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

Direct flights offer convenience by reducing travel time and avoiding layovers, but they are not always the most budget-friendly choice. Flights with one or more connections can often be less expensive. Consider your priorities for cost versus travel time when making your decision.

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 can vary significantly depending on the day of the week or specific times of the 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 meal costs, especially with budget airlines. Also, consider the price of airport transfers and any visa requirements for your destination. These can add to your overall travel expenses.

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 2 days ago

405 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Chicago to Singapore

Explore current cheapest deals departing from Chicago to Singapore

2026-09-01 – 2026-09-17
CHI - Singapore
78% AI deal score
$795
$820
Round trip
2026-09-09 – 2026-09-15
CHI - Singapore
79% AI deal score
$835
$825
Round trip
2026-09-16 – 2026-09-22
CHI - Singapore
79% AI deal score
$843
$839
Round trip
2026-09-02 – 2026-09-09
CHI - Singapore
78% AI deal score
$833
$846
Round trip
2026-09-01 – 2026-09-08
CHI - Singapore
78% AI deal score
$833
$849
Round trip
2026-09-01 – 2026-09-07
CHI - Singapore
78% AI deal score
$833
$853
Round trip
2026-10-07 – 2026-10-19
CHI - Singapore
84% AI deal score
$970
$858
Round trip
2027-01-13 – 2027-01-27
CHI - Singapore
82% AI deal score
$1,020
$867
Round trip
2026-09-06 – 2026-09-23
CHI - Singapore
78% AI deal score
$791
$868
Round trip
2026-11-10 – 2026-11-24
CHI - Singapore
78% AI deal score
$908
$875
Round trip

Chicago to Singapore: Overview

Insights for flights from Chicago to Singapore

The journey from Chicago to Singapore covers a significant distance of 15,050 km, classifying it as a long-haul route. For travelers looking for cheap flights from Chicago to Singapore, fares typically range from $1403 to $1948, with a median price of $1643. Right now, current fares are above the typical level, and 0% of recent fares were classified as a good price.

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. Following closely, May also presents competitive prices, with a median of $858, and January offers a median fare of $878.

For flights from Chicago to Singapore, most itineraries connect at least once, as 0% of recent fares were non-stop. When connections are necessary, the typical number of stopovers is 2.

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 prevalence of connecting flights.

How much is a round trip from Chicago to Singapore

Regular price: $720 - $1,630

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

The regular price range for flights from Chicago to Singapore is USD 720 to USD 1630. The current lowest deal is USD 813 with Cathay Pacific, for travel from Sep 9-Sep 15.

now $813

Low $720

High $1,630

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

Korean Air

Air Canada

Cathay Pacific

Turkish Airlines

Last-minute flights going from Chicago to Singapore

Tue, Aug 4

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

Cathay Pacific

$1,007

$899

One-way

Tue, Aug 4

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

Air Canada

$1,019

$919

One-way

Tue, Aug 4

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

Cathay Pacific

$1,252

$1,222

One-way

Thu, Aug 13

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

Air Canada

$1,037

$956

One-way

Mon, Aug 17

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

Cathay Pacific

$984

$851

One-way

Wed, Aug 19

⌛ Last-Minute

ORD - Singapore

Chicago (ORD) - Singapore (SIN)

Air Canada

$1,078

$915

One-way

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

7 nights

Dec 3 - Dec 10

$1,353 → $1,030

24%

13 nights

Dec 3 - Dec 16

$1,349 → $1,027

24%

12 nights

Dec 2 - Dec 14

$1,321 → $1,012

23%

6 nights

Jan 19 - Jan 25

$1,251 → $984

21%

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 $813.

📅 Best time to fly

April is historically the cheapest month

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

Flights from Chicago to Singapore are typically long-haul, with a median duration of 46h 55m.

✈️ Airlines & availability

Connecting flights are dominant

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

🏆 Airline highlight

Korean Air offers many deals

Korean Air has 20 direct deals from Chicago to Singapore, making it a frequent choice.

🎯 Booking tip

Deals appear regularly

Deals for flights from Chicago to Singapore appear regularly, offering frequent opportunities to book.

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

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 Airport can be a useful alternative, offering cost savings for domestic flights within Malaysia.

📍 ~25 km from Singapore (reachable by car, bus, or taxi)

💸 Flights from ~$1,046

Business & First Class Flight Deals to Singapore

83% AI deal score

$2,697

$2,405

Save $292

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 help you monitor fare changes. Looking into flights with layovers may sometimes offer lower prices than direct routes.

Booking flights in advance often helps secure better prices, though the ideal booking window can vary. Prices may fluctuate based on demand and seasonality. It's usually beneficial to monitor fare trends and book when you see a price that fits your budget.

Comparing nearby airports at both your origin and destination can sometimes reveal more economical flight options. While it may involve additional travel time to and from these airports, the savings on airfare can be significant. Always factor in the cost and convenience of ground transportation.

Related routes

More routes from Chicago

Flights from Chicago to Salt Lake City Flights from Chicago to San Juan Flights from Chicago to Sarasota Flights from Chicago to Savusavu Flights from Chicago to Sydney Flights from Chicago to Taipei Flights from Chicago to Tampa Flights from Chicago to Tel Aviv Flights from Chicago to Thiruvananthapuram Flights from Chicago to Tirana Flights from Chicago to Tokyo Flights from Chicago to Tucson

Flights to Singapore from other cities

Flights from Cairns to Singapore Flights from Cape Town to Singapore Flights from Cedar Rapids to Singapore Flights from Chania to Singapore Flights from Charlotte to Singapore Flights from Chengdu to Singapore Flights from Cheongju to Singapore Flights from Chiang Mai to Singapore Flights from Colombo to Singapore Flights from Copenhagen to Singapore Flights from Da Nang to Singapore Flights from Kochi to Singapore

Chicago to Singapore: Overview

Insights for flights from Chicago to Singapore

For flights from Chicago to Singapore, most itineraries connect at least once, as 0% of recent fares were non-stop. When connections are necessary, the typical number of stopovers is 2.

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 prevalence of connecting flights.

How much is a round trip from Chicago to Singapore

Regular price: $720 - $1,630

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

The regular price range for flights from Chicago to Singapore is USD 720 to USD 1630. The current lowest deal is USD 813 with Cathay Pacific, for travel from Sep 9-Sep 15.

now $813

Low $720

High $1,630

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