What airlines fly to Chicago?

Cathay Pacific, EVA Air and United Airlines are the top three most popular airlines that fly to Chicago from Singapore according to our data. Cathay Pacific is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Singapore to Chicago?

Air Canada, United Airlines, and IndiGo are the most popular carriers operating from Singapore to Chicago

When did momondo last update prices for flights from Singapore to Chicago?

Prices for flights from Singapore to Chicago are updated daily.

How many operators does momondo search for flights from Singapore to Chicago?

As of July 2025, there are 3 operators available to choose from for flights from Singapore to Chicago.

How old do you have to be to fly from Singapore to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Singapore to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$476 Cheap Flights from Singapore to Chicago in 2025

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Find the cheapest flights from Singapore to Chicago

Round-trip

One-way

Last minute

Recent round-trip flight deals from Singapore to Chicago

9:10 am - 9:31 amSIN-ORD

37h 21m2 stops

3:45 pm - 7:05 amORD-SIN

26h 20m1 stop

$671Air Canada

Find Deal

Thu, Sep 25 - Sun, Sep 28

9:10 am - 4:51 pmSIN-ORD

44h 41m2 stops

7:54 pm - 4:00 amORD-SIN

43h 06m2 stops

$672Air Canada

Find Deal

Thu, Sep 25 - Sun, Sep 28

10:10 pm - 3:10 pmSIN-ORD

30h 00m1 stop

11:50 am - 12:45 amORD-SIN

23h 55m1 stop

$815ANA

Find Deal

Wed, Sep 3 - Wed, Sep 24

10:10 pm - 3:10 pmSIN-ORD

30h 00m1 stop

7:19 am - 12:45 amORD-SIN

28h 26m2 stops

$819ANA

Find Deal

Wed, Sep 3 - Wed, Sep 24

9:10 am - 4:49 amSIN-ORD

32h 39m3 stops

12:54 pm - 7:05 amORD-SIN

29h 11m2 stops

$830

Find Deal

Thu, Sep 25 - Sun, Sep 28

1:10 am - 6:37 pmSIN-MDW

30h 27m2 stops

9:35 am - 5:00 amMDW-SIN

30h 25m2 stops

$970Delta

Find Deal

Sun, Sep 7 - Mon, Sep 15

7:30 am - 8:53 amSIN-MDW

38h 23m2 stops

6:00 am - 12:10 amMDW-SIN

28h 10m2 stops

$972Delta

Find Deal

Thu, Sep 25 - Wed, Nov 26

1:10 am - 12:28 pmSIN-MDW

24h 18m2 stops

9:31 am - 11:40 pmMDW-SIN

25h 09m2 stops

$1,974

Find Deal

Mon, Aug 11 - Sun, Aug 31

12:40 am - 3:28 pmSIN-MDW

27h 48m2 stops

7:15 pm - 3:30 pmMDW-SIN

31h 15m2 stops

$2,068KLM

Find Deal

Fri, Sep 5 - Sat, Sep 13

12:40 am - 3:26 pmSIN-MDW

27h 46m2 stops

6:15 pm - 3:30 pmMDW-SIN

32h 15m2 stops

$2,238KLM

Find Deal

Fri, Sep 19 - Sat, Sep 27

Air Canada flights from Singapore to Chicago

Our best Air Canada deals on Singapore to Chicago flight tickets

Air Canada

Sep 25

SIN9:10 amSingapore Changi

37h 21m

2 stops

ORD9:31 amChicago O'Hare Intl

Sep 28

ORD3:45 pmChicago O'Hare Intl

26h 20m

1 stop

SIN7:05 amSingapore Changi

$671

Find similar

Air Canada

Sep 25

SIN9:10 amSingapore Changi

44h 41m

2 stops

ORD4:51 pmChicago O'Hare Intl

Sep 28

ORD7:54 pmChicago O'Hare Intl

43h 06m

2 stops

SIN4:00 amSingapore Changi

$672

Find similar

Air Canada

Sep 25

SIN9:10 amSingapore Changi

37h 21m

2 stops

ORD9:31 amChicago O'Hare Intl

Sep 28

ORD3:40 pmChicago O'Hare Intl

26h 25m

1 stop

SIN7:05 amSingapore Changi

$673

Find similar

EVA Air flights from Singapore to Chicago

Our best EVA Air deals on Singapore to Chicago flight tickets

EVA Air

Aug 6

SIN1:10 pmSingapore Changi

21h 00m

1 stop

ORD9:10 pmChicago O'Hare Intl

Sep 29

ORD12:30 amChicago O'Hare Intl

22h 30m

1 stop

SIN12:00 pmSingapore Changi

$1,155

Find similar

EVA Air

Aug 1

SIN1:10 pmSingapore Changi

21h 00m

1 stop

ORD9:10 pmChicago O'Hare Intl

Aug 9

ORD12:30 amChicago O'Hare Intl

24h 20m

1 stop

SIN1:50 pmSingapore Changi

$1,170

Find similar

EVA Air

Aug 13

SIN1:10 pmSingapore Changi

29h 35m

2 stops

ORD5:45 amChicago O'Hare Intl

Aug 29

ORD12:30 amChicago O'Hare Intl

22h 30m

1 stop

SIN12:00 pmSingapore Changi

$1,206

Find similar

Fly from

Fly to

Route

Depart

Return

Price

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 9/25

9:10 am-9:31 am

2 stops37h 21m

Chicago O'Hare Intl

Sun 9/28

3:45 pm-7:05 am

1 stop26h 20m

$671

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 9/25

9:10 am-4:51 pm

2 stops44h 41m

Chicago O'Hare Intl

Sun 9/28

7:54 pm-4:00 am

2 stops43h 06m

$672

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 9/3

10:10 pm-3:10 pm

1 stop30h 00m

Chicago O'Hare Intl

Wed 9/24

11:50 am-12:45 am

1 stop23h 55m

$815

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 9/3

10:10 pm-3:10 pm

1 stop30h 00m

Chicago O'Hare Intl

Wed 9/24

7:19 am-12:45 am

2 stops28h 26m

$819

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 9/25

9:10 am-4:49 am

3 stops32h 39m

Chicago O'Hare Intl

Sun 9/28

12:54 pm-7:05 am

2 stops29h 11m

$830

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 9/7

1:10 am-6:37 pm

2 stops30h 27m

Chicago Midway

Mon 9/15

9:35 am-5:00 am

2 stops30h 25m

$970

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 9/25

7:30 am-8:53 am

2 stops38h 23m

Chicago Midway

Wed 11/26

6:00 am-12:10 am

2 stops28h 10m

$972

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 8/11

1:10 am-12:28 pm

2 stops24h 18m

Chicago Midway

Sun 8/31

9:31 am-11:40 pm

2 stops25h 09m

$1,974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 9/5

12:40 am-3:28 pm

2 stops27h 48m

Chicago Midway

Sat 9/13

7:15 pm-3:30 pm

2 stops31h 15m

$2,068

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 9/19

12:40 am-3:26 pm

2 stops27h 46m

Chicago Midway

Sat 9/27

6:15 pm-3:30 pm

2 stops32h 15m

$2,238

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Singapore to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Singapore, with most prices found around $906. If you’re not able to fly to Chicago in October, then April is your next best option. Flight prices from Singapore to Chicago during April average around $934.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as $1,114. This is often the case because there is less demand to fly during this day of the week. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Singapore to Chicago for around $1,564.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Singapore to Chicago during this time can be as low as $1,166. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $1,286.

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Singapore when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $1,287 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Singapore for as low as $989 on momondo.

Can stopping save me money on Singapore to Chicago flights?

You could potentially save up to 7% on your flight if you consider stops on a Singapore to Chicago flight.

Cheap Singapore to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Singapore to Chicago

Best Price Found	$476
Fastest flight time	19h 51m
Direct flights	None
Airports in Chicago	2 airports

The best one-way flight to Chicago from Singapore in the past 72 hours is $476. The best round-trip flight deal from Singapore to Chicago found on momondo in the last 72 hours is $671.

The fastest flight from Singapore to Chicago takes 19h 51m

There are no direct flights from Singapore to Chicago. Popular non-direct route for this connection is Singapore Changi Airport - Chicago O'Hare Intl Airport.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Singapore to Chicago?
Prices for flights from Singapore to Chicago are updated daily.
How many operators does momondo search for flights from Singapore to Chicago?
As of July 2025, there are 3 operators available to choose from for flights from Singapore to Chicago.
How old do you have to be to fly from Singapore to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Singapore to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Singapore to Chicago

Compare and see reviews for airlines that fly from Singapore to Chicago with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $802	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
Cathay Pacific	PriceFrom $882	Free Cancellation	Rating 7.6 949 reviews	Search Cathay Pacific flights
EVA Air	PriceFrom $1,011	Free Cancellation	Rating 8.4 1,220 reviews	Search EVA Air flights

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Munster

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Porter

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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Singapore to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Singapore to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Singapore to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Singapore on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Singapore to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Singapore. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Singapore to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Singapore to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.