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$483+ 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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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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 October 14, 2025.

This lol.travel deal was found by Cheapflights users on 10/12. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/259:10 amSIN - ORD
2 stops35h 50mAir Canada
Sun 11/91:10 pmORD - SIN
1 stop27h 50mAir Canada
Deal found 10/12$767
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:35 amSIN - ORD
1 stop21h 15mANA
Sun 11/94:25 pmORD - SIN
1 stop24h 30mANA
Deal found 10/12$806
This Air Canada deal was found by Cheapflights users on 10/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/69:00 pmSIN - ORD
2 stops31h 41mAir Canada
Sun 11/98:45 amORD - SIN
2 stops32h 15mAir Canada
Deal found 10/12$817
This Justfly.com deal was found by Cheapflights users on 10/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2711:10 pmSIN - ORD
2 stops52h 31mAir Canada
Thu 11/133:40 pmORD - SIN
1 stop25h 20mAir Canada
Deal found 10/12$831
This Air Canada deal was found by Cheapflights users on 10/13. 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.
Tue 11/258:50 amSIN - ORD
2 stops22h 11mAir Canada
Wed 2/253:40 pmORD - SIN
1 stop25h 20mAir Canada
Deal found 10/13$844
This Air Canada deal was found by Cheapflights users on 10/13. 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.
Mon 11/249:00 pmSIN - ORD
2 stops33h 44mAir Canada
Wed 2/253:40 pmORD - SIN
1 stop25h 20mAir Canada
Deal found 10/13$846
This Air Canada deal was found by Cheapflights users on 10/13. 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.
Tue 11/258:50 amSIN - ORD
1 stop19h 51mAir Canada
Tue 2/241:00 pmORD - SIN
1 stop28h 00mAir Canada
Deal found 10/13$864
This Gotogate deal was found by Cheapflights users on 10/12. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/268:30 amSIN - ORD
2 stops44h 11mAir Canada
Wed 12/33:40 pmORD - SIN
1 stop25h 20mAir Canada
Deal found 10/12$871
This Air Canada deal was found by Cheapflights users on 10/13. 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.
Tue 11/258:50 amSIN - ORD
2 stops22h 11mAir Canada
Sun 2/223:40 pmORD - SIN
1 stop25h 20mAir Canada
Deal found 10/13$883
This Air Canada deal was found by Cheapflights users on 10/13. 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.
Sun 11/238:50 amSIN - ORD
2 stops28h 00mAir Canada
Wed 2/253:40 pmORD - SIN
1 stop25h 20mAir Canada
Deal found 10/13$888
This Air Canada deal was found by Cheapflights users on 10/13. 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 11/228:50 amSIN - ORD
1 stop19h 51mAir Canada
Wed 2/253:40 pmORD - SIN
1 stop25h 20mAir Canada
Deal found 10/13$903
This Delta deal was found by Cheapflights users on 10/12. 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.
Thu 11/610:40 amSIN - MDW
2 stops36h 15mDelta
Sun 11/96:00 amMDW - SIN
2 stops33h 00mDelta
Deal found 10/12$1,075

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 October 14, 2025.

Round-trip from

$767
(lol.travel)

One-way from

$483
(Kiwi.com)

Popular in

January

Cheapest in

October

Average price

$919
From Singapore to Chicago (CHI)
Search Deals
One-way flight from Singapore to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($138 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 14, 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

Sat 10/25

9:10 am-8:00 am

2 stops35h 50m

Chicago O'Hare Intl

Sun 11/9

1:10 pm-7:00 am

1 stop27h 50m

$767

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 3/8

8:50 am-3:50 pm

2 stops45h 00m

Chicago O'Hare Intl

Sun 3/15

3:40 pm-7:00 am

1 stop26h 20m

$803

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 10/27

11:10 pm-2:41 pm

2 stops52h 31m

Chicago O'Hare Intl

Thu 11/13

3:40 pm-7:00 am

1 stop25h 20m

$831

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 11/25

8:50 am-2:41 pm

1 stop19h 51m

Chicago O'Hare Intl

Tue 2/24

1:00 pm-7:00 am

1 stop28h 00m

$864

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 11/26

8:30 am-2:41 pm

2 stops44h 11m

Chicago O'Hare Intl

Wed 12/3

3:40 pm-7:00 am

1 stop25h 20m

$871

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 11/25

8:50 am-5:01 pm

2 stops22h 11m

Chicago O'Hare Intl

Sun 2/22

3:40 pm-7:00 am

1 stop25h 20m

$883

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 10/27

10:20 pm-6:02 am

1 stop20h 42m

Chicago O'Hare Intl

Thu 11/13

6:15 am-8:15 pm

1 stop24h 00m

$931

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 2/10

10:40 am-9:56 am

2 stops37h 16m

Chicago Midway

Fri 2/20

6:00 am-5:00 am

2 stops33h 00m

$1,073

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 11/27

10:40 am-9:01 am

2 stops36h 21m

Chicago Midway

Thu 12/4

6:00 am-5:00 am

2 stops33h 00m

$1,075

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 11/6

10:40 am-8:55 am

2 stops36h 15m

Chicago Midway

Sun 11/9

6:00 am-5:00 am

2 stops33h 00m

$1,075

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/11

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 May is currently the most expensive (average of $1,148). 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 October 14, 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 October 14, 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
1,250 reviews

Comfort

8.3

Boarding

8.4

Crew

8.6

Overall

8.4

Entertainment

8.0

Food

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
EVA Air
8.4
Very good
1,250 reviews
EVA Air
8.4
Very good
1,250 reviews

Comfort

8.3

Boarding

8.4

Crew

8.6

Overall

8.4

Entertainment

8.0

Food

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Cathay Pacific
7.6
Good
1,023 reviews
EVA Air
8.4
Very good
1,250 reviews

Comfort

8.3

Boarding

8.4

Crew

8.6

Overall

8.4

Entertainment

8.0

Food

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
United Airlines
7.4
Good
8,975 reviews
EVA Air
8.4
Very good
1,250 reviews

Comfort

8.3

Boarding

8.4

Crew

8.6

Overall

8.4

Entertainment

8.0

Food

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak

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 35h 50m. Fly via Air Canada 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.

  • 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 May is currently the most expensive (average of $1,148). 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
Porter
Benton Harbor
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 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$802Average$1,000FlexibilityNo cancel feeOn-time69%

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