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Cheap flights from Chicago to Singapore from S$ 513

CHI — SIN
24 Sep — 1 Oct1
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

Tue 27-1008:40 -
2 stops33h 20m
Tue 3-1108:40 -
2 stops46h 30m
Deal found 22-8S$ 960
Tue 6-1008:49 -
1 stop31h 26m
Tue 13-1007:00 -
2 stops26h 12m
Deal found 21-8S$ 963
Thu 29-1008:40 -
2 stops33h 20m
Thu 5-1108:40 -
2 stops25h 12m
Deal found 22-8S$ 965
Mon 2-1121:21 -
2 stops43h 39m
Mon 9-1121:00 -
2 stops31h 37m
Deal found 22-8S$ 973
Thu 10-911:05 -
2 stops29h 10m
Thu 24-907:00 -
1 stop20h 43m
Deal found 24-8S$ 1,002
Tue 27-1015:30 -
1 stop26h 30m
Tue 10-1108:40 -
1 stop19h 57m
Deal found 25-8S$ 1,008
Tue 27-1006:04 -
2 stops33h 56m
Tue 10-1110:40 -
2 stops37h 44m
Deal found 22-8S$ 1,160
Sun 18-1013:27 -
2 stops50h 33m
Sun 1-1122:30 -
2 stops48h 14m
Deal found 22-8S$ 1,175
Wed 28-1009:29 -
2 stops30h 31m
Tue 3-1101:35 -
2 stops45h 09m
Deal found 22-8S$ 1,177
Wed 28-1009:29 -
2 stops25h 41m
Mon 9-1122:30 -
2 stops51h 20m
Deal found 22-8S$ 1,179
Mon 26-1009:29 -
2 stops30h 31m
Sun 1-1122:30 -
2 stops51h 17m
Deal found 24-8S$ 1,180
Mon 26-1009:29 -
2 stops30h 31m
Sun 8-1110:40 -
2 stops45h 24m
Deal found 22-8S$ 1,181

Find flight deals from Chicago to Singapore

Round-trip from

S$ 960

One-way from

S$ 513

Popular in

December

Cheapest in

April

Average price

S$ 1,608
Air Canada
  • Air Canada
  • 27-10-3-11
  • 4 total stops
  • 79h 50m total
  • Chicago to Singapore
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Cathay Pacific
  • Cathay Pacific
  • 2-11
  • 1 total stop
  • 31h 20m total
  • Chicago to Singapore
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (S$ 162 potential increase over avg. return price).
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Cheapest flight prices on average. 6% potential price decrease (S$ 113 potential savings vs. average return price).
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Average for round-trip flights in August 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

Mon 5-10

16:15-19:05

1 stop37h 50m

Singapore Changi

Mon 12-10

12:45-13:55

1 stop38h 10m

S$ 1,175

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Thu 17-9

16:15-15:40

1 stop34h 25m

Singapore Changi

Mon 21-9

20:05-13:55

1 stop30h 50m

S$ 1,175

ChicagoSingapore

MDW Chicago Midway - SIN Singapore Changi

MDWSIN

Chicago Midway

Wed 28-10

09:29-05:00

2 stops30h 31m

Singapore Changi

Mon 2-11

22:30-12:47

2 stops28h 17m

S$ 1,189

ChicagoSingapore

MDW Chicago Midway - SIN Singapore Changi

MDWSIN

Chicago Midway

Tue 27-10

09:29-05:00

2 stops30h 31m

Singapore Changi

Tue 10-11

10:40-22:54

2 stops26h 14m

S$ 1,189

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Mon 14-9

07:00-05:00

2 stops33h 00m

Singapore Changi

Wed 23-9

07:30-21:33

2 stops27h 03m

S$ 1,189

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Thu 10-9

14:05-05:00

2 stops49h 55m

Singapore Changi

Wed 23-9

01:25-23:59

2 stops35h 34m

S$ 1,223

ChicagoSingapore

MDW Chicago Midway - SIN Singapore Changi

MDWSIN

Chicago Midway

Sat 24-10

16:19-05:00

2 stops47h 41m

Singapore Changi

Thu 5-11

10:40-22:33

2 stops25h 53m

S$ 1,234

ChicagoSingapore

MDW Chicago Midway - SIN Singapore Changi

MDWSIN

Chicago Midway

Mon 7-9

09:24-05:00

2 stops30h 36m

Singapore Changi

Sun 13-9

07:30-22:44

2 stops28h 14m

S$ 1,234
Fastest return journey

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Fri 4-9

20:25-09:40

1 stop24h 15m

Singapore Changi

Wed 16-9

21:00-15:40

1 stop31h 40m

S$ 1,240

ChicagoSingapore

ORD Chicago O'Hare Intl - SIN Singapore Changi

ORDSIN

Chicago O'Hare Intl

Mon 2-11

06:30-00:10

2 stops27h 40m

Singapore Changi

Mon 23-11

10:40-08:30

1 stop35h 50m

S$ 1,367

Flights are sorted by cheapest return flights first.

Deals found on 24-8

Showing 1-10 of 40 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$ 1,194). Flying from Chicago to Singapore in December is currently the most expensive (average of S$ 2,435). 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$ 1,276 and S$ 1,688 in October.
The cheapest return price found within the last 5 days was S$ 960 on Air Canada (27 Oct–3 Nov).

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

Doha (DOH) – chosen by Cheapflights users on 30% 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$ 1,071.

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 19 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
1,515 reviews
Check prices

Overall

7.3

Comfort

7.3

Food

7.1

Crew

7.8

Boarding

7.6

Entertainment

7.2

Reviews

1 / 20
8.0
Excellent

Tom,May 2026

JFK - AUH

Everything was good except the lie flat bed. The bed has a gap and is uncomfortable to lie on. The hostesses were great; the food service was reasonable and the connecting flight services and the baggage service were good. Entertainment service was also good.
Etihad Airways
7.3
Good
1,515 reviews
Etihad Airways
7.3
Good
1,515 reviews
Check prices

Overall

7.3

Comfort

7.3

Food

7.1

Crew

7.8

Boarding

7.6

Entertainment

7.2

Reviews

1 / 20
8.0
Excellent

Tom,May 2026

JFK - AUH

Everything was good except the lie flat bed. The bed has a gap and is uncomfortable to lie on. The hostesses were great; the food service was reasonable and the connecting flight services and the baggage service were good. Entertainment service was also good.

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?

    Cathay Pacific, Delta, and Etihad Airways can get you from Chicago to Singapore in just under 24h 15m. Your travel time can differ by up to 13h 35m. 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$ 2,035. 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$ 1,194). Flying from Chicago to Singapore in December is currently the most expensive (average of S$ 2,435). 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$ 2,035AverageS$ 2,048FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
JetBlueCheapestS$ 2,796AverageS$ 2,796FlexibilityNo cancel feeOn-time62%
Search JetBlue flights

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