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$590+ Cheap flights from Singapore to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
May 19 — May 261
Tue 5/19
Tue 5/26
1 adult, Economy
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Cheap flight deals from Singapore to Chicago

Cheapest flights from Singapore to Chicago
Explore the most affordable flight options available from Singapore to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 19, 2026.

This Gotogate deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:15 am
SIN
-
ORD
1 stop21h 40m
ANA
Wed 10/145:45 pm
ORD
-
SIN
1 stop34h 30m
ANA
Deal found 4/15$825
This Gotogate deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:00 pm
SIN
-
ORD
1 stop23h 40m
ANA
Sun 9/275:45 pm
ORD
-
SIN
1 stop23h 55m
ANA
Deal found 4/16$838
This CheapTickets deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:25 am
SIN
-
ORD
1 stop21h 05m
Multiple Airlines
Wed 10/215:55 pm
ORD
-
SIN
2 stops26h 10m
Multiple Airlines
Deal found 4/15$899
This Korean Air deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Korean Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/291:35 am
SIN
-
ORD
1 stop20h 55m
Korean Air
Mon 1/1111:25 am
ORD
-
SIN
1 stop22h 45m
Korean Air
Deal found 4/19$960
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/131:25 am
SIN
-
ORD
2 stops30h 16m
Delta
Sun 9/277:30 am
ORD
-
SIN
2 stops32h 30m
Delta
Deal found 4/16$963
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/291:35 am
SIN
-
ORD
1 stop20h 55m
Delta
Mon 1/113:00 pm
ORD
-
SIN
2 stops43h 10m
Delta
Deal found 4/19$1,069
This Delta deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/291:35 am
SIN
-
ORD
1 stop20h 55m
Delta
Tue 1/127:00 am
ORD
-
SIN
2 stops27h 10m
Delta
Deal found 4/18$1,071
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/310:00 pm
SIN
-
ORD
2 stops29h 19m
Delta
Sun 10/189:30 am
ORD
-
SIN
2 stops30h 30m
Delta
Deal found 4/19$1,075
This Delta deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/271:35 am
SIN
-
ORD
2 stops36h 11m
Delta
Tue 1/127:00 am
ORD
-
SIN
2 stops27h 10m
Delta
Deal found 4/18$1,081
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:30 am
SIN
-
MDW
2 stops27h 15m
Delta
Wed 10/219:55 am
MDW
-
SIN
2 stops30h 05m
Delta
Deal found 4/15$1,156
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/710:00 pm
SIN
-
MDW
2 stops31h 16m
Delta
Sun 8/96:05 am
MDW
-
SIN
2 stops33h 55m
Delta
Deal found 4/15$1,228
This China Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/71:45 pm
SIN
-
MDW
2 stops34h 40m
Multiple Airlines
Sun 8/98:35 pm
MDW
-
SIN
2 stops27h 00m
Multiple Airlines
Deal found 4/19$1,403

Find flight deals from Singapore to Chicago

Keep the following information in mind while searching for Singapore to Chicago flight deals. Data was last updated April 19, 2026.

Round-trip from

$825
(Gotogate)

One-way from

$590
(Korean Air)

Popular in

January

Cheapest in

February

Average price

$1,060
From Singapore to Chicago (CHI)
Search Deals
One-way flight from Singapore to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Singapore to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 19, 2026.
Use the filters below to find and compare flights from Singapore to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 9/13

1:25 am-6:41 pm

2 stops30h 16m

Chicago O'Hare Intl

Sun 9/27

7:30 am-5:00 am

2 stops32h 30m

$963

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 10/2

7:30 am-9:34 pm

2 stops27h 04m

Chicago O'Hare Intl

Sat 10/17

9:30 am-5:00 am

2 stops30h 30m

$963

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 10/3

10:00 pm-12:08 pm

2 stops27h 08m

Chicago O'Hare Intl

Sun 10/18

12:10 pm-7:15 pm

1 stop42h 05m

$1,075
Quickest round-trip

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 9/24

10:00 pm-9:30 am

1 stop24h 30m

Chicago O'Hare Intl

Mon 9/28

12:10 pm-11:55 pm

1 stop22h 45m

$1,115

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 10/16

7:30 am-9:45 pm

2 stops27h 15m

Chicago Midway

Wed 10/21

9:55 am-5:00 am

2 stops30h 05m

$1,156

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 5/7

7:30 am-9:50 pm

2 stops27h 20m

Chicago O'Hare Intl

Fri 7/31

12:30 pm-5:00 am

1 stop27h 30m

$1,224

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 6/7

10:00 pm-4:34 pm

2 stops31h 34m

Chicago O'Hare Intl

Sun 8/9

5:15 am-5:00 am

2 stops34h 45m

$1,228

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 6/7

10:00 pm-4:16 pm

2 stops31h 16m

Chicago Midway

Sun 8/9

6:05 am-5:00 am

2 stops33h 55m

$1,229

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 5/10

12:10 pm-5:59 am

3 stops30h 49m

Chicago O'Hare Intl

Wed 5/13

1:10 pm-9:15 am

1 stop31h 05m

$1,295

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 6/10

1:30 am-4:50 pm

1 stop28h 20m

Chicago O'Hare Intl

Wed 6/17

4:33 pm-3:45 pm

2 stops34h 12m

$1,327

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 35 resultsSorted by cheapest first
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Best time to book a flight from Singapore to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Singapore with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Singapore to Chicago

What is the cheapest month to book a flight from Singapore to Chicago?

Currently, October is the cheapest month in which you can book a flight from Singapore to Chicago (average of $664). Flying from Singapore to Chicago in May is currently the most expensive (average of $939). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How often are flights from Singapore to Chicago delayed?

About 100% of weekly flights between Singapore and Chicago have experienced delays in the past year, with the average delay time being 1,189 minutes.

What is the most punctual flight time for Singapore to Chicago flights?

Historically, flights departing in the evening are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.

Related info for your journey

Find useful and relevant information for your journey from Singapore to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Singapore to Chicago?

    There are many flights that can get you from Singapore to Chicago in 24h 30m. Fly via Delta or Korean Air to get the fastest option. The distance from Singapore to Chicago is about 9345 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Singapore to Chicago one-way?

    To fly one-way, consider booking your trip with Japan Airlines, which is currently one of the cheapest options available, starting at $428. EVA Air flights start at $459 while deals on United Airlines start at $577 one-way.

  • Can I find deals for flights from Singapore to Chicago that include hotel bookings?

    Yes. In addition to deals on Singapore to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Singapore to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Singapore to Chicago.

  • Can I find deals for business class flights from Singapore to Chicago?

    Yes. Cheapflights offers flight deals from Singapore to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Singapore to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Singapore to Chicago (average of $664). Flying from Singapore to Chicago in May is currently the most expensive (average of $939). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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