Cheap flights from Historic Route 66

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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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is €140 per night from 10 May to 11 May
€140
10 May - 11 May
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 an indoor pool and a gym.
9/10 Wonderful! (4,177 reviews)
The valet guys were top tier!! Staff was nice, we had a small issue in our room and someone was there to resolve it very quickly!

Reviewed on 23 Apr 2026

Opens in a new windowHilton Chicago/Magnificent Mile Suites
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is €116 per night from 26 Apr to 27 Apr
€116
26 Apr - 27 Apr
includes taxes & fees
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.
8.8/10 Excellent! (5,115 reviews)
Clean room

Reviewed on 23 Apr 2026

Opens in a new windowRiver Hotel
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 €114 per night from 10 May to 11 May
€114
10 May - 11 May
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.
8.8/10 Excellent! (3,447 reviews)
Clean room and helpful staff. Best part is the attached restaurant.

Reviewed on 23 Apr 2026

Opens in a new windowClub Quarters Hotel, Central Loop, Chicago
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Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street Chicago IL
The price is €113 per night from 10 May to 11 May
€113
10 May - 11 May
includes taxes & fees
Our customers tell us they can't get enough of Central Loop Hotel's great location. During your stay, you're just a quick walk from Willis Tower. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.
8.6/10 Excellent! (2,090 reviews)
Staff was helpful and friendly

Reviewed on 22 Apr 2026

Opens in a new windowCentral Loop Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
The price is €113 per night from 29 Apr to 30 Apr
€113
29 Apr - 30 Apr
includes taxes & fees
Hotel Felix River North/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 a 24-hour gym and a bar.
8.2/10 Very Good! (2,629 reviews)
The hotel was in great location downtown. The rooms and bedding was also clean and nice. We had to request a room change because the toilet and sink were not working correctly. In the new room, the bathroom sink continued to not drain. It was definitely annoying and disgusting. I probably won’t be ...

Reviewed on 22 Apr 2026

Opens in a new windowHotel Felix River North/Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is €115 per night from 26 Apr to 27 Apr
€115
26 Apr - 27 Apr
includes taxes & fees
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! (10,124 reviews)
The room shown in the picture is not the one they put me on

Reviewed on 21 Apr 2026

Opens in a new windowCongress Plaza 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.