S$ 140+ Flights from Chicago | Cheapflights

What to know about flights from Chicago

Good round-trip deal	S$ 266 or less
Good one-way deal	S$ 82 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 22 February 2025.

Fri 25-418:35ORD - GRR

Nonstop1h 06mUnited Airlines

Mon 28-407:15GRR - ORD

Nonstop1h 07mUnited Airlines

Deal found 20-2S$ 198

Mon 18-806:00ORD - PWM

1 stop6h 23mJetBlue

Tue 26-806:10PWM - ORD

1 stop5h 37mJetBlue

Deal found 20-2S$ 218

Wed 16-406:45ORD - GRR

1 stop5h 49mDelta

Wed 23-406:25GRR - ORD

1 stop3h 59mDelta

Deal found 19-2S$ 236

Tue 15-407:50ORD - ONT

1 stop8h 05mDelta

Wed 23-411:45ONT - ORD

1 stop10h 14mDelta

Deal found 21-2S$ 244

Wed 19-306:00ORD - PWM

1 stop4h 27mDelta

Wed 26-316:30PWM - ORD

1 stop5h 08mDelta

Deal found 20-2S$ 290

Wed 5-311:10ORD - PWM

Nonstop2h 22mUnited Airlines

Fri 25-406:00PWM - ORD

Nonstop2h 52mUnited Airlines

Deal found 19-2S$ 294

Wed 28-519:55ORD - ONT

Nonstop4h 31mUnited Airlines

Mon 2-607:00ONT - ORD

Nonstop4h 03mUnited Airlines

Deal found 21-2S$ 303

Tue 13-513:50ORD - PWM

1 stop7h 40mSouthwest

Tue 20-506:15PWM - ORD

2 stops7h 30mSouthwest

Deal found 20-2S$ 326

Wed 23-406:00ORD - ONT

1 stop11h 32mAlaska Airlines

Tue 29-406:00ONT - ORD

1 stop22h 05mAlaska Airlines

Deal found 21-2S$ 358

Sun 6-422:05ORD - GRR

Nonstop0h 57mAmerican Airlines

Sun 13-415:48GRR - ORD

Nonstop1h 07mAmerican Airlines

Deal found 20-2S$ 369

Mon 7-406:15ORD - ONT

2 stops8h 30mSouthwest

Fri 11-415:15ONT - ORD

1 stop5h 50mSouthwest

Deal found 20-2S$ 403

Fri 4-720:05ORD - PWM

1 stop14h 30mSun Country Air

Mon 7-712:32PWM - ORD

1 stop7h 39mSun Country Air

Deal found 20-2S$ 414

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 22 February 2025.

Fri 25-418:35ORD - GRR

Nonstop1h 06mUnited Airlines

Mon 28-407:15GRR - ORD

Nonstop1h 07mUnited Airlines

Deal found 20-2S$ 198

Mon 18-806:00ORD - PWM

1 stop6h 23mJetBlue

Tue 26-806:10PWM - ORD

1 stop5h 37mJetBlue

Deal found 20-2S$ 218

Wed 16-406:45ORD - GRR

1 stop5h 49mDelta

Wed 23-406:25GRR - ORD

1 stop3h 59mDelta

Deal found 19-2S$ 236

Tue 13-513:50ORD - PWM

1 stop7h 40mSouthwest

Tue 20-506:15PWM - ORD

2 stops7h 30mSouthwest

Deal found 20-2S$ 326

Wed 23-406:00ORD - ONT

1 stop11h 32mAlaska Airlines

Tue 29-406:00ONT - ORD

1 stop22h 05mAlaska Airlines

Deal found 21-2S$ 358

Sun 6-422:05ORD - GRR

Nonstop0h 57mAmerican Airlines

Sun 13-415:48GRR - ORD

Nonstop1h 07mAmerican Airlines

Deal found 20-2S$ 369

Fri 4-720:05ORD - PWM

1 stop14h 30mSun Country Air

Mon 7-712:32PWM - ORD

1 stop7h 39mSun Country Air

Deal found 20-2S$ 414

Wed 12-314:00ORD - ONT

1 stop9h 27mHawaiian Airlines

Tue 18-306:00ONT - ORD

1 stop10h 00mHawaiian Airlines

Deal found 20-2S$ 417

Tue 15-407:50ORD - ONT

1 stop8h 05mDelta

Wed 23-411:45ONT - ORD

1 stop10h 14mDelta

Deal found 21-2S$ 244

Wed 5-311:10ORD - PWM

Nonstop2h 22mUnited Airlines

Fri 25-406:00PWM - ORD

Nonstop2h 52mUnited Airlines

Deal found 19-2S$ 294

Mon 7-420:33ORD - ONT

2 stops29h 26mMultiple Airlines

Mon 14-406:55ONT - ORD

3 stops23h 09mMultiple Airlines

Deal found 21-2S$ 633

Wed 19-306:00ORD - PWM

1 stop4h 27mDelta

Wed 26-316:30PWM - ORD

1 stop5h 08mDelta

Deal found 20-2S$ 290

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 22 February 2025.

Thu 13-308:58ORD - GRR

Nonstop1h 11mUnited Airlines

Mon 17-318:30GRR - ORD

Nonstop1h 16mUnited Airlines

Deal found 21-2S$ 238

Wed 5-311:10ORD - PWM

Nonstop2h 22mUnited Airlines

Fri 25-406:00PWM - ORD

Nonstop2h 52mUnited Airlines

Deal found 19-2S$ 294

Wed 28-519:55ORD - ONT

Nonstop4h 31mUnited Airlines

Mon 2-607:00ONT - ORD

Nonstop4h 03mUnited Airlines

Deal found 21-2S$ 303

Sun 6-422:05ORD - GRR

Nonstop0h 57mAmerican Airlines

Sun 13-415:48GRR - ORD

Nonstop1h 07mAmerican Airlines

Deal found 20-2S$ 369

Sun 3-816:15ORD - ATH

Nonstop10h 15mUnited Airlines

Wed 27-812:35ATH - ORD

Nonstop11h 45mUnited Airlines

Deal found 20-2S$ 1,250

Fri 8-817:05ORD - ATH

Nonstop10h 05mFinnair

Fri 12-911:05ATH - ORD

Nonstop12h 00mFinnair

Deal found 19-2S$ 1,624

Thu 1-516:15ORD - ATH

Nonstop10h 15mLufthansa

Thu 8-512:35ATH - ORD

Nonstop11h 45mLufthansa

Deal found 20-2S$ 1,715

Sat 2-817:00ORD - ATH

Nonstop10h 05mBritish Airways

Fri 12-911:05ATH - ORD

Nonstop12h 00mBritish Airways

Deal found 19-2S$ 1,853

Last-minute flights from Chicago
Discover last-minute flight deals departing from Chicago. Data was last updated 22 February 2025 and is based on user searches.

Wed 26-214:00ORD - ONT

1 stop9h 27mAlaska Airlines

Wed 5-307:00ONT - ORD

2 stops14h 59mAlaska Airlines

Deal found 19-2S$ 672

Wed 26-205:45ORD - ONT

1 stop8h 10mDelta

Thu 27-207:05ONT - ORD

1 stop6h 40mDelta

Deal found 20-2S$ 693

Thu 27-208:45ORD - PWM

1 stop4h 57mUnited Airlines

Tue 4-316:04PWM - ORD

Nonstop3h 06mUnited Airlines

Deal found 20-2S$ 534

Thu 27-211:40ORD - PWM

2 stops11h 15mDelta

Tue 4-306:00PWM - ORD

2 stops7h 55mDelta

Deal found 20-2S$ 653

Fri 28-214:55ORD - PWM

2 stops8h 00mSouthwest

Sun 2-317:10PWM - ORD

1 stop5h 20mSouthwest

Deal found 20-2S$ 460

Fri 28-218:15ORD - GRR

1 stop3h 42mDelta

Sun 2-317:57GRR - ORD

1 stop3h 56mDelta

Deal found 21-2S$ 709

Sat 1-308:45ORD - ONT

1 stop7h 45mUnited Airlines

Sat 1-319:40ONT - ORD

1 stop7h 13mUnited Airlines

Deal found 19-2S$ 815

Sun 2-305:00ORD - ONT

1 stop7h 01mAmerican Airlines

Thu 6-323:59ONT - ORD

1 stop6h 24mAmerican Airlines

Deal found 20-2S$ 636

Mon 3-313:45ORD - ONT

2 stops10h 20mSouthwest

Thu 6-314:50ONT - ORD

1 stop5h 45mSouthwest

Deal found 20-2S$ 578

Mon 3-311:55ORD - ATH

1 stop12h 45mTurkish Airlines

Mon 7-403:55ATH - ORD

1 stop13h 45mTurkish Airlines

Deal found 21-2S$ 809

Mon 3-316:25ORD - ATH

1 stop16h 10mDelta

Tue 18-311:50ATH - ORD

1 stop16h 36mDelta

Deal found 20-2S$ 850

Mon 3-316:25ORD - ATH

1 stop16h 10mKLM

Thu 13-311:50ATH - ORD

1 stop16h 36mKLM

Deal found 20-2S$ 858

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 22 February 2025.

Tue 20-507:10ORD - ONT

1 stop7h 28mUnited Airlines

Deal found 20-2S$ 166

Mon 24-306:45ORD - PWM

1 stop4h 31mDelta

Deal found 21-2S$ 167

Tue 18-306:45ORD - GRR

2 stops8h 30mDelta

Deal found 20-2S$ 167

Sat 17-506:20ORD - PWM

1 stop6h 00mJetBlue

Deal found 19-2S$ 172

Sat 7-613:16ORD - ONT

1 stop8h 26mDelta

Deal found 19-2S$ 172

Mon 12-521:22ORD - GRR

Nonstop1h 08mUnited Airlines

Deal found 20-2S$ 175

Wed 23-406:00ORD - ONT

1 stop11h 32mAlaska Airlines

Deal found 21-2S$ 178

Thu 17-720:10ORD - PWM

1 stop14h 25mSun Country Air

Deal found 20-2S$ 198

Sat 21-613:30ORD - PWM

1 stop9h 05mSouthwest

Deal found 20-2S$ 207

Thu 24-417:56ORD - ONT

1 stop8h 03mHawaiian Airlines

Deal found 21-2S$ 223

Wed 18-613:50ORD - GRR

1 stop7h 10mSouthwest

Deal found 21-2S$ 227

Tue 20-512:40ORD - ONT

2 stops8h 50mSouthwest

Deal found 20-2S$ 232

Find flights from Chicago within your budget

Fly to

Route

Depart

Return

Price

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Tue 15-4

07:50-13:55

1 stop8h 05m

Ontario

Wed 23-4

11:45-23:59

1 stop10h 14m

S$ 244

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 8-7

06:00-13:23

1 stop6h 23m

Portland

Tue 15-7

06:10-10:47

1 stop5h 37m

S$ 247

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Mon 17-3

21:05-23:09

Nonstop1h 04m

Grand Rapids Gerald R. Ford Intl

Sat 22-3

07:25-07:37

Nonstop1h 12m

S$ 258

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Mon 7-4

18:15-22:50

1 stop3h 35m

Grand Rapids Gerald R. Ford Intl

Mon 14-4

14:14-18:10

1 stop4h 56m

S$ 278

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 19-3

06:00-11:27

1 stop4h 27m

Portland

Wed 26-3

16:30-20:38

1 stop5h 08m

S$ 290

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 5-3

11:10-14:32

Nonstop2h 22m

Portland

Fri 25-4

06:00-07:52

Nonstop2h 52m

S$ 294

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Wed 28-5

19:55-22:26

Nonstop4h 31m

Ontario

Mon 2-6

07:00-13:03

Nonstop4h 03m

S$ 303

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 13-5

13:50-22:30

1 stop7h 40m

Portland

Tue 20-5

06:15-12:45

2 stops7h 30m

S$ 326

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Wed 23-4

06:00-15:32

1 stop11h 32m

Ontario

Tue 29-4

06:00-06:05

1 stop22h 05m

S$ 358

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Sun 6-4

22:05-00:02

Nonstop0h 57m

Grand Rapids Gerald R. Ford Intl

Sun 13-4

15:48-15:55

Nonstop1h 07m

S$ 369

Flights are sorted by cheapest return flights first.

Deals found on 20-2

Showing 1-10 of 60 results

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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?

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, February is the cheapest month in which you can book a flight from Chicago (average of S$ 994). Flying from Chicago in June will prove the most costly (average of S$ 1,628). 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

From S$ 836

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,526 flights per day), Detroit (978 flights per day) and Orlando (795 flights per day).

San Francisco

San Francisco

From S$ 107

Rome

Rome

From S$ 719

Atlanta Hartsfield-Jackson

Atlanta Hartsfield-Jackson

From S$ 2,310

Buffalo

Buffalo

From S$ 199

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Orlando, with prices starting at S$ 82. Explore other affordable destinations below.

Orlando

Orlando

From S$ 61

San Francisco

San Francisco

From S$ 107

Buffalo

Buffalo

From S$ 199

Rome

Rome

From S$ 719

Airline reviews for flights from Chicago

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Piotr,Feb 2025

TPE - ORD

It is always a pleasure to travel with EVA Air.

8.4

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Piotr,Feb 2025

TPE - ORD

It is always a pleasure to travel with EVA Air.

8.4

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Piotr,Feb 2025

TPE - ORD

It is always a pleasure to travel with EVA Air.

8.4

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Piotr,Feb 2025

TPE - ORD

It is always a pleasure to travel with EVA Air.

8.3

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Piotr,Feb 2025

TPE - ORD

It is always a pleasure to travel with EVA Air.

8.0

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Piotr,Feb 2025

TPE - ORD

It is always a pleasure to travel with EVA Air.

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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, Mumbai, Ahmedabad. Throughout the year, Atlanta, Boston, Athens 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 February. 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.
Where are the cheapest places to fly to from Chicago?
View the cheapest flight destinations from Chicago:
Fly from Chicago to Singapore from S$ 946 round trip
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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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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