Search Cheap Flights to
Historic Route 66

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Historic Route 66 Flights as Low as $138

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

Frontier Airlines
Tue, Dec 31 - Mon, Jan 6
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 4 hours ago
$138
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Dec 31 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Mon, Jan 6, priced at $138 found 4 hours ago
Frontier Airlines
Mon, Dec 23 - Wed, Jan 1
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$158 Roundtrip, found 3 days ago
$158
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Dec 23 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Wed, Jan 1, priced at $158 found 3 days ago
Frontier Airlines
Sun, Dec 22 - Tue, Dec 24
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Dec 22 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Tue, Dec 24, priced at $164 found 3 days ago
Frontier Airlines
Tue, Dec 31 - Fri, Jan 3
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$168 Roundtrip, found 4 hours ago
$168
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Dec 31 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Fri, Jan 3, priced at $168 found 4 hours ago
Delta
Tue, Dec 24 - Wed, Dec 25
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$176 Roundtrip, found 3 days ago
$176
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Dec 24 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Wed, Dec 25, priced at $176 found 3 days ago
Delta
Thu, Dec 19 - Wed, Dec 25
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$181 Roundtrip, found 3 days ago
$181
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 19 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Wed, Dec 25, priced at $181 found 3 days ago
Delta
Thu, Dec 19 - Mon, Dec 30
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 19 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Mon, Dec 30, priced at $186 found 3 days ago
American Airlines
Wed, Dec 25 - Wed, Dec 25
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Dec 25 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Wed, Dec 25, priced at $197 found 4 hours ago
Frontier Airlines
Sun, Dec 22 - Tue, Dec 24
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Dec 22 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Tue, Dec 24, priced at $208 found 3 days ago
Frontier Airlines
Tue, Dec 31 - Thu, Jan 2
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$208 Roundtrip, found 4 hours ago
$208
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Dec 31 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Thu, Jan 2, priced at $208 found 4 hours ago
American Airlines
Wed, Dec 25 - Mon, Dec 30
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$212 Roundtrip, found 4 hours ago
$212
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Dec 25 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Mon, Dec 30, priced at $212 found 4 hours ago
United
Sun, Dec 22 - Tue, Dec 24
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$213 Roundtrip, found 3 days ago
$213
Roundtrip
found 3 days ago
Select United flight, departing Sun, Dec 22 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Tue, Dec 24, priced at $213 found 3 days ago
American Airlines
Sun, Dec 22 - Tue, Dec 24
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$215 Roundtrip, found 3 days ago
$215
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Dec 22 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Tue, Dec 24, priced at $215 found 3 days ago
Frontier Airlines
Sat, Nov 23 - Wed, Nov 27
CVG
Cincinnati - Northern Kentucky Intl.
OKC
Will Rogers World
$282 Roundtrip, found 11 hours ago
$282
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sat, Nov 23 from Cincinnati - Northern Kentucky Intl. to Will Rogers World, returning Wed, Nov 27, priced at $282 found 11 hours ago
Delta
Fri, Nov 22 - Mon, Nov 25
CVG
Cincinnati - Northern Kentucky Intl.
TUL
Tulsa Intl.
$294 Roundtrip, found 5 days ago
$294
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Nov 22 from Cincinnati - Northern Kentucky Intl. to Tulsa Intl., returning Mon, Nov 25, priced at $294 found 5 days ago
American Airlines
Tue, Nov 26 - Sun, Dec 1
CVG
Cincinnati - Northern Kentucky Intl.
SGF
Springfield-Branson National
$553 Roundtrip, found 4 days ago
$553
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Nov 26 from Cincinnati - Northern Kentucky Intl. to Springfield-Branson National, returning Sun, Dec 1, priced at $553 found 4 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 December, 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 $138, 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 $138 right now, why wait?

Historic Route 66 Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$98

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 $119 per night from Dec 17 to Dec 18
$119
includes taxes & fees
Dec 17 - Dec 18
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 ...
8.4/10 Very Good! (3,249 reviews)
"This was perfect hotel for people traveling who want an easy and convenient stay in central chicago near the loop! Plus also loved the soap / lotion brand they use for there toiletries."

Reviewed on Nov 15, 2024

Club Quarters Hotel, Central Loop, Chicago
Central Loop Hotel
Central Loop Hotel
4 out of 5
111 West Adams Street, Chicago, IL
The price is $119 per night from Dec 17 to Dec 18
$119
includes taxes & fees
Dec 17 - Dec 18
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff ...
8.4/10 Very Good! (1,685 reviews)
"Stayed in a few Club Quarters hotels. Always a pleasure. This one is in a superb location. Room even has a fridge with a small freezer and a microwave. So saves costs in eating out (solo traveller). Only downside is, no tea bags provided. (I do think I had some available when I stayed at one of their ..."

Reviewed on Nov 14, 2024

Central Loop Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $115 per night from Nov 24 to Nov 25
$115
includes taxes & fees
Nov 24 - Nov 25
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! (8,072 reviews)
"Rooms are a little old, toilet got stuck, and has an odd smell to the room. But stuff are nice, and it was in a nice area, but I’ve stayed at hotels around the area for cheaper that have nicer rooms."

Reviewed on Nov 14, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $123 per night from Dec 17 to Dec 18
$123
includes taxes & fees
Dec 17 - Dec 18
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! (3,544 reviews)
"This hotel is a wonderful place, I was there around 8:00 on the 14th of November and The Man Behind The Desk was exceptional! He went above and beyond to get me the room that I was asking for. I did not get the gentleman's name but this hotel needs more people just like him. The River Hotel on Wacker ..."

Reviewed on Nov 16, 2024

River 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
The price is $68 per night from Dec 1 to Dec 2
$68
includes taxes & fees
Dec 1 - Dec 2
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! (5,989 reviews)
I saw goats!
"Location and river view from the California tower was better than expected. An unexpected bonus was seeing a herd of goats on the little island near the Arizona water taxi landing from my 7th floor room. After staying on Fremont Street for the last few decades and seeing how Las Vegas has deteriorated ..."

Reviewed on Nov 13, 2024

The Aquarius Casino Resort, BW Premier Collection
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $158 per night from Dec 16 to Dec 17
$158
includes taxes & fees
Dec 16 - Dec 17
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (2,738 reviews)
"It was beautiful, clean, amazing views staff was great restaurants nearby"

Reviewed on Nov 15, 2024

Eurostars Magnificent Mile
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
The price is $127 per night from Dec 9 to Dec 10
$127
includes taxes & fees
Dec 9 - Dec 10
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 ...
7.8/10 Good! (1,261 reviews)
"Overall is great, especially free luggage storage service even checked out."

Reviewed on Nov 15, 2024

Hotel Felix River North/Magnificent Mile
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is $194 per night from Nov 25 to Nov 26
$194
includes taxes & fees
Nov 25 - Nov 26
Book a stay at this spa 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! (1,002 reviews)
"Location couldn’t be better. Property shows a little wear and our room didn’t have much of a view, but the bed was comfortable and the room was quiet."

Reviewed on Nov 11, 2024

The Westin Michigan Avenue Chicago
See all 18,441 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.