Exclusive Route 66 Raceway Vacation Deals
Route 66 Raceway vacation package deals
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,227, price is now CA $687 per person
CA $687
per person
Jan 31 - Feb 6
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was CA $1,289, price is now CA $707 per person
CA $707
per person
Jan 31 - Feb 6
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Peninsula Chicago
Downtown Chicago
Price was CA $3,192, price is now CA $1,902 per person
CA $1,902
per person
Jan 31 - Feb 6
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,378, price is now CA $841 per person
CA $841
per person
Jan 31 - Feb 6
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago
Downtown Chicago
Price was CA $1,294, price is now CA $808 per person
CA $808
per person
Jan 31 - Feb 6
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,569, price is now CA $988 per person
CA $988
per person
Feb 23 - Feb 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Frequently asked questions
Top Route 66 Raceway hotel deals
Hampton Inn Joliet-Plainfield I-55
3555 Mall Loop Drive Joliet IL
Free cancellation
Reserve now, pay when you stay
The price is CA $98 per night
CA $98
CA $114 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Stay at this hotel in Joliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cinemark Louis Joliet Mall and Westfield Louis Joliet Shopping Mall are located nearby.
Country Inn & Suites by Radisson, Tinley Park, IL
18315 South LaGrange Road Tinley Park IL
Free cancellation
The price is CA $132 per night
CA $132
CA $149 total
Dec 23 - Dec 24
includes taxes & fees
Book a stay at this business-friendly hotel in Tinley Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Odyssey Fun World and Space Golf are located nearby.
Pool
Breakfast included
Hampton Inn Chicago Orland Park
16176 LaGrange Road Orland Park IL
Free cancellation
Reserve now, pay when you stay
The price is CA $146 per night
CA $146
CA $163 total
Jan 2 - Jan 3, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Orland Park. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Space Golf and Centennial Park Aquatic Center are located nearby.
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View all propertiesLowest 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.