$136+ 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 18/7. 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
29 Jul — 5 Aug1
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 29 June 2026. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 19/8

10:00-13:23

Nonstop2h 23m

New York LaGuardia

Sat 22/8

07:20-09:00

Nonstop2h 40m

$271

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 12/9

17:30-20:48

Nonstop2h 18m

New York LaGuardia

Mon 14/9

20:45-22:18

Nonstop2h 33m

$271

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 28/10

13:30-16:55

Nonstop2h 25m

New York John F Kennedy Intl

Thu 29/10

10:50-12:36

Nonstop2h 46m

$271

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Fri 7/8

18:28-21:58

Nonstop2h 30m

Newark

Wed 12/8

21:45-23:22

Nonstop2h 37m

$274
Fastest return journey

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 14/7

07:00-10:14

Nonstop2h 14m

New York LaGuardia

Tue 21/7

06:00-07:32

Nonstop2h 32m

$281

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sat 8/8

06:00-09:17

Nonstop2h 17m

New York John F Kennedy Intl

Sat 15/8

20:00-21:58

Nonstop2h 58m

$286

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 25/7

06:00-09:12

Nonstop2h 12m

Newark

Sat 1/8

18:15-20:10

Nonstop2h 55m

$288

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 9/12

06:00-09:20

Nonstop2h 20m

New York John F Kennedy Intl

Sat 12/12

15:40-17:34

Nonstop2h 54m

$300

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 14/7

20:10-23:44

Nonstop2h 34m

New York LaGuardia

Sun 19/7

06:59-08:31

Nonstop2h 32m

$307

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 18/7

18:12-23:30

1 stop4h 18m

New York LaGuardia

Tue 21/7

10:29-14:29

1 stop5h 00m

$322

Flights are sorted by cheapest return flights first.

Deals found on 27/6

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, May is the cheapest month in which you can book a flight from Chicago (average of $206). Flying from Chicago in October will prove the most costly (average of $1,205). 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 $2,131

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to Detroit (1,230 flights per day), New York (1,190 flights per day) and Los Angeles (827 flights per day).

New York
New York
From $128
Detroit
Detroit
From $1,328
San Francisco
San Francisco
From $629

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Toronto, with prices starting at $99. Explore other affordable destinations below.

Toronto
Toronto
From $99
New York
New York
From $128
Memphis
Memphis
From $169
Denver Intl
Denver Intl
From $250

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

The best time to book flights from Chicago is 46 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.

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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 29 June 2026.

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

    For the current month, the most popular flights from Chicago are Boston, Amman Queen Alia Intl Airport, Atlanta. Atlanta, Boston, 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 $1,429. While Chicago Midway airport is usually cheaper if your destination is Sydney with prices starting at $1,618. 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 United Airlines, Delta, and Qantas Airways to have the cheapest round-trip prices from Chicago. Some of the destinations and prices are as follows: United Airlines flights from Chicago to Sioux City Sioux Gateway ($311). Delta flights from Chicago to Mumbai Chhatrapati Shivaji Intl ($1,328). Qantas Airways flights from Chicago to Melbourne ($1,807).

  • What is the cheapest month to fly from Chicago?

    Currently, the cheapest month for flights from Chicago is May. The most expensive month for flights is October. 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 $1,429 round trip
    Fly from Chicago to Melbourne from $1,576 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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