Cheap Flights To Historic Route 66 2025

Historic Route 66 Flights as Low as $180

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, May 10 - Thu, May 15
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$180 Roundtrip, found 6 days ago
$180
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 10 from Hopkins Intl. to O'Hare Intl., returning Thu, May 15, priced at $180 found 6 days ago
Frontier Airlines
Mon, May 5 - Thu, May 15
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$190 Roundtrip, found 6 days ago
$190
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, May 5 from Hopkins Intl. to O'Hare Intl., returning Thu, May 15, priced at $190 found 6 days ago
Frontier Airlines
Sat, May 10 - Mon, May 12
CLE
Hopkins Intl.
MDW
Midway Intl.
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 10 from Hopkins Intl. to Midway Intl., returning Mon, May 12, priced at $191 found 1 day ago
Frontier Airlines
Mon, May 5 - Sat, May 10
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$198 Roundtrip, found 6 days ago
$198
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, May 5 from Hopkins Intl. to O'Hare Intl., returning Sat, May 10, priced at $198 found 6 days ago
Frontier Airlines
Sun, May 11 - Mon, May 12
CLE
Hopkins Intl.
MDW
Midway Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 11 from Hopkins Intl. to Midway Intl., returning Mon, May 12, priced at $200 found 1 day ago
Frontier Airlines
Thu, May 8 - Sun, May 11
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$208 Roundtrip, found 6 days ago
$208
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, May 8 from Hopkins Intl. to O'Hare Intl., returning Sun, May 11, priced at $208 found 6 days ago
Frontier Airlines
Thu, May 8 - Mon, May 12
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$210 Roundtrip, found 6 days ago
$210
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, May 8 from Hopkins Intl. to O'Hare Intl., returning Mon, May 12, priced at $210 found 6 days ago
Frontier Airlines
Sat, Jun 14 - Mon, Jun 16
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$212 Roundtrip, found 20 hours ago
$212
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sat, Jun 14 from Hopkins Intl. to O'Hare Intl., returning Mon, Jun 16, priced at $212 found 20 hours ago
Frontier Airlines
Thu, May 8 - Sun, May 11
CLE
Hopkins Intl.
MDW
Midway Intl.
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 8 from Hopkins Intl. to Midway Intl., returning Sun, May 11, priced at $220 found 1 day ago
Frontier Airlines
Fri, May 9 - Fri, May 9
CLE
Hopkins Intl.
MDW
Midway Intl.
$225 Roundtrip, found 1 day ago
$225
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, May 9 from Hopkins Intl. to Midway Intl., returning Fri, May 9, priced at $225 found 1 day ago
Frontier Airlines
Fri, Jun 13 - Fri, Jun 13
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$227 Roundtrip, found 20 hours ago
$227
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Fri, Jun 13 from Hopkins Intl. to O'Hare Intl., returning Fri, Jun 13, priced at $227 found 20 hours ago
Frontier Airlines
Thu, May 8 - Mon, May 12
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$228 Roundtrip, found 6 days ago
$228
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, May 8 from Hopkins Intl. to O'Hare Intl., returning Mon, May 12, priced at $228 found 6 days ago
American Airlines
Thu, Jun 12 - Mon, Jun 16
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$263 Roundtrip, found 20 hours ago
$263
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Thu, Jun 12 from Hopkins Intl. to O'Hare Intl., returning Mon, Jun 16, priced at $263 found 20 hours ago
United
Thu, Jun 12 - Mon, Jun 16
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$263 Roundtrip, found 20 hours ago
$263
Roundtrip
found 20 hours ago
Select United flight, departing Thu, Jun 12 from Hopkins Intl. to O'Hare Intl., returning Mon, Jun 16, priced at $263 found 20 hours ago
Delta
Tue, Jun 10 - Sun, Jun 15
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$277 Roundtrip, found 20 hours ago
$277
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Jun 10 from Hopkins Intl. to O'Hare Intl., returning Sun, Jun 15, priced at $277 found 20 hours ago
JetBlue Airways
Wed, May 7 - Tue, May 13
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$373 Roundtrip, found 6 days ago
$373
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, May 7 from Hopkins Intl. to O'Hare Intl., returning Tue, May 13, priced at $373 found 6 days ago

Cheap Historic Route 66 Flights

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See the vast selection of cheap flights for seniors in Historic Route 66 for yourself by simply entering your travel dates and destinations. This time and money-saving search engine will then produce a variety of travel times, airline carriers, and senior flights in Historic Route 66, so you can find the flight best suiting your travel plans. What’s more, on top of these deals, AARP members are exempt from paying any additional booking fees associated with Historic Route 66 senior flights. Snatch these discount airline tickets and embark on your adventure today.