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Historic Route 66

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Historic Route 66 Flights as Low as $129

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

American Airlines
Tue, Sep 9 - Mon, Sep 15
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$129 Roundtrip, found 1 hour ago
$129
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Sep 9 from O'Hare Intl. to Lambert-St. Louis Intl., returning Mon, Sep 15, priced at $129 found 1 hour ago
United
Tue, Sep 9 - Mon, Sep 15
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$129 Roundtrip, found 1 hour ago
$129
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Sep 9 from O'Hare Intl. to Lambert-St. Louis Intl., returning Mon, Sep 15, priced at $129 found 1 hour ago
Sun Country Airlines
Sat, Jun 7 - Mon, Jun 9
MSP
Minneapolis - St. Paul Intl.
STL
Lambert-St. Louis Intl.
$147 Roundtrip, found 1 hour ago
$147
Roundtrip
found 1 hour ago
Select Sun Country Airlines flight, departing Sat, Jun 7 from Minneapolis - St. Paul Intl. to Lambert-St. Louis Intl., returning Mon, Jun 9, priced at $147 found 1 hour ago
Bargain Flight
Thu, Jul 24 - Mon, Jul 28
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 5 hours ago
$153
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Thu, Jul 24 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Jul 28, priced at $153 found 5 hours ago
Delta
Sat, Jul 5 - Sat, Jul 5
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jul 5 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Sat, Jul 5, priced at $179 found 2 days ago
Southern Airways Express
Tue, Sep 9 - Mon, Sep 15
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$185 Roundtrip, found 1 hour ago
$185
Roundtrip
found 1 hour ago
Select Southern Airways Express flight, departing Tue, Sep 9 from O'Hare Intl. to Lambert-St. Louis Intl., returning Mon, Sep 15, priced at $185 found 1 hour ago
Frontier Airlines
Sun, Jun 8 - Sat, Jun 14
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Jun 8 from Minneapolis - St. Paul Intl. to Midway Intl., returning Sat, Jun 14, priced at $197 found 2 days ago
Frontier Airlines
Mon, Jun 16 - Sat, Jun 21
MSP
Minneapolis - St. Paul Intl.
OKC
Will Rogers World
$200 Roundtrip, found 3 days ago
$200
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Jun 16 from Minneapolis - St. Paul Intl. to Will Rogers World, returning Sat, Jun 21, priced at $200 found 3 days ago
American Airlines
Wed, Jul 30 - Tue, Aug 12
ORD
O'Hare Intl.
SGF
Springfield-Branson National
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 30 from O'Hare Intl. to Springfield-Branson National, returning Tue, Aug 12, priced at $217 found 4 days ago
Delta
Wed, Jul 30 - Wed, Aug 6
MSP
Minneapolis - St. Paul Intl.
ABQ
Albuquerque Intl. Sunport
$224 Roundtrip, found 3 days ago
$224
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jul 30 from Minneapolis - St. Paul Intl. to Albuquerque Intl. Sunport, returning Wed, Aug 6, priced at $224 found 3 days ago
Frontier Airlines
Thu, Jun 19 - Sun, Jun 22
ORD
O'Hare Intl.
OKC
Will Rogers World
$235 Roundtrip, found 5 days ago
$235
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Jun 19 from O'Hare Intl. to Will Rogers World, returning Sun, Jun 22, priced at $235 found 5 days ago
United
Tue, Jul 1 - Fri, Jul 4
ORD
O'Hare Intl.
TUL
Tulsa Intl.
$235 Roundtrip, found 1 day ago
$235
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jul 1 from O'Hare Intl. to Tulsa Intl., returning Fri, Jul 4, priced at $235 found 1 day ago
Bargain Flight
Wed, Jul 30 - Wed, Jul 30
MSP
Minneapolis - St. Paul Intl.
TUL
Tulsa Intl.
$240 Roundtrip, found 2 days ago
$240
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, Jul 30 from Minneapolis - St. Paul Intl. to Tulsa Intl., returning Wed, Jul 30, priced at $240 found 2 days ago
American Airlines
Tue, Jul 8 - Mon, Jul 14
MSP
Minneapolis - St. Paul Intl.
SGF
Springfield-Branson National
$254 Roundtrip, found 2 days ago
$254
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jul 8 from Minneapolis - St. Paul Intl. to Springfield-Branson National, returning Mon, Jul 14, priced at $254 found 2 days ago
Alaska Airlines
Tue, Sep 30 - Sat, Oct 4
ORD
O'Hare Intl.
ABQ
Albuquerque Intl. Sunport
$375 Roundtrip, found 6 days ago
$375
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Sep 30 from O'Hare Intl. to Albuquerque Intl. Sunport, returning Sat, Oct 4, priced at $375 found 6 days ago
American Airlines
Sat, Mar 7 - Sat, Mar 14
ORD
O'Hare Intl.
FLG
Flagstaff Pulliam Field
$526 Roundtrip, found 2 days ago
$526
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Mar 7 from O'Hare Intl. to Flagstaff Pulliam Field, returning Sat, Mar 14, priced at $526 found 2 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 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 14 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 $129, 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 $129 right now, why wait?

Historic Route 66 Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$140

Last Minute Hotel Deals in Historic Route 66

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! (8,841 reviews)
"Drawers in room would not close properly."

Reviewed on Jun 4, 2025

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Congress Plaza Hotel
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! (3,132 reviews)
"Nice clean hotel. Close to it all downtown"

Reviewed on Jun 2, 2025

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citizenM Chicago Downtown
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! (2,270 reviews)
"Beautiful space, right near the lake. Also has a cozy little restaurant on the 1st floor"

Reviewed on Jun 3, 2025

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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
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 ...
8.8/10 Excellent! (1,009 reviews)
"Absolutely top tier!! Definitely a whole vibe."

Reviewed on May 30, 2025

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The Westin Michigan Avenue Chicago
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold Coast
4 out of 5
1301 N State Pkwy, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,016 reviews)
"Great environment"

Reviewed on Jun 1, 2025

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The Chicago Hotel Collection Ambassador Gold Coast
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 out of 5
200 North Columbus Drive, Chicago, IL
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 ...
8.6/10 Excellent! (1,750 reviews)
"Room was spacious and clean. Amenities were great. Staff was friendly. We dined at Toro and it was amazing. Highly recommend"

Reviewed on Jun 4, 2025

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Fairmont Chicago at Millennium Park
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! (1,728 reviews)
"Thoroughly enjoyed our stay!! The room was very clean, friendly and accommodating staff, and great location."

Reviewed on May 30, 2025

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Hotel Felix River North/Magnificent Mile
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
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! (2,199 reviews)
"Wonderful accommodations and staff, and the Palm restaurant was great and of course convenient. Will stay there again."

Reviewed on Jun 3, 2025

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Swissotel - Chicago
See all 18,845 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.