jul 24, 2025

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The Aquarius Casino Resort, BW Premier Collection
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,111 reviews)
"Great experience!"

Reviewed on Jul 25, 2025

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InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,528 reviews)
"Convenient to the public transportation and nearby shopping. On-site restaurant was a good breakfast option for us before heading out for the day."

Reviewed on Jul 24, 2025

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Hilton Chicago/Magnificent Mile Suites
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,307 reviews)
"Great location"

Reviewed on Jul 23, 2025

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Crowne Plaza Chicago West Loop by IHG
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,526 reviews)
"Excellent all around"

Reviewed on Jul 23, 2025

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Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,438 reviews)
Fantastic find in Chicago
"What a great hotel -selected from many close to my conference at the Hyatt. It was also walking distance (1.2 miles) from Union Station (Amtrak). Hotel check-in and check-out is seamless -all done at central kiosk. Hotel staff ever-present to assist. Rooms are exceptionally clean and comfortable. ..."

Reviewed on Jul 24, 2025

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citizenM Chicago Downtown
See all 19,122 properties in Historic Route 66
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.