Cheap flights from Historic Route 66

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Historic Route 66 Flight Information
Origin airport IATA code
ORD
Return price
€1,471

Sourcing the best flights from Historic Route 66 on ebookers

If you’re seeking a flight from Historic Route 66, you can swiftly and easily find exactly what you’re looking for using ebookers. Our easy-to-use tool will let you select the destination and ideal travel dates to immediately see which routes and airlines are available. Have a preferred airline in mind for the trip? You can filter your ebookers search to see if they have flights from CHI. For more bespoke options, you can also set your search for multiple destinations and flights that are refundable, so you can have the most relevant information in moments.

Getting the best deal on a cheap flight from CHI

There are a few golden rules for keeping costs low when booking flights from Historic Route 66. The first thing to think about is being flexible on your travel dates. It can help to shift your departure by a day, or even a few hours, as prices can vary by significant amounts. Use ebookers to compare and contrast your options ahead of time, and you can make a savvy decision. Want more savings? If book the hotel at your chosen destination through ebookers while also arranging your flight from Historic Route 66, you can get a discount of up to 15% off the total price. For help on which pad to pick, you can make use of our snappy hotel descriptions, which are accompanied by useful photos.

Getting things going at your destination

With ebookers, you don’t just have access to the latest, constantly updated information on flights from CHI. You can also get inspiration on the most interesting things to get up to when you’re there. Just check out our Things to Do tool and you’ll soon be drawing up an exciting itinerary. And if you’re keen to take in as much of the wider area as possible, you could also look into the best car hire deals and have your very own set of wheels waiting, so you can roam to your heart’s content.

Featured Hotels near Historic Route 66

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is €158 per night from 24 Mar to 25 Mar
€158
per night
24 Mar - 25 Mar
During your stay at Hotel Riu Plaza Chicago, you're just a quick walk from Michigan Avenue. Enjoy features like free breakfast and free WiFi in public areas, plus 2 bars.
9.4/10 Exceptional! (3,488 reviews)
Great location ans staff was amazing!!

Reviewed on 9 Mar 2026

Opens in a new windowHotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is €105 per night from 17 Mar to 18 Mar
€105
per night
17 Mar - 18 Mar
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.
9/10 Wonderful! (3,889 reviews)
Room was clean, but the room was also very hot. Microwave did not work at first. They sent somebody up to fix it, but I still had to sleep in a hot room because the air was not working. I went down to ask the lady at the front desk for a microwave because my work was not working and she rushed me ...

Reviewed on 9 Mar 2026

Opens in a new windowHilton Chicago/Magnificent Mile Suites
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
The price is €146 per night from 23 Mar to 24 Mar
€146
per night
23 Mar - 24 Mar
Eurostars Magnificent Mile's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Free WiFi in public areas, a full-service spa and a gym are available.
9/10 Wonderful! (3,313 reviews)
Great stay. Staff was slightly inattentive at times with requests for things to room.

Reviewed on 9 Mar 2026

Opens in a new windowEurostars Magnificent Mile
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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 €123 per night from 19 Mar to 20 Mar
€123
per night
19 Mar - 20 Mar
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.
8.6/10 Excellent! (5,734 reviews)
Good hotel, good area !

Reviewed on 9 Mar 2026

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

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is €157 per night from 1 Apr to 2 Apr
€157
per night
1 Apr - 2 Apr
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.
8.6/10 Excellent! (2,674 reviews)
Staff was prejudice to black kids in pool area!

Reviewed on 9 Mar 2026

Opens in a new windowHilton Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is €168 per night from 21 Mar to 22 Mar
€168
per night
21 Mar - 22 Mar
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! (9,933 reviews)
Great historic vibe, but feels old.

Reviewed on 9 Mar 2026

Opens in a new windowCongress Plaza Hotel
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See all available properties in Historic Route 66
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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.

Fare, taxes & fees: Fares were found on ebookers.com and are updated daily. They include all taxes and fees, except baggage fees.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a £25.00 / 45.00 Euro service fee charged by ebookers, plus any airline fare and tax increase that may be applicable.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.