$130+ Cheap flights from Chicago
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
What to know about flights from Chicago
Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 6 July 2025.
Good round-trip deal | $498 or less |
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Good one-way deal | $275 or less |
Find flights from Chicago
Cheapest flights from ChicagoExplore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 6 July 2025.
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 6 July 2025.
Find flights from Chicago within your budget
Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 6 July 2025. In the last 7 days, Cheapflights users made a total of 134,765 searches
Fly to
Route
Departure
Return
Price
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Mon 18/8
07:00-15:15
1 stop7h 15m
Miami
Thu 21/8
07:10-11:50
1 stop5h 40m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 20/8
20:47-10:14
1 stop12h 27m
Miami
Tue 26/8
07:00-09:22
Nonstop3h 22m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 2/9
10:54-15:10
Nonstop3h 16m
Miami
Tue 9/9
07:45-14:55
1 stop8h 10m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Sat 8/11
15:05-18:00
Nonstop3h 55m
Phoenix Sky Harbor Intl
Tue 11/11
09:05-13:30
Nonstop3h 25m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Thu 7/8
22:10-23:49
Nonstop3h 39m
Phoenix Sky Harbor Intl
Wed 20/8
12:37-18:17
Nonstop3h 40m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 16/8
13:30-21:28
1 stop6h 58m
Miami
Wed 20/8
06:00-10:04
1 stop5h 04m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Sat 4/10
06:00-12:51
1 stop8h 51m
Phoenix Sky Harbor Intl
Tue 7/10
13:51-23:59
1 stop8h 08m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Thu 31/7
09:15-11:09
Nonstop3h 54m
Phoenix Sky Harbor Intl
Sun 3/8
23:09-04:42
Nonstop3h 33m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Mon 18/8
19:20-23:42
1 stop6h 22m
Phoenix Sky Harbor Intl
Mon 25/8
23:59-08:37
1 stop6h 38m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Fri 7/11
18:14-16:26
1 stop23h 12m
Phoenix Sky Harbor Intl
Sun 9/11
00:59-10:45
1 stop8h 46m
Best time to book a flight from Chicago
Have a flexible travel schedule? Discover the best time to fly from Chicago with our price prediction graph.
Travel insights for flights from Chicago
Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from Chicago?
Currently, January is the cheapest month in which you can book a flight from Chicago (average of $732). Flying from Chicago in September will prove the most costly (average of $2,009). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
What are popular destinations to fly to from Chicago?
Some of the most frequent flights departing from Chicago everyday are: Detroit (708 flights per day), New York (700 flights per day), and Los Angeles (479 flights per day).
What is the cheapest place to fly to from Chicago?
The cheapest city to fly to from Chicago is Mexico City Benito Juarez, with prices starting at $217. Explore other affordable destinations below.
Airline reviews for flights from Chicago
Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 134,765 searches.
Read through reviews of airlines serving Chicago, such as Singapore Airlines, Fiji Airways, andAir New Zealand. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
Boarding
Food
Overall
Comfort
Entertainment
Reviews
Ketan,Nov 2024
SEA - SIN
Crew
Boarding
Food
Overall
Comfort
Entertainment
Reviews
Ketan,Nov 2024
SEA - SIN
Crew
Boarding
Food
Overall
Comfort
Entertainment
Reviews
Ketan,Nov 2024
SEA - SIN
Crew
Boarding
Food
Overall
Comfort
Entertainment
Reviews
Ketan,Nov 2024
SEA - SIN
Crew
Boarding
Food
Overall
Comfort
Entertainment
Reviews
Ketan,Nov 2024
SEA - SIN
Crew
Boarding
Food
Overall
Comfort
Entertainment
Reviews
Ketan,Nov 2024
SEA - SIN
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Direct flights from Illinois
Book a direct flight from one of these other cities located in Illinois.
Related info for your journey
Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 6 July 2025.
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How does Cheapflights help users find flights from Chicago?
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Why should you use Cheapflights to find cheap flight tickets from Chicago?
Cheapflights simply makes it quick and affordable to book flights from Chicago by bringing together all flight options from hundreds of airlines and agencies online — and we put them in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Can Cheapflights find flights from Chicago with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.
Can Cheapflights notify me if prices for flights from Chicago become cheaper?
Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!