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$118+ 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 18/10. 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
17 Oct — 24 Oct1
1 adult
1 adult, Economy

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 17 September 2025.

Cheapest airline

Qantas Airways

Good round-trip deal

$530 or less

Good one-way deal

$87 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago (avg. price of $1,402).
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Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Find flights from Chicago

Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 17 September 2025.

Wed 29/1006:40ORD - JFK
Nonstop2h 23mFrontier
Wed 5/1106:20JFK - ORD
1 stop5h 54mFrontier
Deal found 14/9$174
Wed 15/1013:35ORD - JFK
Nonstop2h 24mJetBlue
Tue 21/1010:30JFK - ORD
Nonstop2h 52mJetBlue
Deal found 16/9$205
Wed 7/109:00ORD - JFK
Nonstop2h 17mJetBlue
Mon 19/111:30JFK - ORD
Nonstop2h 53mJetBlue
Deal found 16/9$207
Thu 8/109:00ORD - JFK
Nonstop2h 17mJetBlue
Mon 19/116:41JFK - ORD
Nonstop2h 53mJetBlue
Deal found 15/9$208
Tue 11/1106:44ORD - JFK
Nonstop2h 15mJetBlue
Mon 17/1119:00JFK - ORD
Nonstop2h 52mJetBlue
Deal found 16/9$213
Mon 9/214:20ORD - JFK
Nonstop2h 23mJetBlue
Fri 13/219:40JFK - ORD
Nonstop2h 53mJetBlue
Deal found 15/9$214
Thu 30/1006:45ORD - JFK
Nonstop2h 14mJetBlue
Tue 4/1119:00JFK - ORD
Nonstop2h 52mJetBlue
Deal found 16/9$216
Tue 2/1207:00ORD - JFK
Nonstop2h 17mJetBlue
Sat 13/1220:00JFK - ORD
Nonstop2h 52mJetBlue
Deal found 15/9$220
Wed 14/109:00ORD - JFK
Nonstop2h 17mJetBlue
Fri 16/116:41JFK - ORD
Nonstop2h 53mJetBlue
Deal found 15/9$229
Tue 16/1207:00ORD - JFK
Nonstop2h 17mJetBlue
Tue 16/1220:00JFK - ORD
Nonstop2h 52mJetBlue
Deal found 15/9$235
Thu 11/1207:00ORD - JFK
Nonstop2h 17mJetBlue
Sat 13/1220:00JFK - ORD
Nonstop2h 52mJetBlue
Deal found 15/9$237
Wed 19/1107:15ORD - EWR
Nonstop2h 10mUnited Airlines
Sun 23/1108:00EWR - ORD
Nonstop2h 48mUnited Airlines
Deal found 14/9$243

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 17 September 2025. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Sydney

Route

Depart

Return

Price

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 24/2

07:00-10:23

Nonstop2h 23m

New York John F Kennedy Intl

Thu 26/2

19:40-21:33

Nonstop2h 53m

$208

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 25/2

07:00-10:23

Nonstop2h 23m

New York John F Kennedy Intl

Thu 26/2

19:40-21:33

Nonstop2h 53m

$208

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 8/1

09:00-12:17

Nonstop2h 17m

New York John F Kennedy Intl

Mon 19/1

16:41-18:34

Nonstop2h 53m

$208

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 24/2

07:00-10:23

Nonstop2h 23m

New York John F Kennedy Intl

Sat 28/2

19:40-21:33

Nonstop2h 53m

$208

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 26/2

07:00-10:23

Nonstop2h 23m

New York John F Kennedy Intl

Thu 26/2

19:40-21:33

Nonstop2h 53m

$208

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 24/2

07:00-10:23

Nonstop2h 23m

New York John F Kennedy Intl

Fri 27/2

19:40-21:33

Nonstop2h 53m

$214

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 26/2

07:00-10:23

Nonstop2h 23m

New York John F Kennedy Intl

Sun 1/3

19:40-21:33

Nonstop2h 53m

$214

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Mon 9/2

14:20-17:43

Nonstop2h 23m

New York John F Kennedy Intl

Fri 13/2

19:40-21:33

Nonstop2h 53m

$214

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Fri 6/2

14:20-17:43

Nonstop2h 23m

New York John F Kennedy Intl

Sun 8/2

11:30-13:23

Nonstop2h 53m

$220

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Fri 7/11

06:44-09:59

Nonstop2h 15m

New York John F Kennedy Intl

Mon 10/11

19:00-20:52

Nonstop2h 52m

$220

Flights are sorted by cheapest return flights first.

Deals found on 15/9

Showing 1-10 of 60 results
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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 12 September 2025.

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 $297). Flying from Chicago in January will prove the most costly (average of $1,287). 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, Air Canada. As they depart for the following popular destinations: Sydney.

Qantas Airways
Qantas Airways
From $868
Air Canada
Air Canada
From $831
American Airlines
American Airlines
From $140
Spirit Airlines
Spirit Airlines
From $59

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to New York (1,680 flights per day), Detroit (1,254 flights per day) and Los Angeles (781 flights per day).

Los Angeles
Los Angeles
From $149
New York
New York
From $96
New Delhi Indira Gandhi Intl
New Delhi Indira Gandhi Intl
From $342

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Toronto, with prices starting at $73. Explore other affordable destinations below.

Toronto
Toronto
From $49
Raleigh-Durham
Raleigh-Durham
From $65
Washington, D.C.
Washington, D.C.
From $73
San Diego
San Diego
From $95

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
907 reviews
Check prices

Entertainment

7.2

Boarding

7.7

Comfort

7.5

Crew

8.2

Overall

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sept 2025

SYD - BNE

Great. Except I haven’t claimed my free lounge passes since 2022 on my Qantas credit card. That’s lots of flights I would have booked if you’d reminded me
Qantas Airways
7.5
Good
907 reviews
Qantas Airways
7.5
Good
907 reviews
Check prices

Entertainment

7.2

Boarding

7.7

Comfort

7.5

Crew

8.2

Overall

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sept 2025

SYD - BNE

Great. Except I haven’t claimed my free lounge passes since 2022 on my Qantas credit card. That’s lots of flights I would have booked if you’d reminded me

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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 17 September 2025.

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

    For the current month, the most popular flights from Chicago are Athens, Boston, 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 Sydney can be found at Chicago Midway airport from $1,548. While Chicago O'Hare Intl airport is usually cheaper if your destination is Melbourne with prices starting at $1,677. 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 ($322). Qantas Airways flights from Chicago to Melbourne ($1,185).

  • 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 January. 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 $1,548 round trip
    Fly from Chicago to Melbourne from $1,701 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

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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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