Find flights
Airlines

$184+ 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 10/10. 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
20 Aug — 27 Aug1
1 adult

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 15 August 2025.

Cheapest airline

Qantas Airways

Good round-trip deal

$368 or less

Good one-way deal

$69 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago (avg. price of $1,468).
Search Deals
Price to beat on a round-trip flight from Chicago.
Search Deals
Price to beat on a one-way flight from Chicago.
Search Deals

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 15 August 2025.

Tue 9/908:00ORD - DCA
Nonstop1h 58mUnited Airlines
Wed 10/908:30DCA - ORD
Nonstop2h 17mUnited Airlines
Deal found 14/8$290
Thu 23/1013:36ORD - DCA
1 stop4h 45mJetBlue
Wed 29/1011:45DCA - ORD
1 stop7h 10mJetBlue
Deal found 15/8$311
Fri 5/913:36ORD - DCA
1 stop8h 20mJetBlue
Wed 10/906:19DCA - ORD
1 stop6h 51mJetBlue
Deal found 14/8$313
Fri 12/913:36ORD - DCA
1 stop8h 20mJetBlue
Tue 16/906:19DCA - ORD
1 stop6h 51mJetBlue
Deal found 14/8$319
Wed 10/905:45ORD - DCA
1 stop4h 35mDelta
Wed 17/906:00DCA - ORD
1 stop5h 19mDelta
Deal found 14/8$320
Wed 3/906:00ORD - DCA
Nonstop1h 58mUnited Airlines
Sat 6/915:59DCA - ORD
1 stop5h 12mUnited Airlines
Deal found 13/8$327
Thu 4/907:00ORD - DCA
Nonstop1h 58mUnited Airlines
Mon 8/920:00DCA - ORD
Nonstop2h 16mUnited Airlines
Deal found 14/8$333
Fri 10/1013:36ORD - DCA
1 stop8h 20mJetBlue
Wed 15/1006:25DCA - ORD
1 stop6h 45mJetBlue
Deal found 13/8$336
Thu 4/907:15ORD - DCA
1 stop3h 19mDelta
Wed 10/913:30DCA - ORD
1 stop6h 44mDelta
Deal found 14/8$342
Thu 23/1013:36ORD - DCA
1 stop4h 45mJetBlue
Fri 24/1006:25DCA - ORD
1 stop6h 45mJetBlue
Deal found 15/8$345
Thu 2/1011:45ORD - DCA
1 stop5h 02mUnited Airlines
Sat 4/1010:30DCA - ORD
Nonstop2h 17mUnited Airlines
Deal found 13/8$348
Tue 11/1115:40ORD - SYD
1 stop24h 55mAir Canada
Tue 18/1111:20SYD - ORD
1 stop20h 21mAir Canada
Deal found 12/8$1,280

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

Fly to

Sydney

Route

Depart

Return

Price

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 17/9

14:00-17:01

Nonstop2h 01m

Washington, D.C. Reagan-National

Wed 24/9

14:00-15:13

Nonstop2h 13m

$290

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Tue 9/9

08:00-10:58

Nonstop1h 58m

Washington, D.C. Reagan-National

Wed 10/9

08:30-09:47

Nonstop2h 17m

$290

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 15/10

07:00-09:58

Nonstop1h 58m

Washington, D.C. Reagan-National

Wed 15/10

20:00-21:16

Nonstop2h 16m

$290

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Fri 24/10

13:36-22:56

1 stop8h 20m

Washington, D.C. Reagan-National

Mon 27/10

16:55-20:52

1 stop4h 57m

$311

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Fri 31/10

06:44-14:50

1 stop7h 06m

Washington, D.C. Reagan-National

Fri 7/11

16:55-20:52

1 stop4h 57m

$311

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Tue 23/9

13:35-19:22

1 stop4h 47m

Washington, D.C. Reagan-National

Wed 1/10

13:20-18:55

1 stop6h 35m

$311

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Tue 16/9

15:00-18:03

Nonstop2h 03m

Washington, D.C. Reagan-National

Sat 20/9

10:30-11:47

Nonstop2h 17m

$311

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 22/10

13:36-22:56

1 stop8h 20m

Washington, D.C. Reagan-National

Wed 29/10

16:55-20:52

1 stop4h 57m

$311

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 8/10

13:36-19:21

1 stop4h 45m

Washington, D.C. Reagan-National

Wed 15/10

06:25-12:10

1 stop6h 45m

$311

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 12/11

11:20-21:00

1 stop8h 40m

Washington, D.C. Reagan-National

Sun 16/11

16:55-20:52

1 stop4h 57m

$311

Flights are sorted by cheapest return flights first.

Deals found on 12/8

Showing 1-10 of 60 results
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 8 August 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 $304). Flying from Chicago in January will prove the most costly (average of $1,319). 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 $854
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 (1,524 flights per day), Detroit (1,096 flights per day) and Los Angeles (739 flights per day).

Seattle/Tacoma Intl
Seattle/Tacoma Intl
From $108
Los Angeles
Los Angeles
From $70
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From $400

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 $45. Explore other affordable destinations below.

New York
New York
From $30
Toronto
Toronto
From $63
Raleigh-Durham
Raleigh-Durham
From $65
Los Angeles
Los Angeles
From $70

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
895 reviews
Check prices

Boarding

7.7

Overall

7.5

Entertainment

7.2

Comfort

7.4

Crew

8.2

Food

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,July 2025

MEL - SYD

Flight cancelled 2hours before take off after checking in. Booked by airline on flight 6 hours later. No compensation or vouchers till we asked just before the flight took off.
Qantas Airways
7.5
Good
895 reviews
Qantas Airways
7.5
Good
895 reviews
Check prices

Boarding

7.7

Overall

7.5

Entertainment

7.2

Comfort

7.4

Crew

8.2

Food

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,July 2025

MEL - SYD

Flight cancelled 2hours before take off after checking in. Booked by airline on flight 6 hours later. No compensation or vouchers till we asked just before the flight took off.

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 15 August 2025.

  • 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. Atlanta, Boston, Mumbai 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 $1,484. While Chicago Midway airport is usually cheaper if your destination is Sydney with prices starting at $1,880. 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 ($83). United Airlines flights from Chicago to Sioux City Sioux Gateway ($329). Qantas Airways flights from Chicago to Melbourne ($1,236).

  • 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 Melbourne from $1,484 round trip
    Fly from Chicago to Sydney from $1,549 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.