Historic Route 66 Vacations from $430
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was $794, price is now $430 per person
$430
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,120 reviews)
Great location and staff
Reviewed on Sep 28, 2025
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $876, price is now $432 per person
$432
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
Room was clean. However was unaware the size and sewer smell in the bathroom. Was put all the way to end of hall by exit door without asking if that room location would be ok. Was told by front desk ok to go to restaurant 10min before close after reconfirming we would still be serviced. Only to be aggressively greeted by staff they were closed.
Reviewed on Sep 30, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,094, price is now $561 per person
$561
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Beautiful new hotel, gorgeous rooftop with delicious food. Hotel staff are super friendly and helpful.
Reviewed on Sep 30, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $2,332, price is now $1,304 per person
$1,304
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on Sep 28, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,342, price is now $767 per person
$767
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.
Reviewed on Sep 29, 2025
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Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $195 total per night from Oct 30 to Oct 31
$195 total
Oct 30 - Oct 31
Total with taxes and fees
8.6/10 Excellent! (3,370 reviews)
"Decent property overall."
Reviewed on Sep 25, 2025
Central Loop Hotel
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $195 total per night from Oct 30 to Oct 31
$195 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (1,878 reviews)
"Loved everything about it. Will definitely stay again in the future."
Reviewed on Sep 30, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Oct 26 to Oct 27
$179 total
Oct 26 - Oct 27
Total with taxes and fees
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."
Reviewed on Sep 25, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.