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Historic Route 66

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Historic Route 66 Flights as Low as $82

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

Spirit Airlines
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Frontier Airlines
Frontier Airlines
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Frontier Airlines
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American Airlines
Delta
United
Alaska Airlines
American Airlines

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 March, 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 $82, 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 $82 right now, why wait?

Historic Route 66 Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$102

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 $113 per night from Feb 1 to Feb 2
$113
includes taxes & fees
Feb 1 - Feb 2
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! (3,316 reviews)
"Nice old hotel in Chicago. Very walkable and easy access to restaurants. We did switch rooms as our first room had a view of some sort of beam or something. But I think that's going to be the case with many of these older buildings that are built tight and right next to each other."

Reviewed on Jan 13, 2025

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 $113 per night from Jan 28 to Jan 29
$113
includes taxes & fees
Jan 28 - Jan 29
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! (1,709 reviews)
"Clean"

Reviewed on Jan 16, 2025

Central Loop Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $126 per night from Jan 19 to Jan 20
$126
includes taxes & fees
Jan 19 - Jan 20
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! (8,385 reviews)
"The view from our room"

Reviewed on Jan 15, 2025

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $100 per night from Feb 17 to Feb 18
$100
includes taxes & fees
Feb 17 - Feb 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! (3,702 reviews)
"The service was excellent!"

Reviewed on Jan 15, 2025

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $110 per night from Feb 16 to Feb 17
$110
includes taxes & fees
Feb 16 - Feb 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! (2,796 reviews)
"It was great"

Reviewed on Jan 14, 2025

Eurostars Magnificent Mile
Pendry Chicago
Pendry Chicago
4.5 out of 5
230 North Michigan Avenue, Chicago, IL
The price is $235 per night from Feb 2 to Feb 3
$235
includes taxes & fees
Feb 2 - Feb 3
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff ...
9.2/10 Wonderful! (1,004 reviews)
"Good and beverage extremely overpriced"

Reviewed on Jan 13, 2025

Pendry Chicago
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
The price is $116 per night from Feb 5 to Feb 6
$116
includes taxes & fees
Feb 5 - Feb 6
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! (2,554 reviews)
"great place"

Reviewed on Jan 15, 2025

citizenM Chicago Downtown
Holiday Inn Chicago Dwtn - The Mart, an IHG Hotel
Holiday Inn Chicago Dwtn - The Mart, an IHG Hotel
3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
The price is $141 per night from Jan 30 to Jan 31
$141
includes taxes & fees
Jan 30 - Jan 31
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,336 reviews)
"They closed the restaurant on property which had really good food in the past. Disappointed in that."

Reviewed on Jan 16, 2025

Holiday Inn Chicago Dwtn - The Mart, an IHG Hotel
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.