Search Deals on
Historic Route 66 Vacation Packages

Build your package with 2 more options

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
Price was $698, price is now $340 per person
$340
per person
Jul 22 - Jul 26
found 21 hours 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 – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,660, price is now $996 per person
$996
per person
Aug 13 - Aug 17
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,064, price is now $649 per person
$649
per person
Sep 3 - Sep 6
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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,093, price is now $669 per person
$669
per person
Sep 3 - Sep 6
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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $877, price is now $537 per person
$537
per person
Sep 3 - Sep 6
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.
The Hacienda & Spa at Hotel Santa Fe

The Hacienda & Spa at Hotel Santa Fe

4.5 out of 5
Save 100% on your flight
Price was $3,705, price is now $2,347 per person
$2,347
per person
Aug 14 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albuquerque (ABQ)
Book a stay at this luxury hotel in Santa Fe. Enjoy free breakfast, a full-service spa, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Santa Fe Plaza and Santa Fe Railyard are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,016, price is now $644 per person
$644
per person
Aug 26 - Aug 29
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 a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Inn at Vanessie

The Inn at Vanessie

4.5 out of 5
Save 100% on your flight
Price was $2,945, price is now $1,888 per person
$1,888
per person
Aug 14 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albuquerque (ABQ)
Book a stay at this luxury hotel in Santa Fe. Enjoy daily housekeeping, concierge services, and satellite TV channels. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Santa Fe Plaza and Loretto Chapel 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
Price was $698, price is now $340 per person
$340
per person
Jul 22 - Jul 26
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,660, price is now $996 per person
$996
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,064, price is now $649 per person
$649
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,093, price is now $669 per person
$669
per person
Sep 3 - Sep 6
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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,093, price is now $653 per person
$653
per person
Sep 2 - Sep 8
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,559, price is now $839 per person
$839
per person
Sep 2 - Sep 8
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,596, price is now $874 per person
$874
per person
Aug 3 - Aug 10
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 $1,566, price is now $932 per person
$932
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Mon, Aug 31 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 18 hours ago
$120
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Los Angeles Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $120 found 18 hours ago
American Airlines
Tue, Aug 25 - Tue, Sep 15
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$137 Roundtrip, found 7 hours ago
$137
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Aug 25 from Los Angeles Intl. to Albuquerque Intl. Sunport, returning Tue, Sep 15, priced at $137 found 7 hours ago
American Airlines
Tue, Aug 11 - Tue, Aug 18
LAX
Los Angeles Intl.
SAF
Santa Fe Municipal
$207 Roundtrip, found 2 hours ago
$207
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Aug 11 from Los Angeles Intl. to Santa Fe Municipal, returning Tue, Aug 18, priced at $207 found 2 hours ago
Delta
Tue, Aug 18 - Tue, Aug 25
LAX
Los Angeles Intl.
MDW
Midway Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 18 from Los Angeles Intl. to Midway Intl., returning Tue, Aug 25, priced at $217 found 1 hour ago

Discover Other Travel Deals