S$ 137+ Flights from Chicago | Cheapflights

What to know about flights from Chicago

Good round-trip deal	S$ 259 or less
Good one-way deal	S$ 155 or less

Price to beat on a round-trip flight from Chicago.

Price to beat on a one-way flight from Chicago.

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 13 May 2025.

Thu 17-719:35ORD - ONT

Nonstop4h 31mUnited Airlines

Sun 27-707:00ONT - ORD

Nonstop4h 03mUnited Airlines

Deal found 12-5S$ 296

Tue 10-618:27ORD - PWM

1 stop5h 19mDelta

Sat 14-618:28PWM - ORD

1 stop6h 30mDelta

Deal found 12-5S$ 312

Wed 11-606:15ORD - PWM

1 stop7h 25mJetBlue

Mon 16-606:10PWM - ORD

1 stop5h 03mJetBlue

Deal found 12-5S$ 317

Tue 10-611:00ORD - GRR

1 stop3h 25mDelta

Tue 17-616:05GRR - ORD

1 stop2h 58mDelta

Deal found 12-5S$ 319

Wed 2-717:56ORD - PWM

1 stop5h 03mUnited Airlines

Tue 8-719:15PWM - ORD

1 stop5h 15mUnited Airlines

Deal found 12-5S$ 321

Tue 19-806:00ORD - ONT

1 stop10h 46mAlaska Airlines

Sun 24-807:10ONT - ORD

1 stop19h 50mAlaska Airlines

Deal found 13-5S$ 321

Thu 3-718:55ORD - ONT

1 stop7h 00mSouthwest

Thu 17-715:20ONT - ORD

1 stop6h 20mSouthwest

Deal found 12-5S$ 322

Wed 20-807:15ORD - ONT

1 stop7h 08mDelta

Thu 28-813:00ONT - ORD

1 stop7h 00mDelta

Deal found 11-5S$ 335

Thu 4-911:25ORD - PWM

2 stops10h 45mSouthwest

Mon 8-908:45PWM - ORD

1 stop5h 00mSouthwest

Deal found 12-5S$ 351

Fri 13-619:30ORD - PWM

1 stop15h 27mSun Country Air

Sat 28-612:58PWM - ORD

1 stop8h 41mSun Country Air

Deal found 11-5S$ 358

Mon 18-806:00ORD - ONT

1 stop9h 27mHawaiian Airlines

Fri 22-819:22ONT - ORD

1 stop9h 41mHawaiian Airlines

Deal found 12-5S$ 373

Mon 23-621:56ORD - ONT

1 stop20h 22mFrontier

Mon 30-606:00ONT - ORD

1 stop12h 56mFrontier

Deal found 12-5S$ 417

Best flights from Chicago
Discover carefully curated flight deals from Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 13 May 2025.

Thu 17-719:35ORD - ONT

Nonstop4h 31mUnited Airlines

Sun 27-707:00ONT - ORD

Nonstop4h 03mUnited Airlines

Deal found 12-5S$ 296

Tue 10-618:27ORD - PWM

1 stop5h 19mDelta

Sat 14-618:28PWM - ORD

1 stop6h 30mDelta

Deal found 12-5S$ 312

Wed 11-606:15ORD - PWM

1 stop7h 25mJetBlue

Mon 16-606:10PWM - ORD

1 stop5h 03mJetBlue

Deal found 12-5S$ 317

Tue 19-806:00ORD - ONT

1 stop10h 46mAlaska Airlines

Sun 24-807:10ONT - ORD

1 stop19h 50mAlaska Airlines

Deal found 13-5S$ 321

Thu 3-718:55ORD - ONT

1 stop7h 00mSouthwest

Thu 17-715:20ONT - ORD

1 stop6h 20mSouthwest

Deal found 12-5S$ 322

Fri 13-619:30ORD - PWM

1 stop15h 27mSun Country Air

Sat 28-612:58PWM - ORD

1 stop8h 41mSun Country Air

Deal found 11-5S$ 358

Mon 18-806:00ORD - ONT

1 stop9h 27mHawaiian Airlines

Fri 22-819:22ONT - ORD

1 stop9h 41mHawaiian Airlines

Deal found 12-5S$ 373

Mon 23-621:56ORD - ONT

1 stop20h 22mFrontier

Mon 30-606:00ONT - ORD

1 stop12h 56mFrontier

Deal found 12-5S$ 417

Tue 10-611:00ORD - GRR

1 stop3h 25mDelta

Tue 17-616:05GRR - ORD

1 stop2h 58mDelta

Deal found 12-5S$ 319

Wed 2-717:56ORD - PWM

1 stop5h 03mUnited Airlines

Tue 8-719:15PWM - ORD

1 stop5h 15mUnited Airlines

Deal found 12-5S$ 321

Thu 4-911:25ORD - PWM

2 stops10h 45mSouthwest

Mon 8-908:45PWM - ORD

1 stop5h 00mSouthwest

Deal found 12-5S$ 351

Wed 20-807:15ORD - ONT

1 stop7h 08mDelta

Thu 28-813:00ONT - ORD

1 stop7h 00mDelta

Deal found 11-5S$ 335

Direct flights from Chicago
Explore direct flight options from Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 13 May 2025.

Thu 17-719:35ORD - ONT

Nonstop4h 31mUnited Airlines

Sun 27-707:00ONT - ORD

Nonstop4h 03mUnited Airlines

Deal found 12-5S$ 296

Sun 15-618:25ORD - PWM

Nonstop2h 31mUnited Airlines

Tue 17-606:00PWM - ORD

Nonstop2h 53mUnited Airlines

Deal found 11-5S$ 323

Mon 4-816:15ORD - ATH

Nonstop10h 15mUnited Airlines

Wed 27-812:35ATH - ORD

Nonstop11h 45mUnited Airlines

Deal found 12-5S$ 1,159

Mon 13-1017:15ORD - ATH

Nonstop9h 55mFinnair

Mon 20-1011:05ATH - ORD

Nonstop12h 00mFinnair

Deal found 12-5S$ 1,384

Sat 2-816:50ORD - ATH

Nonstop10h 20mBritish Airways

Thu 28-811:05ATH - ORD

Nonstop12h 00mBritish Airways

Deal found 11-5S$ 1,534

Thu 24-716:15ORD - ATH

Nonstop10h 15mLufthansa

Tue 5-812:35ATH - ORD

Nonstop11h 45mLufthansa

Deal found 12-5S$ 1,958

Last-minute flights from Chicago
Discover last-minute flight deals departing from Chicago. Data was last updated 13 May 2025 and is based on user searches.

Sun 18-521:20ORD - GRR

Nonstop1h 08mUnited Airlines

Mon 19-511:52GRR - ORD

Nonstop1h 13mUnited Airlines

Deal found 12-5S$ 729

Sun 18-508:40ORD - ATH

1 stop17h 25mUnited Airlines

Thu 12-612:35ATH - ORD

Nonstop11h 45mUnited Airlines

Deal found 12-5S$ 1,159

Sun 18-507:00ORD - ATH

1 stop16h 00mDelta

Thu 5-610:30ATH - ORD

1 stop21h 28mDelta

Deal found 12-5S$ 1,178

Sun 18-508:40ORD - ATH

1 stop17h 25mMultiple Airlines

Mon 16-614:00ATH - ORD

1 stop30h 10mMultiple Airlines

Deal found 12-5S$ 1,180

Sun 18-510:05ORD - ATH

1 stop12h 55mVirgin Atlantic

Sun 8-615:30ATH - ORD

1 stop26h 25mVirgin Atlantic

Deal found 12-5S$ 1,272

Tue 20-514:20ORD - ATH

1 stop17h 25mSWISS

Mon 2-614:00ATH - ORD

1 stop30h 10mSWISS

Deal found 11-5S$ 1,254

Wed 21-507:15ORD - ONT

1 stop9h 00mDelta

Wed 15-1011:29ONT - ORD

1 stop10h 18mDelta

Deal found 12-5S$ 484

Wed 21-514:09ORD - ONT

1 stop11h 48mAlaska Airlines

Tue 27-506:00ONT - ORD

2 stops15h 56mAlaska Airlines

Deal found 13-5S$ 574

Wed 21-515:52ORD - ONT

1 stop8h 08mUnited Airlines

Wed 15-1007:00ONT - ORD

Nonstop4h 03mUnited Airlines

Deal found 12-5S$ 604

Thu 22-507:00ORD - PWM

1 stop5h 50mDelta

Sun 25-506:05PWM - ORD

1 stop5h 07mDelta

Deal found 13-5S$ 472

Fri 23-516:00ORD - PWM

1 stop6h 27mUnited Airlines

Mon 26-506:00PWM - ORD

Nonstop2h 53mUnited Airlines

Deal found 12-5S$ 464

Fri 23-506:00ORD - PWM

2 stops8h 55mSouthwest

Mon 26-505:50PWM - ORD

1 stop7h 00mSouthwest

Deal found 12-5S$ 551

One-way flights from Chicago
Search for one-way flight options from Chicago. Find affordable one-way fares based on user searches. Data last updated 13 May 2025.

Tue 30-918:02ORD - GRR

Nonstop1h 01mUnited Airlines

Deal found 12-5S$ 147

Sat 21-619:55ORD - ONT

Nonstop4h 31mUnited Airlines

Deal found 12-5S$ 149

Thu 12-613:50ORD - PWM

1 stop4h 15mSouthwest

Deal found 11-5S$ 150

Wed 28-507:10ORD - PWM

1 stop3h 47mDelta

Deal found 13-5S$ 155

Wed 4-609:00ORD - GRR

1 stop3h 19mDelta

Deal found 13-5S$ 160

Wed 6-806:00ORD - ONT

1 stop9h 26mAlaska Airlines

Deal found 12-5S$ 160

Wed 28-511:05ORD - PWM

Nonstop2h 26mUnited Airlines

Deal found 13-5S$ 163

Fri 11-712:40ORD - ONT

1 stop10h 10mSouthwest

Deal found 12-5S$ 168

Wed 11-605:35ORD - ONT

1 stop7h 22mDelta

Deal found 13-5S$ 175

Wed 4-606:15ORD - PWM

1 stop7h 25mJetBlue

Deal found 12-5S$ 185

Tue 17-610:00ORD - ONT

1 stop10h 04mHawaiian Airlines

Deal found 12-5S$ 186

Thu 28-817:12ORD - PWM

1 stop17h 22mSun Country Air

Deal found 12-5S$ 219

Find flights from Chicago within your budget

Fly to

Route

Depart

Return

Price

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Thu 17-7

19:35-22:06

Nonstop4h 31m

Ontario

Sun 27-7

07:00-13:03

Nonstop4h 03m

S$ 296

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 10-6

18:27-00:46

1 stop5h 19m

Portland

Sat 14-6

18:28-23:58

1 stop6h 30m

S$ 312

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 11-6

06:15-14:40

1 stop7h 25m

Portland

Mon 16-6

06:10-10:13

1 stop5h 03m

S$ 317

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 10-6

11:00-15:25

1 stop3h 25m

Grand Rapids Gerald R. Ford Intl

Tue 17-6

16:05-18:03

1 stop2h 58m

S$ 319

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Tue 19-8

06:00-14:46

1 stop10h 46m

Ontario

Sun 24-8

07:10-05:00

1 stop19h 50m

S$ 321

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 2-7

17:56-23:59

1 stop5h 03m

Portland

Tue 8-7

19:15-23:30

1 stop5h 15m

S$ 321

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Thu 3-7

18:55-23:55

1 stop7h 00m

Ontario

Thu 17-7

15:20-23:40

1 stop6h 20m

S$ 322

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Wed 20-8

07:15-12:23

1 stop7h 08m

Ontario

Thu 28-8

13:00-22:00

1 stop7h 00m

S$ 335

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 4-9

11:25-23:10

2 stops10h 45m

Portland

Mon 8-9

08:45-12:45

1 stop5h 00m

S$ 351

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 13-6

19:30-11:57

1 stop15h 27m

Portland

Sat 28-6

12:58-20:39

1 stop8h 41m

S$ 358

Flights are sorted by cheapest return flights first.

Deals found on 12-5

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?

The price you pay for your flight from Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 73 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago?

Currently, March is the cheapest month in which you can book a flight from Chicago (average of S$ 950). Flying from Chicago in June will prove the most costly (average of S$ 1,562). 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: United Airlines. As it departs for the following popular destinations: Singapore.

United Airlines

United Airlines

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,718 flights per day), Detroit (1,240 flights per day) and Los Angeles (760 flights per day).

San Francisco

Rome

Buffalo

Amsterdam Schiphol

Amsterdam Schiphol

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is San Francisco, with prices starting at S$ 140. Explore other affordable destinations below.

San Francisco

Buffalo

Rome

Amsterdam Schiphol

Amsterdam Schiphol

Airline reviews for flights from Chicago

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.

8.4

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.

8.4

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.

8.3

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.

8.3

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.

8.0

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.

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Related info for your journey

What are the most popular destinations to fly to from Chicago?
This month, the top selected destinations from Chicago are Atlanta, Boston, Athens. Throughout the year, Atlanta, Boston, Mumbai are some of the top choices made by users flying from Chicago.
What is the cheapest month to fly from Chicago?
Currently, the cheapest month for flights from Chicago is March. The most expensive month for flights is June. The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.
How does Cheapflights help users find flights from Chicago?
When you search for this flight from Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.
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?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.
Can Cheapflights notify me if prices for flights from Chicago become cheaper?
Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

See more FAQs

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How does Cheapflights help users find flights from Chicago?

When you search for this flight from Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

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?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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