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Historic Route 66

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Historic Route 66 Flights as Low as $106

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

Frontier Airlines
Fri, May 9 - Sat, May 10
TPA
Tampa Intl.
ORD
O'Hare Intl.
$106 Roundtrip, just found
$106
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 9 from Tampa Intl. to O'Hare Intl., returning Sat, May 10, priced at $106 just found
Frontier Airlines
Fri, May 9 - Sat, May 10
TPA
Tampa Intl.
ORD
O'Hare Intl.
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 9 from Tampa Intl. to O'Hare Intl., returning Sat, May 10, priced at $112 just found
Frontier Airlines
Sat, May 10 - Mon, May 12
TPA
Tampa Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 10 from Tampa Intl. to O'Hare Intl., returning Mon, May 12, priced at $118 found 2 days ago
Spirit Airlines
Fri, May 9 - Sat, May 10
TPA
Tampa Intl.
ORD
O'Hare Intl.
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, May 9 from Tampa Intl. to O'Hare Intl., returning Sat, May 10, priced at $118 just found
Frontier Airlines
Fri, May 9 - Mon, May 12
TPA
Tampa Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 2 days ago
$124
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, May 9 from Tampa Intl. to O'Hare Intl., returning Mon, May 12, priced at $124 found 2 days ago
Spirit Airlines
Tue, Apr 15 - Sun, Apr 20
TPA
Tampa Intl.
ORD
O'Hare Intl.
$131 Roundtrip, found 6 days ago
$131
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Apr 15 from Tampa Intl. to O'Hare Intl., returning Sun, Apr 20, priced at $131 found 6 days ago
Frontier Airlines
Thu, May 8 - Sun, May 11
TPA
Tampa Intl.
MDW
Midway Intl.
$133 Roundtrip, just found
$133
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, May 8 from Tampa Intl. to Midway Intl., returning Sun, May 11, priced at $133 just found
Delta
Sat, Aug 30 - Sat, Aug 30
TPA
Tampa Intl.
ORD
O'Hare Intl.
$191 Roundtrip, found 17 hours ago
$191
Roundtrip
found 17 hours ago
Select Delta flight, departing Sat, Aug 30 from Tampa Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $191 found 17 hours ago
Delta
Wed, May 7 - Sat, May 10
TPA
Tampa Intl.
STL
Lambert-St. Louis Intl.
$203 Roundtrip, found 6 days ago
$203
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, May 7 from Tampa Intl. to Lambert-St. Louis Intl., returning Sat, May 10, priced at $203 found 6 days ago
United
Tue, Apr 29 - Wed, Apr 30
TPA
Tampa Intl.
ORD
O'Hare Intl.
$209 Roundtrip, found 4 days ago
$209
Roundtrip
found 4 days ago
Select United flight, departing Tue, Apr 29 from Tampa Intl. to O'Hare Intl., returning Wed, Apr 30, priced at $209 found 4 days ago
Frontier Airlines
Tue, May 6 - Thu, May 8
TPA
Tampa Intl.
OKC
Will Rogers World
$210 Roundtrip, found 6 days ago
$210
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, May 6 from Tampa Intl. to Will Rogers World, returning Thu, May 8, priced at $210 found 6 days ago
American Airlines
Fri, May 9 - Sat, May 10
TPA
Tampa Intl.
ORD
O'Hare Intl.
$218 Roundtrip, just found
$218
Roundtrip
just found
Select American Airlines flight, departing Fri, May 9 from Tampa Intl. to O'Hare Intl., returning Sat, May 10, priced at $218 just found
Delta
Tue, Jun 10 - Sun, Jun 15
TPA
Tampa Intl.
SGF
Springfield-Branson National
$249 Roundtrip, found 5 days ago
$249
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jun 10 from Tampa Intl. to Springfield-Branson National, returning Sun, Jun 15, priced at $249 found 5 days ago
American Airlines
Sun, Apr 20 - Tue, Apr 29
TPA
Tampa Intl.
SAF
Santa Fe Municipal
$339 Roundtrip, found 4 days ago
$339
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Apr 20 from Tampa Intl. to Santa Fe Municipal, returning Tue, Apr 29, priced at $339 found 4 days ago
American Airlines
Fri, May 9 - Fri, May 16
TPA
Tampa Intl.
FLG
Flagstaff Pulliam Field
$486 Roundtrip, found 6 days ago
$486
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 9 from Tampa Intl. to Flagstaff Pulliam Field, returning Fri, May 16, priced at $486 found 6 days ago
JetBlue Airways
Thu, Aug 28 - Sun, Aug 31
TPA
Tampa Intl.
ORD
O'Hare Intl.
$496 Roundtrip, found 16 hours ago
$496
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Thu, Aug 28 from Tampa Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $496 found 16 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 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 $106, 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 $106 right now, why wait?

Historic Route 66 Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$120

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 $144 per night from Apr 20 to Apr 21
$144
includes taxes & fees
Apr 20 - Apr 21
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! (3,393 reviews)
"I enjoy staying at this property for work conferences. It is well situated and a great price. I just always forget that the A/C situation can really vary based on room/season."

Reviewed on Apr 10, 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 $159 per night from Apr 20 to Apr 21
$159
includes taxes & fees
Apr 20 - Apr 21
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! (3,873 reviews)
"Excellent quick friendly service! Staff is outstanding:)"

Reviewed on Apr 11, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 $70 per night from Apr 14 to Apr 15
$70
includes taxes & fees
Apr 14 - Apr 15
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! (6,271 reviews)
"It was good for the price, nothing particularly special though."

Reviewed on Apr 11, 2025

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
The price is $139 per night from Apr 21 to Apr 22
$139
includes taxes & fees
Apr 21 - Apr 22
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! (2,112 reviews)
"Hotel was very nice. Convenient to shopping and dining."

Reviewed on Apr 10, 2025

Hilton Chicago/Magnificent Mile Suites
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
The price is $108 per night from Apr 20 to Apr 21
$108
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,009 reviews)
"Excellent property. Safe location. Convenient check in and check out."

Reviewed on Apr 10, 2025

Crowne Plaza Chicago West Loop by IHG
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is $212 per night from Apr 16 to Apr 17
$212
includes taxes & fees
Apr 16 - Apr 17
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! (2,043 reviews)
"The hotel is nice. The amenities are good."

Reviewed on Apr 12, 2025

Swissotel - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $147 per night from Apr 14 to Apr 15
$147
includes taxes & fees
Apr 14 - Apr 15
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! (8,656 reviews)
"Nice place"

Reviewed on Apr 8, 2025

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $136 per night from Apr 20 to Apr 21
$136
includes taxes & fees
Apr 20 - Apr 21
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! (4,036 reviews)
"It was great, but my biggest complaint is you don't seem to be able to change the temperature in your room other than using the fan. Our room was so hot we couldn't sleep the first night, and we ran into another guest down in the lounge having the same problem. Other complaint is the shower; it is ..."

Reviewed on Apr 11, 2025

River Hotel
See all 18,570 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.