Historic Route 66 Holidays from AU$3,640
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$703 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
The Latest Historic Route 66 Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was AU$4,290, price is now AU$3,640 per person
AU$3,640
per person
18 June - 25 June
found 10 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Helpful staff, great location, adequate rooms!
Reviewed on 14 Apr 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was AU$6,811, price is now AU$5,560 per person
AU$5,560
per person
18 June - 25 June
found 10 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on 7 Apr 2026
Level Chicago - River North
Downtown Chicago
Price was AU$7,621, price is now AU$6,416 per person
AU$6,416
per person
18 June - 25 June
found 10 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
The check in process was a little crazy, can’t say I have ever needed a background check to stay somewhere so it was a bit time consuming although I suppose good to know safety is a priority. View from property was the best part hands down! Cost of overall stay was great deal, parking for $65 a night was a bit disappointing because it is nice to have it on site. Overall would stay again.
Reviewed on 14 Apr 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was AU$4,891, price is now AU$4,141 per person
AU$4,141
per person
18 June - 25 June
found 10 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on 14 Apr 2026
Historic Route 66 Holiday
Historic Route 66 Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Arcadia Lake and Flagstaff Convention and Visitors Bureau |
Our pick of the best Historic Route 66 Hotel Deals
Central Loop Hotel
111 West Adams Street Chicago IL
The price is AU$191 per night from 19 Apr to 20 Apr
AU$191
19 Apr - 20 Apr
includes taxes & fees
8.6/10 Excellent! (2,068 reviews)
Hotel was very beautiful staff was really nice Room was clean and etc
Reviewed on 14 Apr 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 26 Apr to 27 Apr
AU$190
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,147 reviews)
The whole hotel was very clean. Everyone was super helpful and nice. Parking was close and affordable.
Reviewed on 15 Apr 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 26 Apr to 27 Apr
AU$197
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,123 reviews)
Very clean
Reviewed on 15 Apr 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
