$376+ Cheap flights from Chicago (CHI) to Singapore (SIN)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Oct 3 — Oct 101
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 September 3, 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 September 3, 2026.
This lol.travel deal was found by Cheapflights users on 8/29. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:49 am -
1 stop31h 26m
Thu 9/247:00 am -
1 stop20h 43m
Deal found 8/29![Air Canada logo]()
$748
This Air Canada deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:30 pm -
1 stop26h 30m
Tue 11/108:40 am -
1 stop19h 57m
Deal found 9/2![Air Canada logo]()
$794
This Air Canada deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:40 pm -
1 stop24h 35m
Thu 10/298:40 am -
2 stops24h 12m
Deal found 8/31![Air Canada logo]()
$797
This Air Canada deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 11/127:05 am -
2 stops33h 55m
Thu 11/198:40 am -
2 stops25h 12m
Deal found 9/1![Air Canada logo]()
$800
This Air Canada deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/143:40 pm -
2 stops48h 35m
Thu 10/17:00 am -
2 stops26h 12m
Deal found 8/31![Air Canada logo]()
$801
This Air Canada deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/298:49 am -
1 stop33h 11m
Mon 11/99:00 pm -
2 stops31h 37m
Deal found 9/1![Air Canada logo]()
$806
This Expedia deal was found by Cheapflights users on 8/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:15 am -
1 stop22h 55m
Mon 12/71:35 am -
1 stop20h 55m
Deal found 8/30![Korean Air logo]()
$808
This Korean Air deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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.
Mon 11/2311:10 am -
1 stop27h 50m
Thu 12/310:30 am -
1 stop36h 00m
Deal found 9/1![Korean Air logo]()
$813
This Air Canada deal was found by Cheapflights users on 8/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/199:20 pm -
2 stops42h 55m
Sun 11/19:00 pm -
2 stops31h 37m
Deal found 8/30![Air Canada logo]()
$814
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:59 am -
2 stops24h 56m
Tue 10/67:30 am -
2 stops28h 03m
Deal found 8/31![Delta logo]()
$824
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/235:13 pm -
2 stops37h 12m
Thu 12/310:40 am -
2 stops44h 10m
Deal found 8/31![Delta logo]()
$829
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/226:44 pm -
2 stops39h 26m
Wed 12/210:40 am -
2 stops36h 15m
Deal found 8/31![Delta logo]()
$835
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 September 3, 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 September 3, 2026.
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/235:13 pm -
2 stops37h 12m
Wed 12/210:40 am -
2 stops39h 19m
Deal found 8/31![Delta logo]()
$829
This Korean Air deal was found by Cheapflights users on 8/29. 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.
Tue 1/1911:25 am -
1 stop43h 00m
Mon 1/2510:30 pm -
1 stop24h 10m
Deal found 8/29![Korean Air logo]()
$833
This Etihad Airways deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Etihad Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:25 pm -
1 stop24h 15m
Mon 9/219:00 pm -
1 stop24h 35m
Deal found 9/2![Etihad Airways logo]()
$913
This China Airlines deal was found by Cheapflights users on 8/30. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/274:45 pm -
3 stops31h 20m
Tue 11/102:25 pm -
2 stops29h 35m
Deal found 8/30![Multiple Airlines logo]()
$1,383
This Korean Air deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Mon 2/111:25 am -
1 stop22h 45m
Mon 3/110:40 am -
1 stop36h 00m
Deal found 8/31![Korean Air logo]()
$833
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 -
2 stops30h 31m
Tue 11/1010:40 am -
2 stops26h 14m
Deal found 8/31![Delta logo]()
$844
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/226:44 pm -
2 stops39h 26m
Fri 12/410:40 am -
2 stops44h 10m
Deal found 8/31![Delta logo]()
$855
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 1/196:00 am -
2 stops28h 10m
Sun 1/241:35 am -
2 stops36h 11m
Deal found 8/31![Delta logo]()
$936
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 2/17:00 am -
2 stops27h 10m
Mon 3/110:30 pm -
2 stops39h 16m
Deal found 9/1![Delta logo]()
$974
This China Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:30 pm -
2 stops32h 00m
Mon 10/52:00 am -
2 stops41h 05m
Deal found 9/2![Multiple Airlines logo]()
$1,404
This Delta deal was found by Cheapflights users on 8/30. 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 2/105:30 am -
2 stops33h 30m
Mon 3/110:30 pm -
1 stop24h 10m
Deal found 8/30![Delta logo]()
$984
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 12/15:30 am -
2 stops28h 40m
Wed 12/91:35 am -
1 stop20h 55m
Deal found 8/31![Delta logo]()
$984
This Delta deal was found by Cheapflights users on 8/29. 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.
Mon 9/1412:10 pm -
1 stop27h 50m
Tue 9/221:25 am -
2 stops35h 32m
Deal found 8/29![Delta logo]()
$989
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 2/246:00 am -
2 stops33h 00m
Mon 3/110:30 pm -
2 stops31h 55m
Deal found 9/1![Delta logo]()
$1,086
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/236:05 am -
2 stops28h 50m
Tue 9/291:25 am -
2 stops27h 50m
Deal found 9/3![Delta logo]()
$1,086
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/149:59 am -
2 stops30h 01m
Wed 9/301:25 am -
2 stops27h 50m
Deal found 8/31![Delta logo]()
$1,244
This Delta deal was found by Cheapflights users on 8/30. 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 9/169:29 am -
2 stops30h 31m
Sun 9/271:25 am -
2 stops27h 50m
Deal found 8/30![Delta logo]()
$1,244
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/209:29 am -
2 stops25h 26m
Thu 10/2910:30 pm -
2 stops30h 44m
Deal found 9/3![Delta logo]()
$1,265
Last-minute flights from Chicago to SingaporeDiscover last-minute flight deals from Chicago to Singapore. Data last updated September 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Singapore. Data last updated September 3, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 8/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:49 am -
1 stop31h 26m
Mon 9/146:15 am -
2 stops26h 57m
Deal found 8/30![Air Canada logo]()
$819
This lol.travel deal was found by Cheapflights users on 8/29. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:49 am -
1 stop31h 26m
Thu 9/247:00 am -
1 stop20h 43m
Deal found 8/29![Air Canada logo]()
$748
This Trip.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Thu 9/108:00 pm -
1 stop24h 40m
Wed 9/239:00 pm -
1 stop31h 40m
Deal found 9/3![Etihad Airways logo]()
$817
This Air Canada deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/143:40 pm -
2 stops48h 35m
Thu 10/17:00 am -
2 stops26h 12m
Deal found 8/31![Air Canada logo]()
$801
This Air Canada deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:43 am -
2 stops55h 32m
Wed 9/306:15 am -
2 stops26h 51m
Deal found 8/31![Air Canada logo]()
$816
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:59 am -
2 stops24h 56m
Tue 10/67:30 am -
2 stops28h 03m
Deal found 8/31![Delta logo]()
$824
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/309:29 am -
2 stops25h 26m
Tue 10/67:30 am -
2 stops28h 03m
Deal found 8/31![Delta logo]()
$936
This Air Canada deal was found by Cheapflights users on 8/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/199:20 pm -
2 stops42h 55m
Sun 11/19:00 pm -
2 stops31h 37m
Deal found 8/29![Air Canada logo]()
$814
This Air Canada deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:40 pm -
1 stop24h 35m
Thu 10/298:40 am -
2 stops24h 12m
Deal found 8/31![Air Canada logo]()
$797
This Air Canada deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:30 pm -
1 stop26h 30m
Tue 11/108:40 am -
1 stop19h 57m
Deal found 9/2![Air Canada logo]()
$794
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 -
2 stops30h 31m
Tue 11/1010:40 am -
2 stops26h 14m
Deal found 8/31![Delta logo]()
$844
This Air Canada deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/298:49 am -
1 stop33h 11m
Mon 11/99:00 pm -
2 stops31h 37m
Deal found 9/1![Air Canada logo]()
$806
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 September 3, 2026.
Search for one-way flight options from Chicago to Singapore. Find affordable one-way fares based on user searches. Data last updated September 3, 2026.
This Kissandfly.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:25 pm -
1 stop24h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Etihad Airways logo]()
$376
This Gotogate deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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.
Mon 10/128:25 pm -
1 stop24h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Etihad Airways logo]()
$377
This IEagle deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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.
Tue 9/222:00 pm -
1 stop30h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Etihad Airways logo]()
$383
This Trip.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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.
Thu 10/152:00 pm -
1 stop30h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Etihad Airways logo]()
$386
This Mytrip deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Tue 1/198:20 pm -
1 stop23h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Etihad Airways logo]()
$389
This oojo deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:15 pm -
1 stop31h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Etihad Airways logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/88:25 pm -
1 stop24h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Etihad Airways logo]()
$402
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/1310:12 am -
2 stops29h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 8/30. 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 10/181:27 pm -
2 stops50h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/30![Delta logo]()
$489
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/259:29 am -
2 stops30h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$514
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/1712:27 pm -
2 stops51h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Delta logo]()
$515
This Kiwi.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/136:21 am -
3 stops50h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$532
Find flight deals from Chicago to Singapore
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Singapore (SIN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $794 (Air Canada) |
One-way from | $376 (Kissandfly.com) |
Popular in | December |
Cheapest in | April |
Average price | $974 |
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 7,457,451 searches. Data last updated September 3, 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
Quickest round-trip
ChicagoSingapore
ORD Chicago O'Hare Intl - SIN Singapore Changi
ORDSIN
Chicago O'Hare Intl
Thu 10/15
8:25 pm-9:40 am
1 stop24h 15m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$392
ChicagoSingapore
MDW Chicago Midway - SIN Singapore Changi
MDWSIN
Chicago Midway
Tue 10/13
10:12 am-5:00 am
2 stops29h 48m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$478
ChicagoSingapore
MDW Chicago Midway - SIN Singapore Changi
MDWSIN
Chicago Midway
Wed 10/14
10:12 am-5:00 am
2 stops29h 48m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$478
ChicagoSingapore
ORD Chicago O'Hare Intl - SIN Singapore Changi
ORDSIN
Chicago O'Hare Intl
Tue 9/8
7:05 am-5:00 am
2 stops32h 55m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$478
ChicagoSingapore
ORD Chicago O'Hare Intl - SIN Singapore Changi
ORDSIN
Chicago O'Hare Intl
Mon 11/30
6:40 am-8:25 pm
2 stops47h 45m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$478
ChicagoSingapore
ORD Chicago O'Hare Intl - SIN Singapore Changi
ORDSIN
Chicago O'Hare Intl
Mon 10/5
8:25 pm-11:55 pm
2 stops38h 30m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$489
ChicagoSingapore
ORD Chicago O'Hare Intl - SIN Singapore Changi
ORDSIN
Chicago O'Hare Intl
Sun 10/25
5:30 pm-5:00 am
2 stops46h 30m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$489
ChicagoSingapore
MDW Chicago Midway - SIN Singapore Changi
MDWSIN
Chicago Midway
Sun 10/25
9:29 am-5:00 am
2 stops30h 31m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$514
ChicagoSingapore
MDW Chicago Midway - SIN Singapore Changi
MDWSIN
Chicago Midway
Sat 10/17
6:44 pm-5:00 am
2 stops45h 16m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$515
ChicagoSingapore
ORD Chicago O'Hare Intl - SIN Singapore Changi
ORDSIN
Chicago O'Hare Intl
Thu 10/15
8:25 pm-8:45 pm
2 stops35h 20m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$521
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Chicago to Singapore
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Singapore in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Singapore flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Singapore flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Singapore flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Singapore flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Singapore flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Singapore
Have a flexible travel schedule? Discover the best time to fly to Singapore from Chicago with our price prediction graph.
CHI-SIN
ORD-SIN
MDW-SIN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Singapore
CHI-SIN
ORD-SIN
MDW-SIN
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 $940). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,906). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Chicago to Singapore?
Airfare is below average for this route at the moment.
Chicago to Singapore flights typically cost between $899 and $1,192 in October.The cheapest round-trip price found within the last 5 days was $794 on Air Canada (Oct 27-Nov 10).
What’s the top layover airport for flights from Chicago to Singapore?
Share of 1-stop round-trip flights from Chicago to Singapore chosen by Cheapflights users in the past 12 months, using the same layover each way.
Incheon (ICN) – chosen by Cheapflights users on 25% of 1-stop itineraries from Chicago to Singapore on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Singapore?
Average round-trip fare for 1-stop flights from Chicago to Singapore, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Hong Kong (HKG) is the most affordable 1-stop option, with an average round-trip price of $882.
What’s the fastest layover option from Chicago to Singapore?
Shortest average travel time for 1-stop one-way flights from Chicago to Singapore, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Incheon (ICN) have the shortest average one-way travel time for 1-stop routes: 22h 45m.
Which airport typically offers the quickest layover for flights from Chicago to Singapore?
Average layover duration for 1-stop one-way flights from Chicago to Singapore, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Incheon (ICN) offer the fastest connection on this route, with an average layover time of 1h 50m.
How far ahead should I book a flight from Chicago to Singapore?
The best time to book flights from Chicago to Singapore is 41 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 September 3, 2026.
Get a feel of what it's like to fly with Cathay Pacific,Turkish Airlines, andUnited Airlines from Chicago to Singapore by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.7
Comfort
7.5
Overall
7.6
Food
7.3
Boarding
7.9
Crew
8.1
Reviews
1 / 20
10.0
ExcellentErnest,Jun 2026
SFO - HKG
Entertainment
7.7
Comfort
7.5
Overall
7.6
Food
7.3
Boarding
7.9
Crew
8.1
Reviews
1 / 20
10.0
ExcellentErnest,Jun 2026
SFO - HKG
Entertainment
7.7
Comfort
7.5
Overall
7.6
Food
7.3
Boarding
7.9
Crew
8.1
Reviews
1 / 20
10.0
ExcellentErnest,Jun 2026
SFO - HKG
Entertainment
7.7
Comfort
7.5
Overall
7.6
Food
7.3
Boarding
7.9
Crew
8.1
Reviews
1 / 20
10.0
ExcellentErnest,Jun 2026
SFO - HKG
Entertainment
7.7
Comfort
7.5
Overall
7.6
Food
7.3
Boarding
7.9
Crew
8.1
Reviews
1 / 20
10.0
ExcellentErnest,Jun 2026
SFO - HKG
Entertainment
7.7
Comfort
7.5
Overall
7.6
Food
7.3
Boarding
7.9
Crew
8.1
Reviews
1 / 20
10.0
ExcellentErnest,Jun 2026
SFO - HKG
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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Popular flights
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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 September 3, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Singapore
Explore flights to Singapore departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 3, 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 7,457,451 searches. Data last updated September 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$698 | Average$1,177 | FlexibilityNo cancel fee | On-time80% | |
| Cheapest$721 | Average$901 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$770 | Average$1,368 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$790 | Average$1,171 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$792 | Average$963 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$822 | Average$1,076 | FlexibilityNo cancel fee | On-time72% | |
| Cheapest$829 | Average$1,055 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$913 | Average$1,450 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$963 | Average$1,077 | FlexibilityNo cancel fee | On-time68% | |
| Cheapest$999 | Average$1,520 | FlexibilityNo cancel fee | On-timeN/A |