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$355+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
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 January 20, 2026.

This IEagle deal was found by Cheapflights users on 1/19. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/21:30 pm
ORD
-
SIN
1 stop42h 15m
Air India
Mon 3/1611:00 pm
SIN
-
ORD
2 stops50h 30m
Air India
Deal found 1/19$648
This IEagle deal was found by Cheapflights users on 1/19. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/271:30 pm
ORD
-
SIN
1 stop27h 30m
Air India
Sun 3/88:00 pm
SIN
-
ORD
2 stops29h 30m
Air India
Deal found 1/19$659
This IEagle deal was found by Cheapflights users on 1/19. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/271:30 pm
ORD
-
SIN
1 stop27h 30m
Air India
Sat 3/711:00 pm
SIN
-
ORD
2 stops50h 30m
Air India
Deal found 1/19$665
This oojo deal was found by Cheapflights users on 1/18. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/91:30 pm
ORD
-
SIN
1 stop42h 15m
Air India
Sun 3/88:00 pm
SIN
-
ORD
2 stops29h 30m
Air India
Deal found 1/18$680
This oojo deal was found by Cheapflights users on 1/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/21:30 pm
ORD
-
SIN
1 stop27h 30m
Air India
Wed 3/1811:00 pm
SIN
-
ORD
2 stops50h 30m
Air India
Deal found 1/20$694
This Trip.com deal was found by Cheapflights users on 1/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/92:30 pm
ORD
-
SIN
1 stop27h 30m
Air India
Mon 3/1611:00 pm
SIN
-
ORD
2 stops50h 30m
Air India
Deal found 1/20$702
This oojo deal was found by Cheapflights users on 1/18. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/201:10 pm
ORD
-
SIN
1 stop41h 20m
Air India
Tue 5/58:30 pm
SIN
-
ORD
2 stops27h 40m
Air India
Deal found 1/18$713
This oojo deal was found by Cheapflights users on 1/19. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/131:30 pm
ORD
-
SIN
1 stop27h 30m
Air India
Sun 2/228:00 pm
SIN
-
ORD
2 stops29h 30m
Air India
Deal found 1/19$734
This Trip.com deal was found by Cheapflights users on 1/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/92:30 pm
ORD
-
SIN
1 stop27h 30m
Air India
Mon 3/2311:00 pm
SIN
-
ORD
2 stops50h 30m
Air India
Deal found 1/20$738
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:40 pm
MDW
-
SIN
2 stops39h 30m
Delta
Sun 3/810:30 pm
SIN
-
MDW
2 stops37h 01m
Delta
Deal found 1/20$894
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/97:16 pm
MDW
-
SIN
2 stops38h 54m
Delta
Sun 3/810:30 pm
SIN
-
MDW
2 stops37h 01m
Delta
Deal found 1/20$900
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:40 pm
MDW
-
SIN
2 stops37h 45m
Delta
Mon 3/2310:30 pm
SIN
-
MDW
2 stops37h 01m
Delta
Deal found 1/20$994

Find flight deals from Chicago to Singapore

Keep the following information in mind while searching for Chicago to Singapore flight deals. Data was last updated January 20, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$648
(IEagle)

One-way from

$355
(oojo)

Popular in

December

Cheapest in

February

Average price

$989
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
Search Deals
One-way flight from Chicago (CHI) to Singapore
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($177 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($73 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 20, 2026.
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

Mon 3/16

2:30 pm-7:00 am

1 stop27h 30m

Singapore Changi

Thu 3/26

8:00 pm-12:30 pm

1 stop29h 30m

$743

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 3/9

2:30 pm-7:00 am

1 stop27h 30m

Singapore Changi

Mon 3/16

11:00 pm-12:30 pm

1 stop50h 30m

$743

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 3/9

2:30 pm-9:45 pm

1 stop42h 15m

Singapore Changi

Mon 3/23

11:00 pm-12:30 pm

1 stop50h 30m

$767

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 7/15

1:10 pm-9:45 pm

1 stop43h 35m

Singapore Changi

Sun 9/6

8:30 pm-11:10 am

1 stop27h 40m

$839

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 3/16

2:30 pm-7:00 am

1 stop27h 30m

Singapore Changi

Fri 3/27

11:00 pm-11:10 am

1 stop49h 10m

$852

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Fri 4/10

1:10 pm-7:30 am

1 stop29h 20m

Singapore Changi

Sat 4/18

11:00 pm-11:10 am

1 stop49h 10m

$857

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 2/1

1:10 pm-9:35 am

1 stop30h 25m

Singapore Changi

Tue 2/10

7:25 pm-7:35 am

1 stop26h 10m

$867

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 3/9

12:50 pm-10:00 am

1 stop32h 10m

Singapore Changi

Thu 3/12

10:15 am-7:25 pm

1 stop46h 10m

$874

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Fri 2/13

1:30 pm-7:00 am

1 stop27h 30m

Singapore Changi

Sun 2/22

8:00 pm-11:30 am

1 stop29h 30m

$877

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 3/4

6:40 pm-8:25 pm

2 stops35h 45m

Singapore Changi

Sun 3/8

10:30 pm-10:31 pm

2 stops37h 01m

$894

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 37 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, September is the cheapest month in which you can book a flight from Chicago to Singapore (average of $661). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,312). 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.

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 January 20, 2026.
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
1,327 reviews

Crew

8.6

Comfort

8.3

Food

8.1

Boarding

8.4

Overall

8.4

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.
EVA Air
8.4
Very good
1,327 reviews
EVA Air
8.4
Very good
1,327 reviews

Crew

8.6

Comfort

8.3

Food

8.1

Boarding

8.4

Overall

8.4

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.
Cathay Pacific
7.6
Good
1,140 reviews
EVA Air
8.4
Very good
1,327 reviews

Crew

8.6

Comfort

8.3

Food

8.1

Boarding

8.4

Overall

8.4

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.
United Airlines
7.4
Good
9,184 reviews
EVA Air
8.4
Very good
1,327 reviews

Crew

8.6

Comfort

8.3

Food

8.1

Boarding

8.4

Overall

8.4

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.
Turkish Airlines
7.3
Good
4,197 reviews
EVA Air
8.4
Very good
1,327 reviews

Crew

8.6

Comfort

8.3

Food

8.1

Boarding

8.4

Overall

8.4

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.
Air Canada
7.1
Good
10,638 reviews
EVA Air
8.4
Very good
1,327 reviews

Crew

8.6

Comfort

8.3

Food

8.1

Boarding

8.4

Overall

8.4

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.

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 27h 30m. Fly via Air India 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 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. Turkish Airlines flights start at $444 while deals on United Airlines start at $446 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 $661). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,312). 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 January 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air IndiaCheapest$675Average$921FlexibilityNo cancel feeOn-timeN/A
Cathay PacificCheapest$698Average$877FlexibilityNo cancel feeOn-time72%
United AirlinesCheapest$709Average$1,200FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$770Average$1,020FlexibilityNo cancel feeOn-time77%
Etihad AirwaysCheapest$830Average$1,172FlexibilityNo cancel feeOn-time75%
Korean AirCheapest$858Average$1,144FlexibilityNo cancel feeOn-time81%
Air CanadaCheapest$872Average$1,340FlexibilityNo cancel feeOn-time67%
Japan AirlinesCheapest$988Average$1,187FlexibilityNo cancel feeOn-time79%
ANACheapest$1,024Average$1,426FlexibilityNo cancel feeOn-time80%
EVA AirCheapest$1,086Average$1,454FlexibilityNo cancel feeOn-time74%

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