Historic Route 66 Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,544, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 8
found 10 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Would have liked coffeemaker in the room and some glasses or cups for water. The bathroom was nice, but for the price, we felt the room was cramped and the window small. Location was convenient.
Reviewed on Jun 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,463, price is now CA $1,624 per person
CA $1,624
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $3,213, price is now CA $2,212 per person
CA $2,212
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.
Reviewed on Jun 23, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $2,026, price is now CA $1,407 per person
CA $1,407
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable
Reviewed on Jun 23, 2026
Historic Route 66 Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Jun 29 to Jun 30
CA $194
CA $231 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very good! (10,129 reviews)
"Great experience! Close to everywhere we wanted to go!"
Reviewed on Jun 26, 2026
The Aquarius Casino Resort, BW Premier Collection
1900 S Casino Dr Laughlin NV
Fully refundableReserve now, pay when you stay
The price is CA $70 per night from Jul 6 to Jul 7
CA $70
CA $115 total
Jul 6 - Jul 7
includes taxes & fees
8.2/10 Very good! (7,786 reviews)
"The room was filthy Dusty coffee maker Whole greasy hand print on blowdryer in the bathroom with a dust covering Water damage on ceiling above the toilet Major Hard water stains on bathtub spout 2 of the elevators were out , massive line to go upstairs Never seen a pillow with a sticker on it saying ..."
Reviewed on Jun 26, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $305 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,824 reviews)
"Great"
Reviewed on Jun 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.
Explore a world of travel with Expedia
- 5 Star Hotels in Quad Cities
- Hotels near Lake Michigan
- Aparthotels in Ohio River Valley
- B&B in Ohio River Valley
- Cabin Rentals in Ohio River Valley
- Chalets in Ohio River Valley
- Condo Rentals in Ohio River Valley
- Adults Only Resorts & in Ohio River Valley
- Beach Hotel Hotels in Ohio River Valley
- Best Western Hotels in Ohio River Valley
- Boutique Hotels in Ohio River Valley
- Cheap Hotels in Ohio River Valley
- Golf Hotels in Ohio River Valley
- Historic Hotels in Ohio River Valley
- Hotels with a Pool in Ohio River Valley
- Hotels with Balconies in Ohio River Valley
- Hotels with Waterslides in Ohio River Valley
- Lake Hotels in Ohio River Valley
- Luxury Hotels in Ohio River Valley
- Marriott Hotels & Resorts in Ohio River Valley
- Motel 6 Hotels in Ohio River Valley
- Pet-Friendly Hotels in Ohio River Valley
- Romantic Hotels in Ohio River Valley
- Spa Hotels in Ohio River Valley
- Waterpark Hotels in Ohio River Valley
- Ohio River Valley Hotels
- Treehouses in Ohio River Valley
- B&B in Quad Cities
- Cabin Rentals in Quad Cities
- Best Western Hotels in Quad Cities
- Boutique Hotels in Quad Cities
- Casino Hotels in Quad Cities
- Hotels & Resorts for Couples in Quad Cities
- Family Hotels in Quad Cities
- Historic Hotels in Quad Cities
- Honeymoon Resorts and in Quad Cities
- Hotels with Early Check-in in Quad Cities
- Hotels with a Pool in Quad Cities
- Hotels with Wifi in Quad Cities
- Hotels with Bar in Quad Cities
- Hotels with Free Airport Shuttle in Quad Cities
- Hotels with Free Breakfast in Quad Cities
- Hotels with Hot Tubs in Quad Cities
- Hotels with an Indoor Pool in Quad Cities
- Hotels with Kitchenettes in Quad Cities
- Luxury Hotels in Quad Cities
- Motel 6 Hotels in Quad Cities
- Pet-Friendly Hotels in Quad Cities
- Romantic Hotels in Quad Cities
- Spa Hotels in Quad Cities
- Waterpark Hotels in Quad Cities
- Quad Cities Hotels
- B&B in Southeast Iowa
- Americinn Hotels in Southeast Iowa
- Luxury Hotels in Southeast Iowa
- Pet-Friendly Hotels in Southeast Iowa
- Romantic Hotels in Southeast Iowa
- Southeast Iowa Hotels
- Flights to Ohio River Valley
- Flights to Quad Cities
- Flights to Southeast Iowa
- Flights from Calgary to Quad Cities
- Flights from Calgary to Ohio River Valley
- Flights from Chicago to Quad Cities
- Flights from Columbus to Quad Cities
- Flights from Dallas to Ohio River Valley
- Flights from Indianapolis to Quad Cities
- Flights from Miami to Ohio River Valley
- Flights from Minneapolis - St. Paul to Quad Cities
- Flights from Minneapolis - St. Paul to Ohio River Valley
- Flights from Orlando to Ohio River Valley
- Flights from Seattle to Quad Cities
- Flights from Toronto to Quad Cities
- Flights from Toronto to Ohio River Valley
- Flights from Vancouver to Ohio River Valley
- Flights from Edmonton to Quad Cities
- Flights from Edmonton to Ohio River Valley
- Flights from Québec City to Ohio River Valley
- Flights from Amarillo to Quad Cities
- Flights from Hamilton to Quad Cities
- Flights from Fort Lauderdale to Ohio River Valley
- Flights from Newark to Ohio River Valley
- Flights from Buffalo to Quad Cities
- Flights from Buffalo to Ohio River Valley
- Flights from Birmingham to Ohio River Valley
- Flights from Quad Cities
- Flights from Winnipeg to Quad Cities
- Flights from Ohio River Valley
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
