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Cheap flights from Chicago to Singapore from S$ 563

CHI — SIN
4 Dec — 11 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Chicago to Singapore

Enter your travel dates to find the best prices.

Cheapest flights from Chicago to Singapore

Wed 18-1109:45 -
1 stop39h 05m
Sat 28-1102:00 -
2 stops43h 40m
Deal found 1-11S$ 1,112
Sun 8-1111:45 -
1 stop31h 00m
Tue 24-1110:25 -
1 stop37h 35m
Deal found 4-11S$ 1,149
Sun 29-1111:45 -
1 stop31h 00m
Tue 15-1223:15 -
1 stop33h 05m
Deal found 31-10S$ 1,154
Thu 19-1109:45 -
1 stop39h 05m
Thu 26-1102:00 -
2 stops43h 40m
Deal found 31-10S$ 1,177
Tue 1-1220:15 -
1 stop44h 35m
Fri 11-1211:40 -
1 stop36h 20m
Deal found 2-11S$ 1,190
Tue 1-1220:15 -
1 stop22h 30m
Tue 8-1210:25 -
1 stop45h 55m
Deal found 3-11S$ 1,191
Thu 19-1109:45 -
1 stop39h 05m
Sat 28-1102:00 -
2 stops43h 40m
Deal found 3-11S$ 1,208
Mon 7-1211:45 -
1 stop39h 55m
Tue 19-104:35 -
1 stop43h 25m
Deal found 31-10S$ 1,209
Mon 9-1120:15 -
1 stop44h 35m
Tue 17-1110:25 -
1 stop37h 35m
Deal found 1-11S$ 1,247
Mon 16-1114:10 -
1 stop31h 40m
Mon 23-1120:20 -
1 stop30h 10m
Deal found 30-10S$ 1,250

Find flight deals from Chicago to Singapore

Round-trip from

S$ 1,112

One-way from

S$ 563

Popular in

December

Cheapest in

April

Average price

S$ 1,272
Ethiopian Air
  • Ethiopian Air
  • 18-11-28-11
  • 3 total stops
  • 82h 45m total
  • Chicago to Singapore
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Cathay Pacific
  • Cathay Pacific
  • 30-11-31-12
  • 1 total stop
  • 35h 30m total
  • Chicago to Singapore
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (S$ 155 potential increase over avg. return price).
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Cheapest flight prices on average. 5% potential price decrease (S$ 111 potential savings vs. average return price).
Search Deals
Average for round-trip flights in November 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Chicago to Singapore that are best for you.

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Route

Depart

Return

Price

Cheapest return flight

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Fri 19-2

07:00-05:00

2 stops32h 00m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 679

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Wed 27-1

06:00-00:15

2 stops28h 15m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 692

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Mon 25-1

06:00-00:15

2 stops28h 15m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 692

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Mon 28-12

14:10-11:50

1 stop31h 40m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 927

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Sun 3-1

21:51-06:55

2 stops43h 04m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 1,078
Fastest return journey

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Tue 29-12

06:25-00:15

2 stops27h 50m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 1,160

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Mon 28-12

18:40-00:15

2 stops39h 35m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 1,174

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Sun 29-11

20:15-17:40

1 stop31h 25m

Singapore Changi

Tue 15-12

23:15-10:00

1 stop24h 45m

S$ 1,190

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Mon 22-3

21:15-17:40

1 stop31h 25m

Singapore Changi

Thu 1-4

10:20-18:10

1 stop44h 50m

S$ 1,201

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Wed 24-3

21:15-10:00

1 stop23h 45m

Singapore Changi

Fri 2-4

10:20-18:10

1 stop44h 50m

S$ 1,202

Flights are sorted by cheapest return flights first.

Deals found on 1-11

Showing 1-10 of 20 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 return 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 S$ 1,211). Flying from Chicago to Singapore in December is currently the most expensive (average of S$ 2,484). 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 for a return flight from Chicago to Singapore?

Airfare is below average for this route at the moment.
Chicago to Singapore flights typically cost between S$ 1,130 and S$ 1,539 in November.
The cheapest return price found within the last 5 days was S$ 1,112 on Ethiopian Air (18 Nov–28 Nov).

What’s the top stopover airport for flights from Chicago to Singapore?

Doha (DOH) – chosen by Cheapflights users on 43% of one-stop itineraries from Chicago to Singapore on Cheapflights.

What’s the cheapest stopover airport for flights from Chicago to Singapore?

Hong Kong (HKG) is the most affordable one-stop option, with an average return flight price of S$ 1,080.

What’s the fastest stopover option from Chicago to Singapore?

Flights via Incheon (ICN) have the shortest average one-way travel time for one-stop routes: 22h 25m.

Which airport typically offers the quickest stopover for flights from Chicago to Singapore?

Flights via Taipei City (TPE) offer the fastest connection on this route, with an average stopover time of 2h 08m.

How far ahead should I book a flight from Chicago to Singapore?

The best time to book flights from Chicago to Singapore is 40 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.

Related info for your journey

  • What airport do you fly into for flights to Singapore from Chicago?

    For a flight from Chicago to Singapore, you will be flying into Changi. Singapore Changi (SIN) is just 16.9 km from the centre vof the city. Changi is the only Singapore airport and it handles 0 inbound flights from Chicago per day. 2 airlines have flights to Singapore Changi from Chicago on a regular basis.

  • How long is the flight from Chicago to Singapore?

    Turkish Airlines and Delta can get you from Chicago to Singapore in just under 23h 05m. Your travel time can differ by up to 8h 20m. The distance from Chicago to Singapore is about 15039 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Singapore round-trip?

    Cheapflights users have booked flights from Chicago to Singapore round-trip from S$ 2,052. Another airline that can offer you cheap pricing is JetBlue.

  • 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 holiday 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 S$ 1,211). Flying from Chicago to Singapore in December is currently the most expensive (average of S$ 2,484). 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

Alternative routes for Chicago to Singapore

St. Louis to Singapore flights

Top 2 airlines flying from Chicago to Singapore

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 2,052AverageS$ 2,065FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
JetBlueCheapestS$ 2,819AverageS$ 2,820FlexibilityNo cancel feeOn-time62%
Search JetBlue flights

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