Cheap flights To Historic Route 66 (CHI) from $40

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Cheap Flights to Historic Route 66 from $40 One Way, $80 Round Trip

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

Tue, May 27 - Fri, May 30
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, May 27 from Newark Liberty Intl. Airport to O'Hare Intl., returning Fri, May 30, priced at $80 just found
Sat, May 31 - Wed, Jun 4
LGA
LaGuardia
ORD
O'Hare Intl.
$81 Roundtrip, found 2 hours ago
$81
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, May 31 from LaGuardia to O'Hare Intl., returning Wed, Jun 4, priced at $81 found 2 hours ago
Wed, May 14 - Tue, May 27
LGA
LaGuardia
ORD
O'Hare Intl.
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
Select United flight, departing Wed, May 14 from LaGuardia to O'Hare Intl., returning Tue, May 27, priced at $139 found 4 days ago
Wed, May 28 - Fri, May 30
LGA
LaGuardia
MDW
Midway Intl.
$140 Roundtrip, just found
$140
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, May 28 from LaGuardia to Midway Intl., returning Fri, May 30, priced at $140 just found
Wed, May 28 - Fri, May 30
LGA
LaGuardia
ORD
O'Hare Intl.
$140 Roundtrip, just found
$140
Roundtrip
just found
Select Delta flight, departing Wed, May 28 from LaGuardia to O'Hare Intl., returning Fri, May 30, priced at $140 just found
Wed, May 21 - Wed, May 21
LGA
LaGuardia
ORD
O'Hare Intl.
$140 Roundtrip, found 2 days ago
$140
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, May 21 from LaGuardia to O'Hare Intl., returning Wed, May 21, priced at $140 found 2 days ago
Sun, May 25 - Wed, May 28
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$159 Roundtrip, just found
$159
Roundtrip
just found
Select Delta flight, departing Sun, May 25 from Newark Liberty Intl. Airport to Midway Intl., returning Wed, May 28, priced at $159 just found
Wed, May 14 - Wed, May 14
LGA
LaGuardia
MDW
Midway Intl.
$205 Roundtrip, found 3 days ago
$205
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, May 14 from LaGuardia to Midway Intl., returning Wed, May 14, priced at $205 found 3 days ago
Wed, May 28 - Thu, Jun 5
EWR
Newark Liberty Intl. Airport
ABQ
Albuquerque Intl. Sunport
$210 Roundtrip, found 2 days ago
$210
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, May 28 from Newark Liberty Intl. Airport to Albuquerque Intl. Sunport, returning Thu, Jun 5, priced at $210 found 2 days ago
Thu, Aug 14 - Sun, Aug 17
LGA
LaGuardia
STL
Lambert-St. Louis Intl.
$210 Roundtrip, found 3 hours ago
$210
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Aug 14 from LaGuardia to Lambert-St. Louis Intl., returning Sun, Aug 17, priced at $210 found 3 hours ago

Historic Route 66 Flight Information

Traveling To
Historic Route 66
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Spirit Airlines, Southwest Airlines, United, Delta, American Airlines, Frontier Airlines
Flight Price
$80
Earliest Departing Flight
Latest Departing Flight

Flights Review

Mar 10, 2018

Great overall service. Smooth landing. Plane was even early.

A verified traveler
Denver to Chicago · United

Book Your Flight & Hotel Together & Save

Historic Route 66 economy flight packages

Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
4.5-star property

Kimpton Gray Hotel by IHG

Jun 14 - Jun 16

2 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Westgate Branson Lakes Resort
4.0-star property

Westgate Branson Lakes Resort

Jun 26 - Jul 1

5 night stay

Newark Liberty Intl. Airport (EWR) to Springfield (SGF)

United • Non-stop • Coach

Springfield (SGF) to Newark Liberty Intl. Airport (EWR)

American Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
Still Waters Resort
4.0-star property

Still Waters Resort

Jun 26 - Jul 1

5 night stay

Newark Liberty Intl. Airport (EWR) to Springfield (SGF)

United • Non-stop • Coach

Springfield (SGF) to Newark Liberty Intl. Airport (EWR)

American Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
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See all available trips from Atlanta to Historic Route 66
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Historic Route 66 premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
3.5-star property

The Wildwood Hotel

9/10 Wonderful! (1,464 reviews)

Jun 15 - Jun 18

3 night stay

Atlanta (ATL) to St. Louis (STL)

Delta • Roundtrip • PremiumEconomy
per person
found 1 hour ago
The staff at this property were incredible. Everyone we talked to was friendly and helpful. I even left something of value behind and they had it shipped to me and I am ever so grateful. The room and the amenities were great and the hotel is in an area that feels safe and has a walking path nearby and also shopping and dining. We would definitely stay here again.

Reviewed on Apr 21, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (1,605 reviews)

Jun 18 - Jun 22

4 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Delta • Non-stop • PremiumEconomy

Chicago (ORD) to Newark Liberty Intl. Airport (EWR)

United • Non-stop • PremiumEconomy
Save 100% on your flight
per person
found 22 hours ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

8.8/10 Excellent! (1,988 reviews)

Jun 18 - Jun 22

4 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Delta • Non-stop • PremiumEconomy

Chicago (ORD) to Newark Liberty Intl. Airport (EWR)

United • Non-stop • PremiumEconomy
per person
found 22 hours ago
Had an amazing stay beautiful hotel

Reviewed on Feb 16, 2025

Don't see what you're looking for?
See all available trips from Atlanta to Historic Route 66
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Historic Route 66 first class flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Branson Lakes Resort
4.0-star property

Westgate Branson Lakes Resort

8/10 Very Good! (685 reviews)

Jun 5 - Jun 9

4 night stay

Philadelphia (PHL) to Springfield (SGF)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
Beautiful lake view!

Reviewed on Apr 14, 2024

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

8.8/10 Excellent! (1,988 reviews)

Jun 18 - Jun 23

5 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Delta • Non-stop • FirstClass

Chicago (ORD) to Newark Liberty Intl. Airport (EWR)

American Airlines • Non-stop • FirstClass
Save 100% on your flight
per person
found 22 hours ago
Had an amazing stay beautiful hotel

Reviewed on Feb 16, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (1,605 reviews)

Jun 18 - Jun 23

5 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Delta • Non-stop • FirstClass

Chicago (ORD) to Newark Liberty Intl. Airport (EWR)

American Airlines • Non-stop • FirstClass
Save 100% on your flight
per person
found 22 hours ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Don't see what you're looking for?
See all available trips from Philadelphia to Historic Route 66
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Historic Route 66

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.