Title: Historic Route 66 Vacation Packages & Trips 2026 from CA $1,004 | 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.

![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Orrington / Evanston

Downtown Evanston

CA $1,004

per person

Apr 3 - Apr 8

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

7.6/10 Good! (1,002 reviews)

I would stay here again if I need to stay in Evanston again. Thanks

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 $1,028

per person

Apr 2 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Clean room. Extremely friendly staff and beautiful atmosphere.

Reviewed on Jan 20, 2026

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,727

per person

Apr 3 - Apr 8

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Exceptional service, great location, beautiful hotel

Reviewed on Jan 20, 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 $2,289

per person

Mar 10 - Mar 17

found 21 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to St. Louis (STL)

2/10 (1 review)

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Peninsula Chicago

Downtown Chicago

CA $2,207

per person

Apr 3 - Apr 8

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.

Reviewed on Jan 11, 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 $126

CA $148 total

Jan 21 - Jan 22

includes taxes & fees

8/10 Very Good! (9,771 reviews)

Front desk was very professional and the room was very tidy, including the bathroom. Staff allowed us to check in early (no fee, if room is cleaned and available, prior to standard check in time.). Overall, not a bad selection based on location and proximity of all the sites to see. Quiet side of ...

Reviewed on Jan 14, 2026

[](https://expedia.ca/Hotel-Search?startDate=21%2F01%2F2026&endDate=22%2F01%2F2026&selected=6452&PinnedHotelID=6452&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 $181

CA $253 total

Feb 1 - Feb 2

includes taxes & fees

8.4/10 Very Good! (2,547 reviews)

Great staff that paid attention quickly to concerns.

Reviewed on Jan 19, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true&regionId=702654640613646336)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Fully refundableReserve now, pay when you stay

CA $147

CA $172 total

Feb 9 - Feb 10

includes taxes & fees

8.4/10 Very Good! (5,575 reviews)

The staff were great! The room was pretty clean. The breakfast was amazing and, the kids loved to pool. The only issue we had was the elevator wait times. As that they were busy it made for long elevator wait times.

Reviewed on Jan 19, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=702654640613646336)

[See all 19,750 properties in Historic Route 66](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=21%2F01%2F2026&endDate=22%2F01%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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- [Visit Southeast Iowa ](https://www.expedia.ca/Southeast-Iowa.dx6234151)

- [Ace Rental Cars in Quad Cities ](https://www.expedia.ca/Ace-Car-Rentals-In-Quad-Cities.d603001-c2.Car-Rental-Guide-Suppliers)
- [Advantage Rent-A-Car Rental Cars in Ohio River Valley ](https://www.expedia.ca/Advantage-Rent-A-Car-Car-Rentals-In-Ohio-River-Valley.d6233674-c3.Car-Rental-Guide-Suppliers)
- [Avis Rental Cars in Quad Cities ](https://www.expedia.ca/Avis-Car-Rentals-In-Quad-Cities.d603001-c41.Car-Rental-Guide-Suppliers)
- [Car rentals near Quad Cities ](https://www.expedia.ca/Car-Rentals-In-Quad-Cities.d603001.Car-Rental-Guide)
- [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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