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Historic Route 66 Vacation Packages

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Historic Route 66 Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $414, price is now $231 per person
$231
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
Book a stay at this business-friendly hotel in Wildwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Six Flags St. Louis and Skid Row are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $2,279, price is now $1,282 per person
$1,282
per person
Jul 24 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $836, price is now $514 per person
$514
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,085, price is now $671 per person
$671
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,265, price is now $788 per person
$788
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $958, price is now $623 per person
$623
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Save 100% on your flight
Price was $1,111, price is now $732 per person
$732
per person
Jul 24 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe Country Club are located nearby.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $643, price is now $430 per person
$430
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.

Historic Route 66 Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $602, price is now $309 per person
$309
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $836, price is now $514 per person
$514
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,085, price is now $671 per person
$671
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,265, price is now $788 per person
$788
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Historic Route 66 Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,522, price is now $822 per person
$822
per person
Aug 12 - Aug 18
found 8 hours ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $2,592, price is now $1,326 per person
$1,326
per person
Jul 24 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,279, price is now $1,282 per person
$1,282
per person
Jul 24 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,809, price is now $1,066 per person
$1,066
per person
Aug 12 - Aug 18
found 8 hours ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Sat, Aug 15 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$176 Roundtrip, found 5 days ago
$176
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 15 from Los Angeles Intl. to O'Hare Intl., returning Wed, Sep 2, priced at $176 found 5 days ago
Bargain Flight
Tue, Aug 25 - Tue, Sep 15
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$198 Roundtrip, found 2 hours ago
$198
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Tue, Aug 25 from Los Angeles Intl. to Albuquerque Intl. Sunport, returning Tue, Sep 15, priced at $198 found 2 hours ago
American Airlines
Tue, Aug 18 - Tue, Aug 25
LAX
Los Angeles Intl.
SAF
Santa Fe Municipal
$207 Roundtrip, found 9 hours ago
$207
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Aug 18 from Los Angeles Intl. to Santa Fe Municipal, returning Tue, Aug 25, priced at $207 found 9 hours ago
Frontier Airlines
Wed, Sep 2 - Tue, Sep 15
LAX
Los Angeles Intl.
OKC
Will Rogers World
$230 Roundtrip, found 7 hours ago
$230
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Will Rogers World, returning Tue, Sep 15, priced at $230 found 7 hours ago

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