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$476+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$671
(Flightnetwork)

One-way from

$486
(Travelocity)

Popular in

January

Cheapest in

October

Average price

$1,190
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. 7% potential increase in price ($95 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Air Canada deal was found by Cheapflights users on 7/30. 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.
Thu 9/259:10 amSIN - ORD
1 stop23h 54mAir Canada
Tue 11/257:10 amORD - SIN
2 stops33h 50mAir Canada
Deal found 7/30$701
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
Wed 9/310:10 pmSIN - ORD
1 stop30h 00mANA
Wed 9/2411:50 amORD - SIN
1 stop23h 55mANA
Deal found 7/29$815
This oojo deal was found by Cheapflights users on 7/30. 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 10/2711:00 amSIN - ORD
1 stop35h 30mKorean Air
Thu 11/1311:05 amORD - SIN
1 stop23h 05mKorean Air
Deal found 7/30$933
This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/143:15 pmSIN - ORD
2 stops33h 44mMultiple Airlines
Mon 9/154:00 pmORD - SIN
1 stop24h 30mMultiple Airlines
Deal found 7/31$940
This Delta deal was found by Cheapflights users on 7/31. 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 9/71:10 amSIN - MDW
2 stops30h 27mDelta
Mon 9/159:35 amMDW - SIN
2 stops30h 25mDelta
Deal found 7/31$970
This Korean Air deal was found by Cheapflights users on 7/31. 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 8/111:10 amSIN - MDW
2 stops24h 18mMultiple Airlines
Sun 8/319:31 amMDW - SIN
2 stops25h 09mMultiple Airlines
Deal found 7/31$1,970
This KLM deal was found by Cheapflights users on 7/31. 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.
Fri 9/512:40 amSIN - MDW
2 stops27h 48mKLM
Sat 9/137:15 pmMDW - SIN
2 stops31h 15mKLM
Deal found 7/31$2,068
This Korean Air deal was found by Cheapflights users on 7/30. 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.
Sun 9/211:10 amSIN - MDW
2 stops33h 26mKorean Air
Mon 11/246:00 amMDW - SIN
2 stops28h 10mKorean Air
Deal found 7/30$4,741

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 July 31, 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

Thu 9/25

9:10 am-9:31 am

2 stops37h 21m

Chicago O'Hare Intl

Sun 9/28

3:45 pm-7:05 am

1 stop26h 20m

$671

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 9/3

10:10 pm-3:10 pm

1 stop30h 00m

Chicago O'Hare Intl

Wed 9/24

11:50 am-12:45 am

1 stop23h 55m

$815

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 9/25

9:10 am-4:49 am

3 stops32h 39m

Chicago O'Hare Intl

Sun 9/28

12:54 pm-7:05 am

2 stops29h 11m

$830

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 9/7

1:10 am-6:37 pm

2 stops30h 27m

Chicago Midway

Mon 9/15

9:35 am-5:00 am

2 stops30h 25m

$970

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 8/11

1:10 am-12:28 pm

2 stops24h 18m

Chicago Midway

Sun 8/31

9:31 am-11:40 pm

2 stops25h 09m

$1,970

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 9/5

12:40 am-3:28 pm

2 stops27h 48m

Chicago Midway

Sat 9/13

7:15 pm-3:30 pm

2 stops31h 15m

$2,068

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 9/21

1:10 am-9:36 pm

2 stops33h 26m

Chicago Midway

Mon 11/24

6:00 am-12:10 am

2 stops28h 10m

$4,741

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 11/27

8:50 am-2:41 pm

1 stop19h 51m

$476

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 11/27

8:50 am-10:03 am

3 stops39h 13m

$504

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 1/13

10:20 pm-5:10 am

1 stop20h 50m

$599

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 18 results
1
2

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 July 31, 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 July 31, 2025.
Read through reviews of airlines operating flights from Singapore to Chicago, such as EVA Air, ANA, and Korean Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
EVA Air
8.4
Very good
1,220 reviews

Comfort

8.3

Boarding

8.4

Food

8.1

Crew

8.6

Overall

8.4

Entertainment

8.0

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
1,220 reviews
EVA Air
8.4
Very good
1,220 reviews

Comfort

8.3

Boarding

8.4

Food

8.1

Crew

8.6

Overall

8.4

Entertainment

8.0

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
ANA
8.4
Very good
922 reviews
EVA Air
8.4
Very good
1,220 reviews

Comfort

8.3

Boarding

8.4

Food

8.1

Crew

8.6

Overall

8.4

Entertainment

8.0

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
Korean Air
8.4
Very good
1,121 reviews
EVA Air
8.4
Very good
1,220 reviews

Comfort

8.3

Boarding

8.4

Food

8.1

Crew

8.6

Overall

8.4

Entertainment

8.0

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
Japan Airlines
8.3
Very good
1,536 reviews
EVA Air
8.4
Very good
1,220 reviews

Comfort

8.3

Boarding

8.4

Food

8.1

Crew

8.6

Overall

8.4

Entertainment

8.0

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
Delta
8.0
Very good
7,981 reviews
EVA Air
8.4
Very good
1,220 reviews

Comfort

8.3

Boarding

8.4

Food

8.1

Crew

8.6

Overall

8.4

Entertainment

8.0

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.

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

    To fly one-way, consider booking your trip with Air Canada, which is currently one of the cheapest options available, starting at $486. United Airlines flights start at $600 while deals on Delta start at $627 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, 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
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$802Average$1,000FlexibilityNo cancel feeOn-time69%
Cathay PacificCheapest$882Average$1,337FlexibilityNo cancel feeOn-time72%
EVA AirCheapest$1,011Average$1,076FlexibilityNo cancel feeOn-time74%

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