Cheap flights from Historic Route 66

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Historic Route 66 Flight Information
Origin airport IATA code
ORD
Return price
€402

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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is €107 per night from 15 Dec to 16 Dec
€107
15 Dec - 16 Dec
includes taxes & fees
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 a gym and a business centre.
8.8/10 Excellent! (3,423 reviews)
Location

Reviewed on 3 Dec 2025

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 €94 per night from 6 Jan to 7 Jan
€94
6 Jan - 7 Jan 2026
includes taxes & fees
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.
8.8/10 Excellent! (3,144 reviews)
Very welcoming

Reviewed on 30 Nov 2025

Opens in a new windowEurostars Magnificent Mile
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
The price is €82 per night from 21 Dec to 22 Dec
€82
21 Dec - 22 Dec
includes taxes & fees
Our customers tell us they can't get enough of Club Quarters Hotel, Central Loop, Chicago'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 a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.
8.6/10 Excellent! (3,294 reviews)
Clean and comfy room with great location

Reviewed on 3 Dec 2025

Opens in a new windowClub Quarters Hotel, Central Loop, Chicago
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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 €84 per night from 11 Dec to 12 Dec
€84
11 Dec - 12 Dec
includes taxes & fees
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! (1,960 reviews)
We enjoyed our weekend stay at Club Quarters very much. Gorgeous 1920's building and our room was very nice as well. Perfect location for EVERYTHING. Highly recommend.

Reviewed on 2 Dec 2025

Opens in a new windowClub Quarters Hotel Wacker at Michigan, 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 €95 per night from 18 Dec to 19 Dec
€95
18 Dec - 19 Dec
includes taxes & fees
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! (5,346 reviews)
Great location, beautiful property, excellent breakfast, spacious rooms.

Reviewed on 3 Dec 2025

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

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
The price is €125 per night from 28 Dec to 29 Dec
€125
28 Dec - 29 Dec
includes taxes & fees
Our customers tell us they can't get enough of Palmer House a Hilton Hotel's great location. During your stay, you're just a quick walk from Millennium Park. You'll find features such as a full-service spa, an indoor pool and a restaurant.
8.4/10 Very Good! (2,116 reviews)
great stay

Reviewed on 5 Dec 2025

Opens in a new windowPalmer House a Hilton Hotel
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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.