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$421+ Cheap flights from Chicago (CHI) to Singapore (SIN)

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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Aug 20 — Aug 271
Thu 8/20
Thu 8/27
1 adult, Economy
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Cheap flight deals from Chicago to Singapore

Cheapest flights from Chicago to Singapore
Explore the most affordable flight options available from Chicago to Singapore. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 21, 2026.

This Gotogate deal was found by Cheapflights users on 7/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:00 pm
ORD
-
SIN
1 stop30h 45m
Multiple Airlines
Sun 9/66:15 am
SIN
-
ORD
2 stops26h 50m
Multiple Airlines
Deal found 7/20$965
This Air Canada deal was found by Cheapflights users on 7/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/23:40 pm
ORD
-
SIN
2 stops33h 50m
Air Canada
Sun 9/66:15 am
SIN
-
ORD
2 stops26h 50m
Air Canada
Deal found 7/20$966
This Priceline deal was found by Cheapflights users on 7/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:10 pm
ORD
-
SIN
1 stop23h 30m
Multiple Airlines
Sun 10/47:00 am
SIN
-
ORD
2 stops26h 12m
Multiple Airlines
Deal found 7/20$967
This Delta deal was found by Cheapflights users on 7/16. 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 9/79:24 am
MDW
-
SIN
2 stops30h 36m
Delta
Sun 9/137:30 am
SIN
-
MDW
2 stops28h 15m
Delta
Deal found 7/16$969
This CheapOair deal was found by Cheapflights users on 7/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:10 pm
ORD
-
SIN
1 stop23h 30m
Multiple Airlines
Wed 9/3010:50 pm
SIN
-
ORD
2 stops34h 16m
Multiple Airlines
Deal found 7/21$969
This FlightHub deal was found by Cheapflights users on 7/20. 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.
Mon 9/217:11 am
ORD
-
SIN
2 stops28h 34m
Air Canada
Fri 9/2510:50 pm
SIN
-
ORD
2 stops52h 53m
Air Canada
Deal found 7/20$971
This FlightHub deal was found by Cheapflights users on 7/16. 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.
Fri 9/48:40 am
ORD
-
SIN
2 stops27h 05m
Air Canada
Sun 9/2010:50 pm
SIN
-
ORD
2 stops52h 53m
Air Canada
Deal found 7/16$973
This Air Canada deal was found by Cheapflights users on 7/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/103:40 pm
ORD
-
SIN
2 stops48h 35m
Air Canada
Tue 8/187:00 am
SIN
-
ORD
2 stops43h 05m
Air Canada
Deal found 7/19$974
This Delta deal was found by Cheapflights users on 7/18. 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 10/257:17 pm
ORD
-
SIN
2 stops39h 53m
Delta
Thu 11/121:35 am
SIN
-
ORD
2 stops36h 15m
Delta
Deal found 7/18$975
This Air Canada deal was found by Cheapflights users on 7/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:48 pm
ORD
-
SIN
1 stop44h 27m
Air Canada
Wed 9/238:10 am
SIN
-
ORD
2 stops43h 33m
Air Canada
Deal found 7/19$977
This Priceline deal was found by Cheapflights users on 7/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/139:10 pm
ORD
-
SIN
1 stop23h 30m
Multiple Airlines
Wed 9/166:15 am
SIN
-
ORD
2 stops26h 57m
Multiple Airlines
Deal found 7/20$978
This Turkish Airlines deal was found by Cheapflights users on 7/16. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:10 pm
ORD
-
SIN
1 stop24h 20m
Turkish Airlines
Wed 9/3011:05 pm
SIN
-
ORD
1 stop23h 35m
Turkish Airlines
Deal found 7/16$979

Find flight deals from Chicago to Singapore

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Singapore (SIN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$969
(Delta)

One-way from

$421
(SmartFares)

Popular in

December

Cheapest in

September

Average price

$1,442
Provider with most accurate pricing for Chicago (CHI)-Singapore Changi flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Singapore Changi flights.
Search Deals
From Chicago (CHI) to Singapore Changi
Search Deals
One-way flight from Chicago (CHI) to Singapore Changi
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($144 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($76 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Singapore 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 July 21, 2026.
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

MDW - SIN

MDWSIN

Chicago Midway

Wed 9/30

5:11 pm-7:15 pm

2 stops37h 04m

Singapore Changi

Tue 10/6

7:30 am-10:25 pm

2 stops27h 55m

$984

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 9/29

8:55 am-5:00 am

2 stops31h 05m

Singapore Changi

Mon 10/5

7:30 am-11:59 pm

2 stops29h 29m

$984

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 8/23

9:59 am-5:00 am

2 stops30h 01m

Singapore Changi

Sat 8/29

7:30 am-10:36 pm

2 stops28h 06m

$1,004

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 10/6

6:00 am-5:00 am

2 stops34h 00m

Singapore Changi

Wed 11/11

1:35 am-4:25 pm

2 stops28h 50m

$1,084

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 11/30

5:30 am-5:00 am

2 stops33h 30m

Singapore Changi

Wed 12/16

10:30 pm-5:14 pm

2 stops32h 44m

$1,084

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Thu 9/10

8:10 pm-9:30 am

1 stop24h 20m

Singapore Changi

Mon 9/14

11:10 am-9:40 am

1 stop35h 30m

$1,100

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 9/23

6:10 am-11:55 pm

2 stops28h 45m

Singapore Changi

Fri 9/25

1:25 am-8:30 pm

2 stops32h 05m

$1,112

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 9/28

6:05 am-11:55 pm

2 stops28h 50m

Singapore Changi

Thu 10/1

1:25 am-4:16 pm

2 stops27h 51m

$1,119

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sat 9/5

6:00 am-3:45 pm

2 stops44h 45m

Singapore Changi

Wed 9/30

7:40 pm-3:05 pm

1 stop32h 25m

$1,148

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Fri 8/14

5:30 am-5:00 am

2 stops34h 30m

Singapore Changi

Fri 8/21

7:30 am-11:29 pm

2 stops28h 59m

$1,154

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/21

Showing 1-10 of 41 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Singapore

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Singapore in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Singapore flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Singapore flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Singapore flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Singapore flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Singapore flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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
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 Chicago to Singapore

What is the cheapest month to book a flight from Chicago to Singapore?

Currently, September is the cheapest month in which you can book a flight from Chicago to Singapore (average of $895). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,995). 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 to fly round-trip from Chicago to Singapore?

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

Share of 1-stop round-trip flights from Chicago to Singapore chosen by Cheapflights users in the past 12 months, using the same layover each way.

Incheon (ICN) – chosen by Cheapflights users on 25% of 1-stop itineraries from Chicago to Singapore on Cheapflights.

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

Average round-trip fare for 1-stop flights from Chicago to Singapore, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Hong Kong (HKG) is the most affordable 1-stop option, with an average round-trip price of $882.

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

Shortest average travel time for 1-stop one-way flights from Chicago to Singapore, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Incheon (ICN) have the shortest average one-way travel time for 1-stop routes: 22h 45m.

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

Average layover duration for 1-stop one-way flights from Chicago to Singapore, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Incheon (ICN) offer the fastest connection on this route, with an average layover time of 1h 50m.

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

The best time to book flights from Chicago to Singapore is 42 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

Get insights into the airlines that provide service to Singapore. 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 Singapore. Reviews last updated July 21, 2026.
Get a feel of what it's like to fly with EVA Air,Cathay Pacific, andTurkish Airlines from Chicago to Singapore by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
EVA Air
8.5
Very good
1,502 reviews

Food

8.1

Comfort

8.3

Crew

8.7

Overall

8.5

Entertainment

8.0

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
EVA Air
8.5
Very good
1,502 reviews
EVA Air
8.5
Very good
1,502 reviews

Food

8.1

Comfort

8.3

Crew

8.7

Overall

8.5

Entertainment

8.0

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
Cathay Pacific
7.6
Good
1,420 reviews
EVA Air
8.5
Very good
1,502 reviews

Food

8.1

Comfort

8.3

Crew

8.7

Overall

8.5

Entertainment

8.0

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
Turkish Airlines
7.4
Good
4,450 reviews
EVA Air
8.5
Very good
1,502 reviews

Food

8.1

Comfort

8.3

Crew

8.7

Overall

8.5

Entertainment

8.0

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
United Airlines
7.4
Good
10,012 reviews
EVA Air
8.5
Very good
1,502 reviews

Food

8.1

Comfort

8.3

Crew

8.7

Overall

8.5

Entertainment

8.0

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
Air Canada
7.1
Good
11,361 reviews
EVA Air
8.5
Very good
1,502 reviews

Food

8.1

Comfort

8.3

Crew

8.7

Overall

8.5

Entertainment

8.0

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Singapore. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Located just 10.5 mi from the city center, Singapore Changi is the airport most travelers will use when flying to Singapore from Chicago. Booking flights from Chicago to Changi (SIN) should be relatively easy as there are 0 daily inbound flights from Chicago from 12 different airlines.

  • How long is the flight from Chicago to Singapore?

    There are many flights that can get you from Chicago to Singapore in 30h 36m. Fly via Air Canada or Delta to get the fastest option. Airlines will cover a distance of 9360 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, ANA ($689), Cathay Pacific ($698), and United Airlines ($705) offers the cheapest pricing from Chicago to Singapore. You may be able to fly from Chicago to Singapore for 42% less than the average price by searching for these airlines.

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

    To fly one-way, consider booking your trip with Cathay Pacific, which is currently one of the cheapest options available, starting at $370. Air Canada flights start at $385 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, September is the cheapest month in which you can book a flight from Chicago to Singapore (average of $895). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,995). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Singapore

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Singapore flights
St. Louis to Singapore flights

Top 10 airlines flying from Chicago to Singapore

Discover the top 10 airlines that operate flights from Chicago to Singapore. 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 July 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
ANACheapest$689Average$1,166FlexibilityNo cancel feeOn-time80%
Cathay PacificCheapest$698Average$932FlexibilityNo cancel feeOn-time72%
United AirlinesCheapest$705Average$1,141FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$721Average$897FlexibilityNo cancel feeOn-time77%
Japan AirlinesCheapest$770Average$1,276FlexibilityNo cancel feeOn-time79%
Korean AirCheapest$792Average$963FlexibilityNo cancel feeOn-time81%
Etihad AirwaysCheapest$829Average$1,032FlexibilityNo cancel feeOn-time75%
Air CanadaCheapest$884Average$1,340FlexibilityNo cancel feeOn-time67%
DeltaCheapest$949Average$1,520FlexibilityNo cancel feeOn-timeN/A
Qatar AirwaysCheapest$963Average$1,064FlexibilityNo cancel feeOn-time68%

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