$189+ Cheap flights from Chicago
This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/2. 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
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 16 January 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 16 January 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 16 January 2025. In the last 7 days, Cheapflights users made a total of 134,765 searches
Fly to
Route
Departure
Return
Price
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Tue 4/3
16:10-19:16
Nonstop4h 06m
Phoenix Sky Harbor Intl
Mon 10/3
00:45-06:05
Nonstop3h 20m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 25/4
08:52-14:44
Nonstop4h 52m
San Juan Luis Munoz Marin Intl
Tue 29/4
01:05-10:48
1 stop10h 43m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Sun 9/2
17:00-23:54
1 stop7h 54m
Phoenix Sky Harbor Intl
Tue 11/2
06:00-15:43
1 stop8h 43m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/3
11:44-21:50
1 stop8h 06m
San Juan Luis Munoz Marin Intl
Sat 8/3
05:10-10:50
1 stop7h 40m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Tue 11/2
07:45-23:59
1 stop17h 14m
Phoenix Sky Harbor Intl
Wed 12/2
06:30-23:59
1 stop16h 29m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Mon 10/2
15:10-18:10
Nonstop4h 00m
Phoenix Sky Harbor Intl
Thu 13/2
18:40-23:05
Nonstop3h 25m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Thu 19/6
20:10-22:44
1 stop28h 34m
Phoenix Sky Harbor Intl
Sun 22/6
18:10-19:11
1 stop23h 01m
ChicagoPhoenix
ORD - PHX
ORDPHX
Chicago O'Hare Intl
Sun 9/2
06:30-12:34
1 stop7h 04m
Phoenix Sky Harbor Intl
Tue 11/2
00:45-05:11
Nonstop3h 26m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/2
07:10-16:55
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Sat 8/2
18:24-23:49
1 stop7h 25m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 24/2
16:00-00:50
1 stop6h 50m
San Juan Luis Munoz Marin Intl
Thu 27/2
05:35-14:00
2 stops10h 25m
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 10 January 2025.
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 $389). Flying from Chicago in June will prove the most costly (average of $2,452). 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 (1,356 flights per day), Detroit (904 flights per day), and Los Angeles (557 flights per day).
What is the cheapest place to fly to from Chicago?
The cheapest city to fly to from Chicago is Las Vegas Harry Reid Intl, with prices starting at $63. 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
Comfort
Crew
Food
Overall
Entertainment
Reviews
Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.
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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 16 January 2025.
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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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