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$507+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheap flight deals from Singapore to Chicago

Keep the following information in mind while searching for Singapore to Chicago flight deals. Data was last updated August 13, 2025.

Round-trip from

$767
(Trip.com)

One-way from

$507
(EaseMyTrip)

Popular in

January

Cheapest in

October

Average price

$1,246
From Singapore to Chicago (CHI)
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One-way flight from Singapore to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($111 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 13, 2025.

This Trip.com deal was found by Cheapflights users on 8/12. 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.
Fri 9/268:45 amSIN - ORD
2 stops26h 58mMultiple Airlines
Fri 10/36:30 amORD - SIN
2 stops46h 55mMultiple Airlines
Deal found 8/12$767
This Air Canada deal was found by Cheapflights users on 8/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/279:10 amSIN - ORD
2 stops40h 22mAir Canada
Sat 10/41:27 pmORD - SIN
2 stops52h 38mAir Canada
Deal found 8/13$796
This Air Canada deal was found by Cheapflights users on 8/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/209:10 amSIN - ORD
2 stops40h 22mAir Canada
Sat 10/41:27 pmORD - SIN
2 stops52h 38mAir Canada
Deal found 8/11$797
This Cheapflightsfares deal was found by Cheapflights users on 8/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/910:10 pmSIN - ORD
1 stop30h 00mANA
Tue 9/1612:40 pmORD - SIN
1 stop29h 00mANA
Deal found 8/11$810
This Gotogate deal was found by Cheapflights users on 8/13. 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.
Tue 9/239:10 amSIN - ORD
2 stops36h 58mAir Canada
Sat 9/273:50 pmORD - SIN
2 stops43h 55mAir Canada
Deal found 8/13$811
This Gotogate deal was found by Cheapflights users on 8/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/86:15 amSIN - ORD
1 stop21h 40mANA
Sun 9/145:45 pmORD - SIN
1 stop23h 55mANA
Deal found 8/11$820
This FlightHub deal was found by Cheapflights users on 8/13. 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.
Tue 9/210:10 pmSIN - ORD
1 stop30h 00mANA
Mon 9/2211:50 amORD - SIN
1 stop23h 55mANA
Deal found 8/13$823
This Gotogate deal was found by Cheapflights users on 8/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:15 amSIN - ORD
1 stop21h 40mANA
Tue 9/235:45 pmORD - SIN
1 stop34h 30mANA
Deal found 8/11$825
This Delta deal was found by Cheapflights users on 8/13. 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.
Tue 9/21:10 amSIN - MDW
2 stops33h 16mDelta
Sat 9/274:25 pmMDW - SIN
2 stops47h 35mDelta
Deal found 8/13$974
This Delta deal was found by Cheapflights users on 8/10. 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.
Mon 9/810:30 pmSIN - MDW
2 stops26h 58mDelta
Sat 9/137:15 pmMDW - SIN
2 stops39h 25mDelta
Deal found 8/10$975
This Delta deal was found by Cheapflights users on 8/13. 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 9/110:30 pmSIN - MDW
2 stops35h 56mDelta
Sat 9/274:25 pmMDW - SIN
2 stops47h 35mDelta
Deal found 8/13$1,083
This Delta deal was found by Cheapflights users on 8/12. 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.
Sun 9/211:10 amSIN - MDW
2 stops33h 26mDelta
Mon 9/299:35 amMDW - SIN
2 stops25h 05mDelta
Deal found 8/12$1,274

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 August 13, 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

Fri 9/26

8:45 am-10:43 pm

2 stops26h 58m

Chicago O'Hare Intl

Fri 10/3

6:30 am-6:25 pm

2 stops46h 55m

$767

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 1/26

10:20 pm-9:13 am

2 stops48h 53m

Chicago O'Hare Intl

Wed 2/11

8:15 pm-7:00 am

2 stops44h 45m

$781

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 1/25

8:50 am-7:30 pm

2 stops24h 40m

Chicago O'Hare Intl

Tue 2/10

3:40 pm-7:00 am

1 stop25h 20m

$789

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 9/27

9:10 am-12:32 pm

2 stops40h 22m

Chicago O'Hare Intl

Sat 10/4

1:27 pm-7:05 am

2 stops52h 38m

$796

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 9/20

9:10 am-12:32 pm

2 stops40h 22m

Chicago O'Hare Intl

Sat 10/4

1:27 pm-7:05 am

2 stops52h 38m

$797

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 9/9

6:15 am-2:55 pm

1 stop21h 40m

Chicago O'Hare Intl

Tue 9/23

5:45 pm-5:15 pm

1 stop34h 30m

$818

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 9/8

6:15 am-2:55 pm

1 stop21h 40m

Chicago O'Hare Intl

Sun 9/14

5:45 pm-6:40 am

1 stop23h 55m

$820

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 9/4

7:30 am-9:26 pm

2 stops26h 56m

Chicago Midway

Sat 9/27

4:25 pm-5:00 am

2 stops47h 35m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 9/2

10:30 pm-9:26 pm

2 stops35h 56m

Chicago Midway

Mon 9/29

9:20 am-5:00 am

2 stops30h 40m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 9/4

7:30 am-9:26 pm

2 stops26h 56m

Chicago Midway

Mon 9/29

9:35 am-5:00 am

2 stops30h 25m

$974

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 32 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, August is the cheapest month in which you can book a flight from Singapore to Chicago (average of $245). Flying from Singapore to Chicago in March is currently the most expensive (average of $321). 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 August 13, 2025.

When flying from Singapore to Chicago, 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 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 August 13, 2025.
Read through reviews of airlines operating flights from Singapore to Chicago, such as EVA Air, Cathay Pacific, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
EVA Air
8.4
Very good
1,230 reviews

Crew

8.6

Comfort

8.3

Boarding

8.4

Entertainment

8.0

Food

8.1

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount
EVA Air
8.4
Very good
1,230 reviews
EVA Air
8.4
Very good
1,230 reviews

Crew

8.6

Comfort

8.3

Boarding

8.4

Entertainment

8.0

Food

8.1

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount
Cathay Pacific
7.6
Good
968 reviews
EVA Air
8.4
Very good
1,230 reviews

Crew

8.6

Comfort

8.3

Boarding

8.4

Entertainment

8.0

Food

8.1

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount
United Airlines
7.4
Good
8,920 reviews
EVA Air
8.4
Very good
1,230 reviews

Crew

8.6

Comfort

8.3

Boarding

8.4

Entertainment

8.0

Food

8.1

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

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.

  • 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, August is the cheapest month in which you can book a flight from Singapore to Chicago (average of $245). Flying from Singapore to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Singapore to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Singapore to Chicago

Discover the top 3 airlines 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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$802Average$1,000FlexibilityNo cancel feeOn-time69%
Cathay PacificCheapest$871Average$1,125FlexibilityNo cancel feeOn-time72%
EVA AirCheapest$1,024Average$1,267FlexibilityNo cancel feeOn-time74%

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