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$81+ 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 12/5. 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
11 Apr — 18 Apr1
1 adult
1 adult, Economy, 0 bags

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 12 March 2026.

Cheapest airline

Qantas Airways

Good round-trip deal

$243 or less

Good one-way deal

$95 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago (avg. price of $2,140).
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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

Enter your travel dates to find the best prices.

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 12 March 2026.

Mon 6/418:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Mon 13/422:54
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
Deal found 7/3$144
Fri 24/412:47
ORD
-
EWR
Nonstop2h 07m
Spirit Airlines
Sat 25/416:05
EWR
-
ORD
1 stop9h 19m
Spirit Airlines
Deal found 7/3$145
Mon 30/318:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Mon 20/410:08
EWR
-
ORD
Nonstop2h 34m
Spirit Airlines
Deal found 10/3$182
Sat 4/418:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Mon 6/422:54
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
Deal found 9/3$183
Fri 1/512:47
ORD
-
EWR
Nonstop2h 07m
Spirit Airlines
Sun 3/510:08
EWR
-
ORD
Nonstop2h 34m
Spirit Airlines
Deal found 8/3$189
Fri 10/418:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Fri 17/410:08
EWR
-
ORD
Nonstop2h 34m
Spirit Airlines
Deal found 11/3$196
Mon 13/418:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Tue 14/419:59
EWR
-
ORD
1 stop14h 37m
Spirit Airlines
Deal found 10/3$198
Fri 3/418:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Mon 6/422:54
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
Deal found 9/3$203
Thu 7/512:47
ORD
-
EWR
Nonstop2h 07m
Spirit Airlines
Mon 11/510:08
EWR
-
ORD
Nonstop2h 34m
Spirit Airlines
Deal found 11/3$204
Sat 28/318:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Wed 1/422:54
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
Deal found 9/3$207
Wed 22/407:30
ORD
-
BNE
2 stops36h 05m
Multiple Airlines
Wed 29/411:35
BNE
-
ORD
2 stops26h 52m
Multiple Airlines
Deal found 11/3$1,139
Sun 3/505:15
ORD
-
MEL
2 stops40h 10m
Multiple Airlines
Wed 13/513:25
MEL
-
ORD
2 stops25h 02m
Multiple Airlines
Deal found 9/3$1,223

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 12 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

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Wed 8/7

05:00-08:13

Nonstop2h 13m

Newark

Wed 15/7

06:00-07:42

Nonstop2h 42m

$247

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Thu 2/4

18:01-21:09

Nonstop2h 08m

Newark

Sun 5/4

12:23-23:17

1 stop11h 54m

$249

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 30/5

20:04-23:36

Nonstop2h 32m

Newark

Tue 2/6

09:20-11:04

Nonstop2h 44m

$275

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Fri 24/4

19:46-23:10

Nonstop2h 24m

Newark

Sun 26/4

07:40-09:23

Nonstop2h 43m

$275

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sun 7/6

06:00-12:53

1 stop5h 53m

Newark

Tue 9/6

14:30-20:18

1 stop6h 48m

$302

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Fri 22/5

21:19-00:42

Nonstop2h 23m

Newark

Sat 23/5

16:45-18:34

Nonstop2h 49m

$302

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Tue 5/5

07:10-14:24

1 stop6h 14m

Newark

Sun 10/5

06:00-10:27

1 stop5h 27m

$331

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Tue 5/5

05:00-08:12

Nonstop2h 12m

Newark

Sun 10/5

07:30-09:14

Nonstop2h 44m

$345

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Wed 8/4

06:00-09:10

Nonstop2h 10m

Newark

Sun 12/4

07:40-09:23

Nonstop2h 43m

$345
Fastest return journey

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Fri 8/5

05:00-08:12

Nonstop2h 12m

Newark

Mon 11/5

15:15-16:55

Nonstop2h 40m

$345

Flights are sorted by cheapest return flights first.

Deals found on 7/3

Showing 1-10 of 60 resultsSorted by cheapest first
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2
3
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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 6 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 $277). Flying from Chicago in October will prove the most costly (average of $1,255). 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 $1,336

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to New York (1,052 flights per day), Detroit (1,030 flights per day) and Toronto (852 flights per day).

New York
New York
From $118
Memphis
Memphis
From $163
Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From $469

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 $118
Memphis
Memphis
From $163
Orlando
Orlando
From $203

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
1,004 reviews
Check prices

Boarding

7.7

Overall

7.5

Entertainment

7.2

Comfort

7.4

Crew

8.1

Food

7.0

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
1,004 reviews
Qantas Airways
7.5
Good
1,004 reviews
Check prices

Boarding

7.7

Overall

7.5

Entertainment

7.2

Comfort

7.4

Crew

8.1

Food

7.0

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

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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 12 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.

  • 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 $1,170. While Chicago Midway airport is usually cheaper if your destination is Sydney with prices starting at $1,364. 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 ($651).

  • 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 $1,170 round trip
    Fly from Chicago to Melbourne from $1,221 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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