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Historic Route 66

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Historic Route 66 Flights as Low as $137

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

American Airlines
Thu, Sep 4 - Mon, Sep 8
PHX
Sky Harbor Intl.
ABQ
Albuquerque Intl. Sunport
$137 Roundtrip, found 1 hour ago
$137
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Sep 4 from Sky Harbor Intl. to Albuquerque Intl. Sunport, returning Mon, Sep 8, priced at $137 found 1 hour ago
Frontier Airlines
Thu, Aug 28 - Thu, Sep 4
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$141 Roundtrip, found 4 days ago
$141
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Aug 28 from Sky Harbor Intl. to Midway Intl., returning Thu, Sep 4, priced at $141 found 4 days ago
Frontier Airlines
Mon, Aug 18 - Mon, Aug 25
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$141 Roundtrip, found 4 days ago
$141
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Aug 18 from Sky Harbor Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $141 found 4 days ago
Spirit Airlines
Sat, Aug 2 - Thu, Aug 14
PHX
Sky Harbor Intl.
STL
Lambert-St. Louis Intl.
$169 Roundtrip, found 3 days ago
$169
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sat, Aug 2 from Sky Harbor Intl. to Lambert-St. Louis Intl., returning Thu, Aug 14, priced at $169 found 3 days ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, just found
$191
Roundtrip
just found
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $191 just found
Delta
Tue, Aug 26 - Tue, Aug 26
DAL
Love Field
STL
Lambert-St. Louis Intl.
$194 Roundtrip, found 2 days ago
$194
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Aug 26 from Love Field to Lambert-St. Louis Intl., returning Tue, Aug 26, priced at $194 found 2 days ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 just found
American Airlines
Tue, Sep 30 - Tue, Oct 7
PHX
Sky Harbor Intl.
OKC
Will Rogers World
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Sep 30 from Sky Harbor Intl. to Will Rogers World, returning Tue, Oct 7, priced at $197 found 1 hour ago
United
Mon, Nov 17 - Thu, Nov 27
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$199 Roundtrip, found 2 hours ago
$199
Roundtrip
found 2 hours ago
Select United flight, departing Mon, Nov 17 from Sky Harbor Intl. to O'Hare Intl., returning Thu, Nov 27, priced at $199 found 2 hours ago
American Airlines
Thu, Aug 7 - Mon, Aug 11
PHX
Sky Harbor Intl.
TUL
Tulsa Intl.
$201 Roundtrip, found 3 days ago
$201
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Aug 7 from Sky Harbor Intl. to Tulsa Intl., returning Mon, Aug 11, priced at $201 found 3 days ago
Hawaiian Airlines
Tue, Aug 5 - Thu, Aug 14
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$218 Roundtrip, found 2 days ago
$218
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Tue, Aug 5 from Sky Harbor Intl. to O'Hare Intl., returning Thu, Aug 14, priced at $218 found 2 days ago
Bargain Flight
Tue, Jul 29 - Wed, Jul 30
PHX
Sky Harbor Intl.
SGF
Springfield-Branson National
$243 Roundtrip, found 4 days ago
$243
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, Jul 29 from Sky Harbor Intl. to Springfield-Branson National, returning Wed, Jul 30, priced at $243 found 4 days ago
Delta
Sat, Aug 2 - Sun, Aug 3
DAL
Love Field
ABQ
Albuquerque Intl. Sunport
$287 Roundtrip, found 4 days ago
$287
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Aug 2 from Love Field to Albuquerque Intl. Sunport, returning Sun, Aug 3, priced at $287 found 4 days ago
Delta
Mon, Sep 15 - Tue, Sep 23
DAL
Love Field
SGF
Springfield-Branson National
$485 Roundtrip, found 3 days ago
$485
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Sep 15 from Love Field to Springfield-Branson National, returning Tue, Sep 23, priced at $485 found 3 days ago
Delta
Thu, Aug 7 - Sat, Aug 30
DAL
Love Field
OKC
Will Rogers World
$542 Roundtrip, found 4 days ago
$542
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Aug 7 from Love Field to Will Rogers World, returning Sat, Aug 30, priced at $542 found 4 days ago
Delta
Sat, Jul 19 - Tue, Jul 22
DAL
Love Field
TUL
Tulsa Intl.
$904 Roundtrip, found 4 hours ago
$904
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Jul 19 from Love Field to Tulsa Intl., returning Tue, Jul 22, priced at $904 found 4 hours 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 September, 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 15 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 $137, 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 $137 right now, why wait?

Historic Route 66 Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$108

Last Minute Hotel Deals in Historic Route 66

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! (6,495 reviews)
"Clean"

Reviewed on Jul 3, 2025

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The Aquarius Casino Resort, BW Premier Collection
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! (2,372 reviews)
"Very nice hotel! No pool though it was out of service"

Reviewed on Jul 3, 2025

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Hilton Chicago/Magnificent Mile Suites
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! (1,970 reviews)
"Even after renovation rooms are still looking dated"

Reviewed on Jul 4, 2025

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InterContinental Chicago Magnificent Mile by IHG
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! (8,872 reviews)
"The history of the hotel is amazing and she might be an old girl with old features but she still shines like a diamond. Plus, the lake side view cannot be beat."

Reviewed on Jul 4, 2025

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Congress Plaza Hotel
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! (4,357 reviews)
"The location is very convenient, close to the train and easy to get to most attractions. The rokms are spacious and clean. The breakfast and happy hour are very good and a nice convenience."

Reviewed on Jul 5, 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! (3,269 reviews)
"Such a fun hotel! Loved the theme carrried through all aspects of the brand and design of the hotel. Super clean. Room might be a bit small for 2. I found for 1 person, it was perfect. Great location!"

Reviewed on Jul 2, 2025

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citizenM Chicago Downtown
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (1,823 reviews)
Loved this hotel!
"This hotel was just perfect! The staff were all very friendly, especially service desk. The rooms were well stocked. The room was a bit small, but it didn't bother us. Within walking distance to everything! Will definitely be staying here again. Thank you for a great experience ❤️"

Reviewed on Jul 2, 2025

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Hotel Felix River North/Magnificent Mile
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 out of 5
105 E Delaware Pl, Chicago, IL
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
8.2/10 Very Good! (3,458 reviews)
"Good"

Reviewed on Jul 3, 2025

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The Whitehall Hotel, BW Premier Collection
See all 18,946 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.