Cheap flights from Historic Route 66

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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 €293 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
CHI

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 €210 per night from 30 Jun to 1 Jul
€210
per night
30 Jun - 1 Jul
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! (4,367 reviews)
"The breakfast, location, and staff were amazing."

Reviewed on 7 Jun 2026

Opens in a new windowHotel Riu Plaza Chicago
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is €134 per night from 28 Jun to 29 Jun
€134
per night
28 Jun - 29 Jun
Our customers tell us that they can't get enough of the helpful staff at Hyatt Regency O'Hare Chicago. During your stay, you'll be connected to the convention centre and just a quick walk from Rosemont Theatre. You'll find features such as free WiFi in public areas and a free round-trip airport shuttle, plus a restaurant.
8.8/10 Excellent! (2,624 reviews)
"N/A"

Reviewed on 7 Jun 2026

Opens in a new windowHyatt Regency O'Hare Chicago
The Aquarius Casino Resort, BW Premier Collection

The Aquarius Casino Resort, BW Premier Collection

3.5 out of 5
1900 S Casino Dr Laughlin NV
The price is €61 per night from 8 Jun to 9 Jun
€61
per night
8 Jun - 9 Jun
Our customers tell us that they can't get enough of the helpful staff at The Aquarius Casino Resort, BW Premier Collection. During your stay, you're just a quick walk from Aquarius Casino Resort. You'll find features such as free WiFi in public areas, plus 7 restaurants and 4 bars.
8.2/10 Very Good! (7,722 reviews)
"My king room on the 18th floor was epic!! Large, clean, and a great view of the water! I stayed in 18060 if you can get it! Paid $36 a night! Will go again!!"

Reviewed on 7 Jun 2026

Opens in a new windowThe Aquarius Casino Resort, BW Premier Collection
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Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is €140 per night from 29 Jun to 30 Jun
€140
per night
29 Jun - 30 Jun
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 Art Institute of Chicago. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
8/10 Very Good! (10,189 reviews)
"The hotel was clean for the most part. Corridors smells like soap because I truly believe the housekeeping works hard to keep them that way. Unfortunately the hotel was just old and needs much needed upgrade. The bathroom was looking noticeably old too and the water in the bath area needs to be at ..."

Reviewed on 7 Jun 2026

Opens in a new windowCongress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
The price is €135 per night from 8 Jul to 9 Jul
€135
per night
8 Jul - 9 Jul
Our customers tell us that they can't get enough of the helpful staff at Freehand Chicago. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.
8/10 Very Good! (3,071 reviews)
"beautiful interior, super cozy and warm. as a frequent solo traveler, with amenities like a washing room and work out area is well appreciated. Bar environment was top tier"

Reviewed on 7 Jun 2026

Opens in a new windowFreehand Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is €157 per night from 28 Jun to 29 Jun
€157
per night
28 Jun - 29 Jun
The Chicago Hotel Collection - Magnificent Mile's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.
7.8/10 Good! (1,530 reviews)
"There isn't a coffee machine in the room one is supposed to be in the lobby but although the machines there were 4 there wasn't any tea or coffee pods."

Reviewed on 7 Jun 2026

Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
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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.