$117+ 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 17/12. 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 31 August 2025.
Good round-trip deal | $511 or less |
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Good one-way deal | $283 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 31 August 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 31 August 2025.
Find flights from Chicago within your budget
Fly to
Route
Departure
Return
Price
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 5/11
07:35-11:49
Nonstop3h 14m
Miami
Wed 12/11
12:23-14:52
Nonstop3h 29m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 27/9
10:54-15:11
Nonstop3h 17m
Miami
Sat 4/10
12:27-14:55
Nonstop3h 28m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 9/9
10:27-14:39
Nonstop3h 12m
Miami
Thu 11/9
07:00-09:18
Nonstop3h 18m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Wed 19/11
15:55-18:53
Nonstop3h 58m
Phoenix Sky Harbor Intl
Fri 21/11
13:55-18:28
Nonstop3h 33m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Wed 19/11
14:40-19:49
1 stop6h 09m
Phoenix Sky Harbor Intl
Sat 22/11
15:30-19:59
Nonstop3h 29m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Wed 22/10
18:28-21:57
1 stop5h 29m
Phoenix Sky Harbor Intl
Sat 25/10
07:00-12:39
Nonstop3h 39m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 27/11
07:35-11:49
Nonstop3h 14m
Miami
Tue 2/12
12:23-14:52
Nonstop3h 29m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Sun 28/9
20:03-22:00
Nonstop3h 57m
Phoenix Sky Harbor Intl
Mon 29/9
07:00-12:39
Nonstop3h 39m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Sat 4/10
11:10-12:59
Nonstop3h 49m
Phoenix Sky Harbor Intl
Tue 14/10
18:30-23:59
Nonstop3h 29m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Thu 2/10
12:50-14:39
Nonstop3h 49m
Phoenix Sky Harbor Intl
Sat 4/10
10:50-16:29
Nonstop3h 39m
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, November is the cheapest month in which you can book a flight from Chicago (average of $788). Flying from Chicago in September will prove the most costly (average of $2,044). 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: New York (1,328 flights per day), Detroit (930 flights per day), and Los Angeles (588 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 $223. 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 Air Canada. 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.
Food
Boarding
Overall
Crew
Comfort
Entertainment
Reviews
Anonymous,Oct 2024
TPA - YYZ
Food
Boarding
Overall
Crew
Comfort
Entertainment
Reviews
Anonymous,Oct 2024
TPA - YYZ
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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 31 August 2025.
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Why should you use Cheapflights to find cheap flight tickets from Chicago?
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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.
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