Cheap flights from Chicago

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Chicago Flight Information
Origin airport IATA code
CHI

Sourcing the best flights from Chicago on ebookers

If you’re seeking a flight from Chicago, 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 Chicago. 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 Chicago, 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 Chicago

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Our customers tell us that they can't get enough of the comfortable beds at Silversmith Hotel Chicago Downtown. 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 24-hour gym and a bar.
9.2/10 Wonderful! (2,148 reviews)
There are plenty of parking garages near by to self park. Staff were friendly and professional. Unfortunately our check in was a little bumpy. We got to the hotel before check in time, room wasn’t ready, but no biggie. I didn’t

Reviewed on 22 Dec 2025

Opens in a new windowSilversmith Hotel Chicago Downtown
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is €89 per night from 5 Jan to 6 Jan
€89
5 Jan - 6 Jan 2026
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! (3,562 reviews)
Great front desk service

Reviewed on 25 Dec 2025

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 €81 per night from 8 Jan to 9 Jan
€81
8 Jan - 9 Jan 2026
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! (1,993 reviews)
Great stay

Reviewed on 19 Dec 2025

Opens in a new windowClub Quarters Hotel Wacker at Michigan, Chicago
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Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
The price is €152 per night from 5 Jan to 6 Jan
€152
5 Jan - 6 Jan 2026
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! (2,174 reviews)
Clean rooms, extremely friendly staff, onsite Starbucks, Lockwood restaurant was amazing, beautiful gathering area in the lounge. Close to all the Christmas must do’s. Decorated so so beautifully for Christmas!

Reviewed on 24 Dec 2025

Opens in a new windowPalmer House a Hilton Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is €147 per night from 2 Jan to 3 Jan
€147
2 Jan - 3 Jan 2026
includes taxes & fees
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! (2,412 reviews)
What a great stay!!

Reviewed on 24 Dec 2025

Opens in a new windowHilton Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is €195 per night from 16 Jan to 17 Jan
€195
16 Jan - 17 Jan 2026
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Hilton Chicago O'Hare Airport. During your stay, you'll be connected to the airport and close to Allstate Arena. Free WiFi in public areas, a free round-trip airport shuttle and 2 restaurants are available.
8.2/10 Very Good! (2,184 reviews)
It was ok. Wouldn’t want to stay longer than a night. Food was pretty bad, room cramped

Reviewed on 23 Dec 2025

Opens in a new windowHilton Chicago O'Hare Airport
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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.