$427+ Cheap flights from Chicago (CHI) to Singapore
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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Aug 23 — Aug 301
Round-trip
1 adult, Economy
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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
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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 July 24, 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 July 24, 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 9/69:15 am
ORD
- SIN
2 stops31h 00m
Air Canada
Wed 9/166:15 am
SIN
- ORD
2 stops26h 57m
Air Canada
Deal found 7/23![Air Canada logo]()
$964
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:00 pm
ORD
- SIN
1 stop30h 45m
Multiple Airlines
Sun 9/66:15 am
SIN
- ORD
2 stops26h 50m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$965
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.
Thu 9/109:15 am
ORD
- SIN
2 stops31h 00m
Air Canada
Mon 9/1410:00 pm
SIN
- ORD
2 stops34h 48m
Air Canada
Deal found 7/21![Air Canada logo]()
$966
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.
Fri 8/213:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Tue 8/257:00 am
SIN
- ORD
2 stops35h 03m
Air Canada
Deal found 7/21![Air Canada logo]()
$967
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.
Sun 9/64:39 pm
MDW
- SIN
2 stops37h 36m
Delta
Wed 9/237:30 am
SIN
- MDW
2 stops28h 14m
Delta
Deal found 7/24![Delta logo]()
$969
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:10 pm
ORD
- SIN
1 stop23h 30m
Multiple Airlines
Wed 9/3010:50 pm
SIN
- ORD
2 stops34h 16m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$969
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:11 am
ORD
- SIN
2 stops28h 34m
Air Canada
Fri 9/2510:50 pm
SIN
- ORD
2 stops52h 53m
Air Canada
Deal found 7/20![Air Canada logo]()
$971
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.
Thu 10/88:40 am
ORD
- SIN
2 stops31h 35m
Air Canada
Sun 10/259:00 pm
SIN
- ORD
2 stops30h 37m
Air Canada
Deal found 7/21![Air Canada logo]()
$972
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.
Wed 9/3012:10 pm
ORD
- SIN
1 stop42h 05m
Korean Air
Mon 10/51:25 am
SIN
- ORD
1 stop21h 05m
Korean Air
Deal found 7/21![Korean Air logo]()
$973
This Air Canada deal was found by Cheapflights users on 7/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:48 pm
ORD
- SIN
1 stop44h 27m
Air Canada
Wed 9/238:10 am
SIN
- ORD
2 stops43h 33m
Air Canada
Deal found 7/19![Air Canada logo]()
$977
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/139:10 pm
ORD
- SIN
1 stop23h 30m
Multiple Airlines
Wed 9/166:15 am
SIN
- ORD
2 stops26h 57m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$978
This Turkish Airlines 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:10 pm
ORD
- SIN
1 stop23h 35m
Turkish Airlines
Wed 9/1611:05 pm
SIN
- ORD
1 stop23h 35m
Turkish Airlines
Deal found 7/20![Turkish Airlines logo]()
$979
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 July 24, 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 July 24, 2026.
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 9/75:10 pm
MDW
- SIN
2 stops37h 05m
Delta
Sun 9/137:30 am
SIN
- MDW
2 stops28h 14m
Delta
Deal found 7/24![Delta logo]()
$969
This Turkish 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:10 pm
ORD
- SIN
1 stop24h 20m
Turkish Airlines
Mon 9/1411:10 am
SIN
- ORD
1 stop35h 30m
Turkish Airlines
Deal found 7/23![Turkish Airlines logo]()
$1,100
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:25 pm
ORD
- SIN
2 stops38h 55m
American Airlines
Sat 9/58:05 am
SIN
- ORD
2 stops28h 54m
American Airlines
Deal found 7/20![American Airlines logo]()
$1,342
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/196:50 pm
ORD
- SIN
1 stop23h 55m
Alaska Airlines
Fri 1/18:15 pm
SIN
- ORD
1 stop32h 15m
Alaska Airlines
Deal found 7/24![Alaska Airlines logo]()
$1,636
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:59 am
MDW
- SIN
2 stops30h 01m
Delta
Tue 10/2710:40 am
SIN
- MDW
2 stops24h 45m
Delta
Deal found 7/22![Delta logo]()
$984
This Singapore 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 Singapore Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:35 am
ORD
- SIN
1 stop30h 55m
Multiple Airlines
Wed 9/2312:10 pm
SIN
- ORD
1 stop34h 48m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$1,999
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:10 pm
MDW
- SIN
2 stops37h 05m
Delta
Wed 9/97:30 am
SIN
- MDW
2 stops28h 14m
Delta
Deal found 7/22![Delta logo]()
$984
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.
Wed 9/305:11 pm
MDW
- SIN
2 stops37h 04m
Delta
Tue 10/67:30 am
SIN
- MDW
2 stops27h 55m
Delta
Deal found 7/21![Delta logo]()
$984
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.
Tue 10/279:29 am
MDW
- SIN
2 stops25h 41m
Delta
Tue 11/1010:40 am
SIN
- MDW
2 stops25h 30m
Delta
Deal found 7/23![Delta logo]()
$984
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.
Thu 9/39:59 am
MDW
- SIN
2 stops30h 01m
Delta
Wed 9/97:30 am
SIN
- MDW
2 stops28h 14m
Delta
Deal found 7/23![Delta logo]()
$984
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.
Tue 1/195:55 pm
ORD
- SIN
2 stops40h 15m
Delta
Sun 1/241:35 am
SIN
- ORD
2 stops36h 11m
Delta
Deal found 7/23![Delta logo]()
$984
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.
Sun 8/239:59 am
MDW
- SIN
2 stops30h 01m
Delta
Sat 8/297:30 am
SIN
- MDW
2 stops28h 06m
Delta
Deal found 7/20![Delta logo]()
$1,004
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am
ORD
- SIN
2 stops36h 45m
Alaska Airlines
Sun 1/38:15 pm
SIN
- ORD
1 stop32h 15m
Alaska Airlines
Deal found 7/24![Alaska Airlines logo]()
$1,982
This Delta deal was found by Cheapflights users on 7/19. 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.
Wed 9/236:10 am
ORD
- SIN
2 stops28h 45m
Delta
Fri 9/251:25 am
SIN
- ORD
2 stops32h 05m
Delta
Deal found 7/19![Delta logo]()
$1,112
This Delta deal was found by Cheapflights users on 7/19. 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 8/256:05 am
MDW
- SIN
2 stops33h 55m
Delta
Sat 8/291:25 am
SIN
- MDW
2 stops27h 50m
Delta
Deal found 7/19![Delta logo]()
$1,119
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.
Tue 8/47:29 am
ORD
- SIN
2 stops32h 31m
Delta
Sat 8/1510:00 pm
SIN
- ORD
2 stops29h 09m
Delta
Deal found 7/21![Delta logo]()
$1,169
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 8/209:59 am
MDW
- SIN
2 stops24h 56m
Delta
Thu 8/277:30 am
SIN
- MDW
2 stops28h 06m
Delta
Deal found 7/21![Delta logo]()
$1,249
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/205:25 pm
MDW
- SIN
2 stops40h 45m
Delta
Sun 1/241:35 am
SIN
- MDW
2 stops34h 35m
Delta
Deal found 7/22![Delta logo]()
$1,249
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.
Sat 12/123:35 pm
ORD
- SIN
2 stops42h 35m
Delta
Sat 1/21:35 am
SIN
- ORD
2 stops30h 57m
Delta
Deal found 7/24![Delta logo]()
$1,813
This Delta deal was found by Cheapflights users on 7/19. 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.
Fri 12/187:10 am
ORD
- SIN
2 stops31h 50m
Delta
Mon 1/410:40 am
SIN
- ORD
2 stops40h 40m
Delta
Deal found 7/19![Delta logo]()
$2,036
Last-minute flights from Chicago to SingaporeDiscover last-minute flight deals from Chicago to Singapore. Data last updated July 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Singapore. Data last updated July 24, 2026 and is based on user searches.
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 8/163:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Sat 8/227:00 am
SIN
- ORD
2 stops26h 01m
Air Canada
Deal found 7/22![Air Canada logo]()
$999
This ScholarTrip 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 ScholarTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:00 pm
ORD
- SIN
1 stop30h 45m
Cathay Pacific
Tue 8/186:00 pm
SIN
- ORD
1 stop33h 20m
Cathay Pacific
Deal found 7/21![Cathay Pacific logo]()
$1,014
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:00 pm
ORD
- SIN
1 stop30h 40m
Etihad Airways
Mon 8/319:00 pm
SIN
- ORD
1 stop31h 40m
Etihad Airways
Deal found 7/20![Etihad Airways logo]()
$996
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.
Fri 8/219:15 am
ORD
- SIN
2 stops31h 00m
Air Canada
Tue 8/257:00 am
SIN
- ORD
2 stops35h 03m
Air Canada
Deal found 7/21![Air Canada logo]()
$967
This ScholarTrip deal was found by Cheapflights users on 7/19. 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 ScholarTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:00 pm
ORD
- SIN
1 stop24h 30m
Cathay Pacific
Tue 8/2512:45 pm
SIN
- ORD
1 stop38h 35m
Cathay Pacific
Deal found 7/19![Cathay Pacific logo]()
$984
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/213:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Sat 8/297:00 am
SIN
- ORD
1 stop20h 36m
Air Canada
Deal found 7/20![Air Canada logo]()
$1,001
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.
Fri 8/219:24 am
MDW
- SIN
2 stops30h 36m
Delta
Sat 8/297:30 am
SIN
- MDW
2 stops28h 06m
Delta
Deal found 7/20![Delta logo]()
$1,004
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:00 pm
ORD
- SIN
1 stop30h 40m
Multiple Airlines
Tue 8/258:50 pm
SIN
- ORD
2 stops30h 46m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$1,004
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.
Sat 8/227:46 pm
ORD
- SIN
2 stops44h 29m
Air Canada
Wed 9/96:15 am
SIN
- ORD
2 stops38h 36m
Air Canada
Deal found 7/23![Air Canada logo]()
$966
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.
Sat 8/227:46 pm
ORD
- SIN
2 stops44h 29m
Air Canada
Sat 8/297:00 am
SIN
- ORD
2 stops43h 05m
Air Canada
Deal found 7/23![Air Canada logo]()
$1,003
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/233:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Sat 8/297:00 am
SIN
- ORD
1 stop20h 36m
Air Canada
Deal found 7/20![Air Canada logo]()
$1,005
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:10 pm
MDW
- SIN
2 stops37h 05m
Delta
Wed 9/97:30 am
SIN
- MDW
2 stops28h 14m
Delta
Deal found 7/22![Delta logo]()
$984
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 July 24, 2026.
Search for one-way flight options from Chicago to Singapore. Find affordable one-way fares based on user searches. Data last updated July 24, 2026.
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/244:00 pm
ORD
- SIN
1 stop24h 30m
Cathay Pacific
Deal found 7/23![Cathay Pacific logo]()
$427
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/204:00 pm
ORD
- SIN
1 stop24h 30m
Cathay Pacific
Deal found 7/22![Cathay Pacific logo]()
$429
This oojo 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 oojo 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 7/22![Cathay Pacific logo]()
$431
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/279:10 pm
ORD
- SIN
1 stop23h 30m
Etihad Airways
Deal found 7/23![Etihad Airways logo]()
$434
This Flightnetwork deal was found by Cheapflights users on 7/19. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:00 pm
ORD
- SIN
1 stop30h 40m
Etihad Airways
Deal found 7/19![Etihad Airways logo]()
$439
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/104:00 pm
ORD
- SIN
1 stop24h 30m
Cathay Pacific
Deal found 7/20![Cathay Pacific logo]()
$442
This ScholarTrip deal was found by Cheapflights users on 7/19. 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 ScholarTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/34:00 pm
ORD
- SIN
1 stop30h 45m
Cathay Pacific
Deal found 7/19![Cathay Pacific logo]()
$444
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/12:00 pm
ORD
- SIN
3 stops39h 05m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$461
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:00 pm
ORD
- SIN
1 stop30h 40m
Etihad Airways
Deal found 7/23![Etihad Airways logo]()
$474
This Korean 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 Korean Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:10 pm
ORD
- SIN
1 stop42h 05m
Korean Air
Deal found 7/23![Korean Air logo]()
$475
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.
Wed 8/195:10 pm
MDW
- SIN
2 stops37h 05m
Delta
Deal found 7/24![Delta logo]()
$477
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.
Wed 1/207:00 am
ORD
- SIN
2 stops27h 10m
Delta
Deal found 7/23![Delta logo]()
$477
Find flight deals from Chicago to Singapore
Keep the following information in mind while searching for Chicago to Singapore flight deals. Data was last updated July 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $964 (Air Canada) |
One-way from | $427 (SmartFares) |
Popular in | December |
Cheapest in | September |
Average price | $1,442 |
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 July 24, 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
MDW - SIN
MDWSIN
Chicago Midway
Mon 9/7
5:10 pm-7:15 pm
2 stops37h 05m
Singapore Changi
Sun 9/13
7:30 am-10:44 pm
2 stops28h 14m
$969
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Mon 10/12
9:59 am-5:00 am
2 stops30h 01m
Singapore Changi
Tue 10/27
10:40 am-10:25 pm
2 stops24h 45m
$984
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Mon 8/24
5:10 pm-7:15 pm
2 stops37h 05m
Singapore Changi
Wed 9/9
7:30 am-10:44 pm
2 stops28h 14m
$984
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Wed 9/30
5:11 pm-7:15 pm
2 stops37h 04m
Singapore Changi
Tue 10/6
7:30 am-10:25 pm
2 stops27h 55m
$984
Quickest round-trip
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Tue 10/27
9:29 am-12:10 am
2 stops25h 41m
Singapore Changi
Tue 11/10
10:40 am-10:10 pm
2 stops25h 30m
$984
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Thu 9/3
9:59 am-5:00 am
2 stops30h 01m
Singapore Changi
Wed 9/9
7:30 am-10:44 pm
2 stops28h 14m
$984
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Tue 1/19
5:55 pm-12:10 am
2 stops40h 15m
Singapore Changi
Sun 1/24
1:35 am-11:46 pm
2 stops36h 11m
$984
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Sun 8/23
9:59 am-5:00 am
2 stops30h 01m
Singapore Changi
Sat 8/29
7:30 am-10:36 pm
2 stops28h 06m
$1,004
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Thu 9/10
8:10 pm-9:30 am
1 stop24h 20m
Singapore Changi
Mon 9/14
11:10 am-9:40 am
1 stop35h 30m
$1,100
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Wed 9/23
6:10 am-11:55 pm
2 stops28h 45m
Singapore Changi
Fri 9/25
1:25 am-8:30 pm
2 stops32h 05m
$1,112
Showing 1-10 of 37 resultsSorted by cheapest first
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.
MDW-SIN
ORD-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-SG0
MDW-SIN
ORD-SIN
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 $895). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,995). 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 far ahead should I book a flight from Chicago to Singapore?
The best time to book flights from Chicago to Singapore is 42 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.
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 July 24, 2026.
Read reviews from past customers who have flown EVA Air,Cathay Pacific, andTurkish Airlines from Chicago to Singapore. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.3
Overall
8.5
Crew
8.7
Boarding
8.4
Food
8.1
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - TPE
Comfort
8.3
Overall
8.5
Crew
8.7
Boarding
8.4
Food
8.1
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - TPE
Comfort
8.3
Overall
8.5
Crew
8.7
Boarding
8.4
Food
8.1
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - TPE
Comfort
8.3
Overall
8.5
Crew
8.7
Boarding
8.4
Food
8.1
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - TPE
Comfort
8.3
Overall
8.5
Crew
8.7
Boarding
8.4
Food
8.1
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - TPE
Comfort
8.3
Overall
8.5
Crew
8.7
Boarding
8.4
Food
8.1
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - 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.
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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 July 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 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 July 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$689 | Average$1,166 | FlexibilityNo cancel fee | On-time80% | |
| Cheapest$698 | Average$932 | FlexibilityNo cancel fee | On-time72% | |
| Cheapest$705 | Average$1,141 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$721 | Average$897 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$770 | Average$1,276 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$792 | Average$963 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$829 | Average$1,032 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$884 | Average$1,340 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$949 | Average$1,520 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$963 | Average$1,064 | FlexibilityNo cancel fee | On-time68% |