S$ 124+ Flights from Chicago | Cheapflights

What to know about flights from Chicago

Good round-trip deal	S$ 255 or less
Good one-way deal	S$ 152 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 June 2025.

Mon 4-807:00ORD - GRR

Nonstop1h 07mUnited Airlines

Mon 11-807:30GRR - ORD

Nonstop1h 08mUnited Airlines

Deal found 12-6S$ 201

Mon 4-819:01ORD - GRR

1 stop3h 45mDelta

Wed 13-805:30GRR - ORD

1 stop3h 34mDelta

Deal found 12-6S$ 227

Tue 1-716:46ORD - PWM

1 stop5h 28mUnited Airlines

Fri 4-705:35PWM - ORD

1 stop7h 08mUnited Airlines

Deal found 12-6S$ 305

Tue 5-811:01ORD - PWM

1 stop4h 10mDelta

Wed 13-806:00PWM - ORD

1 stop13h 02mDelta

Deal found 12-6S$ 310

Sat 26-720:50ORD - GRR

Nonstop1h 21mAmerican Airlines

Sat 2-807:17GRR - ORD

Nonstop1h 07mAmerican Airlines

Deal found 10-6S$ 320

Tue 29-706:16ORD - PWM

1 stop6h 07mJetBlue

Sat 2-814:19PWM - ORD

1 stop9h 09mJetBlue

Deal found 12-6S$ 333

Wed 22-1006:00ORD - ONT

1 stop19h 59mAlaska Airlines

Tue 28-1011:39ONT - ORD

1 stop8h 00mAlaska Airlines

Deal found 11-6S$ 352

Sun 27-721:56ORD - ONT

1 stop24h 56mFrontier

Sat 2-800:59ONT - ORD

1 stop21h 11mFrontier

Deal found 12-6S$ 362

Wed 25-611:50ORD - PWM

1 stop22h 49mSun Country Air

Sat 28-612:58PWM - ORD

1 stop8h 41mSun Country Air

Deal found 11-6S$ 365

Tue 12-811:05ORD - ONT

2 stops13h 15mDelta

Wed 13-811:40ONT - ORD

1 stop10h 11mDelta

Deal found 11-6S$ 387

Fri 12-911:25ORD - PWM

2 stops10h 55mSouthwest

Mon 15-905:50PWM - ORD

1 stop7h 55mSouthwest

Deal found 12-6S$ 399

Thu 24-718:55ORD - ONT

1 stop7h 00mSouthwest

Fri 25-705:40ONT - ORD

1 stop16h 00mSouthwest

Deal found 11-6S$ 429

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 June 2025.

Mon 4-807:00ORD - GRR

Nonstop1h 07mUnited Airlines

Mon 11-807:30GRR - ORD

Nonstop1h 08mUnited Airlines

Deal found 12-6S$ 201

Mon 4-819:01ORD - GRR

1 stop3h 45mDelta

Wed 13-805:30GRR - ORD

1 stop3h 34mDelta

Deal found 12-6S$ 227

Sat 26-720:50ORD - GRR

Nonstop1h 21mAmerican Airlines

Sat 2-807:17GRR - ORD

Nonstop1h 07mAmerican Airlines

Deal found 10-6S$ 320

Tue 29-706:16ORD - PWM

1 stop6h 07mJetBlue

Sat 2-814:19PWM - ORD

1 stop9h 09mJetBlue

Deal found 12-6S$ 333

Wed 22-1006:00ORD - ONT

1 stop19h 59mAlaska Airlines

Tue 28-1011:39ONT - ORD

1 stop8h 00mAlaska Airlines

Deal found 11-6S$ 352

Sun 27-721:56ORD - ONT

1 stop24h 56mFrontier

Sat 2-800:59ONT - ORD

1 stop21h 11mFrontier

Deal found 12-6S$ 362

Wed 25-611:50ORD - PWM

1 stop22h 49mSun Country Air

Sat 28-612:58PWM - ORD

1 stop8h 41mSun Country Air

Deal found 11-6S$ 365

Fri 12-911:25ORD - PWM

2 stops10h 55mSouthwest

Mon 15-905:50PWM - ORD

1 stop7h 55mSouthwest

Deal found 12-6S$ 399

Tue 1-716:46ORD - PWM

1 stop5h 28mUnited Airlines

Fri 4-705:35PWM - ORD

1 stop7h 08mUnited Airlines

Deal found 12-6S$ 305

Tue 5-811:01ORD - PWM

1 stop4h 10mDelta

Wed 13-806:00PWM - ORD

1 stop13h 02mDelta

Deal found 12-6S$ 310

Sat 26-715:18ORD - GRR

3 stops25h 20mMultiple Airlines

Sat 2-814:05GRR - ORD

1 stop27h 42mMultiple Airlines

Deal found 10-6S$ 726

Tue 12-811:05ORD - ONT

2 stops13h 15mDelta

Wed 13-811:40ONT - ORD

1 stop10h 11mDelta

Deal found 11-6S$ 387

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 June 2025.

Mon 4-807:00ORD - GRR

Nonstop1h 07mUnited Airlines

Mon 11-807:30GRR - ORD

Nonstop1h 08mUnited Airlines

Deal found 12-6S$ 201

Tue 1-718:30ORD - PWM

Nonstop2h 31mUnited Airlines

Thu 3-716:56PWM - ORD

Nonstop2h 57mUnited Airlines

Deal found 12-6S$ 311

Sat 26-720:50ORD - GRR

Nonstop1h 21mAmerican Airlines

Sat 2-807:17GRR - ORD

Nonstop1h 07mAmerican Airlines

Deal found 10-6S$ 320

Tue 22-719:40ORD - ONT

Nonstop4h 31mUnited Airlines

Tue 29-707:00ONT - ORD

Nonstop4h 03mUnited Airlines

Deal found 11-6S$ 508

Sun 10-816:15ORD - ATH

Nonstop10h 15mUnited Airlines

Fri 29-812:35ATH - ORD

Nonstop11h 45mUnited Airlines

Deal found 10-6S$ 882

Sat 23-816:55ORD - ATH

Nonstop10h 15mBritish Airways

Mon 1-911:05ATH - ORD

Nonstop11h 45mBritish Airways

Deal found 10-6S$ 1,036

Thu 7-816:55ORD - ATH

Nonstop10h 15mFinnair

Sat 23-811:05ATH - ORD

Nonstop11h 45mFinnair

Deal found 12-6S$ 1,121

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

Wed 18-616:00ORD - ATH

1 stop17h 40mLufthansa

Thu 18-906:50ATH - ORD

1 stop14h 05mLufthansa

Deal found 10-6S$ 1,393

Thu 19-618:25ORD - PWM

Nonstop2h 31mUnited Airlines

Thu 26-606:10PWM - ORD

Nonstop2h 55mUnited Airlines

Deal found 12-6S$ 452

Thu 19-613:50ORD - PWM

1 stop9h 15mSouthwest

Thu 26-605:40PWM - ORD

2 stops11h 45mSouthwest

Deal found 12-6S$ 541

Fri 20-618:27ORD - PWM

1 stop5h 19mDelta

Tue 24-618:56PWM - ORD

1 stop6h 01mDelta

Deal found 11-6S$ 477

Sat 21-607:09ORD - ONT

1 stop9h 16mDelta

Wed 25-606:25ONT - ORD

1 stop8h 55mDelta

Deal found 13-6S$ 1,041

Sun 22-606:00ORD - ONT

1 stop10h 46mAlaska Airlines

Wed 13-812:00ONT - ORD

1 stop15h 40mAlaska Airlines

Deal found 11-6S$ 772

Sun 22-605:02ORD - ONT

1 stop9h 29mUnited Airlines

Thu 21-807:00ONT - ORD

Nonstop4h 03mUnited Airlines

Deal found 12-6S$ 896

Sun 22-616:15ORD - ATH

Nonstop10h 15mUnited Airlines

Wed 17-915:30ATH - ORD

1 stop26h 25mUnited Airlines

Deal found 10-6S$ 1,358

Sun 22-607:00ORD - ATH

1 stop16h 00mDelta

Tue 16-906:30ATH - ORD

2 stops19h 06mDelta

Deal found 11-6S$ 1,402

Mon 23-619:00ORD - GRR

1 stop3h 46mDelta

Wed 25-605:30GRR - ORD

1 stop5h 33mDelta

Deal found 12-6S$ 680

Mon 23-607:00ORD - GRR

Nonstop1h 07mUnited Airlines

Fri 27-615:45GRR - ORD

1 stop18h 56mUnited Airlines

Deal found 12-6S$ 785

Mon 23-619:55ORD - ONT

Nonstop4h 31mMultiple Airlines

Mon 30-612:00ONT - ORD

1 stop9h 59mMultiple Airlines

Deal found 10-6S$ 1,170

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 June 2025.

Tue 19-806:00ORD - PWM

1 stop6h 23mJetBlue

Deal found 11-6S$ 124

Fri 4-713:50ORD - PWM

1 stop5h 30mSouthwest

Deal found 10-6S$ 128

Sun 19-1015:42ORD - GRR

Nonstop1h 01mUnited Airlines

Deal found 11-6S$ 137

Fri 4-718:27ORD - PWM

1 stop5h 19mDelta

Deal found 13-6S$ 140

Tue 1-718:30ORD - PWM

Nonstop2h 31mUnited Airlines

Deal found 11-6S$ 147

Fri 15-819:00ORD - GRR

1 stop3h 46mDelta

Deal found 11-6S$ 150

Wed 24-906:20ORD - ONT

1 stop9h 49mAlaska Airlines

Deal found 10-6S$ 175

Sat 26-718:21ORD - PWM

1 stop16h 14mSun Country Air

Deal found 12-6S$ 177

Sat 1-1107:30ORD - ONT

1 stop8h 27mDelta

Deal found 11-6S$ 187

Wed 16-712:06ORD - ONT

1 stop11h 53mJetBlue

Deal found 10-6S$ 246

Sat 26-719:35ORD - ONT

Nonstop4h 31mUnited Airlines

Deal found 11-6S$ 255

Tue 24-607:00ORD - GRR

Nonstop0h 56mAmerican Airlines

Deal found 12-6S$ 282

Find flights from Chicago within your budget

Fly to

Route

Depart

Return

Price

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Mon 4-8

19:01-23:46

1 stop3h 45m

Grand Rapids Gerald R. Ford Intl

Tue 12-8

05:30-08:04

1 stop3h 34m

S$ 266

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Mon 13-10

19:40-22:00

Nonstop1h 20m

Grand Rapids Gerald R. Ford Intl

Fri 17-10

09:15-09:26

Nonstop1h 11m

S$ 275

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 1-7

16:46-23:14

1 stop5h 28m

Portland

Fri 4-7

05:35-11:43

1 stop7h 08m

S$ 305

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 5-8

11:01-16:11

1 stop4h 10m

Portland

Wed 13-8

06:00-18:02

1 stop13h 02m

S$ 310

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Sat 26-7

20:50-23:11

Nonstop1h 21m

Grand Rapids Gerald R. Ford Intl

Sat 2-8

07:17-07:24

Nonstop1h 07m

S$ 320

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 29-7

06:16-13:23

1 stop6h 07m

Portland

Sat 2-8

14:19-22:28

1 stop9h 09m

S$ 333

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Wed 22-10

06:00-23:59

1 stop19h 59m

Ontario

Tue 28-10

11:39-21:39

1 stop8h 00m

S$ 352

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Sun 27-7

21:56-20:52

1 stop24h 56m

Ontario

Sat 2-8

00:59-00:10

1 stop21h 11m

S$ 362

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 25-6

11:50-11:39

1 stop22h 49m

Portland

Sat 28-6

12:58-20:39

1 stop8h 41m

S$ 365

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Tue 12-8

11:05-22:20

2 stops13h 15m

Ontario

Wed 13-8

11:40-23:51

1 stop10h 11m

S$ 387

Flights are sorted by cheapest return flights first.

Deals found on 11-6

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?

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$ 928). Flying from Chicago in June will prove the most costly (average of S$ 1,564). 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: Detroit (1,226 flights per day), New York (985 flights per day) and Los Angeles (762 flights per day).

San Francisco

Tokyo

Buffalo

Atlanta Hartsfield-Jackson

Atlanta Hartsfield-Jackson

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$ 137. Explore other affordable destinations below.

San Francisco

Buffalo

Atlanta Hartsfield-Jackson

Atlanta Hartsfield-Jackson

Tokyo

Airline reviews for flights from Chicago

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

8.4

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

8.4

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

8.3

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

8.3

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

8.3

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

Browse thousands of different options on Cheapflights for your next trip

Direct flights from Illinois

Direct flights from Los Angeles

Direct flights from San Francisco

Direct flights from Honolulu

Direct flights from Las Vegas

Direct flights from Seattle

Direct flights from Boston

Direct flights from Miami

Direct flights from Orlando

Direct flights from Atlanta

Direct flights from Denver

Direct flights from Austin

Direct flights from Portland

Direct flights from Anchorage

Direct flights from San Diego

Direct flights from Philadelphia

Direct flights from Minneapolis

Direct flights from Charlotte

Direct flights from Pittsburgh

Direct flights from New Orleans

Direct flights from Nashville

Direct flights from Tampa

Direct flights from Indianapolis

Direct flights from Buffalo

Direct flights from Cleveland

Direct flights from Salt Lake City

Direct flights from Cincinnati

Direct flights from Fairbanks

Direct flights from San Antonio

Direct flights from Wichita

Direct flights from Fort Lauderdale

Fly from other United States cities

Flights from New York

Flights from Los Angeles

Flights from Orlando

Flights from Las Vegas

Flights from Miami

Flights from San Francisco

Flights from Boston

Flights from Washington, D.C.

Flights from Denver

Flights from Seattle

Flights from Fort Lauderdale

Flights from Atlanta

Flights from Dallas

Flights from Phoenix

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 Athens, Boston, Amman. 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

Fly with Cheapflights

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.

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.