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$550+ Cheap flights from Singapore to Chicago (CHI)

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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap flight deals from Singapore to Chicago

Cheapest flights from Singapore to Chicago
Explore the most affordable flight options available from Singapore to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 20, 2026.

This lastminute.com 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2210:25 pm
SIN
-
ORD
1 stop23h 10m
Japan Airlines
Wed 2/410:35 am
ORD
-
SIN
1 stop24h 15m
Japan Airlines
Deal found 1/18$923
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1710:20 pm
SIN
-
ORD
1 stop20h 52m
United Airlines
Wed 2/189:01 am
ORD
-
SIN
1 stop32h 59m
United Airlines
Deal found 1/18$932
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:45 am
SIN
-
ORD
1 stop29h 13m
United Airlines
Sat 8/86:25 pm
ORD
-
SIN
1 stop35h 10m
United Airlines
Deal found 1/18$938
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1010:20 pm
SIN
-
ORD
1 stop21h 24m
United Airlines
Fri 2/206:25 am
ORD
-
SIN
1 stop23h 50m
United Airlines
Deal found 1/19$939
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1910:20 pm
SIN
-
ORD
1 stop27h 46m
United Airlines
Wed 3/252:26 pm
ORD
-
SIN
1 stop27h 34m
United Airlines
Deal found 1/20$940
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2210:10 am
SIN
-
ORD
1 stop25h 22m
United Airlines
Wed 2/47:58 pm
ORD
-
SIN
1 stop34h 17m
United Airlines
Deal found 1/20$941
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/281:55 am
SIN
-
ORD
1 stop20h 20m
Japan Airlines
Mon 8/31:30 am
ORD
-
SIN
1 stop27h 00m
Japan Airlines
Deal found 1/18$943
This China Airlines 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/52:25 pm
SIN
-
ORD
2 stops35h 36m
Multiple Airlines
Thu 3/125:29 pm
ORD
-
SIN
2 stops30h 36m
Multiple Airlines
Deal found 1/19$944
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/259:50 pm
SIN
-
ORD
1 stop24h 25m
Japan Airlines
Wed 8/512:30 pm
ORD
-
SIN
1 stop22h 50m
Japan Airlines
Deal found 1/18$946
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/610:40 am
SIN
-
ORD
2 stops24h 50m
Delta
Tue 3/177:10 am
ORD
-
SIN
2 stops28h 00m
Delta
Deal found 1/18$961
This Japan Airlines 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 Japan Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/110:25 pm
SIN
-
ORD
1 stop23h 10m
Japan Airlines
Wed 2/47:00 am
ORD
-
SIN
2 stops27h 50m
Japan Airlines
Deal found 1/18$969
This China Airlines 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/281:45 pm
SIN
-
MDW
2 stops34h 40m
Multiple Airlines
Mon 8/35:15 pm
MDW
-
SIN
2 stops30h 20m
Multiple Airlines
Deal found 1/20$1,098

Find flight deals from Singapore to Chicago

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

Round-trip from

$932
(United Airlines)

One-way from

$550
(FlightHub)

Popular in

January

Cheapest in

September

Average price

$1,581
From Singapore to Chicago (CHI)
Search Deals
One-way flight from Singapore to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($129 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($45 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 Singapore to Chicago 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 Singapore to Chicago that are best for you.

Fly from

Singapore

Fly to

Chicago

Route

Depart

Return

Price

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 2/17

10:20 pm-5:12 am

1 stop20h 52m

Chicago O'Hare Intl

Wed 2/18

9:01 am-8:00 am

1 stop32h 59m

$934

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 3/6

10:10 am-12:59 am

1 stop28h 49m

Chicago O'Hare Intl

Tue 3/17

12:52 pm-7:00 am

1 stop29h 08m

$938

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 2/1

10:20 pm-6:25 am

1 stop22h 05m

Chicago O'Hare Intl

Wed 2/4

4:16 pm-8:00 am

1 stop25h 44m

$938

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 7/1

8:35 pm-11:45 am

1 stop28h 10m

Chicago O'Hare Intl

Sat 8/8

6:25 pm-6:35 pm

1 stop35h 10m

$938

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 6/5

8:45 am-8:17 pm

1 stop24h 32m

Chicago O'Hare Intl

Sun 6/21

9:39 pm-6:35 pm

1 stop31h 56m

$938

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 7/6

8:35 pm-10:55 pm

1 stop39h 20m

Chicago O'Hare Intl

Tue 7/21

6:25 pm-6:35 pm

1 stop35h 10m

$940

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 3/19

10:20 pm-1:06 pm

1 stop27h 46m

Chicago O'Hare Intl

Wed 3/25

2:26 pm-7:00 am

1 stop27h 34m

$940

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 2/1

10:25 pm-7:35 am

1 stop23h 10m

Chicago O'Hare Intl

Wed 2/4

7:00 am-12:50 am

2 stops27h 50m

$969

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 7/6

1:45 pm-2:45 pm

2 stops38h 00m

Chicago O'Hare Intl

Tue 7/21

6:53 pm-12:35 pm

2 stops28h 42m

$984

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 3/19

3:10 pm-12:30 pm

3 stops34h 20m

Chicago O'Hare Intl

Wed 3/25

2:10 pm-9:35 am

1 stop30h 25m

$1,028

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Showing 1-10 of 38 results
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Best time to book a flight from Singapore to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Singapore 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 Singapore to Chicago

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

Currently, June is the cheapest month in which you can book a flight from Singapore to Chicago (average of $695). Flying from Singapore to Chicago in January is currently the most expensive (average of $1,147). 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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated January 20, 2026.
Read through reviews of airlines operating flights from Singapore to Chicago, such as Cathay Pacific and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Cathay Pacific
7.6
Good
1,140 reviews

Crew

8.1

Comfort

7.6

Food

7.3

Boarding

7.9

Overall

7.6

Entertainment

7.7

Reviews

1 / 20
4.0
Okay

Anonymous,Jan 2026

HKG - CTS

I went to sleep without dinner, woke up about 4 hours before landing. I asked for breakfast, waited for an hour, nothing, I asked again, still nothing after 15 minutes. I then asked for coffee, when the coffee came after half an hour, it was cold. Crew manager apologised.
Cathay Pacific
7.6
Good
1,140 reviews
Cathay Pacific
7.6
Good
1,140 reviews

Crew

8.1

Comfort

7.6

Food

7.3

Boarding

7.9

Overall

7.6

Entertainment

7.7

Reviews

1 / 20
4.0
Okay

Anonymous,Jan 2026

HKG - CTS

I went to sleep without dinner, woke up about 4 hours before landing. I asked for breakfast, waited for an hour, nothing, I asked again, still nothing after 15 minutes. I then asked for coffee, when the coffee came after half an hour, it was cold. Crew manager apologised.
United Airlines
7.4
Good
9,180 reviews
Cathay Pacific
7.6
Good
1,140 reviews

Crew

8.1

Comfort

7.6

Food

7.3

Boarding

7.9

Overall

7.6

Entertainment

7.7

Reviews

1 / 20
4.0
Okay

Anonymous,Jan 2026

HKG - CTS

I went to sleep without dinner, woke up about 4 hours before landing. I asked for breakfast, waited for an hour, nothing, I asked again, still nothing after 15 minutes. I then asked for coffee, when the coffee came after half an hour, it was cold. Crew manager apologised.

Related info for your journey

Find useful and relevant information for your journey from Singapore to Chicago. 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 Singapore to Chicago?

    There are many flights that can get you from Singapore to Chicago in 20h 52m. Fly via United Airlines or Delta to get the fastest option. The distance from Singapore to Chicago is about 9345 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Japan Airlines, which is currently one of the cheapest options available, starting at $428. EVA Air flights start at $442 while deals on United Airlines start at $577 one-way.

  • Can I find deals for flights from Singapore to Chicago that include hotel bookings?

    Yes. In addition to deals on Singapore to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Singapore to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Singapore to Chicago.

  • Can I find deals for business class flights from Singapore to Chicago?

    Yes. Cheapflights offers flight deals from Singapore to Chicago 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 Singapore to Chicago?

    Currently, June is the cheapest month in which you can book a flight from Singapore to Chicago (average of $695). Flying from Singapore to Chicago in January is currently the most expensive (average of $1,147). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from Singapore to Chicago

Discover the top airline that operate flights from Singapore to Chicago. 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
United AirlinesCheapest$802Average$1,040FlexibilityNo cancel feeOn-time69%

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