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

Direct flights offer convenience by reducing travel time and avoiding layovers, which can be appealing for long journeys. However, they are not always the most budget-friendly choice. Flights with connections may sometimes offer lower fares, 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 flights. Prices for airfare can vary significantly depending on the day of the week or time of year. Adjusting your departure or return by a few days may result in notable savings.

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 may also charge for meals or entertainment on longer international flights. Understanding these additional fees can help you calculate the true total cost of your journey.

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

459 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 8, 2026.)

Today’s best flight deals from Chicago to Singapore

Explore current cheapest deals departing from Chicago to Singapore

2026-09-10 – 2026-09-24
CHI - Singapore
78% AI deal score
$830
$793
Round trip
2026-11-05 – 2026-11-12
CHI - Singapore
80% AI deal score
$854
$793
Round trip
2026-11-12 – 2026-11-19
CHI - Singapore
79% AI deal score
$854
$797
Round trip
2026-11-01 – 2026-11-11
CHI - Singapore
79% AI deal score
$829
$804
Round trip
2027-02-11 – 2027-02-21
CHI - Singapore
85% AI deal score
$962
$811
Round trip
2026-09-23 – 2026-09-30
CHI - Singapore
77% AI deal score
$838
$815
Round trip
2026-09-17 – 2026-09-22
CHI - Singapore
81% AI deal score
$881
$820
Round trip
2026-10-12 – 2026-10-19
CHI - Singapore
90% AI deal score
$988
$820
Round trip
2026-10-21 – 2026-10-27
CHI - Singapore
90% AI deal score
$987
$820
Round trip
2026-10-20 – 2026-10-29
CHI - Singapore
85% AI deal score
$956
$820
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: $721 - $1,684

Prices are currently within the regular range.

Regular prices for flights from Chicago to Singapore typically range from 721 USD to 1684 USD. The current lowest deal is 793 USD with Air Canada, for travel from September 8 to September 29.

now $793

Low $721

High $1,684

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

Mon, Sep 7

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,288

$1,327

One-way

Thu, Sep 17

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,320

$1,839

One-way

Fri, Sep 18

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,322

$1,531

One-way

Wed, Sep 30

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,149

$936

One-way

Wed, Sep 30

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,148

$1,290

One-way

Sat, Oct 3

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,145

$1,438

One-way

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

11 nights

Mar 10 - Mar 21

$1,458 → $974

33%

15 nights

Mar 19 - Apr 3

$1,457 → $978

33%

8 nights

Mar 28 - Apr 5

$1,468 → $998

32%

7 nights

Mar 29 - Apr 5

$1,457 → $998

31%

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 $793.

📅 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

Flights from Chicago to Singapore typically involve 2 stopovers, with a median duration of 46h 55m.

✈️ Airlines & availability

Connecting flights are dominant

This route is primarily served by connecting flights; direct options are not available.

🏆 Airline highlight

Etihad Airways offers many deals

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

🎯 Booking tip

Deals appear regularly

Deals for flights from Chicago to Singapore appear regularly, so check often for good prices.

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.

📍 ~25 km from Singapore (reachable by car, bus, or taxi, but requires international border crossing).

💸 Flights from ~$874

Business & First Class Flight Deals to Singapore

Discover luxury on the budget with premium cabin class on flights from Chicago to Singapore.

Elite

Best Elite deals to Singapore

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Jan 19

Singapore, Singapore

97% AI deal score

$18,988

$6,377

Save $12,611

Etihad Airways

Business Class

From ORD

Elite

Dec 28

Singapore, Singapore

96% AI deal score

$19,156

$6,877

Save $12,279

Etihad Airways

Business Class

From ORD

Elite

Jan 01

Singapore, Singapore

95% AI deal score

$19,271

$8,527

Save $10,744

Etihad Airways

Business Class

From ORD

Elite

Oct 02

Singapore, Singapore

92% AI deal score

$5,921

$4,032

Save $1,889

Egyptair, +1

Business Class

From ORD

Elite

Sep 16

Singapore, Singapore

89% AI deal score

$4,861

$4,032

Save $829

Egyptair, +1

Business Class

From ORD

Elite

Sep 30

Singapore, Singapore

89% AI deal score

$4,942

$4,032

Save $910

Egyptair, +1

Business Class

From MDW

Elite

Sep 22

Singapore, Singapore

89% AI deal score

$2,594

$2,239

Save $355

Porter Airlines, +1

Business Class

From MDW

Elite

Sep 21

Singapore, Singapore

89% AI deal score

$2,596

$2,240

Save $356

Porter Airlines, +1

Business Class

From ORD

Elite

Feb 03

Singapore, Singapore

88% AI deal score

$2,564

$2,225

Save $339

United Airlines

Business Class

From ORD

Elite

Oct 29

Singapore, Singapore

85% AI deal score

$6,107

$5,166

Save $941

Cathay Pacific

Business Class

From ORD

Elite

Oct 26

Singapore, Singapore

85% AI deal score

$6,105

$5,166

Save $939

Cathay Pacific

Business Class

From ORD

Elite

Oct 27

Singapore, Singapore

85% AI deal score

$6,105

$5,166

Save $939

Cathay Pacific

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 provides more options and potentially better prices, especially for longer international routes. However, last-minute deals can sometimes appear, so monitoring prices is usually beneficial. There isn't a single best time that guarantees the lowest fare.

Comparing nearby airports can sometimes lead to more economical flight options or different route availability. While it may add to your ground travel time, the potential savings on airfare can be significant. Always factor in the total cost and convenience when considering this approach.

Related routes

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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: $721 - $1,684

Prices are currently within the regular range.

Regular prices for flights from Chicago to Singapore typically range from 721 USD to 1684 USD. The current lowest deal is 793 USD with Air Canada, for travel from September 8 to September 29.

now $793

Low $721

High $1,684

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

Mon, Sep 7

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,288

$1,327

One-way

Thu, Sep 17

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,320

$1,839

One-way

Fri, Sep 18

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,322

$1,531

One-way

Wed, Sep 30

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,149

$936

One-way

Wed, Sep 30

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,148

$1,290

One-way

Sat, Oct 3

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,145

$1,438

One-way

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

11 nights

Mar 10 - Mar 21

$1,458 → $974

33%

15 nights

Mar 19 - Apr 3

$1,457 → $978

33%

8 nights

Mar 28 - Apr 5

$1,468 → $998

32%

7 nights

Mar 29 - Apr 5

$1,457 → $998

31%

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 $793.

📅 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

Flights from Chicago to Singapore typically involve 2 stopovers, with a median duration of 46h 55m.

✈️ Airlines & availability

Connecting flights are dominant

This route is primarily served by connecting flights; direct options are not available.

🏆 Airline highlight

Etihad Airways offers many deals

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

🎯 Booking tip

Deals appear regularly

Deals for flights from Chicago to Singapore appear regularly, so check often for good prices.

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

85% AI deal score

$6,105

$5,166

Save $939

Cathay Pacific

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 19

Dec 28

Jan 01

Oct 02

Sep 16

Sep 30

Sep 22

Sep 21

Feb 03

Oct 29

Oct 26

Oct 27

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 19

Dec 28

Jan 01

Oct 02

Sep 16

Sep 30

Sep 22

Sep 21

Feb 03

Oct 29

Oct 26

Oct 27

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?