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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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
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

Sheraton Suites Chicago Elk Grove

3.5 out of 5
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

Level Chicago – Old Town

4 out of 5
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

The Wildwood Hotel

3.5 out of 5
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

Chicago Marriott Suites O'Hare

4 out of 5
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

Hotel Riu Plaza Chicago

4 out of 5
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

Westgate Branson Woods Resort and Cabins

3.5 out of 5
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

Pendry Chicago

4.5 out of 5
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.
Sheraton Suites Chicago Elk Grove

Sheraton Suites Chicago Elk Grove

3.5 out of 5
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)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was $428, price is now $178 per person
$178
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $421, price is now $188 per person
$188
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
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)

Historic Route 66 Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $914, price is now $434 per person
$434
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,019, price is now $522 per person
$522
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,509, price is now $776 per person
$776
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,271, 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)

Top Flight Deals

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

Frontier Airlines
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
Select Frontier Airlines flight, departing Thu, Dec 11 from Los Angeles Intl. to O'Hare Intl., returning Mon, Dec 15, priced at $128 found 3 days ago
Frontier Airlines
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
Select Frontier Airlines flight, departing Wed, Feb 25 from Los Angeles Intl. to Lambert-St. Louis Intl., returning Mon, Mar 9, priced at $192 found 19 hours ago
Bargain Flight
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
Select Bargain Flight flight, departing Tue, Jan 27 from Los Angeles Intl. to Albuquerque Intl. Sunport, returning Sat, Jan 31, priced at $201 found 1 day ago
Frontier Airlines
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
Select Frontier Airlines flight, departing Tue, Jan 6 from Los Angeles Intl. to Tulsa Intl., returning Sun, Jan 11, priced at $231 found 8 hours ago

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