$146+ 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 17/8. 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 17 July 2025.
Good round-trip deal | $507 or less |
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Good one-way deal | $281 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 17 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 17 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 17 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
Tue 29/7
08:09-12:23
Nonstop3h 14m
Miami
Sun 10/8
13:35-16:11
Nonstop3h 36m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Fri 15/8
15:10-16:55
Nonstop3h 45m
Phoenix Sky Harbor Intl
Sun 17/8
16:50-22:20
Nonstop3h 30m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 18/12
15:45-22:05
1 stop5h 20m
Miami
Tue 23/12
07:00-11:10
1 stop5h 10m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Fri 8/8
07:30-09:20
Nonstop3h 50m
Phoenix Sky Harbor Intl
Tue 12/8
06:00-14:42
1 stop6h 42m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 16/8
15:30-21:28
1 stop4h 58m
Miami
Tue 19/8
10:28-16:28
1 stop7h 00m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Wed 3/9
08:00-14:58
1 stop8h 58m
Phoenix Sky Harbor Intl
Thu 4/9
18:10-05:00
1 stop8h 50m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 3/8
18:23-00:06
Nonstop4h 43m
San Juan Luis Munoz Marin Intl
Fri 8/8
15:50-07:04
1 stop16h 14m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Fri 17/10
19:59-09:44
1 stop15h 45m
Phoenix Sky Harbor Intl
Mon 20/10
11:57-23:59
1 stop10h 02m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 1/1
06:00-10:08
Nonstop3h 08m
Miami
Wed 7/1
17:20-23:42
1 stop7h 22m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Thu 7/8
06:00-10:35
1 stop6h 35m
Phoenix Sky Harbor Intl
Mon 11/8
23:59-08:37
1 stop6h 38m
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 $738). Flying from Chicago in September will prove the most costly (average of $2,028). 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 (1,250 flights per day), New York (1,086 flights per day), and Los Angeles (773 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 $221. 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 Tahiti Nui, Fiji Airways, andDelta. 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
Overall
Comfort
Food
Entertainment
Reviews
Isabelle,Apr 2023
AKL - PPT
Crew
Boarding
Overall
Comfort
Food
Entertainment
Reviews
Isabelle,Apr 2023
AKL - PPT
Crew
Boarding
Overall
Comfort
Food
Entertainment
Reviews
Isabelle,Apr 2023
AKL - PPT
Crew
Boarding
Overall
Comfort
Food
Entertainment
Reviews
Isabelle,Apr 2023
AKL - PPT
Crew
Boarding
Overall
Comfort
Food
Entertainment
Reviews
Isabelle,Apr 2023
AKL - PPT
Crew
Boarding
Overall
Comfort
Food
Entertainment
Reviews
Isabelle,Apr 2023
AKL - PPT
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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 17 July 2025.
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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.
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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!