$401+ Cheap flights from Chicago (CHI) to Singapore (SIN)
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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
May 15 — May 221
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Singapore 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Singapore
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to SingaporeExplore the most affordable flight options available from Chicago to Singapore. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2026.
Explore the most affordable flight options available from Chicago to Singapore. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2026.
This FlightHub deal was found by Cheapflights users on 4/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:49 am
ORD
- SIN
1 stop31h 26m
Air Canada
Tue 10/67:00 am
SIN
- ORD
2 stops34h 58m
Air Canada
Deal found 4/10![Air Canada logo]()
$927
This Air Canada deal was found by Cheapflights users on 4/10. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/113:40 pm
ORD
- SIN
1 stop25h 20m
Air Canada
Tue 12/18:50 am
SIN
- ORD
1 stop19h 51m
Air Canada
Deal found 4/10![Air Canada logo]()
$930
This IEagle deal was found by Cheapflights users on 4/14. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/271:15 pm
ORD
- SIN
1 stop43h 30m
Air India
Thu 5/281:10 pm
SIN
- ORD
2 stops35h 00m
Air India
Deal found 4/14![Air India logo]()
$939
This FlightHub deal was found by Cheapflights users on 4/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/253:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Thu 9/107:00 am
SIN
- ORD
2 stops39h 35m
Air Canada
Deal found 4/10![Air Canada logo]()
$940
This IEagle deal was found by Cheapflights users on 4/10. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:30 pm
ORD
- SIN
1 stop41h 15m
Air India
Sat 11/1411:00 pm
SIN
- ORD
2 stops50h 30m
Air India
Deal found 4/10![Air India logo]()
$959
This Travelocity deal was found by Cheapflights users on 4/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/223:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Sun 9/277:00 am
SIN
- ORD
1 stop20h 48m
Air Canada
Deal found 4/10![Air Canada logo]()
$966
This IEagle deal was found by Cheapflights users on 4/11. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:30 pm
ORD
- SIN
1 stop28h 45m
Air India
Wed 11/1111:00 pm
SIN
- ORD
2 stops50h 30m
Air India
Deal found 4/11![Air India logo]()
$968
This FlightHub deal was found by Cheapflights users on 4/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:49 am
ORD
- SIN
1 stop31h 26m
Air Canada
Sat 9/267:00 am
SIN
- ORD
2 stops39h 21m
Air Canada
Deal found 4/10![Air Canada logo]()
$977
This Justfly.com deal was found by Cheapflights users on 4/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:40 pm
ORD
- SIN
2 stops67h 35m
Air Canada
Thu 10/17:00 am
SIN
- ORD
2 stops39h 21m
Air Canada
Deal found 4/12![Air Canada logo]()
$985
This IEagle deal was found by Cheapflights users on 4/10. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:30 pm
ORD
- SIN
1 stop41h 15m
Air India
Fri 11/2711:00 pm
SIN
- ORD
2 stops50h 30m
Air India
Deal found 4/10![Air India logo]()
$988
This Expedia deal was found by Cheapflights users on 4/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Wed 9/166:15 am
SIN
- ORD
2 stops26h 57m
Air Canada
Deal found 4/11![Air Canada logo]()
$992
This Delta deal was found by Cheapflights users on 4/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:30 am
MDW
- SIN
2 stops25h 25m
Delta
Sun 9/67:30 am
SIN
- MDW
2 stops27h 16m
Delta
Deal found 4/11![Delta logo]()
$1,279
Best flights from Chicago to SingaporeDiscover carefully curated flight deals from Chicago to Singapore that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 15, 2026.
Discover carefully curated flight deals from Chicago to Singapore that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 15, 2026.
This United Airlines deal was found by Cheapflights users on 4/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
ORD
- SIN
1 stop23h 35m
United Airlines
Mon 9/148:45 am
SIN
- ORD
1 stop22h 47m
United Airlines
Deal found 4/10![United Airlines logo]()
$1,140
This Delta deal was found by Cheapflights users on 4/10. 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.
Wed 8/268:55 am
ORD
- SIN
2 stops26h 00m
Delta
Mon 9/147:30 am
SIN
- ORD
2 stops26h 00m
Delta
Deal found 4/10![Delta logo]()
$1,154
This Etihad Airways deal was found by Cheapflights users on 4/13. 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 Etihad Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/162:00 pm
ORD
- SIN
1 stop30h 40m
Etihad Airways
Sun 5/319:00 pm
SIN
- ORD
1 stop24h 35m
Etihad Airways
Deal found 4/13![Etihad Airways logo]()
$1,244
This China Airlines deal was found by Cheapflights users on 4/11. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:00 pm
MDW
- SIN
2 stops33h 35m
Multiple Airlines
Wed 9/161:45 pm
SIN
- MDW
2 stops29h 05m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$1,436
This United Airlines deal was found by Cheapflights users on 4/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am
ORD
- SIN
1 stop23h 35m
United Airlines
Thu 9/108:45 am
SIN
- ORD
1 stop22h 47m
United Airlines
Deal found 4/10![United Airlines logo]()
$1,140
This Delta deal was found by Cheapflights users on 4/12. 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 10/129:55 am
MDW
- SIN
2 stops30h 05m
Delta
Sun 10/1810:00 pm
SIN
- MDW
2 stops33h 37m
Delta
Deal found 4/12![Delta logo]()
$1,304
This United Airlines deal was found by Cheapflights users on 4/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:20 pm
ORD
- SIN
1 stop22h 55m
United Airlines
Sat 9/128:35 pm
SIN
- ORD
1 stop21h 26m
United Airlines
Deal found 4/10![United Airlines logo]()
$1,190
This United Airlines deal was found by Cheapflights users on 4/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
ORD
- SIN
1 stop23h 35m
United Airlines
Thu 9/108:35 pm
SIN
- ORD
1 stop21h 26m
United Airlines
Deal found 4/10![United Airlines logo]()
$1,190
This Delta deal was found by Cheapflights users on 4/12. 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 5/108:10 am
ORD
- SIN
2 stops31h 50m
Delta
Sun 5/1710:00 pm
SIN
- ORD
2 stops36h 20m
Delta
Deal found 4/12![Delta logo]()
$1,354
This China Airlines deal was found by Cheapflights users on 4/10. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:20 pm
MDW
- SIN
2 stops32h 15m
Multiple Airlines
Thu 5/141:45 pm
SIN
- MDW
2 stops28h 55m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$1,515
This United Airlines deal was found by Cheapflights users on 4/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:30 am
ORD
- SIN
1 stop43h 05m
United Airlines
Tue 5/128:35 pm
SIN
- ORD
1 stop22h 05m
United Airlines
Deal found 4/11![United Airlines logo]()
$1,200
This Delta deal was found by Cheapflights users on 4/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:05 am
MDW
- SIN
2 stops33h 55m
Delta
Sat 8/1510:00 pm
SIN
- MDW
2 stops31h 27m
Delta
Deal found 4/11![Delta logo]()
$1,479
This United Airlines deal was found by Cheapflights users on 4/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:30 pm
ORD
- SIN
1 stop32h 05m
United Airlines
Sun 8/308:35 pm
SIN
- ORD
2 stops29h 12m
United Airlines
Deal found 4/11![United Airlines logo]()
$1,245
This Korean Air deal was found by Cheapflights users on 4/10. 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 Korean Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/179:17 am
MDW
- SIN
2 stops25h 38m
Multiple Airlines
Fri 6/261:25 am
SIN
- MDW
2 stops24h 11m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$1,693
This Delta deal was found by Cheapflights users on 4/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:07 am
ORD
- SIN
2 stops32h 53m
Delta
Mon 5/2510:00 pm
SIN
- ORD
2 stops35h 26m
Delta
Deal found 4/11![Delta logo]()
$1,499
This United Airlines deal was found by Cheapflights users on 4/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/108:10 pm
ORD
- SIN
2 stops33h 25m
United Airlines
Sun 5/178:35 pm
SIN
- ORD
2 stops26h 45m
United Airlines
Deal found 4/11![United Airlines logo]()
$1,345
This Delta deal was found by Cheapflights users on 4/12. 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 8/76:05 am
MDW
- SIN
2 stops33h 55m
Delta
Sun 8/1610:00 pm
SIN
- MDW
2 stops26h 54m
Delta
Deal found 4/12![Delta logo]()
$1,504
This Delta deal was found by Cheapflights users on 4/13. 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 5/49:29 am
MDW
- SIN
2 stops25h 26m
Delta
Thu 5/77:30 am
SIN
- MDW
2 stops26h 39m
Delta
Deal found 4/13![Delta logo]()
$1,540
This Delta deal was found by Cheapflights users on 4/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:00 am
MDW
- SIN
2 stops28h 55m
Delta
Fri 8/2110:00 pm
SIN
- MDW
2 stops30h 27m
Delta
Deal found 4/11![Delta logo]()
$1,589
This Delta deal was found by Cheapflights users on 4/10. 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.
Thu 5/286:23 am
MDW
- SIN
2 stops33h 37m
Delta
Wed 6/101:25 am
SIN
- MDW
2 stops27h 51m
Delta
Deal found 4/10![Delta logo]()
$1,669
This Delta deal was found by Cheapflights users on 4/13. 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 4/286:00 am
MDW
- SIN
2 stops34h 00m
Delta
Thu 5/77:30 am
SIN
- MDW
2 stops26h 39m
Delta
Deal found 4/13![Delta logo]()
$1,690
This Delta deal was found by Cheapflights users on 4/13. 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 4/306:00 am
MDW
- SIN
2 stops34h 00m
Delta
Thu 5/77:30 am
SIN
- MDW
2 stops26h 39m
Delta
Deal found 4/13![Delta logo]()
$1,690
This Delta deal was found by Cheapflights users on 4/10. 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.
Fri 7/105:10 pm
MDW
- SIN
2 stops41h 45m
Delta
Sun 7/1910:00 pm
SIN
- MDW
2 stops31h 15m
Delta
Deal found 4/10![Delta logo]()
$1,701
Last-minute flights from Chicago to SingaporeDiscover last-minute flight deals from Chicago to Singapore. Data last updated April 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Singapore. Data last updated April 15, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 4/14. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:00 pm
ORD
- SIN
1 stop31h 40m
Etihad Airways
Mon 5/49:00 pm
SIN
- ORD
1 stop24h 35m
Etihad Airways
Deal found 4/14![Etihad Airways logo]()
$1,107
This ScholarTrip deal was found by Cheapflights users on 4/13. 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 ScholarTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/244:15 pm
ORD
- SIN
1 stop31h 10m
Cathay Pacific
Wed 5/612:45 pm
SIN
- ORD
1 stop38h 10m
Cathay Pacific
Deal found 4/13![Cathay Pacific logo]()
$1,056
This IEagle deal was found by Cheapflights users on 4/14. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/271:15 pm
ORD
- SIN
1 stop43h 30m
Air India
Thu 5/281:10 pm
SIN
- ORD
2 stops35h 00m
Air India
Deal found 4/14![Air India logo]()
$939
This Trip.com deal was found by Cheapflights users on 4/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2711:25 am
ORD
- SIN
1 stop32h 20m
Turkish Airlines
Thu 5/2812:50 pm
SIN
- ORD
1 stop33h 50m
Turkish Airlines
Deal found 4/14![Turkish Airlines logo]()
$1,088
This oojo deal was found by Cheapflights users on 4/11. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/511:25 am
ORD
- SIN
1 stop34h 45m
Turkish Airlines
Tue 5/1210:25 am
SIN
- ORD
1 stop36h 15m
Turkish Airlines
Deal found 4/11![Turkish Airlines logo]()
$1,069
This Delta deal was found by Cheapflights users on 4/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- SIN
2 stops34h 00m
Delta
Tue 5/1210:00 pm
SIN
- MDW
2 stops26h 56m
Delta
Deal found 4/11![Delta logo]()
$1,304
This IEagle deal was found by Cheapflights users on 4/14. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:10 pm
ORD
- SIN
1 stop34h 00m
Air India
Thu 5/281:10 pm
SIN
- ORD
2 stops35h 00m
Air India
Deal found 4/14![Air India logo]()
$977
This IEagle deal was found by Cheapflights users on 4/12. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:10 pm
ORD
- SIN
1 stop29h 15m
Air India
Sat 8/2211:00 pm
SIN
- ORD
2 stops49h 10m
Air India
Deal found 4/12![Air India logo]()
$1,071
This FlightHub deal was found by Cheapflights users on 4/14. 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.
Fri 5/151:10 pm
ORD
- SIN
1 stop31h 05m
Air India
Mon 5/2511:00 pm
SIN
- ORD
2 stops49h 10m
Air India
Deal found 4/14![Air India logo]()
$1,101
This eDestinos deal was found by Cheapflights users on 4/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/172:00 pm
ORD
- SIN
1 stop30h 40m
Etihad Airways
Sun 5/319:00 pm
SIN
- ORD
1 stop24h 35m
Etihad Airways
Deal found 4/13![Etihad Airways logo]()
$1,095
This IEagle deal was found by Cheapflights users on 4/14. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:10 pm
ORD
- SIN
1 stop34h 00m
Air India
Tue 6/301:10 pm
SIN
- ORD
2 stops35h 00m
Air India
Deal found 4/14![Air India logo]()
$1,106
This lol.travel deal was found by Cheapflights users on 4/10. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Thu 6/117:00 am
SIN
- ORD
2 stops25h 25m
Air Canada
Deal found 4/10![Air Canada logo]()
$1,078
One-way flights from Chicago to SingaporeSearch for one-way flight options from Chicago to Singapore. Find affordable one-way fares based on user searches. Data last updated April 15, 2026.
Search for one-way flight options from Chicago to Singapore. Find affordable one-way fares based on user searches. Data last updated April 15, 2026.
This CrystalTravel deal was found by Cheapflights users on 4/14. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:00 pm
ORD
- SIN
1 stop31h 40m
Etihad Airways
Deal found 4/14![Etihad Airways logo]()
$401
This SmartFares deal was found by Cheapflights users on 4/13. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/201:00 pm
ORD
- SIN
1 stop31h 50m
Etihad Airways
Deal found 4/13![Etihad Airways logo]()
$418
This oojo deal was found by Cheapflights users on 4/10. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/271:00 pm
ORD
- SIN
1 stop31h 50m
Etihad Airways
Deal found 4/10![Etihad Airways logo]()
$420
This IEagle deal was found by Cheapflights users on 4/12. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/41:10 pm
ORD
- SIN
1 stop29h 15m
Air India
Deal found 4/12![Air India logo]()
$432
This Justfly.com deal was found by Cheapflights users on 4/14. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:10 pm
ORD
- SIN
1 stop43h 35m
Air India
Deal found 4/14![Air India logo]()
$493
This Justfly.com deal was found by Cheapflights users on 4/14. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/151:10 pm
ORD
- SIN
1 stop31h 05m
Air India
Deal found 4/14![Air India logo]()
$502
This CrystalTravel deal was found by Cheapflights users on 4/14. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/194:00 pm
ORD
- SIN
1 stop31h 25m
Cathay Pacific
Deal found 4/14![Cathay Pacific logo]()
$512
This CrystalTravel deal was found by Cheapflights users on 4/13. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/204:00 pm
ORD
- SIN
1 stop31h 25m
Cathay Pacific
Deal found 4/13![Cathay Pacific logo]()
$517
This IEagle deal was found by Cheapflights users on 4/13. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:10 pm
ORD
- SIN
1 stop43h 35m
Air India
Deal found 4/13![Air India logo]()
$527
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:21 pm
ORD
- SIN
3 stops39h 34m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$539
This Delta deal was found by Cheapflights users on 4/12. 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 8/199:20 am
MDW
- SIN
2 stops25h 35m
Delta
Deal found 4/12![Delta logo]()
$638
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:02 pm
MDW
- SIN
2 stops51h 38m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$650
Find flight deals from Chicago to Singapore
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Singapore (SIN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $927 (FlightHub) |
One-way from | $401 (CrystalTravel) |
Popular in | December |
Cheapest in | September |
Average price | $1,034 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Singapore 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 15, 2026.
Use the filters below to find and compare flights from Chicago to Singapore that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Tue 8/25
6:00 am-6:35 pm
1 stop23h 35m
Singapore Changi
Mon 9/14
8:45 am-6:32 pm
1 stop22h 47m
$1,140
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Thu 8/27
6:00 am-6:35 pm
1 stop23h 35m
Singapore Changi
Thu 9/10
8:45 am-6:32 pm
1 stop22h 47m
$1,140
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Wed 8/26
8:55 am-11:55 pm
2 stops26h 00m
Singapore Changi
Mon 9/14
7:30 am-8:30 pm
2 stops26h 00m
$1,154
Quickest round-trip
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Wed 8/26
6:20 pm-6:15 am
1 stop22h 55m
Singapore Changi
Sat 9/12
8:35 pm-5:01 am
1 stop21h 26m
$1,190
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sat 8/22
6:00 am-6:35 pm
1 stop23h 35m
Singapore Changi
Thu 9/10
8:35 pm-5:01 am
1 stop21h 26m
$1,190
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sat 5/9
10:30 am-6:35 pm
1 stop43h 05m
Singapore Changi
Tue 5/12
8:35 pm-5:40 am
1 stop22h 05m
$1,200
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sat 5/16
2:00 pm-9:40 am
1 stop30h 40m
Singapore Changi
Sun 5/31
9:00 pm-8:35 am
1 stop24h 35m
$1,244
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sat 8/15
9:30 pm-6:35 pm
1 stop32h 05m
Singapore Changi
Sun 8/30
8:35 pm-12:47 pm
2 stops29h 12m
$1,245
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Mon 10/12
9:55 am-5:00 am
2 stops30h 05m
Singapore Changi
Sun 10/18
10:00 pm-6:37 pm
2 stops33h 37m
$1,304
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sun 5/10
8:10 pm-6:35 pm
2 stops33h 25m
Singapore Changi
Sun 5/17
8:35 pm-10:20 am
2 stops26h 45m
$1,345
Showing 1-10 of 42 resultsSorted by cheapest first
Compare providers for flights from Chicago to Singapore
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Singapore in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Singapore flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Singapore flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Singapore flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Singapore flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Singapore flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Singapore
Have a flexible travel schedule? Discover the best time to fly to Singapore from Chicago with our price prediction graph.
CHI-SIN
ORD-SIN
MDW-SIN
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 Chicago to Singapore
CHI-SIN
ORD-SIN
MDW-SIN
How far ahead should I book a flight from Chicago to Singapore?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Singapore. Price data was last updated on April 10, 2026.
The best time to book flights from Chicago to Singapore is 6 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Singapore?
Currently, September is the cheapest month in which you can book a flight from Chicago to Singapore (average of $661). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,202). 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 much does it cost to fly round-trip from Chicago to Singapore?
What’s the top layover airport for flights from Chicago to Singapore?
Share of 1-stop round-trip flights from Chicago to Singapore chosen by Cheapflights users in the past 12 months, using the same layover each way.
Incheon (ICN) – chosen by Cheapflights users on 25% of 1-stop itineraries from Chicago to Singapore on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Singapore?
Average round-trip fare for 1-stop flights from Chicago to Singapore, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Hong Kong (HKG) is the most affordable 1-stop option, with an average round-trip price of $882.
What’s the fastest layover option from Chicago to Singapore?
Shortest average travel time for 1-stop one-way flights from Chicago to Singapore, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Incheon (ICN) have the shortest average one-way travel time for 1-stop routes: 22h 45m.
Which airport typically offers the quickest layover for flights from Chicago to Singapore?
Average layover duration for 1-stop one-way flights from Chicago to Singapore, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Incheon (ICN) offer the fastest connection on this route, with an average layover time of 1h 50m.
Reviews of airlines servicing Singapore
Get insights into the airlines that provide service to Singapore. 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 Singapore. Reviews last updated April 15, 2026.
Get a feel of what it's like to fly with EVA Air,Cathay Pacific, andUnited Airlines from Chicago to Singapore by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
8.0
Food
8.1
Boarding
8.4
Crew
8.7
Comfort
8.3
Overall
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
CRK - TPE
Entertainment
8.0
Food
8.1
Boarding
8.4
Crew
8.7
Comfort
8.3
Overall
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
CRK - TPE
Entertainment
8.0
Food
8.1
Boarding
8.4
Crew
8.7
Comfort
8.3
Overall
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
CRK - TPE
Entertainment
8.0
Food
8.1
Boarding
8.4
Crew
8.7
Comfort
8.3
Overall
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
CRK - TPE
Entertainment
8.0
Food
8.1
Boarding
8.4
Crew
8.7
Comfort
8.3
Overall
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
CRK - TPE
Entertainment
8.0
Food
8.1
Boarding
8.4
Crew
8.7
Comfort
8.3
Overall
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
CRK - TPE
Related info for your journey
Find useful and relevant information for your journey from Chicago to Singapore. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Singapore flight routes
Alternative routes for Chicago to Singapore
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Singapore by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Singapore by cabin class
Find flights from Chicago to Singapore, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Singapore flights
Browse other Chicago and Singapore flight options. Last updated on April 15, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on April 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Singapore
Explore flights to Singapore departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 15, 2026.
Top 10 airlines flying from Chicago to Singapore
Discover the top 10 airlines that operate flights from Chicago to Singapore. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$697 | Average$963 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$698 | Average$1,426 | FlexibilityNo cancel fee | On-time80% | |
| Cheapest$698 | Average$877 | FlexibilityNo cancel fee | On-time72% | |
| Cheapest$709 | Average$1,129 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$770 | Average$976 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$814 | Average$1,081 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$829 | Average$1,058 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$872 | Average$1,340 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$949 | Average$1,520 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$1,101 | Average$1,430 | FlexibilityNo cancel fee | On-time74% |