$156+ 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 22/1. 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.
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 December 2024. In the last 7 days, Cheapflights users made a total of 134,765 searches
Fly to
Route
Departure
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 24/1
14:20-20:55
Nonstop4h 35m
San Juan Luis Munoz Marin Intl
Tue 28/1
02:05-09:40
1 stop9h 35m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Mon 13/1
16:58-22:49
1 stop6h 51m
Phoenix Sky Harbor Intl
Wed 15/1
07:15-15:30
1 stop7h 15m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Tue 14/1
20:13-23:14
Nonstop4h 01m
Phoenix Sky Harbor Intl
Sat 18/1
23:59-04:32
Nonstop3h 33m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Tue 28/1
07:45-18:34
2 stops11h 49m
Phoenix Sky Harbor Intl
Thu 30/1
17:40-13:07
1 stop18h 27m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/4
13:22-00:07
1 stop9h 45m
San Juan Luis Munoz Marin Intl
Sun 6/4
04:00-12:27
1 stop9h 27m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Wed 5/2
12:15-19:40
1 stop8h 25m
Phoenix Sky Harbor Intl
Sat 8/2
07:30-16:45
2 stops8h 15m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 1/2
07:00-22:50
2 stops13h 50m
San Juan Luis Munoz Marin Intl
Tue 4/2
06:00-14:00
1 stop10h 00m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Sun 12/1
08:12-15:52
1 stop8h 40m
Phoenix Sky Harbor Intl
Mon 13/1
00:45-05:11
Nonstop3h 26m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 12/3
07:10-19:39
1 stop11h 29m
San Juan Luis Munoz Marin Intl
Thu 20/3
15:10-23:57
1 stop9h 47m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Fri 16/5
20:05-08:55
1 stop14h 50m
Phoenix Sky Harbor Intl
Thu 22/5
09:50-17:51
1 stop6h 01m
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 December 2024.
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 December 2024.
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.
When is the best time to book a flight from Chicago?
Use this chart to determine the optimal time to book a return flight from Chicago to Auckland. Price data was last updated on 13 December 2024.
To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 22 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chicago?
Currently, August is the cheapest month in which you can book a flight from Chicago (average of $377). Flying from Chicago in April will prove the most costly (average of $2,448). 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 (1,148 flights per day), Detroit (820 flights per day), and Toronto (612 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 $228. 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.
Boarding
Crew
Food
Entertainment
Comfort
Overall
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Boarding
Crew
Food
Entertainment
Comfort
Overall
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Boarding
Crew
Food
Entertainment
Comfort
Overall
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Boarding
Crew
Food
Entertainment
Comfort
Overall
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Boarding
Crew
Food
Entertainment
Comfort
Overall
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Boarding
Crew
Food
Entertainment
Comfort
Overall
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
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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 December 2024.
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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.
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