
Historic Route 66 Vacations from $219
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.

The Wildwood Hotel
Save 100% on your flight
Price was $378, price is now $219 per person
$219
per person
May 7 - May 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,620 reviews)
Well, right off the bat, the parking situation was a little bit confusing. My gps took me to a large empty parking lot in the back of the building. Since there were no cars parked there nor an entrance accessible from there, I pulled around the building. There was a small circle driveway off an intersection and some street parking. I kept going and found a parking garage. I got out and walked to the door and there was a sign saying no hotel access, use other door. I went to the second door, got out and there was another small note saying this entrance is closed please use the other door. Finally I found a third door that did access the hotel but only with a key card, so we had to walk up to the front of the hotel to check in and then go get our bags after. No problem. We get to our room.. lovely room, but unfortunately it hadn’t been cleaned. There was trash, the beds were unmade, dirty towels in the bathroom, obviously had not been cleaned at all. Went to front desk, they moved us to a downgraded room but wouldn’t give us any sort of discount or even apology. Okay. Whatever.
The room we went to was fine, but no balcony. The shower head needed replacing, had a weird weak stream, was clogged. I had to twist it to get the water to shoot out of the middle holes, thankfully that worked ok. Breakfast was alright, the standard continental breakfast fare. Waffle irons, etc. Pool and hot tub area was crowded. Desk staff nice. Pictures were misleading on site imo. But not bad hotel.
Reviewed on Mar 30, 2026

Still Waters Resort
Save 100% on your flight
Price was $2,971, price is now $1,491 per person
$1,491
per person
Jun 20 - Jun 27
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (SGF)
8.8/10 Excellent! (4,560 reviews)
We had a great time. Everything was just like advertised.
Reviewed on Mar 29, 2026

Westgate Branson Woods Resort and Cabins
Shepherd of the Hills
Save 100% on your flight
Price was $1,498, price is now $947 per person
$947
per person
Jun 20 - Jun 27
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (SGF)
8.2/10 Very Good! (1,012 reviews)
The room was very clean and nice but the air conditioner didnt work great for the hotter days on Wednesday and Thursdays. Our room was pretty warm but we managed. Dont like to complain.
Reviewed on Mar 29, 2026

Hyatt Vacation Club at The Lodges at Timber Ridge, Branson
Skyview
Save 100% on your flight
Price was $1,445, price is now $939 per person
$939
per person
Jun 20 - Jun 27
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (SGF)
9.2/10 Wonderful! (1,073 reviews)
The room was clean but outside landscaping where the patio was needed some attention. We stayed on a bottom room, and the people above us was pretty loud. Making s’mores with the family was a lot of fun and the events director was amazing. There’s a lot of things that could be offered on the property but it’s all shut down which is a bummer. A bit overpriced for what you get.
Reviewed on Mar 25, 2026
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View all tripsHistoric Route 66 Hotel Deals

Central Loop Hotel
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $128 total per night from Mar 31 to Apr 1
$128 total
Mar 31 - Apr 1
Total with taxes and fees
8.6/10 Excellent! (2,047 reviews)
Clean room and great staff!
Reviewed on Mar 30, 2026

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Apr 1 to Apr 2
$129 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (10,014 reviews)
N/A
Reviewed on Mar 30, 2026

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $143 total per night from Apr 6 to Apr 7
$143 total
Apr 6 - Apr 7
Total with taxes and fees
9/10 Wonderful! (4,020 reviews)
Great location and great service
Reviewed on Mar 30, 2026
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.
Find the Best Historic Route 66 Vacation Packages
Historic Route 66 Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
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