Title: Historic Route 66 Vacation Packages 2026 from $372 | Expedia.com

[Historic Route 66 Travel Guide](https://expedia.com/Historic-Route-66.dx702654640613646336)[Hotels in Historic Route 66](https://expedia.com/Historic-Route-66-Hotels.d702654640613646336.Travel-Guide-Hotels)[Vacation Rentals in Historic Route 66](https://expedia.com/Historic-Route-66-Vacation-Rentals.d702654640613646336.Travel-Guide-VacationRentals)[Flights to Historic Route 66](https://expedia.com/Cheap-Flights-To-Historic-Route-66.d702654640613646336.Travel-Guide-Flights)[Car Rentals in Historic Route 66](https://expedia.com/Car-Rentals-In-Historic-Route-66.d702654640613646336.Car-Rental-Guide)

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# Historic Route 66 Vacations from $372

## Book a Hotel + Flight or Car together to unlock savings

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## The Latest Historic Route 66 vacation packages

Price found within the past 48 hours. Click for updated prices.

![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Felix River North/Magnificent Mile

Downtown Chicago

$372

per person

May 8 - May 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (2,573 reviews)

the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back.

Reviewed on Mar 4, 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

$409

per person

May 8 - May 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (3,422 reviews)

This hotel was super nice and it was clean and we did have to use another hotels valet, but it was no problem because it was right next-door, but the staff was super nice and accommodating. I will definitely stay here again.

Reviewed on Mar 5, 2026

![The Wildwood Hotel](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/800a6847_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Wildwood Hotel

Save 100% on your flight

$476

per person

Apr 21 - Apr 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to St. Louis (STL)

9.2/10 Wonderful! (1,600 reviews)

Clean room, amazing service

Reviewed on Mar 5, 2026

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

$634

per person

May 8 - May 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Had a great stay!! Kelly at the front desk was so sweet

Reviewed on Feb 22, 2026

![JW Marriott Chicago](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/83e4c147_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### JW Marriott Chicago

Downtown Chicago

$396

per person

May 1 - May 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,001 reviews)

The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again .

Reviewed on Feb 17, 2026

Don't see what you're looking for?

See all available trips from Columbus to Historic Route 66

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-05/2026-04-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

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## 

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## Historic Route 66 Hotel Deals

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$101 nightly

$118 total

Mar 30 - Mar 31

Total with taxes and fees

8/10 Very Good! (9,916 reviews)

Great location! Friendly staff

Reviewed on Mar 5, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F30%2F2026&endDate=3%2F31%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=702654640613646336)

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Fully refundableReserve now, pay when you stay

$135 nightly

$159 total

Mar 15 - Mar 16

Total with taxes and fees

9.4/10 Exceptional! (3,459 reviews)

This hotel was super nice and it was clean and we did have to use another hotels valet, but it was no problem because it was right next-door, but the staff was super nice and accommodating. I will definitely stay here again.

Reviewed on Mar 5, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true&regionId=702654640613646336)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

$130 nightly

$153 total

Mar 23 - Mar 24

Total with taxes and fees

8.6/10 Excellent! (5,716 reviews)

Old property bad food long lines

Reviewed on Mar 5, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F23%2F2026&endDate=3%2F24%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=702654640613646336)

[See all 19,781 properties in Historic Route 66](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F6%2F2026&endDate=3%2F7%2F2026&regionId=702654640613646336)

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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