Cheap flights from Historic Route 66

Many airlines offer flexible change policies

Earn BONUS+ rewards on top of your airline points

Enjoy exclusive promotions on the ebookers app!

Cheap round-trip flights from Historic Route 66

The lowest prices found within the past 7 days from Historic Route 66 to were for one-way flights and €311 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

Historic Route 66 Flight Information
Origin airport IATA code
ORD
Return price
€261

Your cheap flight from Historic Route 66 is available right now.

Visit us now at Ebookers to choose from lots of cheap flights leaving Historic Route 66 or our last minute air tickets from Historic Route 66 at unbeatable prices, specially chosen for those who want the best deal possible. Ebookers continuously compares and updates the choice of air tickets available from Historic Route 66, offered by more than 400 airlines worldwide. Ebookers works 24/7 to find the best deals so that our clients don’t have to waste their valuable time. Wherever you are going, you will find your perfect combination for a fantastic holiday at a budget price right here with our extensive flights database and helpful information; star ratings, reviews, maps and more… Many discount flights with a departure from Historic Route 66 and last minute flights from Historic Route 66 are available at Ebookers to help you organise your flights the way you want them at a price you can afford. Come and prepare your perfect holiday now at Ebookers.

Fancy a break from Historic Route 66? Book your flight in advance from Historic Route 66!

Thinking about getting away for a while and leaving from Historic Route 66? Visit Ebookers and discover our selection of inexpensive Historic Route 66 flights and air tickets from Historic Route 66 at unbelievable prices with a great choice of airlines - over 400 in fact. We give excellent service at an affordable price. For a great weekend away from Historic Route 66, visit to Ebookers where we have many available flights departing Historic Route 66 on special offer. Check out our deals and find a flight leaving Historic Route 66 at a price you never imagined. These special Ebookers offers aren’t just about cheap flights. We have over 95,000 hotels worldwide in our database, so why not stay in a Historic Route 66 hotel and start or end your break in style? Combine your choice of flight, hotel and car rental from our vast, reliable database to create your perfect holiday or dream weekend at a discounted price with Ebookers. Don’t wait or you may be too late!

Featured Hotels near Historic Route 66

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is €81 per night from 15 Feb to 16 Feb
€81
per night
15 Feb - 16 Feb
The shopping around Hilton Chicago/Magnificent Mile Suites gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as free WiFi in public areas, plus an indoor pool and a gym.
8.8/10 Excellent! (3,707 reviews)
It was a minus 6 outside temperature did not really run the ac

Reviewed on 12 Jan 2026

Opens in a new windowHilton Chicago/Magnificent Mile Suites
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
The price is €82 per night from 29 Jan to 30 Jan
€82
per night
29 Jan - 30 Jan
Our customers tell us that they can't get enough of the helpful staff at Club Quarters Hotel Wacker at Michigan, Chicago. During your stay, you're just a quick walk from Chicago Riverwalk. You'll find features such as free WiFi in public areas, plus a restaurant and a gym. This property offers pet-friendly amenities, such as food and water bowls.
8.6/10 Excellent! (2,063 reviews)
Helpful staff! Great view of the river from our room.

Reviewed on 13 Jan 2026

Opens in a new windowClub Quarters Hotel Wacker at Michigan, Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is €82 per night from 29 Jan to 30 Jan
€82
per night
29 Jan - 30 Jan
Our customers tell us that they can't get enough of the helpful staff at River Hotel. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a gym. This property offers pet-friendly amenities, such as food and water bowls.
8.6/10 Excellent! (4,908 reviews)
Our stay was A+, the staff was courteous and helpful and always went above and beyond in service. The location was great across from the Riverwalk and central to many other Chicago attractions. We will be back!!

Reviewed on 13 Jan 2026

Opens in a new windowRiver Hotel
Save an average of 15% on thousands of hotels when you're signed in
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is €157 per night from 1 Feb to 2 Feb
€157
per night
1 Feb - 2 Feb
Our customers tell us they can't get enough of Hilton Chicago's great location. During your stay, you're just a quick walk from State Street. Features include free WiFi in public areas, plus 2 restaurants and an indoor pool.
8.4/10 Very Good! (2,538 reviews)
Great staff, good location .

Reviewed on 14 Jan 2026

Opens in a new windowHilton Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
The price is €108 per night from 19 Jan to 20 Jan
€108
per night
19 Jan - 20 Jan
The free breakfast at Embassy Suites by Hilton Chicago Downtown River North gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as a free manager's reception, plus an indoor pool and a restaurant.
8.4/10 Very Good! (5,534 reviews)
I really liked the ambience. The breakfast really good. Everything was fresh. The facility was pretty well kept. The only issue was that the pool had a ring around it.

Reviewed on 11 Jan 2026

Opens in a new windowEmbassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Our customers tell us they can't get enough of Congress Plaza Hotel's great location. During your stay, you're just a quick walk from Millennium Park. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
8/10 Very Good! (9,761 reviews)
Friendly staff and clean rooms. Check in was nice and smooth.

Reviewed on 11 Jan 2026

Opens in a new windowCongress Plaza Hotel
Don't see what you're looking for?
See all available properties in Historic Route 66
View all properties
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.