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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $334, price is now $226 per person
$226
per person
Dec 12 - Dec 15
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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $519, price is now $301 per person
$301
per person
Dec 12 - Dec 15
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.
We stayed for one night and everything from the staff to the room was absolutely perfect. We definitely would stay here again.

Reviewed on Oct 29, 2026

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $1,110, price is now $685 per person
$685
per person
Dec 16 - Dec 23
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.

The Parador

The Parador

3 out of 5
Price was $1,510, price is now $934 per person
$934
per person
Dec 1 - Dec 7
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albuquerque (ABQ)
Stay at this guesthouse in Santa Fe. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Santa Fe Plaza and Loretto Chapel are located nearby.

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was $468, price is now $305 per person
$305
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Staff was great and the room was clean!

Reviewed on Oct 29, 2026

Rosewood Inn of the Anasazi

Rosewood Inn of the Anasazi

5 out of 5
Save 100% on your flight
Price was $1,820, price is now $1,220 per person
$1,220
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albuquerque (ABQ)
Book a stay at this luxury hotel in Santa Fe. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Santa Fe Plaza and Loretto Chapel are located nearby.
The property is ideally situated to enjoy the historic center of Santa Fe with an easy walk to great restaurants and galleries. This was our third visit to the Rosewood Inn and we highly recommend the Inn for its friendly and helpful staff. The Inn has a hotel shuttle that will take and pick up guests to and from destinations as far as three miles away from the hotel, and we used it frequently. We'll definitely be coming back.

Reviewed on Oct 27, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,359, price is now $913 per person
$913
per person
Nov 28 - Dec 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 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.

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Price was $387, price is now $262 per person
$262
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Rooms are very small. You will need to call down for them to bring up a refrigerator. Other than that, everything was okay.

Reviewed on Oct 29, 2026

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 $569, price is now $275 per person
$275
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,455, price is now $443 per person
$443
per person
Dec 20 - Dec 23
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
Price was $519, price is now $301 per person
$301
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $468, price is now $305 per person
$305
per person
Dec 12 - Dec 15
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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $664, price is now $379 per person
$379
per person
Jan 7 - Jan 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $3,147, price is now $734 per person
$734
per person
Dec 21 - Dec 26
found 5 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,091, price is now $546 per person
$546
per person
Jan 18 - Jan 25
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,383, price is now $700 per person
$700
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Tue, Dec 8 - Mon, Dec 14
LAX
Los Angeles Intl.
OKC
Will Rogers World
$112 Roundtrip, found 2 hours ago
$112
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Dec 8 from Los Angeles Intl. to Will Rogers World, returning Mon, Dec 14, priced at $112 found 2 hours ago
American Airlines
Mon, Nov 23 - Wed, Dec 9
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$147 Roundtrip, found 5 hours ago
$147
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Mon, Nov 23 from Los Angeles Intl. to Albuquerque Intl. Sunport, returning Wed, Dec 9, priced at $147 found 5 hours ago
Frontier Airlines
Mon, Dec 7 - Sat, Dec 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$150 Roundtrip, found 1 hour ago
$150
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Dec 7 from Los Angeles Intl. to O'Hare Intl., returning Sat, Dec 12, priced at $150 found 1 hour ago
Frontier Airlines
Wed, Nov 18 - Sat, Dec 5
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$190 Roundtrip, found 9 hours ago
$190
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Nov 18 from Los Angeles Intl. to Lambert-St. Louis Intl., returning Sat, Dec 5, priced at $190 found 9 hours ago

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