To Singapore

Cheap Flights from Chicago to Singapore

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

Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Chicago to Singapore

Explore current cheapest deals departing from Chicago to Singapore

Round trip

Sort by: Cheapest

September 1 - September 8

Cheapest

Earliest

ORD - Singapore

$852

$882

Round trip

September 1 - September 17

Earliest

ORD - Singapore

$820

$888

Round trip

November 3 - November 10

Best

ORD - Singapore

$928

$893

Round trip

September 1 - September 15

Earliest

ORD - Singapore

$823

$901

Round trip

September 15 - September 22

ORD - Singapore

$870

$902

Round trip

September 16 - September 29

ORD - Singapore

$844

$903

Round trip

September 23 - September 30

Best

ORD - Singapore

$885

$906

Round trip

September 1 - September 7

Best

Earliest

ORD - Singapore

$851

$909

Round trip

September 6 - September 14

ORD - Singapore

$842

$925

Round trip

September 2 - September 7

Best

ORD - Singapore

$871

$927

Round trip

Unlock all 500+ flight deals to Singapore and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

Insights for flights from Chicago to Singapore

Flights from Chicago to Singapore cover a substantial distance of 15,050 km, classifying this as a long-haul international route. This significant distance means journeys typically involve multiple connections and extended travel times.

For those seeking cheap flights from Chicago to Singapore, fares typically range from $791–$1789, with a median of $1345. Right now, current fares are significantly above the typical level for this route. Only 1% of recent fares were classified as a good price, indicating that finding exceptional value can be challenging.

When considering the cheapest time to fly from Chicago to Singapore, April stands out 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. Planning your trip during these months could lead to more favorable pricing.

A typical journey from Chicago to Singapore takes approximately 46h 55m, including connections. There are no direct flights from Chicago to Singapore, meaning all itineraries involve at least one stop. Most itineraries on this route connect at least once, with the median number of stopovers being 2 when connecting.

How much is a round trip from Chicago to Singapore

Regular price: $735 - $1,582

Prices for flights from Chicago to Singapore are currently within the regular range.

The regular price range for this route is between $735 and $1582. The current lowest deal is $882 with Air Canada, for travel from Sep 1 to Sep 8.

now $882

Low $735

High $1,582

The cheapest time to fly from Chicago to Singapore

Flights from Chicago to Singapore are cheapest in April, with a median price of $631. The most expensive month to fly 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

Air Canada

Korean Air

Cathay Pacific

All Nippon Airways

Last-minute flights going from Chicago to Singapore

Thu, Jun 18

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

United Airlines

$1,289

$1,136

One-way

Sun, Aug 9

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,191

$1,008

One-way

Mon, Aug 10

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,203

$958

One-way

Mon, Aug 10

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,203

$958

One-way

Mon, Aug 10

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

Air Canada

$1,053

$979

One-way

Mon, Aug 10

⌛ Last-Minute

MDW - Singapore

Chicago (MDW) - Singapore (SIN)

$1,211

$1,008

One-way

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

14 nights

Dec 1 - Dec 15

$1,353 → $986

27%

4 nights

Dec 1 - Dec 5

$1,363 → $1,022

25%

10 nights

Dec 2 - Dec 12

$1,344 → $1,018

24%

10 nights

Dec 1 - Dec 11

$1,340 → $1,016

24%

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, with a median price of $1345.

📅 Best time to fly

April is historically the cheapest month to fly.

Historically, April is the cheapest month to fly from Chicago to Singapore, with a median price of $631.

⏱️ Flight duration

Flights are typically long-haul with 2+ stopovers.

Flights from Chicago to Singapore are typically long-haul, lasting around 46h 55m with 2 or more stopovers.

✈️ Airlines & availability

Connecting flights are available from multiple airlines.

This route is dominated by connecting flights; no direct flights are available from Chicago to Singapore.

🏆 Airline highlight

Air Canada offers connecting flights.

Air Canada has historically offered connecting flights for the Chicago to Singapore route.

🎯 Booking tip

Consider booking during April, May, or January.

Historically, April ($631), May ($858), and January ($878) offer lower median prices.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers the cheapest flights from Chicago to Singapore.

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

💸 Flights from ~$882

Chicago Midway International (MDW)

Chicago Midway International Airport is an alternative option for flights from Chicago to Singapore.

📍 ~15 km from city center (reachable by car or train)

💸 Flights from ~$934

Chicago Rockford International (RFD)

Chicago Rockford International Airport provides another departure choice for flights to Singapore.

📍 ~120 km from city center (reachable by car)

💸 Flights from ~$1275

Singapore main airports to arrive at

Singapore Changi (SIN)

Cheapest

Singapore Changi Airport is a primary gateway for travelers arriving in Singapore from Chicago.

📍 ~17 km from city center (reachable by car, train, bus)

💸 Flights from ~$882

Airports nearby Singapore used as alternative

Senai International (JHB)

Senai International is a useful alternative for regional Malaysia flights due to its land proximity to Singapore.

📍 ~28 km from Singapore (reachable by car, bus, or taxi, requires border crossing)

💸 Flights from ~$1104

Kuala Lumpur International (KUL)

Cheapest

Kuala Lumpur International is a major regional hub, offering an extensive global network and competitive pricing.

📍 ~295 km from Singapore (reachable by flight, bus, or car, requires international transfer)

💸 Flights from ~$905

Seletar Airport (XSP)

Seletar Airport is located within Singapore, offering fast check-in and security for specific regional hops.

📍 ~8 km from Singapore (reachable by car or taxi)

💸 Flights from ~$1457

Hang Nadim (BTH)

Hang Nadim is a viable alternative for domestic Indonesian travel, accessible via frequent ferry services.

📍 ~36 km from Singapore (reachable by ferry and ground transport)

💸 Flights from ~$1306

Sultan Abdul Aziz Shah (SZB)

Sultan Abdul Aziz Shah is closer to Kuala Lumpur city center and has direct turboprop links from Singapore.

📍 ~316 km from Singapore (reachable by flight, bus, or car, requires international transfer)

💸 Flights from ~$1257

Business & First Class Flight Deals to Singapore

78% AI deal score

$5,519

From ORD

Elite

Nov 24

Singapore, Singapore

78% AI deal score

$6,067

$6,013

Save $54

From ORD

Singapore, Singapore

78% AI deal score

$17,782

From ORD

Elite

Jul 02

Singapore, Singapore

78% AI deal score

$21,097

$20,969

Save $128

From ORD

Elite

Jun 22

Singapore, Singapore

78% AI deal score

$2,405

$2,316

Save $89

From ORD

Elite

Jun 27

Singapore, Singapore

78% AI deal score

$2,425

$2,365

Save $60

From ORD

Elite

Oct 07

Singapore, Singapore

78% AI deal score

$2,531

From ORD

Elite

Aug 26

Singapore, Singapore

78% AI deal score

$2,531

From ORD

Elite

Sep 02

Singapore, Singapore

78% AI deal score

$2,531

From ORD

Elite

Jul 01

Singapore, Singapore

78% AI deal score

Elite

Aug 01

Singapore, Singapore

77% AI deal score

Singapore, Singapore

74% AI deal score

$7,013

From ORD

Elite

Nov 04

Singapore, Singapore

74% AI deal score

$8,907

Frequently Asked Questions About Flights to Singapore

To find more affordable flights, consider being flexible with your travel dates and comparing prices across different airlines and booking sites. Setting up price alerts can also notify you of fare drops. Looking into flights with layovers may also present lower-cost options.

Booking flights in advance often provides more options and potentially better prices, especially for longer international routes. However, prices can fluctuate, so monitoring fares over time may help you identify a good booking window. Mid-week bookings are sometimes associated with better deals.

Comparing nearby airports at both your origin and destination can sometimes reveal different flight options and prices. While it may add to travel time, the potential savings could be significant. Always factor in the cost and convenience of ground transportation to and from these alternative airports.

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