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

theWit Chicago, a Hilton Hotel
Save 100% on your flight
Price was $232, price is now $115 per person
$115
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Sheraton Suites Chicago Elk Grove
Save 100% on your flight
Price was $339, price is now $172 per person
$172
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Woodfield Mall and Allstate Arena are located nearby.

Level Chicago – Old Town
Save 100% on your flight
Price was $1,271, price is now $659 per person
$659
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.

The Wildwood Hotel
Save 100% on your flight
Price was $685, price is now $358 per person
$358
per person
Jan 7 - Jan 11
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.

Chicago Marriott Suites O'Hare
Save 100% on your flight
Price was $472, price is now $249 per person
$249
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Rivers Casino are located nearby.

Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $292, price is now $157 per person
$157
per person
Jan 30 - Feb 1
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.

Westgate Branson Woods Resort and Cabins
Price was $1,062, price is now $587 per person
$587
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (SGF)
Book a stay at this family-friendly resort in Branson. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Silver Dollar City and Sight and Sound Theatres are located nearby.

Pendry Chicago
Save 100% on your flight
Price was $310, price is now $174 per person
$174
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms 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.

Thu, Dec 11 - Mon, Dec 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$128 Roundtrip, found 3 days ago
$128
Roundtrip
found 3 days ago

Wed, Feb 25 - Mon, Mar 9
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$192 Roundtrip, found 19 hours ago
$192
Roundtrip
found 19 hours ago

Tue, Jan 27 - Sat, Jan 31
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$201 Roundtrip, found 1 day ago
$201
Roundtrip
found 1 day ago

Tue, Jan 6 - Sun, Jan 11
LAX
Los Angeles Intl.
TUL
Tulsa Intl.
$231 Roundtrip, found 8 hours ago
$231
Roundtrip
found 8 hours ago
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