Title: Historic Route 66 Vacation Packages & Trips 2026 from CA $967 | Expedia.ca

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

![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Historic Route 66 Vacation Packages

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

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Top Historic Route 66 Vacation Deals

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

![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago - River North

Downtown Chicago

CA $967

per person

Mar 14 - Mar 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (766 reviews)

Great stay. Would come again.

Reviewed on Jan 19, 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

CA $981

per person

Apr 13 - Apr 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Staff was extremely polite, rooms were clean. No issues at all

Reviewed on Feb 2, 2026

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $1,175

per person

Mar 11 - Mar 14

found 1 day ago

Roundtrip flight included

Toronto (YTZ) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 2026

![Hermann Grain Bins BNB ](https://images.trvl-media.com/lodging/117000000/116770000/116761300/116761277/27846aee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hermann Grain Bins BNB 

CA $2,246

per person

Mar 13 - Mar 20

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to St. Louis (STL)

2/10 (1 review)

![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Emily Hotel

Downtown Chicago

CA $1,189

per person

Apr 13 - Apr 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,264 reviews)

Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again.

Reviewed on Jan 25, 2026

## Ready to book your vacation to Historic Route 66?

Choose your dates

## Historic Route 66 Hotel Deals

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $122

CA $143 total

Feb 5 - Feb 6

includes taxes & fees

8/10 Very Good! (9,839 reviews)

Great a+++

Reviewed on Feb 1, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F02%2F2026&endDate=06%2F02%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=702654640613646336)

![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

DoubleTree by Hilton Chicago - Magnificent Mile

300 E Ohio St Chicago IL

Fully refundableReserve now, pay when you stay

CA $125

CA $147 total

Feb 11 - Feb 12

includes taxes & fees

8.6/10 Excellent! (2,267 reviews)

2nd time at hotel and will come again.

Reviewed on Jan 28, 2026

[](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=21152&PinnedHotelID=21152&HadPinnedHotel=true&regionId=702654640613646336)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

CA $189

CA $262 total

Feb 21 - Feb 22

includes taxes & fees

8.4/10 Very Good! (2,597 reviews)

Some of the nicest people you'll ever meet! Excellent location for a Bears game stay, walking distance to Soldier Field.

Reviewed on Feb 1, 2026

[](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true&regionId=702654640613646336)

[See all 19,938 properties in Historic Route 66](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F02%2F2026&endDate=06%2F02%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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

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- [Pickup Car Rentals in Ohio River Valley ](https://www.expedia.ca/Pickup-Car-Rentals-In-Ohio-River-Valley.d6233674-tPickup.Car-Rental-Guide-Class)
- [Thrifty Car Rental Rental Cars in Ohio River Valley ](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-Ohio-River-Valley.d6233674-c45.Car-Rental-Guide-Suppliers)

- [Things to do in Quad Cities ](https://www.expedia.ca/Things-To-Do-In-Quad-Cities.d603001.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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