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Cheap flights from Chicago to Singapore from S$ 469

CHI — SIN
27 Oct — 3 Nov1
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

Thu 5-1115:30 -
1 stop25h 30m
Thu 12-1108:40 -
1 stop19h 57m
Deal found 22-9S$ 1,033
Thu 29-1015:30 -
1 stop26h 30m
Thu 12-1108:40 -
1 stop19h 57m
Deal found 24-9S$ 1,034
Thu 12-1108:49 -
1 stop32h 11m
Thu 26-1108:40 -
1 stop19h 57m
Deal found 23-9S$ 1,046
Thu 5-1108:49 -
1 stop32h 11m
Thu 19-1108:40 -
2 stops25h 12m
Deal found 22-9S$ 1,050
Fri 23-1014:00 -
1 stop30h 40m
Wed 4-1119:25 -
1 stop26h 30m
Deal found 22-9S$ 1,065
Sun 1-1115:30 -
1 stop25h 30m
Thu 5-1108:40 -
1 stop19h 57m
Deal found 22-9S$ 1,082
Sat 14-1115:45 -
2 stops49h 15m
Thu 19-1108:40 -
1 stop19h 57m
Deal found 24-9S$ 1,085

Find flight deals from Chicago to Singapore

Round-trip from

S$ 1,033

One-way from

S$ 469

Popular in

December

Cheapest in

April

Average price

S$ 1,244
Air Canada
  • Air Canada
  • 5-11-12-11
  • 2 total stops
  • 45h 27m total
  • Chicago to Singapore
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Etihad Airways
  • Etihad Airways
  • 20-2-31-12
  • 1 total stop
  • 30h 25m total
  • Chicago to Singapore
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (S$ 129 potential increase over avg. return price).
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Cheapest flight prices on average. 5% potential price decrease (S$ 107 potential savings vs. average return price).
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Average for round-trip flights in September 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.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Wed 17-2

13:10-09:35

1 stop30h 25m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 506

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Fri 5-2

13:10-09:35

1 stop30h 25m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 510

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Tue 23-2

13:10-09:35

1 stop30h 25m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 510

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Sun 17-1

13:10-09:35

1 stop30h 25m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 636

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Thu 26-11

11:00-09:35

2 stops32h 35m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 681
Fastest return journey

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Mon 22-2

15:09-09:35

2 stops28h 26m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 684

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Fri 5-2

15:19-19:05

2 stops37h 46m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 696

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Sun 22-11

20:29-20:15

1 stop33h 46m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 761

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Sun 17-1

18:00-20:15

2 stops36h 15m

Singapore Changi

Wed 31-12

00:00-10:30

Nonstop0h 00m

S$ 761

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Wed 10-3

13:10-09:35

1 stop30h 25m

Singapore Changi

Sun 21-3

19:25-08:55

1 stop26h 30m

S$ 1,084

Flights are sorted by cheapest return flights first.

Deals found on 24-9

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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$ 1,214). Flying from Chicago to Singapore in December is currently the most expensive (average of S$ 2,407). 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$ 1,156 and S$ 1,209 in November.
The cheapest return price found within the last 5 days was S$ 1,033 on Air Canada (5 Nov–12 Nov).

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

Doha (DOH) – chosen by Cheapflights users on 38% 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$ 1,077.

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 05m.

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

Check out reviews from past customers who have flown with Etihad Airways from Chicago to Singapore to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Etihad Airways
7.3
Good
1,539 reviews
Check prices

Food

7.1

Entertainment

7.2

Overall

7.3

Crew

7.8

Comfort

7.3

Boarding

7.6

Reviews

1 / 20
10.0
Excellent

Yaacov,Sept 2026

JFK - AUH

Excellent all around. Most comfortable seats in economy I’ve ever experienced. The staff were all very friendly and accommodating in all respects.
Etihad Airways
7.3
Good
1,539 reviews
Etihad Airways
7.3
Good
1,539 reviews
Check prices

Food

7.1

Entertainment

7.2

Overall

7.3

Crew

7.8

Comfort

7.3

Boarding

7.6

Reviews

1 / 20
10.0
Excellent

Yaacov,Sept 2026

JFK - AUH

Excellent all around. Most comfortable seats in economy I’ve ever experienced. The staff were all very friendly and accommodating in all respects.

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?

    Etihad Airways, Turkish Airlines, and United Airlines can get you from Chicago to Singapore in just under 27h. Your travel time can differ by up to 4h. 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$ 2,046. 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$ 1,214). Flying from Chicago to Singapore in December is currently the most expensive (average of S$ 2,407). 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$ 2,046AverageS$ 2,059FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
JetBlueCheapestS$ 2,811AverageS$ 2,812FlexibilityNo cancel feeOn-time62%
Search JetBlue flights

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