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Historic Route 66

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Historic Route 66 Flights as Low as $112

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

Spirit Airlines
Wed, May 21 - Wed, May 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 18 hours ago
$112
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Wed, May 21 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 21, priced at $112 found 18 hours ago
Frontier Airlines
Thu, May 22 - Wed, May 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 18 hours ago
$120
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Thu, May 22 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 28, priced at $120 found 18 hours ago
Spirit Airlines
Sat, May 17 - Thu, May 29
PDX
Portland Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 6 days ago
$154
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sat, May 17 from Portland Intl. to O'Hare Intl., returning Thu, May 29, priced at $154 found 6 days ago
Delta
Tue, Jun 3 - Tue, Jun 10
PDX
Portland Intl.
ABQ
Albuquerque Intl. Sunport
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 3 from Portland Intl. to Albuquerque Intl. Sunport, returning Tue, Jun 10, priced at $159 found 3 days ago
American Airlines
Mon, May 12 - Thu, May 15
PDX
Portland Intl.
ORD
O'Hare Intl.
$182 Roundtrip, found 2 days ago
$182
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, May 12 from Portland Intl. to O'Hare Intl., returning Thu, May 15, priced at $182 found 2 days ago
Alaska Airlines
Mon, May 26 - Sat, May 31
PDX
Portland Intl.
ORD
O'Hare Intl.
$182 Roundtrip, found 4 days ago
$182
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Mon, May 26 from Portland Intl. to O'Hare Intl., returning Sat, May 31, priced at $182 found 4 days ago
Frontier Airlines
Wed, May 14 - Tue, May 20
LAX
Los Angeles Intl.
OKC
Will Rogers World
$190 Roundtrip, found 4 days ago
$190
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, May 14 from Los Angeles Intl. to Will Rogers World, returning Tue, May 20, priced at $190 found 4 days ago
Frontier Airlines
Sun, May 11 - Wed, May 14
PDX
Portland Intl.
OKC
Will Rogers World
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 11 from Portland Intl. to Will Rogers World, returning Wed, May 14, priced at $191 found 1 day ago
Frontier Airlines
Sat, May 10 - Wed, May 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$210 Roundtrip, found 5 days ago
$210
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 10 from Los Angeles Intl. to Midway Intl., returning Wed, May 21, priced at $210 found 5 days ago
Spirit Airlines
Thu, May 8 - Thu, May 15
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, May 8 from Los Angeles Intl. to Albuquerque Intl. Sunport, returning Thu, May 15, priced at $213 found 1 day ago
Frontier Airlines
Thu, May 15 - Wed, May 21
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$221 Roundtrip, found 4 days ago
$221
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, May 15 from Los Angeles Intl. to Lambert-St. Louis Intl., returning Wed, May 21, priced at $221 found 4 days ago
Frontier Airlines
Mon, May 12 - Thu, May 15
PDX
Portland Intl.
MDW
Midway Intl.
$231 Roundtrip, found 2 days ago
$231
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, May 12 from Portland Intl. to Midway Intl., returning Thu, May 15, priced at $231 found 2 days ago
Delta
Wed, Jul 30 - Tue, Aug 5
LAX
Los Angeles Intl.
TUL
Tulsa Intl.
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jul 30 from Los Angeles Intl. to Tulsa Intl., returning Tue, Aug 5, priced at $237 found 3 days ago
Frontier Airlines
Thu, May 22 - Sat, May 31
PDX
Portland Intl.
STL
Lambert-St. Louis Intl.
$265 Roundtrip, found 3 hours ago
$265
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, May 22 from Portland Intl. to Lambert-St. Louis Intl., returning Sat, May 31, priced at $265 found 3 hours ago
Delta
Fri, Jul 25 - Tue, Aug 5
LAX
Los Angeles Intl.
SGF
Springfield-Branson National
$346 Roundtrip, found 4 days ago
$346
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Jul 25 from Los Angeles Intl. to Springfield-Branson National, returning Tue, Aug 5, priced at $346 found 4 days ago
American Airlines
Wed, Dec 17 - Mon, Dec 29
PDX
Portland Intl.
TUL
Tulsa Intl.
$387 Roundtrip, found 1 hour ago
$387
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Dec 17 from Portland Intl. to Tulsa Intl., returning Mon, Dec 29, priced at $387 found 1 hour 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 May, 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 $112, 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 $112 right now, why wait?

Historic Route 66 Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$88

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
The price is $140 per night from May 4 to May 5
$140
includes taxes & fees
May 4 - May 5
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! (3,383 reviews)
"Nice hotel!! Friendly staff and in a great location."

Reviewed on Apr 30, 2025

Club Quarters Hotel, Central Loop, Chicago
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
The price is $189 per night from May 11 to May 12
$189
includes taxes & fees
May 11 - May 12
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. ...
8.2/10 Very Good! (3,982 reviews)
"Excellent hotel"

Reviewed on May 2, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $168 per night from May 11 to May 12
$168
includes taxes & fees
May 11 - May 12
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! (8,730 reviews)
"My stay was good! I did not like that breakfast was so expensive for hotel guests but the stay was good nonetheless."

Reviewed on May 1, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is $179 per night from May 9 to May 10
$179
includes taxes & fees
May 9 - May 10
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! (2,175 reviews)
"We would return for another long weekend, highly recommend"

Reviewed on May 2, 2025

Hilton Chicago/Magnificent Mile Suites
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is $200 per night from May 9 to May 10
$200
includes taxes & fees
May 9 - May 10
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,003 reviews)
"Clean comfortable rooms. The staff was friendly and very accommodating."

Reviewed on Apr 29, 2025

The Westin Michigan Avenue Chicago
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is $231 per night from May 11 to May 12
$231
includes taxes & fees
May 11 - May 12
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
8.8/10 Excellent! (2,075 reviews)
"Stayed at Swissotel but very close to Hyatt Regency Chicago (0.2 miles) where my meeting was held."

Reviewed on Apr 30, 2025

Swissotel - Chicago
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $140 per night from May 4 to May 5
$140
includes taxes & fees
May 4 - May 5
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (4,103 reviews)
"Staff was amazing"

Reviewed on May 2, 2025

River Hotel
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 out of 5
200 North Columbus Drive, Chicago, IL
The price is $240 per night from May 9 to May 10
$240
includes taxes & fees
May 9 - May 10
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,695 reviews)
"The Fairmont was amazing for our weekend vacation. The staff was very nice and accommodating. We needed to check-in early and check-out late and was able to do this for a simple fee. Everything was very clean in this hotel and our view of the parks and Lake Michigan did not disappoint. The massage ..."

Reviewed on May 2, 2025

Fairmont Chicago at Millennium Park
See all 18,720 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.