$498+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
Aug 24 — Aug 311
Round-trip
1 adult, Economy
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Find cheap flights from Singapore to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Singapore to ChicagoExplore 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 July 25, 2026.
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 July 25, 2026.
This lol.travel deal was found by Cheapflights users on 7/22. 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 lol.travel 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
Thu 9/243:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Deal found 7/22![Air Canada logo]()
$745
This Jettzy deal was found by Cheapflights users on 7/25. 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.
Tue 9/86:15 am
SIN
- ORD
2 stops26h 57m
Air Canada
Tue 9/153:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Deal found 7/25![Air Canada logo]()
$765
This Jettzy deal was found by Cheapflights users on 7/23. 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.
Sun 10/47:00 am
SIN
- ORD
1 stop20h 43m
Air Canada
Sun 10/113:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Deal found 7/23![Air Canada logo]()
$773
This Expedia deal was found by Cheapflights users on 7/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 am
SIN
- ORD
1 stop20h 43m
Air Canada
Sun 9/272:15 pm
ORD
- SIN
2 stops26h 00m
Air Canada
Deal found 7/20![Air Canada logo]()
$783
This Delta deal was found by Cheapflights users on 7/25. 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 9/87:30 am
SIN
- MDW
2 stops28h 14m
Delta
Tue 9/159:29 am
MDW
- SIN
2 stops30h 31m
Delta
Deal found 7/25![Delta logo]()
$1,115
This Delta deal was found by Cheapflights users on 7/24. 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.
Mon 9/710:00 pm
SIN
- MDW
2 stops31h 57m
Delta
Mon 9/149:59 am
MDW
- SIN
2 stops24h 56m
Delta
Deal found 7/24![Delta logo]()
$1,187
This Delta deal was found by Cheapflights users on 7/21. 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.
Thu 9/1010:00 pm
SIN
- MDW
2 stops30h 24m
Delta
Thu 9/246:05 am
MDW
- SIN
2 stops28h 50m
Delta
Deal found 7/21![Delta logo]()
$1,223
This China Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 9/101:55 pm
SIN
- MDW
2 stops34h 20m
Multiple Airlines
Thu 9/243:55 pm
MDW
- SIN
2 stops31h 40m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$1,225
This China Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 10/12:00 am
SIN
- MDW
2 stops35h 10m
Multiple Airlines
Sat 10/107:05 pm
MDW
- SIN
2 stops28h 30m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$1,230
This China Airlines deal was found by Cheapflights users on 7/22. 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.
Tue 8/181:55 pm
SIN
- MDW
2 stops28h 50m
Multiple Airlines
Tue 8/259:00 pm
MDW
- SIN
2 stops26h 35m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$1,249
This Delta deal was found by Cheapflights users on 7/25. 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 8/187:30 am
SIN
- MDW
2 stops28h 06m
Delta
Tue 8/256:05 am
MDW
- SIN
2 stops28h 50m
Delta
Deal found 7/25![Delta logo]()
$1,304
This EVA Air deal was found by Cheapflights users on 7/23. 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.
Fri 8/213:20 pm
SIN
- MDW
2 stops27h 30m
Multiple Airlines
Fri 8/289:20 pm
MDW
- SIN
2 stops25h 35m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$1,309
Best flights from Singapore to ChicagoDiscover carefully curated flight deals from Singapore to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 25, 2026.
Discover carefully curated flight deals from Singapore to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 25, 2026.
This United Airlines deal was found by Cheapflights users on 7/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:45 am
SIN
- ORD
1 stop22h 50m
United Airlines
Sat 9/59:40 pm
ORD
- SIN
1 stop31h 55m
United Airlines
Deal found 7/25![United Airlines logo]()
$1,096
This Delta deal was found by Cheapflights users on 7/20. 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.
Wed 9/231:25 am
SIN
- MDW
2 stops34h 19m
Delta
Sun 9/279:59 am
MDW
- SIN
2 stops30h 01m
Delta
Deal found 7/20![Delta logo]()
$1,115
This China Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 9/101:55 pm
SIN
- MDW
2 stops34h 20m
Multiple Airlines
Thu 9/243:55 pm
MDW
- SIN
2 stops31h 40m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$1,225
This Qatar Airways deal was found by Cheapflights users on 7/24. 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 Qatar Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:15 am
SIN
- ORD
1 stop24h 50m
Qatar Airways
Sun 9/273:59 pm
ORD
- SIN
2 stops34h 46m
Qatar Airways
Deal found 7/24![Qatar Airways logo]()
$1,341
This Emirates deal was found by Cheapflights users on 7/24. 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 Emirates is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:30 pm
SIN
- ORD
2 stops55h 25m
Emirates
Tue 8/118:35 pm
ORD
- SIN
2 stops34h 55m
Emirates
Deal found 7/24![Emirates logo]()
$1,695
This Korean Air deal was found by Cheapflights users on 7/21. 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.
Thu 9/2410:00 pm
SIN
- MDW
2 stops27h 39m
Korean Air
Sun 9/279:29 am
MDW
- SIN
2 stops44h 46m
Korean Air
Deal found 7/21![Korean Air logo]()
$1,735
This Ethiopian Air deal was found by Cheapflights users on 7/25. 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 Ethiopian Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/82:00 am
SIN
- ORD
2 stops43h 15m
Ethiopian Air
Wed 8/1210:15 am
ORD
- SIN
1 stop39h 35m
Ethiopian Air
Deal found 7/25![Ethiopian Air logo]()
$1,908
This KAYAK deal was found by Cheapflights users on 7/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:05 am
SIN
- ORD
1 stop36h 40m
Japan Airlines
Fri 12/185:35 pm
ORD
- SIN
1 stop23h 00m
Japan Airlines
Deal found 7/23![Japan Airlines logo]()
$1,929
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:35 pm
SIN
- ORD
1 stop34h 57m
United Airlines
Thu 9/246:07 am
ORD
- SIN
1 stop23h 28m
United Airlines
Deal found 7/21![United Airlines logo]()
$1,101
This Delta deal was found by Cheapflights users on 7/25. 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 9/87:30 am
SIN
- MDW
2 stops28h 14m
Delta
Tue 9/159:29 am
MDW
- SIN
2 stops30h 31m
Delta
Deal found 7/25![Delta logo]()
$1,115
This United Airlines deal was found by Cheapflights users on 7/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:35 pm
SIN
- ORD
1 stop27h 48m
United Airlines
Mon 9/1412:51 pm
ORD
- SIN
1 stop28h 24m
United Airlines
Deal found 7/23![United Airlines logo]()
$1,101
This China Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 10/12:00 am
SIN
- MDW
2 stops35h 10m
Multiple Airlines
Sat 10/107:05 pm
MDW
- SIN
2 stops28h 30m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$1,230
This United Airlines deal was found by Cheapflights users on 7/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:45 am
SIN
- ORD
1 stop22h 50m
United Airlines
Tue 9/1512:51 pm
ORD
- SIN
1 stop28h 24m
United Airlines
Deal found 7/22![United Airlines logo]()
$1,101
This Delta deal was found by Cheapflights users on 7/21. 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.
Thu 9/1010:00 pm
SIN
- MDW
2 stops30h 24m
Delta
Thu 9/246:05 am
MDW
- SIN
2 stops28h 50m
Delta
Deal found 7/21![Delta logo]()
$1,223
This China Airlines deal was found by Cheapflights users on 7/22. 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.
Tue 8/181:55 pm
SIN
- MDW
2 stops28h 50m
Multiple Airlines
Tue 8/259:00 pm
MDW
- SIN
2 stops26h 35m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$1,249
This Delta deal was found by Cheapflights users on 7/20. 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 9/127:30 am
SIN
- MDW
2 stops28h 14m
Delta
Fri 9/186:05 am
MDW
- SIN
2 stops33h 55m
Delta
Deal found 7/20![Delta logo]()
$1,223
This Emirates deal was found by Cheapflights users on 7/21. 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 Emirates is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:30 pm
SIN
- ORD
2 stops40h 15m
Emirates
Sat 8/88:35 pm
ORD
- SIN
2 stops49h 55m
Emirates
Deal found 7/21![Emirates logo]()
$1,742
This China Airlines deal was found by Cheapflights users on 7/21. 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 8/91:55 pm
SIN
- MDW
2 stops34h 20m
Multiple Airlines
Sat 8/156:00 pm
MDW
- SIN
2 stops29h 35m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$1,485
This United Airlines deal was found by Cheapflights users on 7/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:45 am
SIN
- ORD
2 stops29h 30m
United Airlines
Sat 8/88:04 pm
ORD
- SIN
1 stop45h 11m
United Airlines
Deal found 7/22![United Airlines logo]()
$1,463
This Emirates deal was found by Cheapflights users on 7/21. 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 Emirates is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:30 pm
SIN
- ORD
2 stops40h 15m
Emirates
Fri 8/78:35 pm
ORD
- SIN
2 stops25h 55m
Emirates
Deal found 7/21![Emirates logo]()
$1,816
Last-minute flights from Singapore to ChicagoDiscover last-minute flight deals from Singapore to Chicago. Data last updated July 25, 2026 and is based on user searches.
Discover last-minute flight deals from Singapore to Chicago. Data last updated July 25, 2026 and is based on user searches.
This China Airlines deal was found by Cheapflights users on 7/21. 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 8/91:55 pm
SIN
- MDW
2 stops34h 20m
Multiple Airlines
Sat 8/156:00 pm
MDW
- SIN
2 stops29h 35m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$1,485
This Cheapflightsfares deal was found by Cheapflights users on 7/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/171:55 am
SIN
- ORD
2 stops34h 35m
Japan Airlines
Tue 8/252:30 pm
ORD
- SIN
1 stop26h 40m
Japan Airlines
Deal found 7/22![Japan Airlines logo]()
$1,142
This United Airlines deal was found by Cheapflights users on 7/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:45 am
SIN
- ORD
1 stop24h 41m
United Airlines
Tue 8/254:20 pm
ORD
- SIN
1 stop24h 55m
United Airlines
Deal found 7/22![United Airlines logo]()
$1,110
This Air Canada deal was found by Cheapflights users on 7/25. 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 8/187:00 am
SIN
- ORD
1 stop20h 36m
Air Canada
Tue 8/258:40 am
ORD
- SIN
2 stops27h 05m
Air Canada
Deal found 7/25![Air Canada logo]()
$1,132
This China Airlines deal was found by Cheapflights users on 7/22. 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.
Tue 8/181:55 pm
SIN
- MDW
2 stops28h 50m
Multiple Airlines
Tue 8/259:00 pm
MDW
- SIN
2 stops26h 35m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$1,249
This Delta deal was found by Cheapflights users on 7/25. 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 8/187:30 am
SIN
- MDW
2 stops28h 06m
Delta
Tue 8/256:05 am
MDW
- SIN
2 stops28h 50m
Delta
Deal found 7/25![Delta logo]()
$1,304
This Delta deal was found by Cheapflights users on 7/23. 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 8/217:30 am
SIN
- ORD
2 stops28h 59m
Delta
Fri 8/287:44 pm
ORD
- SIN
2 stops39h 11m
Delta
Deal found 7/23![Delta logo]()
$1,115
This Gotogate deal was found by Cheapflights users on 7/23. 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.
Fri 8/218:05 am
SIN
- ORD
1 stop36h 40m
Japan Airlines
Fri 8/2810:40 am
ORD
- SIN
1 stop24h 40m
Japan Airlines
Deal found 7/23![Japan Airlines logo]()
$1,159
This EVA Air deal was found by Cheapflights users on 7/23. 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.
Fri 8/213:20 pm
SIN
- MDW
2 stops27h 30m
Multiple Airlines
Fri 8/289:20 pm
MDW
- SIN
2 stops25h 35m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$1,309
This Air Canada deal was found by Cheapflights users on 7/25. 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.
Sat 8/227:00 am
SIN
- ORD
2 stops26h 01m
Air Canada
Sat 8/293:40 pm
ORD
- SIN
2 stops33h 50m
Air Canada
Deal found 7/25![Air Canada logo]()
$891
This Gotogate deal was found by Cheapflights users on 7/22. 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 8/258:50 pm
SIN
- ORD
2 stops30h 46m
Air Canada
Tue 9/153:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Deal found 7/22![Air Canada logo]()
$812
This United Airlines deal was found by Cheapflights users on 7/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:45 am
SIN
- ORD
1 stop22h 50m
United Airlines
Tue 9/1512:51 pm
ORD
- SIN
1 stop28h 24m
United Airlines
Deal found 7/22![United Airlines logo]()
$1,101
One-way flights from Singapore to ChicagoSearch for one-way flight options from Singapore to Chicago. Find affordable one-way fares based on user searches. Data last updated July 25, 2026.
Search for one-way flight options from Singapore to Chicago. Find affordable one-way fares based on user searches. Data last updated July 25, 2026.
This Air Canada deal was found by Cheapflights users on 7/23. 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.
Sun 9/137:00 am
SIN
- ORD
2 stops39h 12m
Air Canada
Deal found 7/23![Air Canada logo]()
$498
This Jettzy deal was found by Cheapflights users on 7/22. 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 9/96:15 am
SIN
- ORD
2 stops26h 57m
Air Canada
Deal found 7/22![Air Canada logo]()
$503
This FlightHub deal was found by Cheapflights users on 7/22. 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 12/138:40 am
SIN
- ORD
1 stop19h 57m
Air Canada
Deal found 7/22![Air Canada logo]()
$512
This Air Canada deal was found by Cheapflights users on 7/23. 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 9/158:50 pm
SIN
- ORD
2 stops30h 53m
Air Canada
Deal found 7/23![Air Canada logo]()
$513
This Expedia deal was found by Cheapflights users on 7/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:40 am
SIN
- ORD
2 stops37h 14m
Air Canada
Deal found 7/22![Air Canada logo]()
$520
This Air Canada deal was found by Cheapflights users on 7/21. 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 12/158:40 am
SIN
- ORD
2 stops29h 17m
Air Canada
Deal found 7/21![Air Canada logo]()
$522
This FlightHub deal was found by Cheapflights users on 7/22. 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.
Mon 9/146:15 am
SIN
- ORD
2 stops38h 36m
Air Canada
Deal found 7/22![Air Canada logo]()
$527
This FlightHub deal was found by Cheapflights users on 7/21. 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.
Tue 1/126:35 am
SIN
- ORD
2 stops27h 17m
Air Canada
Deal found 7/21![Air Canada logo]()
$528
This Booking.com deal was found by Cheapflights users on 7/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/106:35 am
SIN
- ORD
2 stops27h 23m
Air Canada
Deal found 7/23![Air Canada logo]()
$531
This Air Canada deal was found by Cheapflights users on 7/22. 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 1/136:35 am
SIN
- ORD
2 stops41h 09m
Air Canada
Deal found 7/22![Air Canada logo]()
$532
This Air Canada deal was found by Cheapflights users on 7/22. 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.
Mon 1/1110:20 pm
SIN
- ORD
2 stops47h 30m
Air Canada
Deal found 7/22![Air Canada logo]()
$534
This Air Canada deal was found by Cheapflights users on 7/22. 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 1/146:35 am
SIN
- ORD
2 stops29h 24m
Air Canada
Deal found 7/22![Air Canada logo]()
$538
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 July 25, 2026.
Round-trip from | $745 (lol.travel) |
|---|---|
One-way from | $498 (Air Canada) |
Popular in | August |
Cheapest in | September |
Average price | $1,210 |
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 July 25, 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
Cheapest round-trip
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Sat 9/5
8:45 am-6:35 pm
1 stop22h 50m
Chicago O'Hare Intl
Sat 9/5
9:40 pm-6:35 pm
1 stop31h 55m
$1,096
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Tue 9/1
8:35 pm-6:32 pm
1 stop34h 57m
Chicago O'Hare Intl
Thu 9/24
6:07 am-6:35 pm
1 stop23h 28m
$1,101
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Mon 9/7
8:35 pm-11:23 am
1 stop27h 48m
Chicago O'Hare Intl
Mon 9/14
12:51 pm-6:15 am
1 stop28h 24m
$1,101
Quickest round-trip
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Tue 8/25
8:45 am-6:35 pm
1 stop22h 50m
Chicago O'Hare Intl
Tue 9/15
12:51 pm-6:15 am
1 stop28h 24m
$1,101
SingaporeChicago
SIN - MDW
SINMDW
Singapore Changi
Wed 9/23
1:25 am-10:44 pm
2 stops34h 19m
Chicago Midway
Sun 9/27
9:59 am-5:00 am
2 stops30h 01m
$1,115
SingaporeChicago
SIN - MDW
SINMDW
Singapore Changi
Tue 9/8
7:30 am-10:44 pm
2 stops28h 14m
Chicago Midway
Tue 9/15
9:29 am-5:00 am
2 stops30h 31m
$1,115
SingaporeChicago
SIN - MDW
SINMDW
Singapore Changi
Thu 9/10
10:00 pm-3:24 pm
2 stops30h 24m
Chicago Midway
Thu 9/24
6:05 am-11:55 pm
2 stops28h 50m
$1,223
SingaporeChicago
SIN - MDW
SINMDW
Singapore Changi
Sat 9/12
7:30 am-10:44 pm
2 stops28h 14m
Chicago Midway
Fri 9/18
6:05 am-5:00 am
2 stops33h 55m
$1,223
SingaporeChicago
SIN - MDW
SINMDW
Singapore Changi
Thu 9/10
1:55 pm-11:15 am
2 stops34h 20m
Chicago Midway
Thu 9/24
3:55 pm-12:35 pm
2 stops31h 40m
$1,225
SingaporeChicago
SIN - MDW
SINMDW
Singapore Changi
Thu 10/1
2:00 am-12:10 am
2 stops35h 10m
Chicago Midway
Sat 10/10
7:05 pm-12:35 pm
2 stops28h 30m
$1,230
Showing 1-10 of 35 resultsSorted by cheapest first
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.
SIN-ORD
SIN-MDW
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
SG0-CHI
SIN-ORD
SIN-MDW
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 July 25, 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.
Entertainment
7.8
Boarding
8.4
Crew
8.7
Food
7.7
Overall
8.3
Comfort
8.2
Reviews
1 / 20
4.0
OkayPaul,Jun 2026
HND - DFW
Entertainment
7.8
Boarding
8.4
Crew
8.7
Food
7.7
Overall
8.3
Comfort
8.2
Reviews
1 / 20
4.0
OkayPaul,Jun 2026
HND - DFW
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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