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

Direct flights offer convenience and save time, but they are not always the most budget-friendly choice. Flights with layovers or connecting flights can sometimes be considerably cheaper. Evaluate whether the time saved is worth the potential extra cost.

Can flexible travel dates help on Singapore to Chicago flights?

Absolutely, being flexible with your travel dates can significantly impact flight prices. Mid-week flights or those during the off-season are often less expensive than weekend or holiday travel. Adjusting your departure or return by a few days may lead to substantial savings.

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

Before booking, always check for potential extra costs such as baggage fees, seat selection charges, and in-flight meal expenses. Some airlines may also charge for amenities like Wi-Fi or entertainment. Factor these into your total travel budget.

Flights From Singapore

To Chicago

Cheap Flights from Singapore to Chicago

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

Deals from

Singapore

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

Prices updated 7 days ago

483 airlines compared

80%+ AI score for best value

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

Today’s best flight deals from Singapore to Chicago

Explore current cheapest deals departing from Singapore to Chicago

2026-11-09 – 2026-11-12
SIN - Chicago
81% AI deal score
$1,062
$983
Round trip
2026-11-01 – 2026-11-08
SIN - Chicago
77% AI deal score
$1,038
$1,016
Round trip
2026-10-29 – 2026-11-08
SIN - Chicago
78% AI deal score
$1,041
$1,024
Round trip
2026-10-31 – 2026-11-08
SIN - Chicago
78% AI deal score
$1,033
$1,024
Round trip
2026-11-05 – 2026-11-08
SIN - Chicago
80% AI deal score
$1,096
$1,030
Round trip
2026-11-03 – 2026-11-08
SIN - Chicago
78% AI deal score
$1,050
$1,030
Round trip
2026-11-04 – 2026-11-08
SIN - Chicago
80% AI deal score
$1,096
$1,031
Round trip
2026-11-10 – 2026-11-14
SIN - Chicago
77% AI deal score
$1,049
$1,041
Round trip
2026-11-08 – 2026-11-24
SIN - Chicago
75% AI deal score
$920
$1,057
Round trip
2026-11-08 – 2026-11-27
SIN - Chicago
75% AI deal score
$912
$1,061
Round trip

Singapore to Chicago: Overview

Insights for flights from Singapore to Chicago

Flights from Singapore to Chicago cover a substantial distance of 15,074 km, classifying this as a long-haul journey. This significant distance means that itineraries typically involve extended travel times and multiple connections to reach the destination.

When looking for cheap flights from Singapore to Chicago, fares typically range from $1537–$2276, with a median of $1941. Right now, current fares are above the typical level for this route. Only 1% of recent fares were classified as a good price, indicating that finding deals can be challenging.

If you are wondering when is the cheapest time to fly from Singapore to Chicago, July stands out as the most affordable month, with a median fare of $1158. Other relatively cheaper months include December, with a median fare of $1969, and November, where the median fare is $2386.

For flights from Singapore to Chicago, most itineraries connect at least once. In fact, 0% of recent fares were for direct flights from Singapore to Chicago. For connecting itineraries, the median number of stopovers is 2, meaning you should expect multiple stops on your journey.

A typical journey from Singapore to Chicago takes approximately 29h 35m, including connections. This median duration reflects the long-haul nature of the route and the necessity of connecting flights, as there are no direct options available.

How much is a round trip from Singapore to Chicago

Regular price: $823 - $1,581

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

The regular price range for flights from Singapore to Chicago is between $823 and $1581. The current lowest deal is $1012 with Air Canada, for travel from Nov 8-Nov 27.

now $1,012

Low $823

High $1,581

The cheapest time to fly from Singapore to Chicago

The cheapest month to fly from Singapore to Chicago is July, with a median price of $1158. The most expensive month is November, with a median price of $2386. Prices are generally lower from July to December.

July

Cheapest

Flights from $1,158

November

Most Expensive

Flights from $2,386

Jul

Nov

Dec

Direct flights from Singapore to Chicago

Air Canada

Cathay Pacific

Korean Air

Turkish Airlines

Last-minute flights going from Singapore to Chicago

Tue, Nov 3

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

All Nippon Airways

$986

$1,163

One-way

Wed, Nov 4

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

Korean Air

$972

$1,091

One-way

Wed, Nov 4

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

Korean Air

$969

$1,143

One-way

Wed, Nov 4

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

Korean Air

$969

$1,192

One-way

Thu, Nov 5

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

Etihad Airways

$972

$1,009

One-way

Thu, Nov 5

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

Etihad Airways

$969

$1,066

One-way

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

5 nights

Dec 2 - Dec 7

$1,167 → $1,079

3 nights

Nov 9 - Nov 12

$1,062 → $983

3 nights

Nov 1 - Nov 4

$1,153 → $1,080

3 nights

Nov 5 - Nov 8

$1,096 → $1,030

Popular Airports to fly from Singapore to Chicago

Singapore - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares are above the typical level for this route, with a median price of $1941.

📅 Best time to fly

July is historically cheapest at $1158

Historically, July offers the lowest median prices at $1158, followed by December at $1969.

⏱️ Flight duration

Connecting flights average 29h 35m

Flights on this long-haul route typically involve connecting, with a median duration of 29h 35m.

✈️ Airlines & availability

Connecting flights are dominant

This route is connecting dominant; 0% of recent fares were for direct flights.

🏆 Airline highlight

Air Canada offers the most deals

Air Canada has 69 deals, followed by Cathay Pacific with 10 deals for this route.

🎯 Booking tip

Deals are rare for this route

Deals for flights on this route are rare, so consider booking when you see a good price.

Singapore main airports to depart from

Singapore Changi (SIN)

Cheapest

Singapore Changi Airport is a key departure point for flights from Singapore to Chicago.

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

💸 Flights from ~$814

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a good option for flights from Singapore to Chicago.

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

💸 Flights from ~$817

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International offers a major international alternative with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$1,088

Business & First Class Flight Deals to Chicago

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

Elite

Best Elite deals to Chicago

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

From SIN

Elite

Nov 25

Chicago, United States

89% AI deal score

$4,565

$3,890

Save $675

Vietnam Airlines, +1

Business Class

From SIN

Elite

Nov 25

Chicago, United States

89% AI deal score

$4,485

$3,930

Save $555

Vietnam Airlines, +1

Business Class

From SIN

Elite

Nov 25

Chicago, United States

88% AI deal score

$4,352

$3,930

Save $422

Vietnam Airlines, +1

Business Class

From SIN

Elite

Dec 16

Chicago, United States

88% AI deal score

$6,539

$4,722

Save $1,817

From SIN

Elite

Jan 20

Chicago, United States

84% AI deal score

$2,236

$1,908

Save $328

Cathay Pacific

Business Class

From SIN

Elite

Dec 27

Chicago, United States

83% AI deal score

$5,555

$4,968

Save $587

All Nippon Airways

Business Class

From SIN

Elite

Dec 21

Chicago, United States

81% AI deal score

$5,249

$4,868

Save $381

Korean Air

Business Class

From SIN

Elite

Dec 25

Chicago, United States

81% AI deal score

$5,253

$4,965

Save $288

All Nippon Airways

Business Class

From SIN

Elite

Dec 23

Chicago, United States

81% AI deal score

$5,317

$4,965

Save $352

All Nippon Airways

Business Class

From SIN

Elite

Oct 27

Chicago, United States

80% AI deal score

$5,252

$4,875

Save $377

Korean Air

Business Class

From SIN

Elite

Oct 28

Chicago, United States

80% AI deal score

$5,197

$4,882

Save $315

Korean Air

Business Class

From SIN

Elite

Dec 02

Chicago, United States

80% AI deal score

$5,198

$4,964

Save $234

All Nippon Airways

Business Class

Frequently Asked Questions About Flights to Chicago

To find more affordable flights, consider being flexible with your travel dates and times. Comparing prices across various airlines and booking platforms can also help you identify better deals. Setting up price alerts may notify you when fares drop for your desired route.

Booking flights in advance, often several months before your intended travel date, may result in lower fares. Prices can fluctuate, so monitoring trends and booking during off-peak seasons might also be beneficial. Last-minute bookings usually carry a higher cost.

Yes, comparing flights to and from airports near your origin and destination cities can sometimes uncover more economical options. While it may add to your travel time, the potential savings on airfare can be significant. Always factor in ground transportation costs and convenience.

Related routes

More routes from Singapore

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Flights to Chicago from other cities

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Singapore to Chicago: Overview

Insights for flights from Singapore to Chicago

How much is a round trip from Singapore to Chicago

Regular price: $823 - $1,581

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

The regular price range for flights from Singapore to Chicago is between $823 and $1581. The current lowest deal is $1012 with Air Canada, for travel from Nov 8-Nov 27.

now $1,012

Low $823

High $1,581

The cheapest time to fly from Singapore to Chicago

July

Cheapest

Flights from $1,158

November

Most Expensive

Flights from $2,386

Jul

Nov

Dec

Direct flights from Singapore to Chicago

Air Canada

Cathay Pacific

Korean Air

Turkish Airlines

Last-minute flights going from Singapore to Chicago

Tue, Nov 3

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

All Nippon Airways

$986

$1,163

One-way

Wed, Nov 4

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

Korean Air

$972

$1,091

One-way

Wed, Nov 4

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

Korean Air

$969

$1,143

One-way

Wed, Nov 4

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

Korean Air

$969

$1,192

One-way

Thu, Nov 5

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

Etihad Airways

$972

$1,009

One-way

Thu, Nov 5

⌛ Last-Minute

SIN - Chicago

Singapore (SIN) - Chicago (ORD)

Etihad Airways

$969

$1,066

One-way

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

5 nights

Dec 2 - Dec 7

$1,167 → $1,079

3 nights

Nov 9 - Nov 12

$1,062 → $983

3 nights

Nov 1 - Nov 4

$1,153 → $1,080

3 nights

Nov 5 - Nov 8

$1,096 → $1,030

Popular Airports to fly from Singapore to Chicago

Singapore - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares are above the typical level for this route, with a median price of $1941.

📅 Best time to fly

July is historically cheapest at $1158

Historically, July offers the lowest median prices at $1158, followed by December at $1969.

⏱️ Flight duration

Connecting flights average 29h 35m

Flights on this long-haul route typically involve connecting, with a median duration of 29h 35m.

✈️ Airlines & availability

Connecting flights are dominant

This route is connecting dominant; 0% of recent fares were for direct flights.

🏆 Airline highlight

Air Canada offers the most deals

Air Canada has 69 deals, followed by Cathay Pacific with 10 deals for this route.

🎯 Booking tip

Deals are rare for this route

Deals for flights on this route are rare, so consider booking when you see a good price.

Singapore main airports to depart from

Singapore Changi (SIN)

Cheapest

Singapore Changi Airport is a key departure point for flights from Singapore to Chicago.

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

💸 Flights from ~$814

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a good option for flights from Singapore to Chicago.

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

💸 Flights from ~$817

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International offers a major international alternative with significant carrier presence and direct flight options.

Chicago, United States

80% AI deal score

$5,198

$4,964

Save $234

All Nippon Airways

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Singapore to Chicago

Today’s best flight deals from Singapore to Chicago

Singapore to Chicago: Overview

Insights for flights from Singapore to Chicago

How much is a round trip from Singapore to Chicago

The cheapest time to fly from Singapore to Chicago

Direct flights from Singapore to Chicago

Last-minute flights going from Singapore to Chicago

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

Popular Airports to fly from Singapore to Chicago

Singapore - Chicago route insights

Recent fares are above the typical level

July is historically cheapest at $1158

Connecting flights average 29h 35m

Connecting flights are dominant

Air Canada offers the most deals

Deals are rare for this route

Singapore main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Nov 25

Nov 25

Nov 25

Dec 16

Jan 20

Dec 27

Dec 21

Dec 25

Dec 23

Oct 27

Oct 28

Dec 02

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Singapore to Chicago?

When should I book flights from Singapore to Chicago?

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

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

Can flexible travel dates help on Singapore to Chicago flights?

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

Related routes

More routes from Singapore

Flights to Chicago from other cities

Singapore to Chicago: Overview

Insights for flights from Singapore to Chicago

How much is a round trip from Singapore to Chicago

The cheapest time to fly from Singapore to Chicago

Direct flights from Singapore to Chicago

Last-minute flights going from Singapore to Chicago

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

Popular Airports to fly from Singapore to Chicago

Singapore - Chicago route insights

Recent fares are above the typical level

July is historically cheapest at $1158

Connecting flights average 29h 35m

Connecting flights are dominant

Air Canada offers the most deals

Deals are rare for this route

Singapore main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Nov 25

Nov 25

Nov 25

Dec 16

Jan 20

Dec 27

Dec 21

Dec 25

Dec 23

Oct 27

Oct 28

Dec 02

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Singapore to Chicago?

When should I book flights from Singapore to Chicago?

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