$478+ 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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
May 31 — Jun 71
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
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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 May 1, 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 May 1, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Wed 11/1110:45 pm
ORD
- SIN
1 stop24h 55m
Philippine Airlines
Mon 11/3010:30 am
SIN
- ORD
1 stop20h 25m
Philippine Airlines
Deal found 4/29![Philippine Airlines logo]()
$967
This KAYAK deal was found by Cheapflights users on 4/28. 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.
Mon 8/244:00 pm
ORD
- SIN
1 stop34h 40m
Cathay Pacific
Mon 9/149:45 am
SIN
- ORD
1 stop41h 35m
Cathay Pacific
Deal found 4/28![Cathay Pacific logo]()
$975
This oojo deal was found by Cheapflights users on 4/29. 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.
Sun 11/19:20 pm
ORD
- SIN
1 stop21h 25m
Turkish Airlines
Wed 11/1111:25 pm
SIN
- ORD
1 stop24h 40m
Turkish Airlines
Deal found 4/29![Turkish Airlines logo]()
$981
This CrystalTravel deal was found by Cheapflights users on 4/30. 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 11/1110:45 pm
ORD
- SIN
1 stop24h 55m
Philippine Airlines
Thu 11/1912:30 am
SIN
- ORD
1 stop30h 25m
Philippine Airlines
Deal found 4/30![Philippine Airlines logo]()
$982
This Trip.com deal was found by Cheapflights users on 4/29. 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 11/1610:45 pm
ORD
- SIN
1 stop34h 25m
Philippine Airlines
Tue 11/247:45 pm
SIN
- ORD
1 stop35h 10m
Philippine Airlines
Deal found 4/29![Philippine Airlines logo]()
$984
This FlightHub deal was found by Cheapflights users on 4/27. 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 9/83:40 pm
ORD
- SIN
1 stop24h 35m
Air Canada
Tue 9/297:00 am
SIN
- ORD
2 stops39h 43m
Air Canada
Deal found 4/27![Air Canada logo]()
$987
This FlightHub deal was found by Cheapflights users on 4/30. 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 10/1811:25 am
ORD
- SIN
1 stop32h 20m
Turkish Airlines
Thu 10/2210:25 am
SIN
- ORD
1 stop36h 15m
Turkish Airlines
Deal found 4/30![Turkish Airlines logo]()
$995
This FlightHub deal was found by Cheapflights users on 4/30. 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 10/1911:25 am
ORD
- SIN
1 stop41h 30m
Turkish Airlines
Thu 10/2210:25 am
SIN
- ORD
1 stop36h 15m
Turkish Airlines
Deal found 4/30![Turkish Airlines logo]()
$1,000
This FlightHub deal was found by Cheapflights users on 4/29. 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 11/1011:50 am
ORD
- SIN
1 stop30h 55m
Turkish Airlines
Mon 11/3011:40 am
SIN
- ORD
1 stop36h 25m
Turkish Airlines
Deal found 4/29![Turkish Airlines logo]()
$1,004
This Delta deal was found by Cheapflights users on 4/30. 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 8/205:25 pm
MDW
- SIN
2 stops36h 50m
Delta
Thu 9/107:30 am
SIN
- MDW
2 stops27h 16m
Delta
Deal found 4/30![Delta logo]()
$1,154
This Delta deal was found by Cheapflights users on 4/29. 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 9/139:20 am
MDW
- SIN
2 stops30h 40m
Delta
Thu 10/87:30 am
SIN
- MDW
2 stops27h 15m
Delta
Deal found 4/29![Delta logo]()
$1,204
This Delta deal was found by Cheapflights users on 4/26. 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 10/149:55 am
MDW
- SIN
2 stops30h 05m
Delta
Sun 10/2510:30 pm
SIN
- MDW
2 stops33h 07m
Delta
Deal found 4/26![Delta logo]()
$1,229
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 May 1, 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 May 1, 2026.
This Turkish Airlines deal was found by Cheapflights users on 4/30. 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 10/228:10 pm
ORD
- SIN
1 stop24h 20m
Turkish Airlines
Sat 10/3110:25 am
SIN
- ORD
1 stop38h 40m
Turkish Airlines
Deal found 4/30![Turkish Airlines logo]()
$1,100
This United Airlines deal was found by Cheapflights users on 4/30. 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 10/215:00 am
ORD
- SIN
2 stops24h 35m
United Airlines
Mon 10/2610:20 pm
SIN
- ORD
1 stop20h 58m
United Airlines
Deal found 4/30![United Airlines logo]()
$1,145
This Delta deal was found by Cheapflights users on 4/30. 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 10/258:55 am
ORD
- SIN
2 stops31h 05m
Delta
Fri 10/3010:30 pm
SIN
- ORD
2 stops34h 54m
Delta
Deal found 4/30![Delta logo]()
$1,254
This Korean Air deal was found by Cheapflights users on 4/28. 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 10/289:30 am
MDW
- SIN
2 stops30h 30m
Korean Air
Sun 11/110:40 am
SIN
- MDW
2 stops39h 53m
Korean Air
Deal found 4/28![Korean Air logo]()
$1,459
This Korean Air deal was found by Cheapflights users on 4/30. 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 6/39:22 am
MDW
- SIN
2 stops25h 33m
Multiple Airlines
Tue 6/91:25 am
SIN
- MDW
2 stops24h 16m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$1,638
This United Airlines deal was found by Cheapflights users on 4/30. 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 10/214:17 pm
ORD
- SIN
1 stop24h 58m
United Airlines
Sun 11/110:20 pm
SIN
- ORD
1 stop21h 07m
United Airlines
Deal found 4/30![United Airlines logo]()
$1,190
This United Airlines deal was found by Cheapflights users on 4/29. 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 9/139:40 pm
ORD
- SIN
2 stops31h 55m
United Airlines
Sat 10/38:35 pm
SIN
- ORD
1 stop21h 23m
United Airlines
Deal found 4/29![United Airlines logo]()
$1,195
This Delta deal was found by Cheapflights users on 4/29. 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 9/1310:35 am
MDW
- SIN
2 stops53h 25m
Delta
Wed 10/710:00 pm
SIN
- MDW
2 stops27h 33m
Delta
Deal found 4/29![Delta logo]()
$1,354
This United Airlines deal was found by Cheapflights users on 4/30. 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 10/15:00 am
ORD
- SIN
2 stops24h 35m
United Airlines
Fri 10/98:35 pm
SIN
- ORD
2 stops26h 04m
United Airlines
Deal found 4/30![United Airlines logo]()
$1,195
This Delta deal was found by Cheapflights users on 4/29. 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 9/135:25 pm
MDW
- SIN
2 stops36h 50m
Delta
Fri 10/27:30 am
SIN
- MDW
2 stops27h 16m
Delta
Deal found 4/29![Delta logo]()
$1,364
This United Airlines deal was found by Cheapflights users on 4/27. 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 9/69:40 pm
ORD
- SIN
2 stops31h 55m
United Airlines
Fri 9/1811:05 am
SIN
- ORD
2 stops26h 50m
United Airlines
Deal found 4/27![United Airlines logo]()
$1,204
This Delta deal was found by Cheapflights users on 4/26. 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 9/276:45 pm
MDW
- SIN
2 stops40h 10m
Delta
Wed 10/710:00 pm
SIN
- MDW
2 stops31h 25m
Delta
Deal found 4/26![Delta logo]()
$1,384
This Delta deal was found by Cheapflights users on 4/26. 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 6/96:35 am
ORD
- SIN
2 stops28h 20m
Delta
Mon 6/157:30 am
SIN
- ORD
2 stops29h 09m
Delta
Deal found 4/26![Delta logo]()
$1,449
This United Airlines deal was found by Cheapflights users on 4/28. 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 7/259:35 pm
ORD
- SIN
1 stop32h 00m
United Airlines
Sun 8/96:15 am
SIN
- ORD
2 stops31h 44m
United Airlines
Deal found 4/28![United Airlines logo]()
$1,398
This Delta deal was found by Cheapflights users on 4/29. 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 6/115:30 am
ORD
- SIN
2 stops29h 25m
Delta
Thu 9/177:30 am
SIN
- ORD
2 stops27h 28m
Delta
Deal found 4/29![Delta logo]()
$1,449
This Delta deal was found by Cheapflights users on 4/30. 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 6/156:35 am
ORD
- SIN
2 stops28h 20m
Delta
Mon 6/227:30 am
SIN
- ORD
2 stops29h 09m
Delta
Deal found 4/30![Delta logo]()
$1,449
This Delta deal was found by Cheapflights users on 4/27. 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 5/117:07 am
ORD
- SIN
2 stops32h 53m
Delta
Sun 5/241:25 am
SIN
- ORD
2 stops30h 10m
Delta
Deal found 4/27![Delta logo]()
$1,454
This Delta deal was found by Cheapflights users on 4/27. 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 6/116:00 am
MDW
- SIN
2 stops28h 55m
Delta
Wed 6/171:25 am
SIN
- MDW
2 stops33h 52m
Delta
Deal found 4/27![Delta logo]()
$1,559
This Delta deal was found by Cheapflights users on 4/30. 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 6/106:00 am
MDW
- SIN
2 stops34h 00m
Delta
Fri 6/261:25 am
SIN
- MDW
2 stops33h 52m
Delta
Deal found 4/30![Delta logo]()
$1,574
This Delta deal was found by Cheapflights users on 4/26. 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
Sun 8/161:25 am
SIN
- MDW
2 stops33h 21m
Delta
Deal found 4/26![Delta logo]()
$1,605
This Delta deal was found by Cheapflights users on 4/29. 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 6/136:00 am
MDW
- SIN
2 stops34h 00m
Delta
Sat 6/2010:00 pm
SIN
- MDW
2 stops31h 16m
Delta
Deal found 4/29![Delta logo]()
$1,624
This Delta deal was found by Cheapflights users on 4/27. 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 5/116:23 am
MDW
- SIN
2 stops33h 37m
Delta
Mon 5/2510:00 pm
SIN
- MDW
2 stops26h 56m
Delta
Deal found 4/27![Delta logo]()
$1,630
This Delta deal was found by Cheapflights users on 4/26. 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 7/96:00 am
MDW
- SIN
2 stops28h 55m
Delta
Mon 8/1010:00 pm
SIN
- MDW
2 stops31h 27m
Delta
Deal found 4/26![Delta logo]()
$1,646
This Delta deal was found by Cheapflights users on 4/26. 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 5/126:23 am
MDW
- SIN
2 stops33h 37m
Delta
Sat 5/2310:00 pm
SIN
- MDW
2 stops30h 26m
Delta
Deal found 4/26![Delta logo]()
$1,680
Last-minute flights from Chicago to SingaporeDiscover last-minute flight deals from Chicago to Singapore. Data last updated May 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Singapore. Data last updated May 1, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 4/27. 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 4/304:15 pm
ORD
- SIN
1 stop33h 50m
Cathay Pacific
Sat 5/166:00 pm
SIN
- ORD
1 stop32h 55m
Cathay Pacific
Deal found 4/27![Cathay Pacific logo]()
$1,027
This ScholarTrip deal was found by Cheapflights users on 4/29. 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.
Sat 5/24:15 pm
ORD
- SIN
1 stop24h 15m
Cathay Pacific
Wed 5/139:45 am
SIN
- ORD
1 stop41h 10m
Cathay Pacific
Deal found 4/29![Cathay Pacific logo]()
$1,056
This Air Canada deal was found by Cheapflights users on 4/27. 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 5/43:40 pm
ORD
- SIN
2 stops48h 35m
Air Canada
Mon 5/1110:50 pm
SIN
- ORD
2 stops34h 25m
Air Canada
Deal found 4/27![Air Canada logo]()
$1,011
This BusinessClass deal was found by Cheapflights users on 4/28. 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 BusinessClass is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:15 pm
ORD
- SIN
1 stop31h 10m
Cathay Pacific
Mon 5/111:45 am
SIN
- ORD
1 stop25h 10m
Cathay Pacific
Deal found 4/28![Cathay Pacific logo]()
$1,134
This Delta deal was found by Cheapflights users on 4/28. 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 5/45:53 pm
ORD
- SIN
2 stops36h 22m
Delta
Tue 5/1210:00 pm
SIN
- ORD
2 stops35h 26m
Delta
Deal found 4/28![Delta logo]()
$1,154
This United Airlines deal was found by Cheapflights users on 4/26. 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 5/64:35 pm
ORD
- SIN
1 stop25h 10m
United Airlines
Mon 6/18:35 pm
SIN
- ORD
1 stop22h 22m
United Airlines
Deal found 4/26![United Airlines logo]()
$1,140
This United Airlines deal was found by Cheapflights users on 4/26. 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 5/61:43 pm
ORD
- SIN
2 stops28h 02m
United Airlines
Wed 6/38:45 am
SIN
- ORD
1 stop22h 50m
United Airlines
Deal found 4/26![United Airlines logo]()
$1,145
This United Airlines deal was found by Cheapflights users on 4/26. 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 5/64:35 pm
ORD
- SIN
1 stop25h 10m
United Airlines
Thu 6/411:05 am
SIN
- ORD
2 stops30h 42m
United Airlines
Deal found 4/26![United Airlines logo]()
$1,150
This FlightHub deal was found by Cheapflights users on 4/26. 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 5/101:10 pm
ORD
- SIN
1 stop43h 35m
Air India
Tue 6/28:25 am
SIN
- ORD
2 stops39h 45m
Air India
Deal found 4/26![Air India logo]()
$1,133
This FlightHub deal was found by Cheapflights users on 4/26. 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 5/101:10 pm
ORD
- SIN
1 stop43h 35m
Air India
Sun 5/311:10 pm
SIN
- ORD
2 stops35h 00m
Air India
Deal found 4/26![Air India logo]()
$1,141
This Korean Air deal was found by Cheapflights users on 4/29. 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 5/139:23 am
MDW
- SIN
2 stops25h 32m
Multiple Airlines
Fri 5/151:25 am
SIN
- MDW
2 stops24h 17m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$1,508
This oojo deal was found by Cheapflights users on 4/30. 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.
Fri 5/151:10 pm
ORD
- SIN
1 stop34h 00m
Air India
Mon 5/2511:00 pm
SIN
- ORD
2 stops49h 10m
Air India
Deal found 4/30![Air India logo]()
$1,118
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 May 1, 2026.
Search for one-way flight options from Chicago to Singapore. Find affordable one-way fares based on user searches. Data last updated May 1, 2026.
This IEagle deal was found by Cheapflights users on 4/29. 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 7/271:10 pm
ORD
- SIN
1 stop29h 15m
Air India
Deal found 4/29![Air India logo]()
$478
This oojo deal was found by Cheapflights users on 4/30. 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 stop34h 05m
Cathay Pacific
Deal found 4/30![Cathay Pacific logo]()
$529
This FlightHub deal was found by Cheapflights users on 4/30. 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 7/261:10 pm
ORD
- SIN
1 stop29h 15m
Air India
Deal found 4/30![Air India logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Wed 8/54:00 pm
ORD
- SIN
1 stop24h 30m
Cathay Pacific
Deal found 4/30![Cathay Pacific logo]()
$541
This Cathay Pacific deal was found by Cheapflights users on 4/30. 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 Cathay Pacific 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 4/30![Cathay Pacific logo]()
$542
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Tue 8/189:48 pm
ORD
- SIN
2 stops42h 27m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$544
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 8/109:57 pm
ORD
- SIN
3 stops37h 58m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$577
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Tue 8/119:57 pm
ORD
- SIN
3 stops50h 18m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$587
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Wed 8/199:48 pm
ORD
- SIN
2 stops44h 52m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$590
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sat 8/83:22 pm
MDW
- SIN
2 stops48h 53m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$631
This Delta deal was found by Cheapflights users on 4/28. 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 8/195:25 pm
MDW
- SIN
2 stops36h 50m
Delta
Deal found 4/28![Delta logo]()
$638
This Delta deal was found by Cheapflights users on 4/29. 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 9/136:45 pm
MDW
- SIN
2 stops40h 10m
Delta
Deal found 4/29![Delta logo]()
$649
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 May 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $967 (FlightHub) |
One-way from | $478 (IEagle) |
Popular in | December |
Cheapest in | September |
Average price | $1,192 |
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 May 1, 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
Thu 10/22
8:10 pm-9:30 am
1 stop24h 20m
Singapore Changi
Sat 10/31
10:25 am-12:05 pm
1 stop38h 40m
$1,100
Quickest round-trip
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Wed 10/21
5:00 am-6:35 pm
2 stops24h 35m
Singapore Changi
Mon 10/26
10:20 pm-6:18 am
1 stop20h 58m
$1,145
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Wed 10/21
4:17 pm-6:15 am
1 stop24h 58m
Singapore Changi
Sun 11/1
10:20 pm-5:27 am
1 stop21h 07m
$1,190
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sun 9/13
9:40 pm-6:35 pm
2 stops31h 55m
Singapore Changi
Sat 10/3
8:35 pm-4:58 am
1 stop21h 23m
$1,195
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Thu 10/1
5:00 am-6:35 pm
2 stops24h 35m
Singapore Changi
Fri 10/9
8:35 pm-9:39 am
2 stops26h 04m
$1,195
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sun 9/6
9:40 pm-6:35 pm
2 stops31h 55m
Singapore Changi
Fri 9/18
11:05 am-12:55 am
2 stops26h 50m
$1,204
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sun 10/25
8:55 am-5:00 am
2 stops31h 05m
Singapore Changi
Fri 10/30
10:30 pm-8:24 pm
2 stops34h 54m
$1,254
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Sun 9/13
10:35 am-5:00 am
2 stops53h 25m
Singapore Changi
Wed 10/7
10:00 pm-12:33 pm
2 stops27h 33m
$1,354
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Sun 9/13
5:25 pm-7:15 pm
2 stops36h 50m
Singapore Changi
Fri 10/2
7:30 am-9:46 pm
2 stops27h 16m
$1,364
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Sun 9/27
6:45 pm-11:55 pm
2 stops40h 10m
Singapore Changi
Wed 10/7
10:00 pm-4:25 pm
2 stops31h 25m
$1,384
Showing 1-10 of 40 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.
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-SG0
ORD-SIN
MDW-SIN
How far ahead should I book a flight from Chicago to Singapore?
The best time to book flights from Chicago to Singapore is 60 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, January is the cheapest month in which you can book a flight from Chicago to Singapore (average of $492). Flying from Chicago to Singapore in July is currently the most expensive (average of $875). 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.
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 May 1, 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.
Food
8.1
Comfort
8.3
Crew
8.6
Overall
8.5
Boarding
8.4
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
TPE - SFO
Food
8.1
Comfort
8.3
Crew
8.6
Overall
8.5
Boarding
8.4
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
TPE - SFO
Food
8.1
Comfort
8.3
Crew
8.6
Overall
8.5
Boarding
8.4
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
TPE - SFO
Food
8.1
Comfort
8.3
Crew
8.6
Overall
8.5
Boarding
8.4
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
TPE - SFO
Food
8.1
Comfort
8.3
Crew
8.6
Overall
8.5
Boarding
8.4
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
TPE - SFO
Food
8.1
Comfort
8.3
Crew
8.6
Overall
8.5
Boarding
8.4
Entertainment
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
TPE - SFO
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.
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Alternative routes for Chicago to Singapore
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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 May 1, 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 May 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$698 | Average$864 | FlexibilityNo cancel fee | On-time72% | |
| Cheapest$705 | Average$1,132 | 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$983 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$860 | Average$1,426 | FlexibilityNo cancel fee | On-time80% | |
| 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$1,454 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$1,909 | Average$2,109 | FlexibilityNo cancel fee | On-time70% |