Are direct flights from Chicago to Singapore always the best option?

Direct flights often offer convenience by reducing travel time and avoiding layovers. However, they are not always the most budget-friendly option. Flights with one or more connections can sometimes be significantly cheaper, depending on the route and airline.

Can flexible travel dates help on Chicago to Singapore flights?

Yes, being flexible with your travel dates can often lead to finding more affordable flight options. Prices for flights can vary significantly depending on the day of the week or time of year. Avoiding peak travel periods usually results in lower fares.

What extra costs should I check before booking Chicago to Singapore flights?

Before booking, always check for potential extra costs such as baggage fees, seat selection charges, and in-flight services. Some airlines, especially budget carriers, may charge separately for these amenities. Factor these into your total travel budget to avoid surprises.

Flights From Chicago

To Singapore

Cheap Flights from Chicago to Singapore

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to Singapore

Prices updated 1 day ago

461 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Chicago to Singapore

Explore current cheapest deals departing from Chicago to Singapore

2026-11-05 – 2026-11-12
CHI - Singapore
79% AI deal score
$844
$790
Round trip
2026-10-12 – 2026-10-26
CHI - Singapore
85% AI deal score
$943
$812
Round trip
2026-10-19 – 2026-10-26
CHI - Singapore
90% AI deal score
$987
$812
Round trip
2027-02-17 – 2027-02-22
CHI - Singapore
85% AI deal score
$940
$813
Round trip
2026-10-12 – 2026-10-27
CHI - Singapore
84% AI deal score
$933
$818
Round trip
2027-03-15 – 2027-03-22
CHI - Singapore
91% AI deal score
$1,074
$818
Round trip
2026-11-17 – 2026-11-22
CHI - Singapore
79% AI deal score
$874
$824
Round trip
2026-10-20 – 2026-10-29
CHI - Singapore
82% AI deal score
$955
$836
Round trip
2026-10-12 – 2026-10-22
CHI - Singapore
84% AI deal score
$953
$844
Round trip
2026-10-08 – 2026-10-20
CHI - Singapore
83% AI deal score
$944
$847
Round trip

Chicago to Singapore: Overview

Insights for flights from Chicago to Singapore

The journey from Chicago to Singapore covers a substantial distance of 15,050 km, classifying it as a long-haul route. This considerable distance means that itineraries typically involve multiple connections.

For travelers seeking cheap flights from Chicago to Singapore, fares right now are above the typical level. Prices for this route typically range from $1403–$1948, with a median of $1643. New deals for this route show up several times a week, indicating a regular cadence of price changes.

If you are wondering when is the cheapest time to fly from Chicago to Singapore, the data indicates that April is often the most affordable month, with a median fare of $631. Other cost-effective months include May, with a median fare of $858, and January, where the median fare is $878.

When flying from Chicago to Singapore, most itineraries connect at least once, as 0% of recent fares were non-stop. For connecting flights, the typical number of stopovers is 2. This means you should expect to make multiple stops on your journey.

A typical journey from Chicago to Singapore, including connections, takes approximately 46h 55m. This duration reflects the long-haul nature of the route and the common necessity of multiple stopovers between the two cities.

How much is a round trip from Chicago to Singapore

Regular price: $744 - $1,621

Prices are currently within the regular range.

The regular price range for flights from Chicago to Singapore is $744-$1621. The current lowest deal is $789 with Air Canada, for travel from Nov 5-Nov 12.

now $789

Low $744

High $1,621

The cheapest time to fly from Chicago to Singapore

The cheapest month to fly from Chicago to Singapore is April, with a median price of $631. The most expensive month is June, with a median price of $1871. Generally, prices are lower from January to September.

April

Cheapest

Flights from $631

June

Most Expensive

Flights from $1,871

Jan

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Singapore

Etihad Airways

Air Canada

Cathay Pacific

Korean Air

Last-minute flights going from Chicago to Singapore

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

Etihad Airways

$864

$899

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

Cathay Pacific

$864

$905

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

$1,018

$937

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

$942

$937

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

$943

$937

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

$894

$937

One-way

Biggest price drops on these dates for flights from Chicago to Singapore

7 nights

Mar 15 - Mar 22

$1,132 → $818

28%

3 nights

Dec 4 - Dec 7

$1,251 → $1,031

18%

7 nights

Dec 1 - Dec 8

$1,203 → $997

17%

7 nights

Oct 19 - Oct 26

$987 → $811

18%

Popular Airports to fly from Chicago to Singapore

Chicago - Singapore route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Chicago to Singapore are above the typical level at $789.

📅 Best time to fly

April offers the lowest median price

Historically, April has the lowest median price at $631 for flights from Chicago to Singapore.

⏱️ Flight duration

Connecting flights average 46h 55m

The median flight duration for connecting flights from Chicago to Singapore is 46h 55m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights are dominant, with a median of 2 stopovers on this route.

🏆 Airline highlight

Etihad Airways offers many deals

Etihad Airways has 40 direct deals, making it a frequent option for this route.

🎯 Booking tip

Deals appear regularly

Deals for flights from Chicago to Singapore appear regularly within a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International offers a wide range of flights from Chicago to Singapore, often with competitive pricing.

📍 ~25 km from city center (reachable by car or train)

💸 Flights from ~$791

Chicago Midway International (MDW)

Chicago Midway International is a convenient option for flights from Chicago to Singapore.

📍 ~14 km from city center (reachable by car or train)

💸 Flights from ~$824

Chicago Rockford International (RFD)

Chicago Rockford International is an alternative departure point for flights from Chicago to Singapore.

📍 ~126 km from city center (reachable by car)

💸 Flights from ~$1,224

Singapore main airports to arrive at

Singapore Changi (SIN)

Cheapest

Singapore Changi Airport is a primary gateway to Singapore, offering convenient access for your trip from Chicago.

📍 ~19 km from city center (reachable by car, train, bus)

💸 Flights from ~$791

Airports nearby Singapore used as alternative

Senai International (JHB)

Singapore, Singapore

95% AI deal score

$18,855

$8,177

Save $10,678

Etihad Airways

Business Class

From ORD

Elite

Oct 07

Singapore, Singapore

94% AI deal score

$5,934

$3,548

Save $2,386

Air Canada, +1

Business Class

From ORD

Elite

Oct 05

Singapore, Singapore

94% AI deal score

$5,903

$3,548

Save $2,355

Air Canada, +1

Business Class

From ORD

Elite

Oct 06

Singapore, Singapore

94% AI deal score

$5,929

$3,548

Save $2,381

Air Canada, +1

Business Class

From ORD

Elite

Oct 11

Singapore, Singapore

93% AI deal score

$5,988

$3,704

Save $2,284

Air Canada, +1

Business Class

From ORD

Elite

Oct 07

Singapore, Singapore

93% AI deal score

$5,945

$3,730

Save $2,215

Air Canada, +1

Business Class

From ORD

Elite

Oct 05

Singapore, Singapore

93% AI deal score

$5,926

$3,730

Save $2,196

Air Canada, +1

Business Class

From ORD

Elite

Oct 06

Singapore, Singapore

93% AI deal score

$5,938

$3,730

Save $2,208

Air Canada, +1

Business Class

From ORD

Elite

Oct 11

Singapore, Singapore

93% AI deal score

$6,187

$3,885

Save $2,302

Air Canada, +1

Business Class

From ORD

Elite

Sep 27

Singapore, Singapore

91% AI deal score

$4,971

$3,517

Save $1,454

Air Canada, +1

Business Class

From ORD

Elite

Sep 30

Singapore, Singapore

91% AI deal score

$4,927

$3,548

Save $1,379

Air Canada, +1

Business Class

Frequently Asked Questions About Flights to Singapore

To find more affordable flights, consider being flexible with your travel dates and times. Comparing prices across different airlines and booking platforms can often reveal better deals. Setting up price alerts may also help you catch drops in fares.

Booking flights in advance, often several months out, can sometimes lead to lower prices. However, prices can fluctuate, so monitoring fares over time may help you identify an opportune booking window. Last-minute deals are less common for international routes.

Comparing nearby airports at both your origin and destination can sometimes offer more flight options or different pricing. While it may require additional travel to and from these airports, it could potentially lead to savings on airfare. Always factor in the total cost and convenience.

Related routes

More routes from Chicago

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Flights to Singapore from other cities

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Chicago to Singapore: Overview

Insights for flights from Chicago to Singapore

How much is a round trip from Chicago to Singapore

Regular price: $744 - $1,621

Prices are currently within the regular range.

The regular price range for flights from Chicago to Singapore is $744-$1621. The current lowest deal is $789 with Air Canada, for travel from Nov 5-Nov 12.

now $789

Low $744

High $1,621

The cheapest time to fly from Chicago to Singapore

April

Cheapest

Flights from $631

June

Most Expensive

Flights from $1,871

Jan

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Singapore

Etihad Airways

Air Canada

Cathay Pacific

Korean Air

Last-minute flights going from Chicago to Singapore

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

Etihad Airways

$864

$899

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

Cathay Pacific

$864

$905

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

$1,018

$937

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

$942

$937

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

$943

$937

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

$894

$937

One-way

Biggest price drops on these dates for flights from Chicago to Singapore

7 nights

Mar 15 - Mar 22

$1,132 → $818

28%

3 nights

Dec 4 - Dec 7

$1,251 → $1,031

18%

7 nights

Dec 1 - Dec 8

$1,203 → $997

17%

7 nights

Oct 19 - Oct 26

$987 → $811

18%

Popular Airports to fly from Chicago to Singapore

Chicago - Singapore route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Chicago to Singapore are above the typical level at $789.

📅 Best time to fly

April offers the lowest median price

Historically, April has the lowest median price at $631 for flights from Chicago to Singapore.

⏱️ Flight duration

Connecting flights average 46h 55m

The median flight duration for connecting flights from Chicago to Singapore is 46h 55m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights are dominant, with a median of 2 stopovers on this route.

🏆 Airline highlight

Etihad Airways offers many deals

Etihad Airways has 40 direct deals, making it a frequent option for this route.

🎯 Booking tip

Deals appear regularly

Deals for flights from Chicago to Singapore appear regularly within a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International offers a wide range of flights from Chicago to Singapore, often with competitive pricing.

📍 ~25 km from city center (reachable by car or train)

💸 Flights from ~$791

Chicago Midway International (MDW)

Chicago Midway International is a convenient option for flights from Chicago to Singapore.

📍 ~14 km from city center (reachable by car or train)

💸 Flights from ~$824

Chicago Rockford International (RFD)

Chicago Rockford International is an alternative departure point for flights from Chicago to Singapore.

📍 ~126 km from city center (reachable by car)

💸 Flights from ~$1,224

Singapore main airports to arrive at

Singapore Changi (SIN)

Cheapest

Singapore Changi Airport is a primary gateway to Singapore, offering convenient access for your trip from Chicago.

📍 ~19 km from city center (reachable by car, train, bus)

💸 Flights from ~$791

Airports nearby Singapore used as alternative

Senai International (JHB)

Senai International Airport (JHB) is a useful alternative, often providing cost savings for domestic flights within Malaysia.

Singapore, Singapore

91% AI deal score

$4,927

$3,548

Save $1,379

Air Canada, +1

Business Class

Frequently Asked Questions About Flights to Singapore

Cheap Flights from Chicago to Singapore

Today’s best flight deals from Chicago to Singapore

Chicago to Singapore: Overview

Insights for flights from Chicago to Singapore

How much is a round trip from Chicago to Singapore

The cheapest time to fly from Chicago to Singapore

Direct flights from Chicago to Singapore

Last-minute flights going from Chicago to Singapore

Biggest price drops on these dates for flights from Chicago to Singapore

Popular Airports to fly from Chicago to Singapore

Chicago - Singapore route insights

Recent fares are above the typical level

April offers the lowest median price

Connecting flights average 46h 55m

Connecting flights are dominant

Etihad Airways offers many deals

Deals appear regularly

Chicago main airports to depart from

Singapore main airports to arrive at

Airports nearby Singapore used as alternative

Business & First Class Flight Deals to Singapore

Best Elite deals to Singapore

Jan 21

Feb 20

Oct 07

Oct 05

Oct 06

Oct 11

Oct 07

Oct 05

Oct 06

Oct 11

Sep 27

Sep 30

Frequently Asked Questions About Flights to Singapore

How can I find cheap flights from Chicago to Singapore?

When should I book flights from Chicago to Singapore?

Should I compare nearby airports for flights from Chicago to Singapore?

Are direct flights from Chicago to Singapore always the best option?

Can flexible travel dates help on Chicago to Singapore flights?

What extra costs should I check before booking Chicago to Singapore flights?

Related routes

More routes from Chicago

Flights to Singapore from other cities

Chicago to Singapore: Overview

Insights for flights from Chicago to Singapore

How much is a round trip from Chicago to Singapore

The cheapest time to fly from Chicago to Singapore

Direct flights from Chicago to Singapore

Last-minute flights going from Chicago to Singapore

Biggest price drops on these dates for flights from Chicago to Singapore

Popular Airports to fly from Chicago to Singapore

Chicago - Singapore route insights

Recent fares are above the typical level

April offers the lowest median price

Connecting flights average 46h 55m

Connecting flights are dominant

Etihad Airways offers many deals

Deals appear regularly

Chicago main airports to depart from

Singapore main airports to arrive at

Airports nearby Singapore used as alternative

Business & First Class Flight Deals to Singapore

Best Elite deals to Singapore

Jan 21

Feb 20

Oct 07

Oct 05

Oct 06

Oct 11

Oct 07

Oct 05

Oct 06

Oct 11

Sep 27

Sep 30

Frequently Asked Questions About Flights to Singapore

How can I find cheap flights from Chicago to Singapore?

When should I book flights from Chicago to Singapore?

Should I compare nearby airports for flights from Chicago to Singapore?