Title: Historic Route 66 Vacation Packages & Trips 2026 from CA $1,181 | 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)

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# Historic Route 66 Vacation Packages

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

- ##  
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Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
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## Top Historic Route 66 Vacation Deals

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

![Sports Illustrated Resorts Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/d70b1c1f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sports Illustrated Resorts Chicago

Downtown Chicago

CA $1,181

per person

May 16 - May 19

found 12 hours ago

Roundtrip flight included

Hamilton (YHM) to Chicago (ORD)

9.2/10 Wonderful! (1,414 reviews)

Check in was quick and easy, room was clean and spacious

Reviewed on Mar 9, 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 $1,226

per person

Jun 5 - Jun 8

found 23 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

The property is located within a short walk to the Magnificent Mile, restaurants, the north side of the river, Target, AMC theaters, Walgreens, Northwestern Medicine and the bus line. They have figured out convenience. The property was as beautiful as it was immaculate. The rooms were spacious with a fantastic shower and amazing shampoo, conditioner and lotion! I’ve even looked into buying it for my home. The breakfast buffet was unbelievable! The food was plentiful with more options than I thought possible. Even more impressive was the breakfast staff who kept the tables clean and the food available, hot and fresh. The hosts took a special interest in knowing the guests, and I know this first hand. My birthday fell during our stay, and the breakfast staff had a table waiting for my family and presented a birthday brownie with the words “Happy Birthday” written in chocolate sauce! Unfortunately, I had unexpectedly been hospitalized for emergency surgery so I missed the opportunity to experience their grand gesture, but the first morning I walked into breakfast after being discharged from the hospital, the host having never see me, asked if my family had given me the brownie. l was blown away! Will I stay again? Without any hesitation!!! Excellent choice!!

Reviewed on Mar 22, 2026

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,272

per person

Jun 5 - Jun 8

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,401 reviews)

We only stayed for 1 night but the room was exceptionally clean, smelled fresh, and we had an amazing view! Would highly recommend

Reviewed on Mar 22, 2026

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $1,572

per person

Jun 5 - Jun 8

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.2/10 Wonderful! (421 reviews)

Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago.

Reviewed on Mar 14, 2026

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $1,284

per person

Jun 5 - Jun 8

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (441 reviews)

Spacious room with great views and washer and dryer

Reviewed on Mar 17, 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/1000000/10000/6500/6452/11b63ec2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $143

CA $168 total

Apr 1 - Apr 2

includes taxes & fees

8/10 Very Good! (9,984 reviews)

It’s an old hotel. It needs a quality paint job and new carpets in the hallways among many other things. But the lake view rooms makes up for a lot of what’s missing.

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%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

CA $181

CA $251 total

Apr 6 - Apr 7

includes taxes & fees

9.4/10 Exceptional! (3,591 reviews)

The property is located within a short walk to the Magnificent Mile, restaurants, the north side of the river, Target, AMC theaters, Walgreens, Northwestern Medicine and the bus line. They have figured out convenience. The property was as beautiful as it was immaculate. The rooms were spacious with ...

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%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

Fully refundableReserve now, pay when you stay

CA $179

CA $210 total

Mar 29 - Mar 30

includes taxes & fees

8.6/10 Excellent! (5,766 reviews)

Spent three nights with husband and teenage son over spring break. Young man who checked us in was not friendly, did not mention happy hour, or breakfast. He did not give us any information except room number. Breakfast staff was nice and polite. Recommend getting to breakfast early or there will ...

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=702654640613646336)

[See all 19,734 properties in Historic Route 66](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F03%2F2026&endDate=24%2F03%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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- [Flights from Quad Cities ](https://www.expedia.ca/lp/flights/603001/flights-from-quad-cities)
- [Flights from Winnipeg to Quad Cities ](https://www.expedia.ca/lp/flights/6141041/603001/winnipeg-to-quad-cities)
- [Flights from Ohio River Valley ](https://www.expedia.ca/lp/flights/6233674/flights-from-ohio-river-valley)

- [Lake Michigan ](https://www.expedia.ca/Lake-Michigan-United-States-of-America.d6338716.Vacation-Attraction)
- [Visit Ohio River Valley ](https://www.expedia.ca/Ohio-River-Valley.dx6233674)
- [Quad Cities Vacations ](https://www.expedia.ca/Quad-Cities.d603001.Destination-Travel-Guides)
- [Visit Quad Cities ](https://www.expedia.ca/Quad-Cities.dx603001)
- [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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