Singapore

$448+ Cheap flights from Chicago (CHI) to Singapore

CHI — SIN
Dec 13 — Dec 201
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Cheap flight deals from Chicago to Singapore

Cheapest flights from Chicago to Singapore

Sun 11/2911:45 am -
1 stop31h 00m
Tue 12/1511:15 pm -
1 stop24h 45m
Deal found 11/10$900
Mon 11/308:15 pm -
1 stop23h 45m
Mon 12/711:15 pm -
1 stop24h 45m
Deal found 11/11$945
Wed 12/28:15 pm -
1 stop23h 45m
Tue 12/811:15 pm -
1 stop33h 05m
Deal found 11/11$953
Wed 12/211:45 am -
1 stop39h 55m
Wed 12/911:40 am -
1 stop44h 40m
Deal found 11/8$963
Mon 12/711:45 am -
1 stop39h 55m
Fri 12/1111:40 am -
1 stop36h 20m
Deal found 11/10$969
Mon 12/711:45 am -
1 stop39h 55m
Tue 12/1510:25 am -
1 stop37h 35m
Deal found 11/10$979
Sat 11/219:35 am -
2 stops55h 25m
Thu 11/268:40 am -
2 stops42h 49m
Deal found 11/11$1,004
Mon 12/711:45 am -
1 stop32h 15m
Mon 12/1411:40 am -
1 stop36h 20m
Deal found 11/12$1,005
Wed 12/26:00 am -
2 stops28h 15m
Mon 12/71:40 am -
2 stops35h 14m
Deal found 11/11$1,222
Wed 12/26:00 am -
2 stops33h 00m
Wed 12/910:30 am -
2 stops26h 24m
Deal found 11/8$1,358
Sun 12/66:41 pm -
2 stops44h 19m
Sun 12/1310:30 am -
2 stops26h 24m
Deal found 11/8$1,361
Tue 12/16:00 am -
2 stops33h 00m
Tue 12/810:30 pm -
2 stops33h 31m
Deal found 11/10$1,408

Find flight deals from Chicago to Singapore

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$897
(IEagle)

One-way from

$448
(FlightHub)

Popular in

December

Cheapest in

April

Average price

$976
Provider with most accurate pricing for Chicago (CHI)-Singapore Changi flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Singapore Changi flights.
From Chicago (CHI) to Singapore
One-way flight from Chicago (CHI) to Singapore
Highest demand for flights based on searches. 6% potential increase in price ($83 potential increase over avg. RT price).
Cheapest flight prices on average. 5% potential price decrease ($65 potential savings vs. average RT price).
Average for round-trip flights in November 2026

Cheapflights Fare Finder

 
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

Price

Cheapest round-trip

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Mon 1/25

2:10 pm-11:50 am

1 stop31h 40m

Singapore Changi

Wed 12/31

12:00 am-10:30 am

Nonstop0h 00m

$448

ChicagoSingapore

MDW Chicago Midway - SIN Singapore Changi

MDWSIN

Chicago Midway

Mon 3/15

9:30 am-5:00 am

2 stops30h 30m

Singapore Changi

Wed 12/31

12:00 am-10:30 am

Nonstop0h 00m

$490

ChicagoSingapore

MDW Chicago Midway - SIN Singapore Changi

MDWSIN

Chicago Midway

Tue 3/16

9:30 am-8:25 pm

2 stops45h 55m

Singapore Changi

Wed 12/31

12:00 am-10:30 am

Nonstop0h 00m

$490

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Tue 3/16

6:30 am-5:00 am

2 stops33h 30m

Singapore Changi

Wed 12/31

12:00 am-10:30 am

Nonstop0h 00m

$490

ChicagoSingapore

MDW Chicago Midway - SIN Singapore Changi

MDWSIN

Chicago Midway

Sun 3/14

5:35 pm-8:25 pm

2 stops61h 50m

Singapore Changi

Wed 12/31

12:00 am-10:30 am

Nonstop0h 00m

$501

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Fri 2/19

7:00 am-5:00 am

2 stops32h 00m

Singapore Changi

Wed 12/31

12:00 am-10:30 am

Nonstop0h 00m

$540
Quickest round-trip

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Thu 1/7

8:15 pm-8:45 am

1 stop22h 30m

Singapore Changi

Wed 12/31

12:00 am-10:30 am

Nonstop0h 00m

$658

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Mon 11/23

1:05 pm-6:55 am

1 stop27h 50m

Singapore Changi

Wed 12/31

12:00 am-10:30 am

Nonstop0h 00m

$694

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Thu 1/7

7:00 am-11:40 pm

2 stops26h 40m

Singapore Changi

Wed 12/31

12:00 am-10:30 am

Nonstop0h 00m

$702

ChicagoSingapore

MDW Chicago Midway - SIN Singapore Changi

MDWSIN

Chicago Midway

Thu 11/26

4:13 pm-8:25 pm

2 stops38h 12m

Singapore Changi

Wed 12/31

12:00 am-10:30 am

Nonstop0h 00m

$722

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/8

Showing 1-10 of 44 resultsSorted by cheapest first
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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.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Chicago to Singapore

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 $946). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,920). 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

Read reviews from past customers who have flown Cathay Pacific,Turkish Airlines, andEtihad Airways from Chicago to Singapore. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Comfort

7.6

Entertainment

7.8

Food

7.3

Boarding

7.9

Crew

8.1

Overall

7.6

Reviews

1 / 20
4.0
Okay

Paden,Oct 2026

SEA - HKG

Ground staff at Seattle counter were excellent . Business class on board experience was very disappointing. There was no pajamas, no bed turn down service and the service was very mediocre took long time to get one extra roll of bread. Not very forthcoming quite curt in general. Also was situated in the middle row first row whole night being right next to the toilet not able to get any sleep. The entertainment wad very outdated too! Sorry to complain but I had high hopes for Cathay as I have flow years ago and the experience then was like night and day. Usually fly Qatar or Emirates the service doesn't compare. My flight from HKG to Delhi was much better. Thanks

Comfort

7.6

Entertainment

7.8

Food

7.3

Boarding

7.9

Crew

8.1

Overall

7.6

Reviews

1 / 20
4.0
Okay

Paden,Oct 2026

SEA - HKG

Ground staff at Seattle counter were excellent . Business class on board experience was very disappointing. There was no pajamas, no bed turn down service and the service was very mediocre took long time to get one extra roll of bread. Not very forthcoming quite curt in general. Also was situated in the middle row first row whole night being right next to the toilet not able to get any sleep. The entertainment wad very outdated too! Sorry to complain but I had high hopes for Cathay as I have flow years ago and the experience then was like night and day. Usually fly Qatar or Emirates the service doesn't compare. My flight from HKG to Delhi was much better. Thanks

Comfort

7.6

Entertainment

7.8

Food

7.3

Boarding

7.9

Crew

8.1

Overall

7.6

Reviews

1 / 20
4.0
Okay

Paden,Oct 2026

SEA - HKG

Ground staff at Seattle counter were excellent . Business class on board experience was very disappointing. There was no pajamas, no bed turn down service and the service was very mediocre took long time to get one extra roll of bread. Not very forthcoming quite curt in general. Also was situated in the middle row first row whole night being right next to the toilet not able to get any sleep. The entertainment wad very outdated too! Sorry to complain but I had high hopes for Cathay as I have flow years ago and the experience then was like night and day. Usually fly Qatar or Emirates the service doesn't compare. My flight from HKG to Delhi was much better. Thanks

Comfort

7.6

Entertainment

7.8

Food

7.3

Boarding

7.9

Crew

8.1

Overall

7.6

Reviews

1 / 20
4.0
Okay

Paden,Oct 2026

SEA - HKG

Ground staff at Seattle counter were excellent . Business class on board experience was very disappointing. There was no pajamas, no bed turn down service and the service was very mediocre took long time to get one extra roll of bread. Not very forthcoming quite curt in general. Also was situated in the middle row first row whole night being right next to the toilet not able to get any sleep. The entertainment wad very outdated too! Sorry to complain but I had high hopes for Cathay as I have flow years ago and the experience then was like night and day. Usually fly Qatar or Emirates the service doesn't compare. My flight from HKG to Delhi was much better. Thanks

Comfort

7.6

Entertainment

7.8

Food

7.3

Boarding

7.9

Crew

8.1

Overall

7.6

Reviews

1 / 20
4.0
Okay

Paden,Oct 2026

SEA - HKG

Ground staff at Seattle counter were excellent . Business class on board experience was very disappointing. There was no pajamas, no bed turn down service and the service was very mediocre took long time to get one extra roll of bread. Not very forthcoming quite curt in general. Also was situated in the middle row first row whole night being right next to the toilet not able to get any sleep. The entertainment wad very outdated too! Sorry to complain but I had high hopes for Cathay as I have flow years ago and the experience then was like night and day. Usually fly Qatar or Emirates the service doesn't compare. My flight from HKG to Delhi was much better. Thanks

Comfort

7.6

Entertainment

7.8

Food

7.3

Boarding

7.9

Crew

8.1

Overall

7.6

Reviews

1 / 20
4.0
Okay

Paden,Oct 2026

SEA - HKG

Ground staff at Seattle counter were excellent . Business class on board experience was very disappointing. There was no pajamas, no bed turn down service and the service was very mediocre took long time to get one extra roll of bread. Not very forthcoming quite curt in general. Also was situated in the middle row first row whole night being right next to the toilet not able to get any sleep. The entertainment wad very outdated too! Sorry to complain but I had high hopes for Cathay as I have flow years ago and the experience then was like night and day. Usually fly Qatar or Emirates the service doesn't compare. My flight from HKG to Delhi was much better. Thanks

Related info for your journey

  • How long is the flight from Chicago to Singapore?

    There are many flights that can get you from Chicago to Singapore in 31h. Fly via Turkish Airlines or Delta to get the fastest option. Airlines will cover a distance of 9345 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Singapore one-way?

    To fly one-way, consider booking your trip with Philippine Airlines, which is currently one of the cheapest options available, starting at $322. Etihad Airways flights start at $400 while deals on ANA start at $438 one-way.

  • Can I find deals for flights from Chicago to Singapore that include hotel bookings?

    Yes. In addition to deals on Chicago to Singapore flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Singapore?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Singapore.

  • Can I find deals for business class flights from Chicago to Singapore?

    Yes. Cheapflights offers flight deals from Chicago to Singapore by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $946). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,920). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Top 10 airlines flying from Chicago to Singapore

AirlineCheapestAverageFlexibilityOn-time
Japan AirlinesCheapest$770Average$1,746FlexibilityNo cancel feeOn-time79%
Korean AirCheapest$792Average$963FlexibilityNo cancel feeOn-time81%
United AirlinesCheapest$795Average$1,055FlexibilityNo cancel feeOn-time69%
Etihad AirwaysCheapest$829Average$1,032FlexibilityNo cancel feeOn-time75%
Turkish AirlinesCheapest$829Average$976FlexibilityNo cancel feeOn-time77%
Cathay PacificCheapest$838Average$1,080FlexibilityNo cancel feeOn-time72%
Air CanadaCheapest$843Average$1,497FlexibilityNo cancel feeOn-time67%
ANACheapest$860Average$1,177FlexibilityNo cancel feeOn-time80%
DeltaCheapest$949Average$1,613FlexibilityNo cancel feeOn-timeN/A
Qatar AirwaysCheapest$963Average$1,078FlexibilityNo cancel feeOn-time68%

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