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Cheap flights from Singapore to Chicago from S$ 661

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 20-8. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
21 Jun — 28 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 22 May 2026.

Sun 4-1007:00
SIN
-
ORD
1 stop20h 43m
Air Canada
Sat 31-1015:55
ORD
-
SIN
2 stops50h 05m
Air Canada
Deal found 19-5S$ 1,046
Tue 16-607:00
SIN
-
ORD
2 stops24h 19m
Air Canada
Sat 20-621:54
ORD
-
SIN
2 stops42h 21m
Air Canada
Deal found 21-5S$ 1,132
Sat 20-607:00
SIN
-
ORD
2 stops26h 16m
Air Canada
Tue 23-606:00
ORD
-
SIN
2 stops34h 15m
Air Canada
Deal found 21-5S$ 1,139
Tue 16-607:00
SIN
-
ORD
2 stops24h 19m
Air Canada
Tue 23-606:00
ORD
-
SIN
2 stops34h 15m
Air Canada
Deal found 21-5S$ 1,149
Sun 21-607:00
SIN
-
ORD
2 stops35h 46m
Air Canada
Sat 27-621:50
ORD
-
SIN
2 stops42h 25m
Air Canada
Deal found 21-5S$ 1,155
Mon 22-606:15
SIN
-
ORD
2 stops38h 35m
Air Canada
Sat 27-621:50
ORD
-
SIN
2 stops42h 25m
Air Canada
Deal found 21-5S$ 1,158
Sun 1-1122:30
SIN
-
ORD
1 stop24h 00m
Korean Air
Mon 16-1111:15
ORD
-
SIN
1 stop43h 10m
Korean Air
Deal found 18-5S$ 1,185
Thu 11-607:00
SIN
-
ORD
2 stops43h 07m
Air Canada
Sat 20-621:54
ORD
-
SIN
2 stops42h 21m
Air Canada
Deal found 21-5S$ 1,197
Thu 16-707:00
SIN
-
ORD
2 stops30h 44m
Air Canada
Sun 16-815:40
ORD
-
SIN
1 stop24h 35m
Air Canada
Deal found 21-5S$ 1,199
Wed 15-706:15
SIN
-
ORD
2 stops26h 50m
Air Canada
Sat 15-819:45
ORD
-
SIN
2 stops44h 30m
Air Canada
Deal found 21-5S$ 1,212
Thu 18-607:00
SIN
-
ORD
1 stop20h 41m
Air Canada
Sat 27-621:50
ORD
-
SIN
2 stops42h 25m
Air Canada
Deal found 21-5S$ 1,214
Thu 8-1001:25
SIN
-
MDW
2 stops33h 20m
Delta
Sun 11-1009:55
MDW
-
SIN
2 stops44h 20m
Delta
Deal found 22-5S$ 1,612

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 22 May 2026.

Round-trip from

S$ 1,046

One-way from

S$ 661

Popular in

August

Cheapest in

February

Average price

S$ 1,369
Air Canada
  • Air Canada
  • 4-10-31-10
  • 3 total stops
  • 70h 48m total
  • Singapore to Chicago
Search Deals
Air Canada
  • Air Canada
  • 20-8
  • 1 total stop
  • 20h 36m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (S$ 347 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 8% 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 22 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

Thu 22-10

01:25-09:30

1 stop21h 05m

Chicago O'Hare Intl

Sun 25-10

12:15-20:25

1 stop43h 10m

S$ 1,220

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 9-10

07:30-23:46

2 stops29h 16m

Chicago O'Hare Intl

Sun 11-10

07:30-05:00

2 stops32h 30m

S$ 1,365

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$ 1,507

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 7-6

20:05-13:55

1 stop30h 50m

Chicago O'Hare Intl

Sun 9-8

16:00-15:05

1 stop34h 05m

S$ 1,586
Fastest return journey

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 21-6

13:10-21:00

1 stop20h 50m

Chicago O'Hare Intl

Mon 22-6

00:30-11:55

1 stop22h 25m

S$ 1,602

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 8-10

01:25-21:45

2 stops33h 20m

Chicago Midway

Sun 11-10

09:55-19:15

2 stops44h 20m

S$ 1,612

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 18-6

18:15-07:45

2 stops26h 30m

Chicago O'Hare Intl

Wed 24-6

10:40-09:05

2 stops33h 25m

S$ 1,649

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$ 1,673

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 3-6

15:20-05:45

2 stops27h 25m

Chicago Midway

Sat 6-6

21:00-11:55

2 stops25h 55m

S$ 1,681

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$ 1,686

Flights are sorted by cheapest return flights first.

Deals found on 21-5

Showing 1-10 of 33 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$ 849). Flying from Singapore to Chicago in December is currently the most expensive (average of S$ 1,228). 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 1,095 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 22 May 2026.
Read reviews from past customers who have flown with EVA Air and United 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
1,457 reviews
Check prices

Boarding

8.4

Crew

8.7

Comfort

8.3

Entertainment

8.0

Food

8.1

Overall

8.5

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
1,457 reviews
EVA Air
8.5
Very Good
1,457 reviews
Check prices

Boarding

8.4

Crew

8.7

Comfort

8.3

Entertainment

8.0

Food

8.1

Overall

8.5

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
9,752 reviews
EVA Air
8.5
Very Good
1,457 reviews
Check prices

Boarding

8.4

Crew

8.7

Comfort

8.3

Entertainment

8.0

Food

8.1

Overall

8.5

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?

    Korean Air, Delta, and Cathay Pacific can get you from Singapore to Chicago in just under 21h 05m. Your travel time can differ by up to 9h 45m. The distance between Singapore and Chicago is about 15039 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$ 849). Flying from Singapore to Chicago in December is currently the most expensive (average of S$ 1,228). 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

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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.
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 22 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 883AverageS$ 1,377FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 889AverageS$ 1,489FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
EVA AirCheapestS$ 1,326AverageS$ 1,700FlexibilityNo 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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