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$570+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
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 December 3, 2025.

This United Airlines deal was found by Cheapflights users on 12/2. 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.
Wed 12/310:10 amSIN - ORD
1 stop20h 50mUnited Airlines
Wed 12/37:35 pmORD - SIN
1 stop34h 40mUnited Airlines
Deal found 12/2$932
This Expedia deal was found by Cheapflights users on 12/2. 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 12/318:15 amSIN - ORD
2 stops39h 29mMultiple Airlines
Wed 1/74:25 pmORD - SIN
1 stop24h 30mMultiple Airlines
Deal found 12/2$1,076
This United Airlines deal was found by Cheapflights users on 12/3. 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.
Sat 12/1310:20 pmSIN - ORD
1 stop20h 40mUnited Airlines
Mon 1/510:10 pmORD - SIN
1 stop32h 05mUnited Airlines
Deal found 12/3$1,093
This United Airlines deal was found by Cheapflights users on 12/2. 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.
Wed 12/3110:20 pmSIN - ORD
2 stops29h 55mUnited Airlines
Wed 1/76:47 amORD - SIN
1 stop23h 28mUnited Airlines
Deal found 12/2$1,151
This Cathay Pacific deal was found by Cheapflights users on 12/2. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:15 pmSIN - ORD
1 stop30h 40mCathay Pacific
Wed 12/312:35 pmORD - SIN
1 stop38h 40mCathay Pacific
Deal found 12/2$1,157
This United Airlines deal was found by Cheapflights users on 12/2. 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.
Mon 12/1510:10 amSIN - ORD
1 stop32h 50mUnited Airlines
Tue 12/309:40 pmORD - SIN
2 stops32h 35mUnited Airlines
Deal found 12/2$1,161
This EVA Air deal was found by Cheapflights users on 12/2. 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 EVA Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/93:45 pmSIN - ORD
1 stop41h 50mEVA Air
Wed 12/3111:30 pmORD - SIN
1 stop25h 00mEVA Air
Deal found 12/2$1,170
This Cathay Pacific deal was found by Cheapflights users on 12/2. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:15 pmSIN - ORD
1 stop30h 40mCathay Pacific
Wed 12/312:35 pmORD - SIN
1 stop35h 10mCathay Pacific
Deal found 12/2$1,254
This KLM deal was found by Cheapflights users on 12/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:40 amSIN - MDW
2 stops28h 38mMultiple Airlines
Wed 12/316:08 pmMDW - SIN
2 stops24h 52mMultiple Airlines
Deal found 12/2$2,231
This KLM deal was found by Cheapflights users on 12/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/91:40 amSIN - MDW
2 stops30h 20mMultiple Airlines
Mon 12/296:08 pmMDW - SIN
2 stops32h 47mMultiple Airlines
Deal found 12/2$2,240
This KLM deal was found by Cheapflights users on 12/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:40 amSIN - MDW
2 stops29h 46mMultiple Airlines
Wed 1/76:14 pmMDW - SIN
2 stops24h 46mMultiple Airlines
Deal found 12/2$2,248
This Delta deal was found by Cheapflights users on 12/2. 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.
Sat 12/131:35 amSIN - MDW
2 stops36h 12mDelta
Mon 12/296:00 amMDW - SIN
2 stops33h 00mDelta
Deal found 12/2$3,317

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 December 3, 2025.

Round-trip from

$860
(Air Canada)

One-way from

$570
(oojo)

Popular in

January

Cheapest in

October

Average price

$1,284
From Singapore to Chicago (CHI)
Search Deals
One-way flight from Singapore to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($170 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 3, 2025.
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

Sun 1/25

10:10 am-4:57 pm

1 stop20h 47m

Chicago O'Hare Intl

Fri 1/30

5:16 pm-8:15 pm

1 stop36h 59m

$931

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 2/18

10:20 pm-2:45 pm

1 stop30h 25m

Chicago O'Hare Intl

Sun 2/22

6:25 am-8:15 pm

1 stop23h 50m

$931

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 2/26

10:10 am-6:41 pm

1 stop22h 31m

Chicago O'Hare Intl

Sun 3/1

6:18 pm-8:00 am

1 stop23h 42m

$931

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 2/10

10:10 am-6:48 pm

1 stop22h 38m

Chicago O'Hare Intl

Fri 2/20

6:25 am-8:15 pm

1 stop23h 50m

$934

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 1/17

8:15 am-1:45 pm

1 stop19h 30m

Chicago O'Hare Intl

Sat 1/24

5:40 pm-5:25 pm

1 stop33h 45m

$954

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 1/25

10:30 pm-10:22 pm

2 stops37h 52m

Chicago Midway

Fri 1/30

6:35 pm-12:10 am

2 stops39h 35m

$955

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 1/19

10:30 pm-12:51 pm

2 stops28h 21m

Chicago Midway

Tue 3/31

9:30 am-5:00 am

2 stops30h 30m

$955

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 1/18

1:35 am-11:53 pm

2 stops36h 18m

Chicago O'Hare Intl

Tue 3/31

7:20 am-11:40 pm

2 stops27h 20m

$955

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 1/25

10:30 pm-11:53 pm

2 stops39h 23m

Chicago O'Hare Intl

Fri 1/30

7:30 am-12:10 am

2 stops26h 40m

$955

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 2/18

11:15 am-6:25 pm

2 stops45h 10m

Chicago O'Hare Intl

Sun 2/22

1:30 pm-6:55 pm

1 stop39h 25m

$959

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/30

Showing 1-10 of 34 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 $1,031). 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 SG to CHI?

Find hourly flight availability from Singapore to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 3, 2025.

One of the essential ways to save on airfare from Singapore to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 21% on airfare.

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 December 3, 2025.
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
1,080 reviews

Comfort

7.6

Boarding

7.9

Overall

7.6

Food

7.3

Crew

8.1

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Anonymous,Sep 2025

PNH - HKG

Everything was good except the typhoon that cause cancelation of my return flight with i had not got any compensation for
Cathay Pacific
7.6
Good
1,080 reviews
Cathay Pacific
7.6
Good
1,080 reviews

Comfort

7.6

Boarding

7.9

Overall

7.6

Food

7.3

Crew

8.1

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Anonymous,Sep 2025

PNH - HKG

Everything was good except the typhoon that cause cancelation of my return flight with i had not got any compensation for
United Airlines
7.4
Good
9,063 reviews
Cathay Pacific
7.6
Good
1,080 reviews

Comfort

7.6

Boarding

7.9

Overall

7.6

Food

7.3

Crew

8.1

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Anonymous,Sep 2025

PNH - HKG

Everything was good except the typhoon that cause cancelation of my return flight with i had not got any compensation for

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 47m. 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 $1,031). 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 December 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$802Average$999FlexibilityNo cancel feeOn-time69%

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