$354+ 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Mar 26 — Apr 21
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 February 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 February 24, 2026.
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:20 pm
ORD
- SIN
1 stop33h 55m
United Airlines
Wed 3/410:10 am
SIN
- ORD
1 stop28h 35m
United Airlines
Deal found 2/23![United Airlines logo]()
$841
This CrystalTravel deal was found by Cheapflights users on 2/23. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:50 am
ORD
- SIN
1 stop22h 30m
ANA
Wed 10/2112:50 am
SIN
- ORD
1 stop27h 05m
ANA
Deal found 2/23![ANA logo]()
$847
This KAYAK deal was found by Cheapflights users on 2/20. 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.
Wed 4/81:10 pm
ORD
- SIN
1 stop29h 15m
Air India
Sun 4/191:10 pm
SIN
- ORD
2 stops35h 00m
Air India
Deal found 2/20![Air India logo]()
$848
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:45 pm
ORD
- SIN
1 stop42h 30m
United Airlines
Mon 9/218:35 pm
SIN
- ORD
1 stop21h 23m
United Airlines
Deal found 2/23![United Airlines logo]()
$849
This KAYAK deal was found by Cheapflights users on 2/20. 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.
Mon 4/61:10 pm
ORD
- SIN
1 stop34h 00m
Air India
Wed 4/2211:00 pm
SIN
- ORD
2 stops49h 10m
Air India
Deal found 2/20![Air India logo]()
$853
This Delta deal was found by Cheapflights users on 2/22. 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.
Sat 8/227:15 am
ORD
- SIN
2 stops32h 45m
Delta
Thu 9/177:30 am
SIN
- ORD
2 stops26h 50m
Delta
Deal found 2/22![Delta logo]()
$854
This Air India deal was found by Cheapflights users on 2/23. 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 India is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/101:10 pm
ORD
- SIN
1 stop34h 00m
Air India
Fri 4/1711:00 pm
SIN
- ORD
1 stop49h 10m
Air India
Deal found 2/23![Air India logo]()
$856
This Gurufare deal was found by Cheapflights users on 2/23. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:45 pm
ORD
- SIN
1 stop37h 50m
Multiple Airlines
Wed 6/38:35 pm
SIN
- ORD
1 stop23h 41m
Multiple Airlines
Deal found 2/23![Multiple Airlines logo]()
$859
This KAYAK deal was found by Cheapflights users on 2/20. 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 4/31:10 pm
ORD
- SIN
1 stop31h 05m
Air India
Sun 4/191:10 pm
SIN
- ORD
2 stops35h 00m
Air India
Deal found 2/20![Air India logo]()
$860
This oojo deal was found by Cheapflights users on 2/22. 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 10/71:10 pm
ORD
- SIN
1 stop29h 15m
Air India
Mon 10/1211:00 pm
SIN
- ORD
2 stops49h 10m
Air India
Deal found 2/22![Air India logo]()
$862
This FlightHub deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/162:30 pm
ORD
- SIN
1 stop27h 30m
Air India
Thu 3/268:00 pm
SIN
- ORD
2 stops29h 30m
Air India
Deal found 2/21![Air India logo]()
$865
This Delta deal was found by Cheapflights users on 2/24. 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 10/286:00 am
MDW
- SIN
2 stops29h 10m
Delta
Sun 11/1510:30 pm
SIN
- MDW
2 stops31h 55m
Delta
Deal found 2/24![Delta logo]()
$954
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 February 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 February 24, 2026.
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:10 pm
ORD
- SIN
2 stops34h 05m
United Airlines
Wed 3/410:10 am
SIN
- ORD
2 stops27h 49m
United Airlines
Deal found 2/23![United Airlines logo]()
$845
This China Airlines deal was found by Cheapflights users on 2/20. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/65:40 pm
MDW
- SIN
2 stops29h 55m
Multiple Airlines
Mon 4/201:45 pm
SIN
- MDW
2 stops29h 10m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$1,230
This Delta deal was found by Cheapflights users on 2/24. 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 3/156:00 am
MDW
- SIN
2 stops34h 00m
Delta
Thu 3/2610:30 pm
SIN
- MDW
2 stops37h 01m
Delta
Deal found 2/24![Delta logo]()
$1,304
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/92:35 pm
ORD
- SIN
2 stops27h 25m
United Airlines
Thu 3/1210:10 am
SIN
- ORD
1 stop23h 05m
United Airlines
Deal found 2/23![United Airlines logo]()
$870
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:17 am
ORD
- SIN
1 stop24h 58m
United Airlines
Mon 3/1610:10 am
SIN
- ORD
2 stops27h 48m
United Airlines
Deal found 2/22![United Airlines logo]()
$870
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/39:25 pm
ORD
- SIN
1 stop32h 10m
United Airlines
Sat 4/188:35 pm
SIN
- ORD
1 stop21h 52m
United Airlines
Deal found 2/20![United Airlines logo]()
$891
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:20 pm
ORD
- SIN
1 stop33h 55m
United Airlines
Sun 3/810:20 pm
SIN
- ORD
2 stops27h 28m
United Airlines
Deal found 2/21![United Airlines logo]()
$895
This China Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/810:00 am
MDW
- SIN
2 stops37h 35m
Multiple Airlines
Wed 4/151:45 pm
SIN
- MDW
2 stops34h 40m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$1,242
This Delta deal was found by Cheapflights users on 2/24. 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 3/166:00 am
MDW
- SIN
2 stops34h 00m
Delta
Thu 3/2610:30 pm
SIN
- MDW
2 stops37h 01m
Delta
Deal found 2/24![Delta logo]()
$1,304
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/149:15 pm
ORD
- SIN
1 stop44h 45m
United Airlines
Sun 3/2210:20 pm
SIN
- ORD
1 stop27h 46m
United Airlines
Deal found 2/23![United Airlines logo]()
$899
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:25 am
ORD
- SIN
1 stop23h 10m
United Airlines
Fri 4/179:00 am
SIN
- ORD
1 stop27h 29m
United Airlines
Deal found 2/20![United Airlines logo]()
$916
This Delta deal was found by Cheapflights users on 2/23. 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 3/246:00 am
MDW
- SIN
2 stops34h 00m
Delta
Mon 3/301:25 am
SIN
- MDW
2 stops34h 06m
Delta
Deal found 2/23![Delta logo]()
$1,354
This China Airlines deal was found by Cheapflights users on 2/23. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:50 am
MDW
- SIN
2 stops35h 15m
Multiple Airlines
Fri 3/132:25 pm
SIN
- MDW
2 stops33h 35m
Multiple Airlines
Deal found 2/23![Multiple Airlines logo]()
$1,454
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/69:15 pm
ORD
- SIN
1 stop33h 00m
United Airlines
Wed 3/1110:10 am
SIN
- ORD
2 stops25h 45m
United Airlines
Deal found 2/23![United Airlines logo]()
$920
This Delta deal was found by Cheapflights users on 2/23. 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 3/266:00 am
MDW
- SIN
2 stops34h 00m
Delta
Wed 4/11:25 am
SIN
- MDW
2 stops34h 06m
Delta
Deal found 2/23![Delta logo]()
$1,393
This China Airlines deal was found by Cheapflights users on 2/20. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1611:50 am
MDW
- SIN
2 stops36h 15m
Multiple Airlines
Tue 3/242:25 pm
SIN
- MDW
2 stops34h 15m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$1,460
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:20 pm
ORD
- SIN
1 stop33h 55m
United Airlines
Sat 3/710:10 am
SIN
- ORD
1 stop28h 49m
United Airlines
Deal found 2/21![United Airlines logo]()
$966
This Delta deal was found by Cheapflights users on 2/21. 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.
Sat 3/216:00 am
MDW
- SIN
2 stops34h 00m
Delta
Fri 3/2710:40 am
SIN
- MDW
2 stops36h 16m
Delta
Deal found 2/21![Delta logo]()
$1,460
This Delta deal was found by Cheapflights users on 2/21. 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 3/186:00 am
MDW
- SIN
2 stops34h 00m
Delta
Sat 3/2810:30 pm
SIN
- MDW
2 stops31h 52m
Delta
Deal found 2/21![Delta logo]()
$1,504
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/145:45 pm
ORD
- SIN
2 stops37h 30m
United Airlines
Sun 3/298:35 pm
SIN
- ORD
2 stops37h 00m
United Airlines
Deal found 2/21![United Airlines logo]()
$1,045
This China Airlines deal was found by Cheapflights users on 2/23. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/244:35 pm
MDW
- SIN
3 stops31h 00m
Multiple Airlines
Wed 4/291:45 pm
SIN
- MDW
2 stops28h 55m
Multiple Airlines
Deal found 2/23![Multiple Airlines logo]()
$1,689
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:00 am
MDW
- SIN
2 stops34h 00m
Delta
Fri 3/2710:40 am
SIN
- MDW
2 stops36h 16m
Delta
Deal found 2/20![Delta logo]()
$1,510
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1210:50 am
ORD
- SIN
2 stops31h 10m
United Airlines
Mon 3/1610:10 am
SIN
- ORD
2 stops25h 50m
United Airlines
Deal found 2/22![United Airlines logo]()
$1,084
Last-minute flights from Chicago to SingaporeDiscover last-minute flight deals from Chicago to Singapore. Data last updated February 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Singapore. Data last updated February 24, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:20 pm
ORD
- SIN
1 stop33h 55m
United Airlines
Sun 3/810:20 pm
SIN
- ORD
1 stop20h 59m
United Airlines
Deal found 2/21![United Airlines logo]()
$891
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:20 pm
ORD
- SIN
1 stop33h 55m
United Airlines
Wed 3/410:10 am
SIN
- ORD
1 stop28h 35m
United Airlines
Deal found 2/23![United Airlines logo]()
$841
This ScholarTrip deal was found by Cheapflights users on 2/23. 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 ScholarTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/62:35 pm
ORD
- SIN
1 stop32h 30m
Cathay Pacific
Wed 3/116:00 pm
SIN
- ORD
1 stop32h 55m
Cathay Pacific
Deal found 2/23![Cathay Pacific logo]()
$872
This FlightHub deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/119:20 pm
ORD
- SIN
1 stop23h 40m
Turkish Airlines
Mon 3/1611:25 pm
SIN
- ORD
1 stop24h 40m
Turkish Airlines
Deal found 2/22![Turkish Airlines logo]()
$853
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/149:15 pm
ORD
- SIN
1 stop44h 45m
United Airlines
Sun 3/2210:20 pm
SIN
- ORD
1 stop27h 46m
United Airlines
Deal found 2/23![United Airlines logo]()
$899
This Delta deal was found by Cheapflights users on 2/24. 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 3/156:00 am
MDW
- SIN
2 stops34h 00m
Delta
Thu 3/2610:30 pm
SIN
- MDW
2 stops37h 01m
Delta
Deal found 2/24![Delta logo]()
$1,304
This FlightHub deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/162:30 pm
ORD
- SIN
1 stop27h 30m
Air India
Thu 3/268:00 pm
SIN
- ORD
2 stops29h 30m
Air India
Deal found 2/21![Air India logo]()
$865
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/164:00 pm
ORD
- SIN
2 stops26h 00m
United Airlines
Thu 3/2610:20 pm
SIN
- ORD
1 stop20h 59m
United Airlines
Deal found 2/22![United Airlines logo]()
$870
This Delta deal was found by Cheapflights users on 2/23. 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.
Mon 3/236:00 am
MDW
- SIN
2 stops34h 00m
Delta
Mon 3/3010:00 pm
SIN
- MDW
2 stops27h 02m
Delta
Deal found 2/23![Delta logo]()
$1,254
This FlightHub deal was found by Cheapflights users on 2/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/249:20 pm
ORD
- SIN
1 stop22h 15m
Turkish Airlines
Tue 3/3110:25 am
SIN
- ORD
1 stop36h 15m
Turkish Airlines
Deal found 2/23![Turkish Airlines logo]()
$848
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:17 am
ORD
- SIN
1 stop24h 58m
United Airlines
Wed 4/18:35 pm
SIN
- ORD
1 stop22h 45m
United Airlines
Deal found 2/23![United Airlines logo]()
$866
This IEagle deal was found by Cheapflights users on 2/20. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/272:30 pm
ORD
- SIN
1 stop32h 40m
Air India
Sun 4/121:10 pm
SIN
- ORD
2 stops35h 00m
Air India
Deal found 2/20![Air India logo]()
$878
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 February 24, 2026.
Search for one-way flight options from Chicago to Singapore. Find affordable one-way fares based on user searches. Data last updated February 24, 2026.
This Orbitz deal was found by Cheapflights users on 2/24. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:00 am
ORD
- SIN
2 stops37h 35m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$354
This oojo deal was found by Cheapflights users on 2/24. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/271:10 pm
ORD
- SIN
1 stop34h 00m
Air India
Deal found 2/24![Air India logo]()
$361
This FlightHub deal was found by Cheapflights users on 2/20. 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 3/21:30 pm
ORD
- SIN
1 stop27h 30m
Air India
Deal found 2/20![Air India logo]()
$366
This FlightHub deal was found by Cheapflights users on 2/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/92:30 pm
ORD
- SIN
1 stop42h 15m
Air India
Deal found 2/24![Air India logo]()
$368
This FlightHub deal was found by Cheapflights users on 2/20. 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.
Sun 3/11:30 pm
ORD
- SIN
1 stop42h 15m
Air India
Deal found 2/20![Air India logo]()
$371
This oojo deal was found by Cheapflights users on 2/21. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/241:10 pm
ORD
- SIN
1 stop43h 35m
Air India
Deal found 2/21![Air India logo]()
$374
This CrystalTravel deal was found by Cheapflights users on 2/20. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:00 pm
ORD
- SIN
1 stop30h 40m
Etihad Airways
Deal found 2/20![Etihad Airways logo]()
$398
This Gurufare deal was found by Cheapflights users on 2/22. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/32:00 pm
ORD
- SIN
1 stop30h 40m
Etihad Airways
Deal found 2/22![Etihad Airways logo]()
$401
This EaseMyTrip deal was found by Cheapflights users on 2/23. 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 EaseMyTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/101:10 pm
ORD
- SIN
1 stop31h 05m
Air India
Deal found 2/23![Air India logo]()
$404
This Trip.com deal was found by Cheapflights users on 2/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:20 am
MDW
- SIN
2 stops28h 35m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 2/20. 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.
Mon 3/26:20 pm
MDW
- SIN
2 stops39h 50m
Delta
Deal found 2/20![Delta logo]()
$474
This Delta deal was found by Cheapflights users on 2/22. 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 7/299:30 am
MDW
- SIN
2 stops30h 30m
Delta
Deal found 2/22![Delta logo]()
$537
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 February 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $841 (United Airlines) |
One-way from | $354 (Orbitz) |
Popular in | December |
Cheapest in | September |
Average price | $881 |
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 February 24, 2026.
Use the filters below to find and compare flights from Chicago to Singapore that are best for you.
Fly from
Chicago
Fly to
Singapore
Route
Depart
Return
Price
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sat 2/28
8:10 pm-8:15 pm
2 stops34h 05m
Singapore Changi
Wed 3/4
10:10 am-11:59 pm
2 stops27h 49m
$845
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Mon 3/9
2:35 pm-7:00 am
2 stops27h 25m
Singapore Changi
Thu 3/12
10:10 am-8:15 pm
1 stop23h 05m
$870
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Wed 3/11
6:17 am-8:15 pm
1 stop24h 58m
Singapore Changi
Mon 3/16
10:10 am-12:58 am
2 stops27h 48m
$870
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Fri 4/3
9:25 pm-6:35 pm
1 stop32h 10m
Singapore Changi
Sat 4/18
8:35 pm-5:27 am
1 stop21h 52m
$891
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Fri 2/27
8:20 pm-8:15 pm
1 stop33h 55m
Singapore Changi
Sun 3/8
10:20 pm-12:48 pm
2 stops27h 28m
$895
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sat 3/14
9:15 pm-7:00 am
1 stop44h 45m
Singapore Changi
Sun 3/22
10:20 pm-1:06 pm
1 stop27h 46m
$899
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Tue 4/7
6:25 am-6:35 pm
1 stop23h 10m
Singapore Changi
Fri 4/17
9:00 am-11:29 pm
1 stop27h 29m
$916
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Fri 3/6
9:15 pm-8:15 pm
1 stop33h 00m
Singapore Changi
Wed 3/11
10:10 am-10:55 pm
2 stops25h 45m
$920
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sat 2/28
8:20 pm-8:15 pm
1 stop33h 55m
Singapore Changi
Sat 3/7
10:10 am-12:59 am
1 stop28h 49m
$966
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sat 3/14
5:45 pm-8:15 pm
2 stops37h 30m
Singapore Changi
Sun 3/29
8:35 pm-8:35 pm
2 stops37h 00m
$1,045
Showing 1-10 of 39 results
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
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 $662). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,314). 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 February 24, 2026.
Read reviews from past customers who have flown EVA Air, Cathay Pacific, and United 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
Food
8.1
Entertainment
8.0
Boarding
8.4
Crew
8.6
Overall
8.4
Reviews
1 / 20
8.0
ExcellentJolene,Jan 2026
SGN - TPE
Comfort
8.3
Food
8.1
Entertainment
8.0
Boarding
8.4
Crew
8.6
Overall
8.4
Reviews
1 / 20
8.0
ExcellentJolene,Jan 2026
SGN - TPE
Comfort
8.3
Food
8.1
Entertainment
8.0
Boarding
8.4
Crew
8.6
Overall
8.4
Reviews
1 / 20
8.0
ExcellentJolene,Jan 2026
SGN - TPE
Comfort
8.3
Food
8.1
Entertainment
8.0
Boarding
8.4
Crew
8.6
Overall
8.4
Reviews
1 / 20
8.0
ExcellentJolene,Jan 2026
SGN - TPE
Comfort
8.3
Food
8.1
Entertainment
8.0
Boarding
8.4
Crew
8.6
Overall
8.4
Reviews
1 / 20
8.0
ExcellentJolene,Jan 2026
SGN - TPE
Comfort
8.3
Food
8.1
Entertainment
8.0
Boarding
8.4
Crew
8.6
Overall
8.4
Reviews
1 / 20
8.0
ExcellentJolene,Jan 2026
SGN - 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.
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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
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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 February 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Singapore flights
Consider these flights traveling from Chicago to Singapore.
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 February 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$675 | Average$925 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$698 | Average$1,426 | FlexibilityNo cancel fee | On-time80% | |
| Cheapest$698 | Average$882 | FlexibilityNo cancel fee | On-time72% | |
| Cheapest$705 | Average$1,180 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$799 | Average$1,103 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$829 | Average$983 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$858 | Average$1,153 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$872 | Average$1,340 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$981 | Average$1,081 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$1,086 | Average$1,389 | FlexibilityNo cancel fee | On-time74% |