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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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $995, price is now $648 per person
$648
per person
Aug 6 - Aug 9
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 $1,488, price is now $893 per person
$893
per person
Jul 2 - Jul 8
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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,180, price is now $717 per person
$717
per person
Jul 2 - Jul 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,471, price is now $934 per person
$934
per person
Jul 2 - Jul 8
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 parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,302, price is now $840 per person
$840
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,108, price is now $747 per person
$747
per person
Jul 2 - Jul 8
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 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,791, price is now $1,208 per person
$1,208
per person
Jun 26 - Jun 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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,258, price is now $850 per person
$850
per person
Jul 2 - Jul 8
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 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue 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
Save 100% on your flight
Price was $1,174, price is now $672 per person
$672
per person
Jul 8 - Jul 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,192, price is now $741 per person
$741
per person
Jun 26 - Jun 29
found 1 day 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 $1,556, price is now $984 per person
$984
per person
Jul 29 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,302, price is now $840 per person
$840
per person
Jun 26 - Jun 29
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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,349, price is now $734 per person
$734
per person
Jul 23 - Jul 28
found 14 hours 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 $2,233, price is now $1,148 per person
$1,148
per person
Jul 10 - Jul 17
found 1 day ago
Roundtrip flight included
Houston (HOU) to St. Louis (STL)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,525, price is now $849 per person
$849
per person
Jul 23 - Jul 28
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Inn at Vanessie

The Inn at Vanessie

4.5 out of 5
Downtown Santa Fe
Save 100% on your flight
Price was $1,910, price is now $1,120 per person
$1,120
per person
Aug 10 - Aug 15
found 4 hours ago
Roundtrip flight included
New York (NYC) to Albuquerque (ABQ)

Top Flight Deals

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

American Airlines
Tue, Aug 11 - Tue, Aug 18
LAX
Los Angeles Intl.
SAF
Santa Fe Municipal
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day 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 1 day ago
Bargain Flight
Tue, Aug 25 - Tue, Sep 15
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$210 Roundtrip, found 6 hours ago
$210
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Tue, Aug 25 from Los Angeles Intl. to Albuquerque Intl. Sunport, returning Tue, Sep 15, priced at $210 found 6 hours ago
Delta
Tue, Jul 14 - Wed, Jul 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$219 Roundtrip, found 2 hours ago
$219
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Jul 14 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 15, priced at $219 found 2 hours ago
Frontier Airlines
Wed, Sep 2 - Wed, Sep 16
LAX
Los Angeles Intl.
OKC
Will Rogers World
$230 Roundtrip, found 2 days ago
$230
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Will Rogers World, returning Wed, Sep 16, priced at $230 found 2 days ago

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