Search Deals onHistoric Route 66 Vacation Packages
Historic Route 66 Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Hilton Grand Vacations Club Chicago Magnificent Mile
Price was $444, price is now $217 per person
$217
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

The Westin Michigan Avenue Chicago
Price was $1,560, price is now $624 per person
$624
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Westgate Branson Lakes Resort
Save 100% on your flight
Price was $991, price is now $527 per person
$527
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (SGF)
Stay at this 4-star family-friendly hotel in Hollister. Enjoy free parking, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Table Rock Lake and Top of the Rock Golf Course are located nearby.

Pendry Chicago
Save 100% on your flight
Price was $480, price is now $258 per person
$258
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

The Emily Hotel
Save 100% on your flight
Price was $1,262, price is now $685 per person
$685
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.

Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $423, price is now $230 per person
$230
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.

Trump International Hotel & Tower Chicago
Price was $1,833, price is now $1,015 per person
$1,015
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Arlo Chicago
Save 100% on your flight
Price was $788, price is now $441 per person
$441
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Historic Route 66 Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Historic Route 66 Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



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

Sat, Nov 8 - Sat, Nov 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago

Wed, Nov 19 - Sat, Dec 6
LAX
Los Angeles Intl.
OKC
Will Rogers World
$120 Roundtrip, found 1 hour ago
$120
Roundtrip
found 1 hour ago

Thu, Nov 13 - Mon, Nov 17
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$120 Roundtrip, found 4 hours ago
$120
Roundtrip
found 4 hours ago

Sat, Nov 1 - Thu, Nov 6
LAX
Los Angeles Intl.
MDW
Midway Intl.
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
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