Historic Route 66 Vacations from $371
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $658, price is now $371 per person
$371
per person
Jul 6 - Jul 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
It’s all good but they didn’t allow me to take just a cup of coffee to my room and that I did not like at all. After seeing the tiktok where girls washes underwear in hotel room coffee machine I will never make coffee in hotels rooms ever and that’s why I wanted to enjoy the morning coffee from dining hall but wasn’t allowed therefore my rating is F
Reviewed on Apr 15, 2026
Level Chicago – Old Town
Downtown Chicago
Price was $1,613, price is now $917 per person
$917
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!
Reviewed on Apr 13, 2026
The Wildwood Hotel
Save 100% on your flight
Price was $940, price is now $552 per person
$552
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,627 reviews)
The breakfaat was average, thou fresh. There was enough street parking nearby, safe.
Reviewed on Mar 30, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $964, price is now $574 per person
$574
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Nice hotel I would stay here again
Reviewed on Apr 15, 2026
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Central Loop Hotel
111 West Adams Street Chicago IL
$116 nightly
The price is $136 total per night from Apr 19 to Apr 20
$136 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (2,068 reviews)
Hotel was very beautiful staff was really nice Room was clean and etc
Reviewed on Apr 14, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $137 total per night from Apr 26 to Apr 27
$137 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (10,147 reviews)
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Reviewed on Apr 14, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Apr 26 to Apr 27
$140 total
Apr 26 - Apr 27
Total with taxes and fees
9/10 Wonderful! (4,123 reviews)
We stayed after seeing Hamilton at CIBC Easter weekend. The hotel was busy, but service was quick and representatives were very friendly. The remodeled pool was great for my 11 year old niece.
Reviewed on Apr 15, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.