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$327+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
May 18 — May 251
Mon 5/18
Mon 5/25
1 adult, Economy
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Find cheap flights from Chicago to Singapore with Cheapflights

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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 April 18, 2026.

This IEagle deal was found by Cheapflights users on 4/17. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:10 pm
ORD
-
SIN
1 stop34h 00m
Air India
Mon 6/811:00 pm
SIN
-
ORD
2 stops49h 10m
Air India
Deal found 4/17$891
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:50 am
ORD
-
SIN
2 stops27h 45m
Multiple Airlines
Wed 9/166:40 pm
SIN
-
ORD
1 stop23h 20m
Multiple Airlines
Deal found 4/16$914
This IEagle deal was found by Cheapflights users on 4/18. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:10 pm
ORD
-
SIN
1 stop43h 35m
Air India
Wed 6/1011:00 pm
SIN
-
ORD
2 stops49h 10m
Air India
Deal found 4/18$920
This IEagle deal was found by Cheapflights users on 4/17. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/241:10 pm
ORD
-
SIN
1 stop34h 00m
Air India
Mon 9/1411:00 pm
SIN
-
ORD
2 stops49h 10m
Air India
Deal found 4/17$938
This IEagle deal was found by Cheapflights users on 4/14. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/271:15 pm
ORD
-
SIN
1 stop43h 30m
Air India
Thu 5/281:10 pm
SIN
-
ORD
2 stops35h 00m
Air India
Deal found 4/14$939
This IEagle deal was found by Cheapflights users on 4/18. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:10 pm
ORD
-
SIN
1 stop34h 00m
Air India
Sun 6/148:25 am
SIN
-
ORD
2 stops39h 45m
Air India
Deal found 4/18$947
This FlightHub deal was found by Cheapflights users on 4/17. 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 8/241:10 pm
ORD
-
SIN
1 stop29h 15m
Air India
Tue 9/151:10 pm
SIN
-
ORD
2 stops35h 00m
Air India
Deal found 4/17$963
This Justfly.com deal was found by Cheapflights users on 4/15. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/151:10 pm
ORD
-
SIN
1 stop43h 35m
Air India
Mon 5/2511:00 pm
SIN
-
ORD
2 stops49h 10m
Air India
Deal found 4/15$965
This IEagle deal was found by Cheapflights users on 4/16. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:10 pm
ORD
-
SIN
1 stop43h 35m
Air India
Wed 7/811:00 pm
SIN
-
ORD
2 stops49h 10m
Air India
Deal found 4/16$968
This FlightHub deal was found by Cheapflights users on 4/17. 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 8/241:10 pm
ORD
-
SIN
1 stop29h 15m
Air India
Sun 9/131:10 pm
SIN
-
ORD
2 stops35h 00m
Air India
Deal found 4/17$970
This KAYAK deal was found by Cheapflights users on 4/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:00 pm
ORD
-
SIN
1 stop30h 45m
Cathay Pacific
Wed 9/1612:45 pm
SIN
-
ORD
1 stop38h 10m
Cathay Pacific
Deal found 4/18$975
This Gurufare deal was found by Cheapflights users on 4/17. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:15 pm
ORD
-
SIN
1 stop24h 15m
Cathay Pacific
Tue 5/198:05 pm
SIN
-
ORD
1 stop30h 50m
Cathay Pacific
Deal found 4/17$977

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 April 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$891
(IEagle)

One-way from

$327
(oojo)

Popular in

December

Cheapest in

September

Average price

$1,034
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 ($134 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($74 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 18, 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

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 9/14

4:20 pm-6:15 am

1 stop24h 55m

Singapore Changi

Thu 9/17

8:45 am-9:47 pm

1 stop26h 02m

$1,141

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 8/26

5:00 am-6:35 pm

2 stops24h 35m

Singapore Changi

Thu 9/10

8:35 pm-5:01 am

1 stop21h 26m

$1,145

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 8/19

8:51 am-6:15 am

2 stops32h 24m

Singapore Changi

Mon 9/7

6:15 am-9:07 pm

2 stops27h 52m

$1,157
Quickest round-trip

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Fri 8/21

6:00 am-6:35 pm

1 stop23h 35m

Singapore Changi

Tue 9/15

8:35 pm-5:01 am

1 stop21h 26m

$1,191

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 5/3

6:20 am-6:35 pm

1 stop23h 15m

Singapore Changi

Tue 5/5

8:35 pm-10:55 am

2 stops27h 20m

$1,195

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Thu 8/20

7:20 pm-10:15 am

2 stops25h 55m

Singapore Changi

Mon 9/21

3:15 am-3:05 pm

1 stop24h 50m

$1,301

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sat 9/5

7:20 pm-10:15 am

2 stops25h 55m

Singapore Changi

Wed 9/23

3:15 am-3:05 pm

1 stop24h 50m

$1,341

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Fri 7/3

6:55 am-11:55 pm

2 stops28h 00m

Singapore Changi

Mon 7/13

10:00 pm-9:48 pm

2 stops36h 48m

$1,349

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sat 7/4

8:46 am-12:45 am

2 stops26h 59m

Singapore Changi

Tue 7/14

8:35 pm-9:36 am

2 stops26h 01m

$1,352

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 5/11

7:20 pm-9:20 am

1 stop25h 00m

Singapore Changi

Mon 5/18

9:15 pm-4:50 pm

2 stops32h 35m

$1,366

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

Showing 1-10 of 40 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Singapore. Price data was last updated on April 10, 2026.

The best time to book flights from Chicago to Singapore is 6 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.

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 $492). Flying from Chicago to Singapore in July is currently the most expensive (average of $875). 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.

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 April 18, 2026.
Get a feel of what it's like to fly with EVA Air,Cathay Pacific, andUnited 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
1,419 reviews

Comfort

8.3

Crew

8.7

Entertainment

8.0

Overall

8.5

Boarding

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

CRK - TPE

What about midnight snacks to add? Used to have that before..
EVA Air
8.5
Very good
1,419 reviews
EVA Air
8.5
Very good
1,419 reviews

Comfort

8.3

Crew

8.7

Entertainment

8.0

Overall

8.5

Boarding

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

CRK - TPE

What about midnight snacks to add? Used to have that before..
Cathay Pacific
7.6
Good
1,280 reviews
EVA Air
8.5
Very good
1,419 reviews

Comfort

8.3

Crew

8.7

Entertainment

8.0

Overall

8.5

Boarding

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

CRK - TPE

What about midnight snacks to add? Used to have that before..
United Airlines
7.4
Good
9,604 reviews
EVA Air
8.5
Very good
1,419 reviews

Comfort

8.3

Crew

8.7

Entertainment

8.0

Overall

8.5

Boarding

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

CRK - TPE

What about midnight snacks to add? Used to have that before..
Etihad Airways
7.3
Good
1,431 reviews
EVA Air
8.5
Very good
1,419 reviews

Comfort

8.3

Crew

8.7

Entertainment

8.0

Overall

8.5

Boarding

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

CRK - TPE

What about midnight snacks to add? Used to have that before..
Turkish Airlines
7.3
Good
4,308 reviews
EVA Air
8.5
Very good
1,419 reviews

Comfort

8.3

Crew

8.7

Entertainment

8.0

Overall

8.5

Boarding

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

CRK - TPE

What about midnight snacks to add? Used to have that before..

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 11 different airlines.

  • How long is the flight from Chicago to Singapore?

    There are many flights that can get you from Chicago to Singapore in 24h 35m. Fly via United 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 flying from Chicago to Singapore round-trip?

    According to our current data, Air India ($697), ANA ($698), and Cathay Pacific ($698) offers the cheapest pricing from Chicago to Singapore. You may be able to fly from Chicago to Singapore for 38% 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. ANA flights start at $438 while deals on Turkish Airlines start at $444 one-way.

  • Where are the most common layover locations when flying from Chicago to Singapore?

    Of the flights from Chicago to Singapore that have layovers, most of them stop in Hong Kong.

  • What are some popular things to do or see while on a layover in Hong Kong?

    The majority of Hong Kong visitors spend their time at Shatin Baptist Church, Fa Yeun Street Market, and Temple Street Night Market. Travelers on a layover in Hong Kong can visit Shatin Baptist Church, Fa Yeun Street Market, and Temple Street Night Market, by traveling 18.3 mi, 16.2 mi, and 16.1 mi, respectively after landing at Hong Kong Intl.

  • Where are the least popular layover locations for Chicago to Singapore flights?

    Of the flights from Chicago to Singapore that have layovers, the fewest flights stop in Istanbul.

  • 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 $492). Flying from Chicago to Singapore in July is currently the most expensive (average of $875). 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

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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 April 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air IndiaCheapest$697Average$963FlexibilityNo cancel feeOn-timeN/A
ANACheapest$698Average$1,426FlexibilityNo cancel feeOn-time80%
Cathay PacificCheapest$698Average$877FlexibilityNo cancel feeOn-time72%
United AirlinesCheapest$709Average$1,129FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$770Average$976FlexibilityNo cancel feeOn-time77%
Japan AirlinesCheapest$814Average$1,081FlexibilityNo cancel feeOn-time79%
Etihad AirwaysCheapest$829Average$1,058FlexibilityNo cancel feeOn-time75%
Air CanadaCheapest$872Average$1,340FlexibilityNo cancel feeOn-time67%
DeltaCheapest$949Average$1,520FlexibilityNo cancel feeOn-timeN/A
EVA AirCheapest$1,101Average$1,430FlexibilityNo cancel feeOn-time74%

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