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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.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $409, price is now $240 per person
$240
per person
Feb 3 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois Beach State Park and Carmel Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $677, price is now $367 per person
$367
per person
Mar 4 - Mar 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $760, price is now $418 per person
$418
per person
Jan 23 - Jan 28
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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $656, price is now $370 per person
$370
per person
Jan 23 - Jan 28
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.
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Save 100% on your flight
Price was $562, price is now $326 per person
$326
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $659, price is now $383 per person
$383
per person
Feb 26 - Mar 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 WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $970, price is now $569 per person
$569
per person
Feb 26 - Mar 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 Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $665, price is now $390 per person
$390
per person
Mar 6 - Mar 9
found 21 hours ago
Roundtrip flight included
Dallas (DFW) 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.

Historic Route 66 Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $677, price is now $367 per person
$367
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $659, price is now $383 per person
$383
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $970, price is now $569 per person
$569
per person
Feb 26 - Mar 1
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 $665, price is now $390 per person
$390
per person
Mar 6 - Mar 9
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)

Historic Route 66 Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $656, price is now $370 per person
$370
per person
Jan 23 - Jan 28
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 $980, price is now $518 per person
$518
per person
Feb 10 - Feb 17
found 24 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $965, price is now $526 per person
$526
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $760, price is now $418 per person
$418
per person
Jan 23 - Jan 28
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
Wed, Jan 28 - Sat, Jan 31
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$160 Roundtrip, found 5 hours ago
$160
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Jan 28 from Los Angeles Intl. to Lambert-St. Louis Intl., returning Sat, Jan 31, priced at $160 found 5 hours ago
Frontier Airlines
Tue, Feb 10 - Wed, Feb 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 12 hours ago
$163
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Feb 10 from Los Angeles Intl. to O'Hare Intl., returning Wed, Feb 18, priced at $163 found 12 hours ago
American Airlines
Tue, Feb 10 - Tue, Feb 17
LAX
Los Angeles Intl.
SAF
Santa Fe Municipal
$187 Roundtrip, found 1 hour ago
$187
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Feb 10 from Los Angeles Intl. to Santa Fe Municipal, returning Tue, Feb 17, priced at $187 found 1 hour ago
Frontier Airlines
Tue, Jan 13 - Thu, Jan 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$196 Roundtrip, found 4 days ago
$196
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Jan 13 from Los Angeles Intl. to Midway Intl., returning Thu, Jan 15, priced at $196 found 4 days ago

Discover Other Travel Deals