Find flights
Airlines

$127+ 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 18/4. 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
20 Apr — 27 Apr1
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 21 March 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 - JFK

ORDJFK

Chicago O'Hare Intl

Sat 2/5

06:00-12:55

1 stop5h 55m

New York John F Kennedy Intl

Mon 4/5

06:00-07:41

Nonstop2h 41m

$283

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Fri 3/4

17:50-21:15

Nonstop2h 25m

New York John F Kennedy Intl

Tue 7/4

15:15-17:10

Nonstop2h 55m

$314

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 29/4

09:41-16:13

1 stop5h 32m

New York John F Kennedy Intl

Thu 30/4

06:00-07:41

Nonstop2h 41m

$314

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 4/6

06:00-09:15

Nonstop2h 15m

New York John F Kennedy Intl

Sun 7/6

20:59-22:56

Nonstop2h 57m

$341
Fastest return journey

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 5/5

08:31-11:49

Nonstop2h 18m

New York John F Kennedy Intl

Sat 9/5

06:00-07:41

Nonstop2h 41m

$350

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sat 11/7

18:10-21:49

Nonstop2h 39m

New York John F Kennedy Intl

Mon 13/7

12:59-18:41

1 stop6h 42m

$378

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 23/7

07:30-10:53

Nonstop2h 23m

New York John F Kennedy Intl

Sun 26/7

08:10-10:00

Nonstop2h 50m

$392

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Fri 19/6

07:30-10:53

Nonstop2h 23m

New York John F Kennedy Intl

Tue 23/6

12:59-18:41

1 stop6h 42m

$407

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 21/5

07:00-11:59

1 stop3h 59m

New York John F Kennedy Intl

Wed 27/5

12:59-18:05

1 stop6h 06m

$424

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sat 4/4

07:10-11:50

1 stop3h 40m

New York John F Kennedy Intl

Wed 8/4

12:59-16:43

1 stop4h 44m

$424

Flights are sorted by cheapest return flights first.

Deals found on 19/3

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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 13 March 2026.

The best time to book flights from Chicago is 2 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 $280). Flying from Chicago in October will prove the most costly (average of $1,272). 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 $1,916

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to New York (1,600 flights per day), Detroit (1,050 flights per day) and Orlando (964 flights per day).

New York
New York
From $120
Memphis
Memphis
From $165
Calgary
Calgary
From $247

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Toronto, with prices starting at $96. Explore other affordable destinations below.

Toronto
Toronto
From $96
New York
New York
From $120
Memphis
Memphis
From $165
Boston Logan Intl
Boston Logan Intl
From $190

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 647,157 searches.
See what other customers who have flown with Qantas Airways from Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Qantas Airways
7.5
Good
1,006 reviews
Check prices

Entertainment

7.2

Overall

7.5

Food

7.0

Comfort

7.4

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Midhat,Feb 2026

WYA - ADL

Frequent delays, 3rd week in a row. Flight attendants not at all friendly.
Qantas Airways
7.5
Good
1,006 reviews
Qantas Airways
7.5
Good
1,006 reviews
Check prices

Entertainment

7.2

Overall

7.5

Food

7.0

Comfort

7.4

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Midhat,Feb 2026

WYA - ADL

Frequent delays, 3rd week in a row. Flight attendants not at all friendly.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 21 March 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.

  • 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 ($82). United Airlines flights from Chicago to Sioux City Sioux Gateway ($304). Qantas Airways flights from Chicago to Melbourne ($660).

  • 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 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 $1,261 round trip
    Fly from Chicago to Melbourne from $1,289 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.

See more FAQs

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.