
Historic Route 66 Vacations from $474
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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
Price was $762, price is now $474 per person
$474
per person
May 11 - May 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Stayed at the Hotel Riu Plaza Chicago and had a great experience. The hotel was very nice, clean, and comfortable, and the price was much cheaper compared to similar hotels in the area
Reviewed on Mar 24, 2026

Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,469, price is now $924 per person
$924
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Everything was perfect. We own a cleaning company so when traveling or staycationing we check the beds for bedbugs, lice and any other critters. Everything was pristine. I also let the phone staff know we were staying for my wife’s birthday and requested a higher room and they did say they couldn’t guarantee that but not only did they give us a higher floor they gave us a corner room also! Probably on of the best views in the building. Thank you for that. The area is also less congested than other parts of downtown. There’s SOME street parking nearby. Walkable distance to 7Eleven, Whole Foods and Jewel. Love this boutique hotel better than the large chain ones. Customer service was also great. We will be back.
Reviewed on Mar 23, 2026


Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,698, price is now $1,094 per person
$1,094
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
This was a nice hotel but some staff made us feel uncomfortable and the rooms had flaws (dirt). I expected better for the money however, I met someone who stayed at Travelodge and their hotel flooded. So, I'd recommend this hotel.
Reviewed on Mar 23, 2026

Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $2,488, price is now $1,654 per person
$1,654
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Clean rooms and friendly staff
Reviewed on Mar 22, 2026
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Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $151 total per night from Apr 1 to Apr 2
$151 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (10,006 reviews)
I always stay at the Congress Hotel when I participate in the Shamrock Shuffle. This was my sixth time. This year's experience was the best. The check in was clear, concise, and professional. The room I stayed in was recently updated.
Reviewed on Mar 24, 2026

Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $183 total per night from Apr 6 to Apr 7
$183 total
Apr 6 - Apr 7
Total with taxes and fees
9.4/10 Exceptional! (3,615 reviews)
Nice front desk staff, great breakfast
Reviewed on Mar 24, 2026

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$130 nightly
The price is $153 total per night from Apr 5 to Apr 6
$153 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (5,783 reviews)
I liked this hotel
Reviewed on Mar 24, 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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