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$369+ Cheap flights from Chicago (CHI) to Singapore

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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Chicago to Singapore

Keep the following information in mind while searching for Chicago to Singapore flight deals. Data was last updated September 11, 2025.

Round-trip from

$703
(IEagle)

One-way from

$369
(FlightHub)

Popular in

December

Cheapest in

February

Average price

$885
From Chicago (CHI) to Singapore
Search Deals
One-way flight from Chicago (CHI) to Singapore
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($198 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($64 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This IEagle deal was found by Cheapflights users on 9/10. 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 10/201:10 pmORD - SIN
1 stop43h 35mAir India
Mon 11/311:00 pmSIN - ORD
1 stop45h 30mAir India
Deal found 9/10$703
This Gotogate deal was found by Cheapflights users on 9/10. 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.
Sun 10/2612:15 pmORD - SIN
1 stop22h 55mKorean Air
Sun 11/210:40 amSIN - ORD
1 stop35h 50mKorean Air
Deal found 9/10$712
This oojo deal was found by Cheapflights users on 9/11. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/32:40 pmORD - SIN
1 stop25h 00mCathay Pacific
Mon 11/101:25 amSIN - ORD
1 stop25h 35mCathay Pacific
Deal found 9/11$713
This lastminute.com deal was found by Cheapflights users on 9/11. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/32:40 pmORD - SIN
1 stop25h 00mCathay Pacific
Mon 11/178:15 pmSIN - ORD
1 stop30h 45mCathay Pacific
Deal found 9/11$718
This oojo deal was found by Cheapflights users on 9/10. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/214:00 pmORD - SIN
1 stop38h 05mCathay Pacific
Mon 11/101:25 amSIN - ORD
1 stop25h 35mCathay Pacific
Deal found 9/10$720
This Korean Air deal was found by Cheapflights users on 9/9. 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 Korean Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2611:15 amORD - SIN
1 stop27h 45mKorean Air
Wed 12/310:30 pmSIN - ORD
1 stop24h 00mKorean Air
Deal found 9/9$723
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 9/179:20 amMDW - SIN
2 stops25h 20mDelta
Tue 9/231:10 amSIN - MDW
2 stops33h 26mDelta
Deal found 9/10$734
This Delta deal was found by Cheapflights users on 9/8. 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 9/221:35 pmORD - SIN
2 stops45h 05mDelta
Mon 9/297:30 amSIN - ORD
2 stops29h 24mDelta
Deal found 9/8$734
This Korean Air deal was found by Cheapflights users on 9/8. 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 Korean Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1711:15 amORD - SIN
1 stop43h 10mKorean Air
Sat 11/2210:30 pmSIN - ORD
1 stop24h 00mKorean Air
Deal found 9/8$735
This oojo deal was found by Cheapflights users on 9/9. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/104:00 pmORD - SIN
1 stop31h 25mCathay Pacific
Tue 9/161:50 amSIN - ORD
1 stop25h 35mCathay Pacific
Deal found 9/9$736
This Expedia deal was found by Cheapflights users on 9/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/174:00 pmORD - SIN
1 stop24h 30mCathay Pacific
Tue 9/231:50 amSIN - ORD
1 stop25h 35mCathay Pacific
Deal found 9/10$739
This Delta deal was found by Cheapflights users on 9/11. 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 11/36:00 amMDW - SIN
2 stops33h 00mDelta
Tue 11/1110:30 pmSIN - MDW
2 stops32h 09mDelta
Deal found 9/11$884

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 September 11, 2025.
Use the filters below to find and compare flights from Chicago to Singapore that are best for you.

Fly from

Chicago

Fly to

Singapore

Route

Depart

Return

Price

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 11/26

11:15 am-5:00 am

1 stop27h 45m

Singapore Changi

Wed 12/3

10:30 pm-8:30 am

1 stop24h 00m

$723

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 9/24

11:00 am-11:40 pm

2 stops23h 40m

Singapore Changi

Tue 9/30

7:30 am-11:55 pm

2 stops29h 25m

$734

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 9/22

7:59 pm-11:40 pm

2 stops38h 41m

Singapore Changi

Sun 9/28

1:10 am-11:55 pm

2 stops35h 45m

$734

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 11/26

11:15 am-5:00 am

1 stop27h 45m

Singapore Changi

Thu 12/18

1:35 am-8:30 am

1 stop20h 55m

$735

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 11/2

11:15 am-5:00 am

1 stop27h 45m

Singapore Changi

Mon 11/10

1:35 am-8:30 am

1 stop20h 55m

$735

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 2/8

2:40 pm-1:05 pm

1 stop32h 25m

Singapore Changi

Wed 2/25

1:25 am-1:00 pm

1 stop25h 35m

$798

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 11/3

6:45 am-5:00 am

2 stops32h 15m

Singapore Changi

Tue 11/11

10:30 pm-8:30 am

1 stop24h 00m

$874

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 10/7

6:45 am-11:40 pm

2 stops27h 55m

Singapore Changi

Tue 10/21

7:30 am-9:30 am

1 stop39h 00m

$874

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 11/3

6:00 am-5:00 am

2 stops33h 00m

Singapore Changi

Tue 11/11

10:30 pm-4:39 pm

2 stops32h 09m

$884

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 10/20

6:45 am-5:00 am

2 stops33h 15m

Singapore Changi

Mon 11/3

10:30 pm-5:10 pm

2 stops32h 40m

$884

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 40 results
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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 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, October is the cheapest month in which you can book a flight from Chicago to Singapore (average of $1,002). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,665). 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.

What is the cheapest time of day to fly from CHI to SG?

Find hourly flight availability from Chicago to Singapore. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

When flying from Chicago to Singapore, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 11, 2025.
Read reviews from past customers who have flown EVA Air, Cathay Pacific, and United Airlines from Chicago to Singapore. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
EVA Air
8.4
Very good
1,236 reviews

Comfort

8.3

Entertainment

8.0

Overall

8.4

Food

8.1

Crew

8.6

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
EVA Air
8.4
Very good
1,236 reviews
EVA Air
8.4
Very good
1,236 reviews

Comfort

8.3

Entertainment

8.0

Overall

8.4

Food

8.1

Crew

8.6

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Cathay Pacific
7.6
Good
993 reviews
EVA Air
8.4
Very good
1,236 reviews

Comfort

8.3

Entertainment

8.0

Overall

8.4

Food

8.1

Crew

8.6

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
United Airlines
7.4
Good
8,937 reviews
EVA Air
8.4
Very good
1,236 reviews

Comfort

8.3

Entertainment

8.0

Overall

8.4

Food

8.1

Crew

8.6

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Turkish Airlines
7.3
Good
3,968 reviews
EVA Air
8.4
Very good
1,236 reviews

Comfort

8.3

Entertainment

8.0

Overall

8.4

Food

8.1

Crew

8.6

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Air Canada
7.1
Good
10,000 reviews
EVA Air
8.4
Very good
1,236 reviews

Comfort

8.3

Entertainment

8.0

Overall

8.4

Food

8.1

Crew

8.6

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak

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.

  • How long is the flight from Chicago to Singapore?

    There are many flights that can get you from Chicago to Singapore in 23h 40m. Fly via Korean Air 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.

  • 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, October is the cheapest month in which you can book a flight from Chicago to Singapore (average of $1,002). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,665). 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.
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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air IndiaCheapest$675Average$921FlexibilityNo cancel feeOn-timeN/A
Cathay PacificCheapest$708Average$888FlexibilityNo cancel feeOn-time72%
United AirlinesCheapest$709Average$1,283FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$729Average$839FlexibilityNo cancel feeOn-time77%
Japan AirlinesCheapest$791Average$1,081FlexibilityNo cancel feeOn-time79%
Qatar AirwaysCheapest$850Average$1,204FlexibilityNo cancel feeOn-time68%
Air CanadaCheapest$884Average$1,340FlexibilityNo cancel feeOn-time67%
Korean AirCheapest$940Average$1,400FlexibilityNo cancel feeOn-time81%
ANACheapest$1,024Average$1,427FlexibilityNo cancel feeOn-time80%
EVA AirCheapest$1,080Average$1,448FlexibilityNo cancel feeOn-time74%

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