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S$ 142+ 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 5-2. 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 — SIN
27 Dec — 3 Jan1
1 adult

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 December 2024.

Tue 4-206:45ORD - GRR
1 stop6h 10mDelta
Tue 11-214:00GRR - ORD
1 stop3h 13mDelta
Deal found 21-12S$ 238
Wed 5-213:55ORD - GRR
Nonstop1h 09mUnited Airlines
Wed 12-212:56GRR - ORD
Nonstop1h 18mUnited Airlines
Deal found 21-12S$ 267
Fri 24-115:35ORD - ONT
1 stop8h 38mAlaska Airlines
Mon 27-106:00ONT - ORD
1 stop9h 59mAlaska Airlines
Deal found 21-12S$ 333
Tue 21-119:20ORD - ONT
1 stop6h 33mDelta
Sat 22-213:05ONT - ORD
1 stop8h 43mDelta
Deal found 22-12S$ 346
Sun 16-215:35ORD - PWM
1 stop6h 40mUnited Airlines
Sat 22-216:04PWM - ORD
Nonstop3h 06mUnited Airlines
Deal found 21-12S$ 391
Sat 31-508:55ORD - PWM
2 stops8h 56mDelta
Mon 2-617:59PWM - ORD
1 stop5h 43mDelta
Deal found 21-12S$ 410
Mon 17-216:20ORD - ONT
1 stop9h 35mSouthwest
Sat 22-205:05ONT - ORD
2 stops9h 40mSouthwest
Deal found 22-12S$ 429
Wed 5-306:30ORD - ONT
1 stop9h 59mUnited Airlines
Tue 11-306:00ONT - ORD
1 stop9h 06mUnited Airlines
Deal found 22-12S$ 449
Sat 18-112:40ORD - PWM
1 stop8h 25mSouthwest
Sun 19-105:35PWM - ORD
2 stops12h 10mSouthwest
Deal found 22-12S$ 457
Mon 7-419:15ORD - ATH
1 stop15h 35mScandinavian Airlines
Sat 26-421:05ATH - ORD
1 stop27h 05mScandinavian Airlines
Deal found 21-12S$ 758
Wed 5-211:55ORD - ATH
1 stop24h 50mTurkish Airlines
Thu 20-221:35ATH - ORD
1 stop29h 00mTurkish Airlines
Deal found 21-12S$ 777
Tue 4-318:26ORD - ATH
1 stop22h 49mMultiple Airlines
Mon 10-319:35ATH - ORD
1 stop25h 30mMultiple Airlines
Deal found 22-12S$ 857

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 22 December 2024. In the last 7 days, Cheapflights users made a total of 200,618 searches

Fly to

Any airport

Route

Depart

Return

Price

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 4-2

06:45-13:55

1 stop6h 10m

Grand Rapids Gerald R. Ford Intl

Tue 11-2

14:00-16:13

1 stop3h 13m

S$ 238

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Wed 5-2

13:55-16:04

Nonstop1h 09m

Grand Rapids Gerald R. Ford Intl

Wed 12-2

12:56-13:14

Nonstop1h 18m

S$ 267

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Fri 24-1

15:35-22:13

1 stop8h 38m

Ontario

Mon 27-1

06:00-17:59

1 stop9h 59m

S$ 333

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Tue 21-1

19:20-23:53

1 stop6h 33m

Ontario

Sat 22-2

13:05-23:48

1 stop8h 43m

S$ 346

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 16-2

15:35-23:15

1 stop6h 40m

Portland

Sat 22-2

16:04-18:10

Nonstop3h 06m

S$ 391

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 31-5

08:55-18:51

2 stops8h 56m

Portland

Mon 2-6

17:59-22:42

1 stop5h 43m

S$ 410

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Mon 17-2

16:20-23:55

1 stop9h 35m

Ontario

Sat 22-2

05:05-16:45

2 stops9h 40m

S$ 429

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Wed 5-3

06:30-14:29

1 stop9h 59m

Ontario

Tue 11-3

06:00-17:06

1 stop9h 06m

S$ 449

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 18-1

12:40-22:05

1 stop8h 25m

Portland

Sun 19-1

05:35-16:45

2 stops12h 10m

S$ 457

ChicagoAthens

ORD - ATH

ORDATH

Chicago O'Hare Intl

Mon 7-4

19:15-18:50

1 stop15h 35m

Athens Eleftherios V.

Sat 26-4

21:05-16:10

1 stop27h 05m

S$ 758

Flights are sorted by cheapest return flights first.

Deals found on 21-12

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?

Use this chart to determine the optimal time to book a return flight from Chicago to Singapore. Price data was last updated on 13 December 2024.

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 56 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$ 1,007). Flying from Chicago in July will prove the most costly (average of S$ 1,708). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: Detroit (800 flights per day), New York (754 flights per day) and Orlando (719 flights per day).

Rome

Rome

From S$ 719

Atlanta Hartsfield-Jackson

Atlanta Hartsfield-Jackson

From S$ 2,310

San Francisco

San Francisco

From S$ 107

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$ 83. 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

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 200,618 searches.
EVA Air
8.4
Very Good
1,265 reviews
Check prices

Overall

8.4

Crew

8.6

Entertainment

8.0

Food

8.0

Boarding

8.4

Comfort

8.3

Reviews

1 / 10

The food was HORRIBLE, the flight crew looked as though they’d rather be getting a root canal, and the bathrooms were disgusting.

EVA Air
8.4
Very Good
1,265 reviews
EVA Air
8.4
Very Good
1,265 reviews
Check prices

Overall

8.4

Crew

8.6

Entertainment

8.0

Food

8.0

Boarding

8.4

Comfort

8.3

Reviews

1 / 10

The food was HORRIBLE, the flight crew looked as though they’d rather be getting a root canal, and the bathrooms were disgusting.

Korean Air
8.4
Very Good
1,025 reviews
EVA Air
8.4
Very Good
1,265 reviews
Check prices

Overall

8.4

Crew

8.6

Entertainment

8.0

Food

8.0

Boarding

8.4

Comfort

8.3

Reviews

1 / 10

The food was HORRIBLE, the flight crew looked as though they’d rather be getting a root canal, and the bathrooms were disgusting.

Japan Airlines
8.3
Very Good
1,440 reviews
EVA Air
8.4
Very Good
1,265 reviews
Check prices

Overall

8.4

Crew

8.6

Entertainment

8.0

Food

8.0

Boarding

8.4

Comfort

8.3

Reviews

1 / 10

The food was HORRIBLE, the flight crew looked as though they’d rather be getting a root canal, and the bathrooms were disgusting.

Delta
8.0
Very Good
8,594 reviews
EVA Air
8.4
Very Good
1,265 reviews
Check prices

Overall

8.4

Crew

8.6

Entertainment

8.0

Food

8.0

Boarding

8.4

Comfort

8.3

Reviews

1 / 10

The food was HORRIBLE, the flight crew looked as though they’d rather be getting a root canal, and the bathrooms were disgusting.

KLM
7.8
Good
1,342 reviews
EVA Air
8.4
Very Good
1,265 reviews
Check prices

Overall

8.4

Crew

8.6

Entertainment

8.0

Food

8.0

Boarding

8.4

Comfort

8.3

Reviews

1 / 10

The food was HORRIBLE, the flight crew looked as though they’d rather be getting a root canal, and the bathrooms were disgusting.

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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 22 December 2024.

  • What are the most popular destinations to fly to from Chicago?

    This month, the top selected destinations from Chicago are Mumbai, Ahmedabad, Atlanta. 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 July. 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$ 1,005 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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