$506+ Cheap flights from Singapore to Chicago (CHI)
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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
Apr 5 — Apr 121
Round-trip
1 adult, Economy
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Find cheap flights from Singapore to Chicago 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 Singapore to Chicago
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Cheapest flights from Singapore to ChicagoExplore the most affordable flight options available from Singapore to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 6, 2026.
Explore the most affordable flight options available from Singapore to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 6, 2026.
This FlightHub deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 10/2111:05 am
SIN
- ORD
1 stop34h 35m
ANA
Sun 11/84:25 pm
ORD
- SIN
1 stop24h 30m
ANA
Deal found 3/4![ANA logo]()
$828
This ANA deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ANA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:05 am
SIN
- ORD
2 stops25h 15m
Multiple Airlines
Sun 11/84:25 pm
ORD
- SIN
1 stop24h 30m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$861
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:00 am
SIN
- ORD
1 stop35h 07m
United Airlines
Mon 4/66:25 am
ORD
- SIN
1 stop23h 10m
United Airlines
Deal found 3/3![United Airlines logo]()
$945
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:35 pm
SIN
- ORD
1 stop23h 41m
United Airlines
Wed 7/156:10 am
ORD
- SIN
1 stop23h 25m
United Airlines
Deal found 3/4![United Airlines logo]()
$946
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1910:10 am
SIN
- ORD
1 stop21h 42m
United Airlines
Wed 4/13:45 pm
ORD
- SIN
1 stop26h 00m
United Airlines
Deal found 3/3![United Airlines logo]()
$948
This United Airlines deal was found by Cheapflights users on 3/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:20 pm
SIN
- ORD
1 stop20h 57m
United Airlines
Fri 5/16:20 am
ORD
- SIN
1 stop23h 15m
United Airlines
Deal found 3/2![United Airlines logo]()
$949
This United Airlines deal was found by Cheapflights users on 3/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1010:10 am
SIN
- ORD
1 stop24h 27m
United Airlines
Wed 4/12:15 pm
ORD
- SIN
1 stop27h 30m
United Airlines
Deal found 3/2![United Airlines logo]()
$954
This United Airlines deal was found by Cheapflights users on 3/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:00 am
SIN
- ORD
1 stop27h 29m
United Airlines
Thu 4/239:40 pm
ORD
- SIN
1 stop31h 55m
United Airlines
Deal found 3/1![United Airlines logo]()
$955
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/19:00 am
SIN
- ORD
1 stop24h 18m
United Airlines
Wed 4/154:40 pm
ORD
- SIN
1 stop25h 05m
United Airlines
Deal found 3/4![United Airlines logo]()
$958
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 10/2110:00 pm
SIN
- MDW
2 stops27h 33m
Delta
Sun 11/85:59 pm
MDW
- SIN
2 stops40h 11m
Delta
Deal found 3/4![Delta logo]()
$959
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/147:30 am
SIN
- ORD
2 stops26h 48m
Delta
Tue 4/217:09 pm
ORD
- SIN
2 stops39h 46m
Delta
Deal found 3/4![Delta logo]()
$959
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/227:30 am
SIN
- ORD
2 stops29h 28m
Delta
Sun 4/267:15 am
ORD
- SIN
2 stops27h 40m
Delta
Deal found 3/5![Delta logo]()
$960
Best flights from Singapore to ChicagoDiscover carefully curated flight deals from Singapore to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 6, 2026.
Discover carefully curated flight deals from Singapore to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 6, 2026.
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:00 am
SIN
- ORD
1 stop35h 07m
United Airlines
Mon 4/66:25 am
ORD
- SIN
1 stop23h 10m
United Airlines
Deal found 3/3![United Airlines logo]()
$945
This Delta deal was found by Cheapflights users on 3/1. 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.
Tue 4/141:25 am
SIN
- ORD
2 stops32h 53m
Delta
Wed 4/225:15 am
ORD
- SIN
2 stops29h 40m
Delta
Deal found 3/1![Delta logo]()
$969
This China Airlines deal was found by Cheapflights users on 3/3. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/171:45 pm
SIN
- MDW
2 stops28h 55m
Multiple Airlines
Fri 4/2411:00 am
MDW
- SIN
2 stops36h 35m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$1,082
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 6/258:35 pm
SIN
- ORD
1 stop23h 41m
United Airlines
Wed 7/156:10 am
ORD
- SIN
1 stop23h 25m
United Airlines
Deal found 3/4![United Airlines logo]()
$946
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1910:10 am
SIN
- ORD
1 stop21h 42m
United Airlines
Wed 4/13:45 pm
ORD
- SIN
1 stop26h 00m
United Airlines
Deal found 3/3![United Airlines logo]()
$948
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/2210:00 pm
SIN
- MDW
2 stops31h 26m
Delta
Sun 4/269:27 am
MDW
- SIN
2 stops25h 28m
Delta
Deal found 3/5![Delta logo]()
$1,069
This China Airlines deal was found by Cheapflights users on 3/1. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:45 pm
SIN
- MDW
2 stops28h 55m
Multiple Airlines
Thu 4/236:10 pm
MDW
- SIN
2 stops29h 25m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$1,131
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:45 am
SIN
- ORD
1 stop22h 50m
United Airlines
Sat 7/49:33 pm
ORD
- SIN
1 stop43h 42m
United Airlines
Deal found 3/3![United Airlines logo]()
$949
This Delta deal was found by Cheapflights users on 3/1. 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 4/1510:00 pm
SIN
- MDW
2 stops27h 07m
Delta
Wed 4/229:29 am
MDW
- SIN
2 stops25h 26m
Delta
Deal found 3/1![Delta logo]()
$1,079
This China Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/151:45 pm
SIN
- MDW
2 stops28h 55m
Multiple Airlines
Thu 4/306:10 pm
MDW
- SIN
2 stops29h 25m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$1,131
This United Airlines deal was found by Cheapflights users on 3/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:35 pm
SIN
- ORD
1 stop21h 50m
United Airlines
Fri 5/86:20 pm
ORD
- SIN
1 stop35h 15m
United Airlines
Deal found 3/2![United Airlines logo]()
$949
This United Airlines deal was found by Cheapflights users on 3/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:00 am
SIN
- ORD
1 stop27h 29m
United Airlines
Thu 4/239:40 pm
ORD
- SIN
1 stop31h 55m
United Airlines
Deal found 3/1![United Airlines logo]()
$955
This EVA Air deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure EVA Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/63:20 pm
SIN
- MDW
2 stops26h 40m
Multiple Airlines
Sat 6/139:00 pm
MDW
- SIN
2 stops25h 55m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$1,197
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/1410:00 pm
SIN
- MDW
2 stops31h 29m
Delta
Tue 4/216:00 am
MDW
- SIN
2 stops28h 55m
Delta
Deal found 3/4![Delta logo]()
$1,222
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/1910:00 pm
SIN
- MDW
2 stops32h 58m
Delta
Sun 4/265:21 pm
MDW
- SIN
2 stops36h 54m
Delta
Deal found 3/4![Delta logo]()
$1,327
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:35 pm
SIN
- ORD
1 stop27h 56m
United Airlines
Sun 7/129:33 pm
ORD
- SIN
1 stop43h 42m
United Airlines
Deal found 3/4![United Airlines logo]()
$1,178
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 6/258:45 am
SIN
- ORD
1 stop25h 50m
United Airlines
Mon 7/131:00 pm
ORD
- SIN
2 stops28h 15m
United Airlines
Deal found 3/4![United Airlines logo]()
$1,178
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:45 am
SIN
- ORD
1 stop22h 50m
United Airlines
Thu 7/25:00 am
ORD
- SIN
2 stops24h 35m
United Airlines
Deal found 3/3![United Airlines logo]()
$1,182
Last-minute flights from Singapore to ChicagoDiscover last-minute flight deals from Singapore to Chicago. Data last updated March 6, 2026 and is based on user searches.
Discover last-minute flight deals from Singapore to Chicago. Data last updated March 6, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 3/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:20 pm
SIN
- ORD
1 stop20h 57m
United Airlines
Sun 4/2610:45 pm
ORD
- SIN
1 stop30h 50m
United Airlines
Deal found 3/2![United Airlines logo]()
$949
This United Airlines deal was found by Cheapflights users on 3/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1010:10 am
SIN
- ORD
1 stop24h 27m
United Airlines
Wed 4/12:15 pm
ORD
- SIN
1 stop27h 30m
United Airlines
Deal found 3/2![United Airlines logo]()
$954
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1910:10 am
SIN
- ORD
1 stop21h 42m
United Airlines
Wed 4/13:45 pm
ORD
- SIN
1 stop26h 00m
United Airlines
Deal found 3/3![United Airlines logo]()
$948
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/19:00 am
SIN
- ORD
1 stop24h 18m
United Airlines
Wed 4/154:40 pm
ORD
- SIN
1 stop25h 05m
United Airlines
Deal found 3/4![United Airlines logo]()
$958
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:00 am
SIN
- ORD
1 stop35h 07m
United Airlines
Mon 4/66:25 am
ORD
- SIN
1 stop23h 10m
United Airlines
Deal found 3/3![United Airlines logo]()
$945
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/147:30 am
SIN
- ORD
2 stops26h 48m
Delta
Tue 4/217:09 pm
ORD
- SIN
2 stops39h 46m
Delta
Deal found 3/4![Delta logo]()
$959
This CheapTickets deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/141:45 pm
SIN
- ORD
2 stops29h 05m
Multiple Airlines
Tue 4/212:00 pm
ORD
- SIN
1 stop30h 40m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$974
This Delta deal was found by Cheapflights users on 3/3. 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 4/157:30 am
SIN
- ORD
2 stops26h 48m
Delta
Wed 4/227:15 am
ORD
- SIN
2 stops27h 40m
Delta
Deal found 3/3![Delta logo]()
$963
This Delta deal was found by Cheapflights users on 3/1. 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 4/1510:00 pm
SIN
- MDW
2 stops27h 07m
Delta
Wed 4/229:29 am
MDW
- SIN
2 stops25h 26m
Delta
Deal found 3/1![Delta logo]()
$1,079
This United Airlines deal was found by Cheapflights users on 3/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:00 am
SIN
- ORD
1 stop27h 29m
United Airlines
Thu 4/239:40 pm
ORD
- SIN
1 stop31h 55m
United Airlines
Deal found 3/1![United Airlines logo]()
$955
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/227:30 am
SIN
- ORD
2 stops29h 28m
Delta
Sun 4/267:15 am
ORD
- SIN
2 stops27h 40m
Delta
Deal found 3/5![Delta logo]()
$960
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/2210:00 pm
SIN
- MDW
2 stops31h 26m
Delta
Sun 4/269:27 am
MDW
- SIN
2 stops25h 28m
Delta
Deal found 3/5![Delta logo]()
$1,069
One-way flights from Singapore to ChicagoSearch for one-way flight options from Singapore to Chicago. Find affordable one-way fares based on user searches. Data last updated March 6, 2026.
Search for one-way flight options from Singapore to Chicago. Find affordable one-way fares based on user searches. Data last updated March 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:45 pm
SIN
- ORD
1 stop21h 50m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$506
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 4/147:55 am
SIN
- ORD
3 stops34h 55m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$516
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 5/510:20 am
SIN
- ORD
3 stops50h 07m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$533
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:05 am
SIN
- ORD
3 stops55h 22m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$538
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/49:20 pm
SIN
- ORD
3 stops45h 30m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$545
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/168:50 pm
SIN
- ORD
3 stops44h 59m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$551
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/2010:00 pm
SIN
- MDW
2 stops27h 43m
Delta
Deal found 3/6![Delta logo]()
$591
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:40 am
SIN
- MDW
3 stops53h 39m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$592
This Delta deal was found by Cheapflights users on 3/2. 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 4/187:30 am
SIN
- MDW
2 stops27h 58m
Delta
Deal found 3/2![Delta logo]()
$598
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:40 am
SIN
- MDW
3 stops53h 34m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$599
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/131:10 am
SIN
- MDW
3 stops55h 21m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$605
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1911:05 pm
SIN
- MDW
3 stops57h 26m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$613
Find flight deals from Singapore to Chicago
Keep the following information in mind while searching for Singapore to Chicago flight deals. Data was last updated March 6, 2026.
Round-trip from | $945 (United Airlines) |
|---|---|
One-way from | $506 (Kiwi.com) |
Popular in | January |
Cheapest in | February |
Average price | $1,076 |
Cheapflights Fare Finder
Customize your flight search to find flights from Singapore to Chicago 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 March 6, 2026.
Use the filters below to find and compare flights from Singapore to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Thu 4/2
9:00 am-7:07 am
1 stop35h 07m
Chicago O'Hare Intl
Mon 4/6
6:25 am-6:35 pm
1 stop23h 10m
$945
Quickest round-trip
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Thu 6/25
8:35 pm-7:16 am
1 stop23h 41m
Chicago O'Hare Intl
Wed 7/15
6:10 am-6:35 pm
1 stop23h 25m
$946
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Thu 3/19
10:10 am-6:52 pm
1 stop21h 42m
Chicago O'Hare Intl
Wed 4/1
3:45 pm-6:45 am
1 stop26h 00m
$948
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Wed 6/17
8:45 am-6:35 pm
1 stop22h 50m
Chicago O'Hare Intl
Sat 7/4
9:33 pm-6:15 am
1 stop43h 42m
$949
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Sat 5/2
8:35 pm-5:25 am
1 stop21h 50m
Chicago O'Hare Intl
Fri 5/8
6:20 pm-6:35 pm
1 stop35h 15m
$949
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Thu 4/16
9:00 am-11:29 pm
1 stop27h 29m
Chicago O'Hare Intl
Thu 4/23
9:40 pm-6:35 pm
1 stop31h 55m
$955
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Tue 4/14
1:25 am-9:18 pm
2 stops32h 53m
Chicago O'Hare Intl
Wed 4/22
5:15 am-11:55 pm
2 stops29h 40m
$969
SingaporeChicago
SIN - MDW
SINMDW
Singapore Changi
Wed 4/22
10:00 pm-4:26 pm
2 stops31h 26m
Chicago Midway
Sun 4/26
9:27 am-11:55 pm
2 stops25h 28m
$1,069
SingaporeChicago
SIN - MDW
SINMDW
Singapore Changi
Wed 4/15
10:00 pm-12:07 pm
2 stops27h 07m
Chicago Midway
Wed 4/22
9:29 am-11:55 pm
2 stops25h 26m
$1,079
SingaporeChicago
SIN - MDW
SINMDW
Singapore Changi
Fri 4/17
1:45 pm-5:40 am
2 stops28h 55m
Chicago Midway
Fri 4/24
11:00 am-12:35 pm
2 stops36h 35m
$1,082
Showing 1-10 of 38 resultsSorted by cheapest first
Best time to book a flight from Singapore to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Singapore with our price prediction graph.
SIN-ORD
SIN-MDW
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 Singapore to Chicago
SG0-CHI
SIN-ORD
SIN-MDW
What is the cheapest month to book a flight from Singapore to Chicago?
Currently, June is the cheapest month in which you can book a flight from Singapore to Chicago (average of $695). Flying from Singapore to Chicago in January is currently the most expensive (average of $1,200). 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 Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated March 6, 2026.
Read through reviews of airlines operating flights from Singapore to Chicago, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Food
6.6
Entertainment
7.1
Comfort
7.3
Overall
7.4
Crew
8.1
Reviews
1 / 20
6.0
GoodGerry,Jan 2026
YVR - DEN
Boarding
7.7
Food
6.6
Entertainment
7.1
Comfort
7.3
Overall
7.4
Crew
8.1
Reviews
1 / 20
6.0
GoodGerry,Jan 2026
YVR - DEN
Related info for your journey
Find useful and relevant information for your journey from Singapore to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Singapore to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on March 6, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Singapore to Chicago by cabin class
Find flights from Singapore to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Singapore and Chicago flights
Browse other Singapore and Chicago flight options. Last updated on March 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Singapore to Chicago
Discover the top airline that operate flights from Singapore to Chicago. 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 March 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$802 | Average$1,040 | FlexibilityNo cancel fee | On-time69% |