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Top Historic Route 66 Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Westin Michigan Avenue Chicago
Downtown Chicago
per person
Aug. 10 - Aug. 13
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,004 reviews)
Perfect area to go shopping, check out tourist attractions, or relax at the beach. Very convenient area to head to Lakefront Trail as well for a morning run. Staff was helpful and friendly during every interaction. I really loved all the benefits you received through the destination fee. Property was clean and attentive. In a very walkable area and close to public transportation.
Reviewed on Jun. 3, 2024
Where to stay in Historic Route 66
Find the best Historic Route 66 areas and neighborhoods for the activities you enjoy most. Learn more about Historic Route 66
Downtown Chicago
2 out of top 10 points of interest in this area
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Historic Route 66 Hotel Deals
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Jun. 16 to Jun. 17
CA $211
CA $247 total
includes taxes & fees
Jun 16 - Jun 17
8.4/10 Very Good! (3,080 reviews)
"Front desk help was amazing"
Reviewed on Jun. 2, 2024
Central Loop Hotel
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Jun. 16 to Jun. 17
CA $211
CA $248 total
includes taxes & fees
Jun 16 - Jun 17
8.4/10 Very Good! (1,627 reviews)
"Very central location, clean, friendly staff, and affordable."
Reviewed on Jun. 5, 2024
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Jun. 17 to Jun. 18
CA $205
CA $240 total
includes taxes & fees
Jun 17 - Jun 18
7.6/10 Good! (6,849 reviews)
"Great location, historic feel. Pleasant stay"
Reviewed on Jun. 4, 2024
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.
Frequently asked questions
Discover the most popular places to visit in Historic Route 66
Wrigley Field
4.5/5(158 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
McCormick Place
4.5/5(141 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Navy Pier
4.5/5(459 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
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Hotels
Flights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.