Cheap flights To Historic Route 66 (CHI) from $50

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Cheap Flights to Historic Route 66 from $50 One Way, $101 Round Trip

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

Tue, Aug 11 - Sat, Aug 15
DFW
Dallas-Fort Worth Intl.
STL
Lambert-St. Louis Intl.
$101 Roundtrip, found 18 hours ago
$101
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Dallas-Fort Worth Intl. to Lambert-St. Louis Intl., returning Sat, Aug 15, priced at $101 found 18 hours ago
Sat, Oct 10 - Tue, Oct 13
DAL
Love Field
TUL
Tulsa Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Oct 10 from Love Field to Tulsa Intl., returning Tue, Oct 13, priced at $117 found 5 days ago
Sat, Jul 25 - Sat, Jul 25
DFW
Dallas-Fort Worth Intl.
TUL
Tulsa Intl.
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 25 from Dallas-Fort Worth Intl. to Tulsa Intl., returning Sat, Jul 25, priced at $120 found 3 days ago
Sat, Jul 25 - Tue, Jul 28
DFW
Dallas-Fort Worth Intl.
OKC
Will Rogers World
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 25 from Dallas-Fort Worth Intl. to Will Rogers World, returning Tue, Jul 28, priced at $120 found 3 days ago
Sat, Jul 25 - Tue, Jul 28
DAL
Love Field
OKC
Will Rogers World
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Jul 25 from Love Field to Will Rogers World, returning Tue, Jul 28, priced at $130 found 3 days ago
Sat, Sep 12 - Sat, Sep 19
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$148 Roundtrip, found 22 hours ago
$148
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Sat, Sep 12 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Sep 19, priced at $148 found 22 hours ago
Sat, Sep 5 - Sat, Sep 12
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 18 hours ago
$148
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Sep 12, priced at $148 found 18 hours ago
Tue, Aug 18 - Tue, Aug 25
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$171 Roundtrip, found 23 hours ago
$171
Roundtrip
found 23 hours ago
Select United flight, departing Tue, Aug 18 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Aug 25, priced at $171 found 23 hours ago
Sat, Oct 31 - Tue, Nov 3
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 31 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Nov 3, priced at $191 found 1 day ago
Tue, Aug 11 - Tue, Aug 18
DAL
Love Field
STL
Lambert-St. Louis Intl.
$212 Roundtrip, found 3 days ago
$212
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Aug 11 from Love Field to Lambert-St. Louis Intl., returning Tue, Aug 18, priced at $212 found 3 days ago

Historic Route 66 Flight Information

Traveling To
Historic Route 66
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Southwest Airlines, American Airlines, Delta, United
Flight Price
$101
Earliest Departing Flight
Latest Departing Flight

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Historic Route 66 premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (512 reviews)

Aug 7 - Aug 9

2 night stay

San Francisco (SFO) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,011, price is now $881 per person
$881
per person
found 1 day ago
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on Jul 2, 2026

The Peninsula Chicago
5.0-star property

The Peninsula Chicago

9.8/10 Exceptional! (1,003 reviews)

Aug 7 - Aug 9

2 night stay

San Francisco (SFO) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,632, price is now $1,296 per person
$1,296
per person
found 1 day ago
This beautiful hotel never fails to live up to their reputation. Old school quality and service never disappoints.

Reviewed on Jul 3, 2026

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,002 reviews)

Aug 7 - Aug 9

2 night stay

San Francisco (SFO) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,435, price is now $1,260 per person
$1,260
per person
found 1 day ago
Arrived 4:30PM, room not ready. Left bags with Bell Desk and went to a business dinner. Returned at 8pm, Bell Desk could not find my bags. Arrived an hour later, they had put them in the wrong room. No offer of any kind to remedy or try to remedy, just “sorry”. Shameful.

Reviewed on Jul 3, 2026

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Historic Route 66 first class flight packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago
2.0-star property

Travelodge by Wyndham Downtown Chicago

7.6/10 Good! (2,643 reviews)

Aug 5 - Aug 9

4 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,151, price is now $996 per person
$996
per person
found 23 hours ago
Rooms are small and dismal; carpets are well worn. Hotel offers no food or coffee or water. Location is good, but that’s the only real positive to this hotel; it’s not a nice place to stay nor a good value.

Reviewed on Jul 3, 2026

LondonHouse Chicago, Curio Collection by Hilton
4.5-star property

LondonHouse Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (3,764 reviews)

Aug 5 - Aug 9

4 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,525, price is now $1,177 per person
$1,177
per person
found 23 hours ago
Enjoyed!

Reviewed on Jul 3, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (1,899 reviews)

Aug 21 - Aug 23

2 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,307, price is now $1,062 per person
$1,062
per person
found 21 hours ago
The shower temp was about on the hot side no matter how low you had it. The bed& room were overall great

Reviewed on Jul 3, 2026

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Historic Route 66

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