$148+ 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 26/8. 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.
CHI — SYD
1 Sep — 8 Sep1
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 2 August 2026. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Wed 9/9

21:35-00:57

Nonstop2h 22m

Newark

Sun 13/9

07:30-09:13

Nonstop2h 43m

$323
Fastest return journey

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Thu 3/9

05:00-08:14

Nonstop2h 14m

Newark

Mon 7/9

23:00-00:28

Nonstop2h 28m

$351

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Fri 23/10

17:29-23:16

1 stop4h 47m

Newark

Wed 28/10

09:40-12:59

1 stop4h 19m

$380

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 29/8

05:00-08:14

Nonstop2h 14m

Newark

Wed 2/9

16:55-18:39

Nonstop2h 44m

$408

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 22/8

07:05-10:22

Nonstop2h 17m

Newark

Sun 23/8

21:45-23:22

Nonstop2h 37m

$432

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Tue 8/9

20:36-23:59

Nonstop2h 23m

Newark

Thu 10/9

05:23-07:13

Nonstop2h 50m

$436

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 21/11

20:40-23:59

Nonstop2h 19m

Newark

Fri 27/11

21:59-23:49

Nonstop2h 50m

$438

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Thu 3/9

05:00-08:14

Nonstop2h 14m

Newark

Tue 8/9

08:00-09:44

Nonstop2h 44m

$451

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Tue 27/10

21:48-00:59

Nonstop2h 11m

Newark

Sun 1/11

09:00-10:48

Nonstop2h 48m

$451

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Mon 21/9

05:00-08:14

Nonstop2h 14m

Newark

Fri 25/9

19:45-21:32

Nonstop2h 47m

$455

Flights are sorted by cheapest return flights first.

Deals found on 1/8

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.

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 $1,821). Flying from Chicago in December will prove the most costly (average of $2,454). 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 $2,089

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to New York (1,110 flights per day), Detroit (982 flights per day) and Los Angeles (795 flights per day).

Los Angeles Los Angeles
Los Angeles Los Angeles
From $175
New York
New York
From $121
Vancouver Intl
Vancouver Intl
From $1,148

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is New York, with prices starting at $121. Explore other affordable destinations below.

New York
New York
From $121
Denver Intl
Denver Intl
From $173
Los Angeles Los Angeles
Los Angeles Los Angeles
From $175
Calgary
Calgary
From $247

When is the best time to book a flight from Chicago?

The best time to book flights from Chicago is 82 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.
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 2 August 2026.

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

    For the current month, the most popular flights from Chicago are Boston, Atlanta, Athens. 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 $1,392. While Chicago Midway airport is usually cheaper if your destination is Sydney with prices starting at $1,549. Reference our flight search to find the best deals in real time.

  • What is the cheapest month to fly from Chicago?

    Currently, the cheapest month for flights from Chicago is February. The most expensive month for flights is December. 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 $1,392 round trip
    Fly from Chicago to Melbourne from $1,629 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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