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Cheap flights from Singapore to Chicago from S$ 667

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 25-8. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
16 Jun — 23 Jun1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Singapore to Chicago

Enter your travel dates to find the best prices.

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 17 May 2026.

Fri 30-1008:50
SIN
-
ORD
2 stops24h 20m
Air Canada
Sat 14-1115:55
ORD
-
SIN
2 stops49h 05m
Air Canada
Deal found 16-5S$ 1,051
Tue 18-807:00
SIN
-
ORD
2 stops28h 46m
Air Canada
Sun 6-907:00
ORD
-
SIN
2 stops33h 15m
Air Canada
Deal found 15-5S$ 1,054
Tue 18-807:00
SIN
-
ORD
2 stops29h 59m
Air Canada
Mon 7-921:22
ORD
-
SIN
2 stops42h 53m
Air Canada
Deal found 15-5S$ 1,064
Thu 20-807:00
SIN
-
ORD
2 stops29h 59m
Air Canada
Tue 8-909:50
ORD
-
SIN
2 stops30h 25m
Air Canada
Deal found 12-5S$ 1,068
Tue 18-807:00
SIN
-
ORD
2 stops29h 59m
Air Canada
Wed 9-907:09
ORD
-
SIN
2 stops34h 31m
Air Canada
Deal found 15-5S$ 1,075
Thu 20-807:00
SIN
-
ORD
2 stops28h 46m
Air Canada
Mon 7-908:45
ORD
-
SIN
2 stops27h 00m
Air Canada
Deal found 12-5S$ 1,077
Thu 20-807:00
SIN
-
ORD
2 stops28h 46m
Air Canada
Wed 9-907:09
ORD
-
SIN
2 stops34h 31m
Air Canada
Deal found 12-5S$ 1,079
Wed 14-1022:00
SIN
-
ORD
1 stop24h 30m
Korean Air
Mon 19-1012:10
ORD
-
SIN
1 stop27h 50m
Korean Air
Deal found 13-5S$ 1,191
Mon 26-1001:35
SIN
-
ORD
1 stop20h 55m
Korean Air
Wed 11-1111:15
ORD
-
SIN
1 stop27h 45m
Korean Air
Deal found 13-5S$ 1,192
Fri 23-1007:30
SIN
-
ORD
1 stop39h 00m
Korean Air
Sun 25-1012:15
ORD
-
SIN
1 stop27h 45m
Korean Air
Deal found 16-5S$ 1,223
Wed 14-1007:30
SIN
-
MDW
2 stops27h 15m
Delta
Mon 19-1017:25
MDW
-
SIN
2 stops36h 50m
Delta
Deal found 13-5S$ 1,231
Wed 23-1201:35
SIN
-
MDW
2 stops34h 10m
Delta
Sat 9-117:35
MDW
-
SIN
2 stops40h 35m
Delta
Deal found 14-5S$ 1,530

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 17 May 2026.

Round-trip from

S$ 1,051

One-way from

S$ 667

Popular in

August

Cheapest in

February

Average price

S$ 1,370
Air Canada
  • Air Canada
  • 30-10-14-11
  • 4 total stops
  • 73h 25m total
  • Singapore to Chicago
Search Deals
Air Canada
  • Air Canada
  • 25-8
  • 2 total stops
  • 35h 03m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (S$ 349 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (S$ 139 potential savings vs. average return price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customise 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 200,618 searches. Data last updated 17 May 2026.
Use the filters below to find and compare flights from Singapore to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 7-6

13:45-06:20

2 stops29h 35m

Chicago O'Hare Intl

Sun 9-8

20:20-12:35

2 stops27h 15m

S$ 1,514

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 21-8

15:35-07:45

2 stops29h 10m

Chicago O'Hare Intl

Sat 26-9

10:15-11:25

2 stops36h 10m

S$ 1,658

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 20-8

16:35-07:45

2 stops28h 10m

Chicago O'Hare Intl

Sun 20-9

10:15-09:05

2 stops33h 50m

S$ 1,658

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 7-6

13:45-11:25

2 stops34h 40m

Chicago Midway

Sun 9-8

20:35-12:35

2 stops27h 00m

S$ 1,682

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 19-8

15:20-05:50

2 stops27h 30m

Chicago Midway

Thu 10-9

20:55-11:55

2 stops26h 00m

S$ 1,697

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 10-6

01:30-16:50

1 stop28h 20m

Chicago O'Hare Intl

Wed 17-6

16:33-08:50

2 stops27h 17m

S$ 1,720

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 4-8

15:20-05:50

2 stops27h 30m

Chicago Midway

Thu 27-8

20:55-11:55

2 stops26h 00m

S$ 1,726

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 3-8

13:45-05:00

2 stops28h 15m

Chicago Midway

Sat 29-8

18:25-12:35

2 stops29h 10m

S$ 1,726

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 7-6

01:30-16:50

1 stop28h 20m

Chicago O'Hare Intl

Tue 23-6

06:00-21:15

2 stops26h 15m

S$ 1,726

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 28-6

03:15-18:58

2 stops28h 43m

Chicago O'Hare Intl

Mon 6-7

19:20-15:45

1 stop31h 25m

S$ 1,744

Flights are sorted by cheapest return flights first.

Deals found on 17-5

Showing 1-10 of 35 resultsSorted by cheapest first
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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 return 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, October is the cheapest month in which you can book a flight from Singapore to Chicago (average of S$ 850). Flying from Singapore to Chicago in April is currently the most expensive (average of S$ 1,208). 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.

How often are flights from Singapore to Chicago delayed?

About 100% of weekly flights between Singapore and Chicago have experienced delays in the past year, with the average delay time being 1,189 minutes.

What is the most punctual flight time for Singapore to Chicago flights?

Historically, flights departing in the evening are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.

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 17 May 2026.
Read reviews from past customers who have flown with EVA Air,Japan Airlines, andUnited Airlines from Singapore to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
EVA Air
8.5
Very Good
1,451 reviews
Check prices

Comfort

8.3

Overall

8.5

Entertainment

8.0

Food

8.1

Boarding

8.4

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
EVA Air
8.5
Very Good
1,451 reviews
EVA Air
8.5
Very Good
1,451 reviews
Check prices

Comfort

8.3

Overall

8.5

Entertainment

8.0

Food

8.1

Boarding

8.4

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
Japan Airlines
8.3
Very Good
1,824 reviews
EVA Air
8.5
Very Good
1,451 reviews
Check prices

Comfort

8.3

Overall

8.5

Entertainment

8.0

Food

8.1

Boarding

8.4

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
United Airlines
7.4
Good
9,736 reviews
EVA Air
8.5
Very Good
1,451 reviews
Check prices

Comfort

8.3

Overall

8.5

Entertainment

8.0

Food

8.1

Boarding

8.4

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!

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?

    Malaysia Airlines and Delta can get you from Singapore to Chicago in just under 26h 51m. Your travel time can differ by up to 2h 19m. The distance between Singapore and Chicago is about 15063 km. 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 holiday 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, October is the cheapest month in which you can book a flight from Singapore to Chicago (average of S$ 850). Flying from Singapore to Chicago in April is currently the most expensive (average of S$ 1,208). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Singapore to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Singapore to O'Hare Intl flights
Singapore to Midway flights

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 200,618 searches. Data last updated 17 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 883AverageS$ 1,378FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 889AverageS$ 1,490FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
EVA AirCheapestS$ 1,327AverageS$ 1,701FlexibilityNo cancel feeOn-time74%
Search EVA Air flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Singapore to Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Singapore today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Singapore to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Singapore to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Singapore to Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from Singapore to Chicago with no change fees.

Can Cheapflights notify me if prices for flights from Singapore to Chicago become cheaper?

Not ready to book yet? You can track prices for flights from Singapore to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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