$88+ 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 29/10. 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.
CHI — SYD
8 Nov — 15 Nov1
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 9 October 2026. In the last 7 days, Cheapflights users made a total of 7,457,451 searches
Fly to
Route
Depart
Return
Cheapest return flight
ChicagoFort Lauderdale
ORD Chicago O'Hare Intl - FLL Fort Lauderdale
ORDFLL
Chicago O'Hare Intl
Wed 18/11
13:00-22:32
1 stop8h 32m
Fort Lauderdale
Wed 31/12
00:00-23:00
Nonstop0h 00m
$101
ChicagoFort Lauderdale
ORD Chicago O'Hare Intl - FLL Fort Lauderdale
ORDFLL
Chicago O'Hare Intl
Wed 18/11
05:55-13:08
1 stop6h 13m
Fort Lauderdale
Wed 31/12
00:00-23:00
Nonstop0h 00m
$105
ChicagoFort Lauderdale
ORD Chicago O'Hare Intl - FLL Fort Lauderdale
ORDFLL
Chicago O'Hare Intl
Sat 14/11
05:30-15:46
1 stop9h 16m
Fort Lauderdale
Wed 31/12
00:00-23:00
Nonstop0h 00m
$105
ChicagoLos Angeles
ORD Chicago O'Hare Intl - LAX Los Angeles
ORDLAX
Chicago O'Hare Intl
Fri 30/10
14:03-18:12
1 stop6h 09m
Los Angeles
Wed 31/12
00:00-02:00
Nonstop0h 00m
$142
ChicagoLos Angeles
ORD Chicago O'Hare Intl - LAX Los Angeles
ORDLAX
Chicago O'Hare Intl
Fri 13/11
06:49-12:44
1 stop7h 55m
Los Angeles
Wed 31/12
00:00-02:00
Nonstop0h 00m
$142
ChicagoLos Angeles
ORD Chicago O'Hare Intl - LAX Los Angeles
ORDLAX
Chicago O'Hare Intl
Wed 10/2
13:35-20:31
1 stop8h 56m
Los Angeles
Wed 31/12
00:00-02:00
Nonstop0h 00m
$142
ChicagoLos Angeles
ORD Chicago O'Hare Intl - LAX Los Angeles
ORDLAX
Chicago O'Hare Intl
Fri 11/12
19:18-23:56
1 stop6h 38m
Los Angeles
Wed 31/12
00:00-02:00
Nonstop0h 00m
$142
ChicagoLos Angeles
ORD Chicago O'Hare Intl - LAX Los Angeles
ORDLAX
Chicago O'Hare Intl
Sat 20/2
07:00-14:50
1 stop9h 50m
Los Angeles
Wed 31/12
00:00-02:00
Nonstop0h 00m
$142
ChicagoLos Angeles
ORD Chicago O'Hare Intl - LAX Los Angeles
ORDLAX
Chicago O'Hare Intl
Thu 26/11
12:58-20:18
1 stop9h 20m
Los Angeles
Wed 31/12
00:00-02:00
Nonstop0h 00m
$142
ChicagoFort Lauderdale
ORD Chicago O'Hare Intl - FLL Fort Lauderdale
ORDFLL
Chicago O'Hare Intl
Tue 3/11
09:00-13:18
Nonstop3h 18m
Fort Lauderdale
Wed 31/12
00:00-23:00
Nonstop0h 00m
$150
Showing 1-10 of 60 resultsSorted by cheapest first
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.
CHI-SYD
ORD-FLL
ORD-LAX
ORD-EWR
ORD-LAS
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Travel insights for flights from Chicago
Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.
CHI-SYD
ORD-FLL
ORD-LAX
ORD-EWR
ORD-LAS
What is the cheapest month to book a flight from Chicago?
Currently, February is the cheapest month in which you can book a flight from Chicago (average of $1,768). Flying from Chicago in December will prove the most costly (average of $2,537). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
Which airlines fly from Chicago?
When flying from Chicago check dates and pricing for the following: Qantas Airways. As it departs for the following popular destinations: Sydney.
What are popular destinations to fly to from Chicago?
Chicago offers frequent flights to Detroit (1,048 flights per day), New York (1,018 flights per day) and Los Angeles (816 flights per day).
What is the cheapest place to fly to from Chicago?
The cheapest city to fly to from Chicago is Fort Lauderdale, with prices starting at $76. Explore other affordable destinations below.
When is the best time to book a flight from Chicago?
The best time to book flights from Chicago is 84 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Browse thousands of different options on Cheapflights for your next trip
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Direct flights from Illinois
Book a direct flight from one of these other cities located in Illinois.
Airports servicing Chicago
Fly out of one of these airports located in Chicago.
Fly from other United States cities
Consider departing from one of these cities also located in United States. Flight origins are based on user searches made on Cheapflights and were last updated on 9 October 2026.
Popular Return Flight Destinations
Consider these popular destinations that Cheapflights users have chosen when departing from Chicago. Routes are based on user searches and were last updated on 9 October 2026.
Popular flight searches
Check out other popular destinations found by fellow travellers in 2026
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 9 October 2026.
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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?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.
Can Cheapflights find flights from Chicago with no change fees?
Yes! Cheapflights helps users easily find flights from Chicago with no change fees.
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