$378+ Cheap flights from Chicago (CHI) to Singapore
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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Oct 17 — Oct 241
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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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 17, 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 17, 2026.
This lol.travel deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/298:40 am -
2 stops33h 20m
Thu 11/128:40 am -
1 stop25h 19m
Deal found 9/16![Air Canada logo]()
$778
This Air Canada deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 9/13![Air Canada logo]()
$794
This Air Canada deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:30 pm -
1 stop26h 30m
Thu 11/58:40 am -
1 stop19h 57m
Deal found 9/14![Air Canada logo]()
$796
This Priceline deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:40 pm -
1 stop24h 35m
Thu 10/87:00 am -
2 stops26h 12m
Deal found 9/13![Air Canada logo]()
$807
This Air Canada deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:40 am -
2 stops32h 20m
Wed 11/1811:10 pm -
2 stops34h 49m
Deal found 9/16![Air Canada logo]()
$811
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/1312:49 pm -
2 stops41h 26m
Mon 10/2610:30 pm -
2 stops27h 17m
Deal found 9/15![Delta logo]()
$937
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:31 pm -
2 stops60h 44m
Mon 10/2610:30 pm -
2 stops37h 03m
Deal found 9/15![Delta logo]()
$942
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/276:04 am -
2 stops29h 11m
Mon 11/91:40 am -
2 stops28h 38m
Deal found 9/16![Delta logo]()
$1,086
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/119:29 am -
2 stops30h 31m
Mon 10/2610:30 pm -
2 stops27h 17m
Deal found 9/15![Delta logo]()
$1,116
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/105:31 pm -
2 stops46h 29m
Mon 10/2610:30 pm -
2 stops27h 17m
Deal found 9/15![Delta logo]()
$1,122
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
2 stops33h 00m
Tue 11/241:40 am -
2 stops28h 38m
Deal found 9/12![Delta logo]()
$1,123
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 9/309:59 am -
2 stops24h 56m
Tue 10/67:30 am -
2 stops28h 03m
Deal found 9/16![Delta logo]()
$1,140
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 17, 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 17, 2026.
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:29 am -
2 stops30h 31m
Tue 11/1010:30 am -
2 stops26h 24m
Deal found 9/13![Delta logo]()
$937
This Etihad Airways deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Etihad Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/13:59 pm -
2 stops27h 36m
Mon 3/17:25 pm -
1 stop26h 30m
Deal found 9/13![Multiple Airlines logo]()
$1,000
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/185:30 am -
2 stops33h 30m
Sun 2/2110:30 am -
1 stop36h 00m
Deal found 9/12![Delta logo]()
$1,076
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/197:00 am -
2 stops27h 15m
Sun 1/241:40 am -
1 stop20h 50m
Deal found 9/13![Delta logo]()
$1,076
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:49 am -
2 stops32h 11m
Mon 12/710:30 am -
1 stop36h 00m
Deal found 9/12![Delta logo]()
$1,076
This China Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1010:25 am -
3 stops36h 40m
Sun 3/212:25 pm -
2 stops34h 00m
Deal found 9/13![Multiple Airlines logo]()
$1,321
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 3/1011:10 am -
1 stop23h 05m
Sun 3/2110:30 pm -
2 stops33h 02m
Deal found 9/16![Delta logo]()
$1,082
This China Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 30m
Deal found 9/16![Multiple Airlines logo]()
$1,351
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 2/46:00 am -
2 stops33h 00m
Sun 2/141:40 am -
2 stops28h 45m
Deal found 9/15![Delta logo]()
$1,087
This China Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/610:05 am -
2 stops37h 00m
Tue 1/122:00 am -
3 stops35h 00m
Deal found 9/12![Multiple Airlines logo]()
$1,435
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:00 am -
2 stops28h 15m
Mon 12/710:30 pm -
2 stops27h 35m
Deal found 9/12![Delta logo]()
$1,087
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:04 am -
2 stops33h 56m
Tue 10/2710:30 pm -
2 stops26h 24m
Deal found 9/12![Delta logo]()
$1,087
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/212:55 pm -
2 stops39h 30m
Mon 1/251:40 am -
2 stops30h 52m
Deal found 9/12![Delta logo]()
$1,087
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/138:05 am -
2 stops31h 55m
Tue 10/207:30 am -
2 stops29h 04m
Deal found 9/15![Delta logo]()
$1,087
Last-minute flights from Chicago to SingaporeDiscover last-minute flight deals from Chicago to Singapore. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Singapore. Data last updated September 17, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 9/238:49 am -
1 stop26h 41m
Wed 9/306:15 am -
2 stops26h 51m
Deal found 9/15![Air Canada logo]()
$817
This Priceline deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:40 pm -
1 stop24h 35m
Thu 10/87:00 am -
2 stops26h 12m
Deal found 9/13![Air Canada logo]()
$807
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 9/309:59 am -
2 stops24h 56m
Tue 10/67:30 am -
2 stops28h 03m
Deal found 9/16![Delta logo]()
$1,140
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/105:31 pm -
2 stops46h 29m
Mon 10/2610:30 pm -
2 stops27h 17m
Deal found 9/15![Delta logo]()
$1,122
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/119:29 am -
2 stops30h 31m
Mon 10/2610:30 pm -
2 stops27h 17m
Deal found 9/15![Delta logo]()
$1,116
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:31 pm -
2 stops60h 44m
Mon 10/2610:30 pm -
2 stops37h 03m
Deal found 9/15![Delta logo]()
$942
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/1312:49 pm -
2 stops41h 26m
Mon 10/2610:30 pm -
2 stops27h 17m
Deal found 9/15![Delta logo]()
$937
This Air Canada deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 9/13![Air Canada logo]()
$794
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/276:04 am -
2 stops29h 11m
Mon 11/91:40 am -
2 stops28h 38m
Deal found 9/16![Delta logo]()
$1,086
This lol.travel deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/298:40 am -
2 stops33h 20m
Thu 11/128:40 am -
1 stop25h 19m
Deal found 9/16![Air Canada logo]()
$778
This Air Canada deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:30 pm -
1 stop26h 30m
Thu 11/58:40 am -
1 stop19h 57m
Deal found 9/14![Air Canada logo]()
$796
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:04 am -
2 stops29h 11m
Sat 11/1410:30 pm -
2 stops31h 48m
Deal found 9/16![Delta logo]()
$1,159
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 17, 2026.
Search for one-way flight options from Chicago to Singapore. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This IEagle deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 9/218:05 pm -
1 stop24h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Etihad Airways logo]()
$378
This deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:05 pm -
1 stop24h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Etihad Airways logo]()
$380
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/1810:45 pm -
1 stop24h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Philippine Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/2311:00 am -
2 stops32h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Etihad Airways logo]()
$438
This SmartFares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/224:15 pm -
1 stop24h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Cathay Pacific logo]()
$442
This Philippine Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Philippine Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2310:45 pm -
1 stop30h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Philippine Airlines logo]()
$445
This FlightHub deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/232:10 pm -
1 stop35h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Cathay Pacific logo]()
$448
This oojo deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:25 pm -
1 stop24h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Etihad Airways logo]()
$449
This oojo deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/191:10 pm -
1 stop30h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Etihad Airways logo]()
$451
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/242:10 pm -
1 stop31h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Cathay Pacific logo]()
$456
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/2311:27 am -
2 stops42h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/229:30 am -
2 stops53h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Delta logo]()
$489
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $778 (lol.travel) |
One-way from | $378 (IEagle) |
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 17, 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 Chicago O'Hare Intl - SIN Singapore Changi
ORDSIN
Chicago O'Hare Intl
Tue 11/24
2:10 pm-3:40 pm
1 stop35h 30m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$459
ChicagoSingapore
ORD Chicago O'Hare Intl - SIN Singapore Changi
ORDSIN
Chicago O'Hare Intl
Tue 11/24
8:29 am-5:00 am
2 stops30h 31m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$473
ChicagoSingapore
ORD Chicago O'Hare Intl - SIN Singapore Changi
ORDSIN
Chicago O'Hare Intl
Mon 11/23
6:23 am-5:00 am
2 stops32h 37m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$473
ChicagoSingapore
MDW Chicago Midway - SIN Singapore Changi
MDWSIN
Chicago Midway
Thu 11/26
4:13 pm-5:00 am
2 stops46h 47m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$478
ChicagoSingapore
MDW Chicago Midway - SIN Singapore Changi
MDWSIN
Chicago Midway
Mon 11/23
11:27 am-8:25 pm
2 stops42h 58m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$478
ChicagoSingapore
MDW Chicago Midway - SIN Singapore Changi
MDWSIN
Chicago Midway
Tue 11/24
11:27 am-8:25 pm
2 stops42h 58m
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 9/23
9:59 am-5:00 am
2 stops30h 01m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$478
Quickest round-trip
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
Wed 10/14
8:29 am-5:00 am
2 stops31h 31m
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
Wed 10/14
2:00 pm-9:40 am
1 stop30h 40m
Singapore Changi
Wed 12/31
12:00 am-10:30 am
Nonstop0h 00m
$479
Showing 1-10 of 32 resultsSorted by cheapest first
Best time to book a flight from Chicago to Singapore
Have a flexible travel schedule? Discover the best time to fly to Singapore from Chicago with our price prediction graph.
MDW-SIN
ORD-SIN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Singapore
CHI-SG0
MDW-SIN
ORD-SIN
What is the cheapest month to book a flight from Chicago to Singapore?
Currently, 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 $1,873). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How far ahead should I book a flight from Chicago to Singapore?
The best time to book flights from Chicago to Singapore is 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 17, 2026.
Read reviews from past customers who have flown Cathay Pacific,Turkish Airlines, andUnited 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.
Overall
7.6
Comfort
7.6
Crew
8.1
Food
7.3
Boarding
7.9
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentErnest,Jun 2026
SFO - HKG
Overall
7.6
Comfort
7.6
Crew
8.1
Food
7.3
Boarding
7.9
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentErnest,Jun 2026
SFO - HKG
Overall
7.6
Comfort
7.6
Crew
8.1
Food
7.3
Boarding
7.9
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentErnest,Jun 2026
SFO - HKG
Overall
7.6
Comfort
7.6
Crew
8.1
Food
7.3
Boarding
7.9
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentErnest,Jun 2026
SFO - HKG
Overall
7.6
Comfort
7.6
Crew
8.1
Food
7.3
Boarding
7.9
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentErnest,Jun 2026
SFO - HKG
Overall
7.6
Comfort
7.6
Crew
8.1
Food
7.3
Boarding
7.9
Entertainment
7.8
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.
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Alternative routes for Chicago to Singapore
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Singapore by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Singapore by cabin class
Find flights from Chicago to Singapore, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Singapore flights
Browse other Chicago and Singapore flight options. Last updated on September 17, 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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$721 | Average$901 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$770 | Average$1,368 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$792 | Average$963 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$820 | Average$1,127 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$829 | Average$1,032 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$838 | Average$1,107 | FlexibilityNo cancel fee | On-time72% | |
| Cheapest$843 | Average$1,497 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$860 | Average$1,177 | FlexibilityNo cancel fee | On-time80% | |
| Cheapest$963 | Average$1,077 | FlexibilityNo cancel fee | On-time68% | |
| Cheapest$999 | Average$1,520 | FlexibilityNo cancel fee | On-timeN/A |