$135+ 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 28/9. 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
19 May — 26 May1
1 adult
1 adult, Economy, 0 bags

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 19 April 2026. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

ChicagoLos Angeles

ORD - LAX

ORDLAX

Chicago O'Hare Intl

Mon 11/5

23:00-01:41

Nonstop4h 41m

Los Angeles Los Angeles

Tue 12/5

22:53-05:06

Nonstop4h 13m

$307

ChicagoLos Angeles

ORD - LAX

ORDLAX

Chicago O'Hare Intl

Mon 1/6

18:20-23:55

1 stop7h 35m

Los Angeles Los Angeles

Wed 10/6

17:15-23:18

Nonstop4h 03m

$333

ChicagoLos Angeles

ORD - LAX

ORDLAX

Chicago O'Hare Intl

Wed 6/5

11:55-21:10

2 stops11h 15m

Los Angeles Los Angeles

Sat 9/5

05:35-14:30

1 stop6h 55m

$342

ChicagoLos Angeles

ORD - LAX

ORDLAX

Chicago O'Hare Intl

Wed 27/5

07:45-13:00

1 stop7h 15m

Los Angeles Los Angeles

Mon 1/6

07:25-23:55

2 stops14h 30m

$350

ChicagoLos Angeles

ORD - LAX

ORDLAX

Chicago O'Hare Intl

Thu 28/5

17:19-22:42

1 stop7h 23m

Los Angeles Los Angeles

Sat 6/6

14:05-23:55

1 stop7h 50m

$364

ChicagoLos Angeles

ORD - LAX

ORDLAX

Chicago O'Hare Intl

Fri 29/5

07:45-12:34

1 stop6h 49m

Los Angeles Los Angeles

Fri 29/5

23:59-08:36

1 stop6h 37m

$386

ChicagoLos Angeles

ORD - LAX

ORDLAX

Chicago O'Hare Intl

Fri 8/5

06:24-10:55

1 stop6h 31m

Los Angeles Los Angeles

Mon 11/5

23:59-08:36

1 stop6h 37m

$431

ChicagoLos Angeles

ORD - LAX

ORDLAX

Chicago O'Hare Intl

Wed 24/6

14:45-17:15

Nonstop4h 30m

Los Angeles Los Angeles

Sun 5/7

06:00-16:34

1 stop8h 34m

$456

ChicagoLos Angeles

ORD - LAX

ORDLAX

Chicago O'Hare Intl

Tue 26/5

10:30-19:45

2 stops11h 15m

Los Angeles Los Angeles

Thu 28/5

07:25-23:55

2 stops14h 30m

$509

ChicagoLos Angeles

ORD - LAX

ORDLAX

Chicago O'Hare Intl

Thu 21/5

13:35-22:30

2 stops10h 55m

Los Angeles Los Angeles

Sat 30/5

11:50-22:20

2 stops8h 30m

$563

Flights are sorted by cheapest return flights first.

Deals found on 17/4

Showing 1-10 of 60 resultsSorted by cheapest first
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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.
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.

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 Sydney. Price data was last updated on 17 April 2026.

The best time to book flights from Chicago is 7 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.

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 $192). Flying from Chicago in July will prove the most costly (average of $1,178). 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.

Qantas Airways
Qantas Airways
From $1,886

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to Detroit (1,336 flights per day), New York (1,120 flights per day) and Minneapolis (686 flights per day).

Toronto
Toronto
From $95
Tampa
Tampa
From $348
Los Angeles
Los Angeles
From $233

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Toronto, with prices starting at $95. Explore other affordable destinations below.

Toronto
Toronto
From $95
New York
New York
From $123
Memphis
Memphis
From $162
Los Angeles
Los Angeles
From $233

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Direct flights from Illinois

Book a direct flight from one of these other cities located in Illinois.
Direct flights from Moline

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 19 April 2026.

  • What are the most popular destinations to fly to from Chicago?

    For the current month, the most popular flights from Chicago are Atlanta, Boston, Austin. Boston, Atlanta, Ahmedabad are the most popular locations from Chicago year round.

  • Which is the cheapest airport to catch a flight from Chicago?

    The cheapest routes to Melbourne can be found at Chicago O'Hare Intl airport from $1,345. While Chicago Midway airport is usually cheaper if your destination is Sydney with prices starting at $1,642. Reference our flight search to find the best deals in real time.

  • What are the cheapest airlines flying from Chicago to anywhere?

    According to our data, users have found Spirit Airlines, United Airlines, and Qantas Airways to have the cheapest round-trip prices from Chicago. Some of the destinations and prices are as follows: Spirit Airlines flights from Chicago to New York ($81). United Airlines flights from Chicago to Sioux City Sioux Gateway ($300). Qantas Airways flights from Chicago to Melbourne ($1,738).

  • What is the cheapest month to fly from Chicago?

    Currently, the cheapest month for flights from Chicago is August. The most expensive month for flights is July. The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.

  • Where are the cheapest places to fly to from Chicago?

    View the cheapest flight destinations from Chicago:
    Fly from Chicago to Sydney from $1,345 round trip
    Fly from Chicago to Melbourne from $1,640 round trip

  • How does Cheapflights help users find flights from Chicago?

    Cheapflights helps you search for flights from Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

  • 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.

  • Can Cheapflights notify me if prices for flights from Chicago become cheaper?

    Yes! Start tracking prices for flights from Chicago today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago?

Cheapflights helps you search for flights from Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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.

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Yes! Start tracking prices for flights from Chicago today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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