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$488+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
Jul 11 — Jul 181
Sat 7/11
Sat 7/18
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 June 11, 2026.

This Jettzy deal was found by Cheapflights users on 6/9. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:45 am
SIN
-
ORD
1 stop34h 35m
ANA
Tue 11/104:25 pm
ORD
-
SIN
1 stop24h 30m
ANA
Deal found 6/9$795
This Air Canada deal was found by Cheapflights users on 6/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:00 am
SIN
-
ORD
2 stops41h 25m
Air Canada
Tue 10/203:40 pm
ORD
-
SIN
1 stop24h 35m
Air Canada
Deal found 6/9$797
This Air Canada deal was found by Cheapflights users on 6/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:00 am
SIN
-
ORD
2 stops36h 56m
Air Canada
Sat 10/2410:00 pm
ORD
-
SIN
2 stops44h 00m
Air Canada
Deal found 6/9$801
This Flightnetwork deal was found by Cheapflights users on 6/9. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:30 am
SIN
-
ORD
2 stops44h 11m
Air Canada
Tue 11/108:00 am
ORD
-
SIN
2 stops32h 55m
Air Canada
Deal found 6/9$808
This Air Canada deal was found by Cheapflights users on 6/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am
SIN
-
ORD
1 stop20h 43m
Air Canada
Mon 9/147:48 pm
ORD
-
SIN
1 stop44h 27m
Air Canada
Deal found 6/7$809
This Air Canada deal was found by Cheapflights users on 6/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am
SIN
-
ORD
1 stop22h 45m
Air Canada
Tue 10/203:40 pm
ORD
-
SIN
1 stop24h 35m
Air Canada
Deal found 6/9$810
This Air Canada deal was found by Cheapflights users on 6/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:00 am
SIN
-
ORD
2 stops36h 56m
Air Canada
Sun 10/257:10 am
ORD
-
SIN
2 stops32h 45m
Air Canada
Deal found 6/9$812
This Air Canada deal was found by Cheapflights users on 6/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:50 pm
SIN
-
ORD
2 stops34h 16m
Air Canada
Sun 10/253:40 pm
ORD
-
SIN
1 stop26h 20m
Air Canada
Deal found 6/9$817
This Air Canada deal was found by Cheapflights users on 6/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am
SIN
-
ORD
2 stops24h 30m
Air Canada
Sun 10/253:40 pm
ORD
-
SIN
1 stop26h 20m
Air Canada
Deal found 6/9$818
This FlightHub deal was found by Cheapflights users on 6/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2011:05 am
SIN
-
ORD
1 stop34h 35m
ANA
Sun 10/45:45 pm
ORD
-
SIN
1 stop34h 30m
ANA
Deal found 6/7$820
This Delta deal was found by Cheapflights users on 6/10. 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 11/2110:40 am
SIN
-
MDW
2 stops39h 53m
Delta
Mon 11/235:25 pm
MDW
-
SIN
2 stops45h 35m
Delta
Deal found 6/10$1,155
This EVA Air deal was found by Cheapflights users on 6/11. 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 EVA Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/113:20 pm
SIN
-
MDW
2 stops26h 40m
Multiple Airlines
Sat 7/189:00 pm
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 6/11$1,306

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 June 11, 2026.

Round-trip from

$795
(Jettzy)

One-way from

$488
(Jettzy)

Popular in

August

Cheapest in

February

Average price

$1,246
From Singapore to Chicago (CHI)
Search Deals
One-way flight from Singapore to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($212 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($83 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 11, 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

Thu 10/29

1:35 am-9:30 am

1 stop20h 55m

Chicago O'Hare Intl

Tue 11/3

11:15 am-5:00 am

1 stop27h 45m

$1,153

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 11/21

10:40 am-12:33 pm

2 stops39h 53m

Chicago Midway

Mon 11/23

5:25 pm-5:00 am

2 stops45h 35m

$1,155

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 11/21

2:25 pm-5:01 pm

2 stops40h 36m

Chicago O'Hare Intl

Mon 11/23

5:55 pm-1:05 pm

2 stops29h 10m

$1,164

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 7/4

8:45 am-7:16 am

1 stop35h 31m

Chicago O'Hare Intl

Sat 7/11

9:35 pm-6:35 pm

1 stop32h 00m

$1,187

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 7/11

8:45 am-9:38 pm

1 stop25h 53m

Chicago O'Hare Intl

Sat 7/18

8:50 am-6:15 am

1 stop32h 25m

$1,187

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 7/4

1:45 pm-12:03 pm

2 stops35h 18m

Chicago O'Hare Intl

Sat 7/11

8:20 pm-12:35 pm

2 stops27h 15m

$1,188

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 7/6

8:45 am-10:59 pm

1 stop27h 14m

Chicago O'Hare Intl

Tue 7/21

6:20 pm-6:15 am

1 stop22h 55m

$1,188

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 11/23

1:35 am-11:50 pm

2 stops36h 15m

Chicago O'Hare Intl

Wed 12/9

7:00 am-5:00 am

2 stops32h 00m

$1,234

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 7/26

8:45 am-5:57 am

1 stop34h 12m

Chicago O'Hare Intl

Sun 8/2

9:35 pm-6:15 am

1 stop43h 40m

$1,264

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 7/4

3:20 pm-5:00 am

2 stops26h 40m

Chicago Midway

Sat 7/11

9:00 pm-11:55 am

2 stops25h 55m

$1,309

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/6

Showing 1-10 of 37 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 April is currently the most expensive (average of $944). 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 1,095 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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 11, 2026.
Read through reviews of airlines operating flights from Singapore to Chicago, such as Japan Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Japan Airlines
8.3
Very good
1,838 reviews

Crew

8.7

Overall

8.3

Comfort

8.2

Food

7.7

Boarding

8.4

Entertainment

7.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2026

HND - DFW

When it says Japan Airlines, I expect Japan Airlines!! Not a code share with American Airlines.
Japan Airlines
8.3
Very good
1,838 reviews
Japan Airlines
8.3
Very good
1,838 reviews

Crew

8.7

Overall

8.3

Comfort

8.2

Food

7.7

Boarding

8.4

Entertainment

7.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2026

HND - DFW

When it says Japan Airlines, I expect Japan Airlines!! Not a code share with American Airlines.

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 20h 55m. Fly via Korean Air, Delta, or United Airlines 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 April is currently the most expensive (average of $944). 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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