Search Deals onHistoric Route 66 Vacation Packages
Historic Route 66 Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Chicago/Alsip
Save 100% on your flight
Price was $436, price is now $264 per person
$264
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (MDW)
Book a stay at this business-friendly hotel in Alsip. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hollywood Park and Gaelic Park are located nearby.
Chicago Athletic Association, a Hyatt Hotel
Price was $1,598, price is now $845 per person
$845
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star 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.
Westgate Branson Woods Resort and Cabins
Save 100% on your flight
Price was $711, price is now $382 per person
$382
per person
Nov 10 - Nov 15
found 1 hour ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (SGF)
Stay at this 3.5-star 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 Branson Landing and Silver Dollar City are located nearby.
Hyatt Regency Deerfield
Save 100% on your flight
Price was $724, price is now $420 per person
$420
per person
Nov 10 - Nov 16
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Deerfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sportsman's Country Club and Northbrook Sports Complex are located nearby.
THE BRANSINN Entertainment District
Save 100% on your flight
Price was $753, price is now $452 per person
$452
per person
Nov 10 - Nov 15
found 1 hour ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (SGF)
Book a stay at this spa hotel in Branson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Branson Landing and Table Rock Lake are located nearby.
Still Waters Resort
Save 100% on your flight
Price was $654, price is now $398 per person
$398
per person
Nov 10 - Nov 15
found 1 hour ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (SGF)
Stay at this 4-star family-friendly condo in Branson. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Silver Dollar City and Table Rock Lake are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,695, price is now $1,042 per person
$1,042
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Staybridge Suites, Lincolnshire by IHG
Save 100% on your flight
Price was $494, price is now $313 per person
$313
per person
Oct 31 - Nov 5
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Lincolnshire. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Marriott Theatre and Valentino Vineyards are located nearby.
Historic Route 66 Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Historic Route 66 Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Sep 13 - Sat, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$122 Roundtrip, found 10 hours ago
$122
Roundtrip
found 10 hours ago
Sat, Oct 25 - Tue, Oct 28
LAX
Los Angeles Intl.
OKC
Will Rogers World
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Sat, Oct 25 - Mon, Oct 27
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$163 Roundtrip, found 1 hour ago
$163
Roundtrip
found 1 hour ago
Sun, Sep 14 - Mon, Sep 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$179 Roundtrip, found 12 hours ago
$179
Roundtrip
found 12 hours ago
Discover Other Travel Deals
- Popular Vacation Attractions
- Popular Destinations
- Nearby Destinations
- Areas of Historic Route 66
- Hotwire Picks
- Route 66 Raceway Vacations
- Route 66 Casino Vacations
- Springfield Expo Center Vacations
- National Route 66 Museum Vacations
- El Rey Theater Vacations
- Symphony Center Vacations
- Route 66 Carousel Park Vacations
- Chicago Board of Trade Building Vacations
- The Blue Whale Vacations
- Coleman Theater Vacations
- Downtown Kingman's First Friday Vacations
- Route 66 Vintage Iron Motorcycle Museum Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Chicago Vacations
- San Francisco Vacations
- Los Angeles Vacations
- Boston Vacations
- Miami Vacations
- Nashville Vacations
- Atlantic City Vacations
- Houston Vacations
- Atlanta Vacations
- Seattle Vacations
- San Antonio Vacations
- New Orleans Vacations
- Austin Vacations