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Cheap flights from Singapore to Chicago from S$ 595

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 14-9. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
3 Jul — 10 Jul1
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 3 June 2026.

Fri 13-1108:50
SIN
-
ORD
1 stop19h 51m
Air Canada
Sat 28-1118:30
ORD
-
SIN
2 stops46h 30m
Air Canada
Deal found 30-5S$ 1,018
Tue 9-620:35
SIN
-
ORD
1 stop22h 18m
United Airlines
Tue 7-715:57
ORD
-
SIN
1 stop37h 38m
United Airlines
Deal found 2-6S$ 1,031
Mon 6-708:45
SIN
-
ORD
1 stop25h 53m
United Airlines
Mon 20-706:10
ORD
-
SIN
1 stop23h 25m
United Airlines
Deal found 30-5S$ 1,036
Wed 8-706:15
SIN
-
ORD
2 stops26h 50m
Air Canada
Wed 22-709:50
ORD
-
SIN
2 stops25h 55m
Air Canada
Deal found 29-5S$ 1,043
Sat 14-1108:50
SIN
-
ORD
1 stop19h 51m
Air Canada
Sun 29-1115:40
ORD
-
SIN
1 stop25h 20m
Air Canada
Deal found 31-5S$ 1,046
Mon 22-608:45
SIN
-
ORD
1 stop25h 43m
Lufthansa
Wed 8-706:10
ORD
-
SIN
1 stop23h 25m
Lufthansa
Deal found 29-5S$ 1,051
Fri 11-906:15
SIN
-
ORD
1 stop21h 40m
ANA
Sun 13-917:45
ORD
-
SIN
1 stop23h 55m
ANA
Deal found 28-5S$ 1,052
Wed 2-906:15
SIN
-
ORD
2 stops26h 50m
Air Canada
Sat 12-920:40
ORD
-
SIN
2 stops39h 05m
Air Canada
Deal found 2-6S$ 1,063
Tue 16-607:00
SIN
-
ORD
1 stop35h 40m
Air Canada
Tue 23-606:00
ORD
-
SIN
2 stops34h 15m
Air Canada
Deal found 31-5S$ 1,065
Thu 10-901:25
SIN
-
MDW
2 stops33h 21m
Delta
Sun 13-913:05
MDW
-
SIN
2 stops41h 10m
Delta
Deal found 28-5S$ 1,225
Fri 2-1001:25
SIN
-
MDW
2 stops34h 00m
Delta
Mon 5-1009:49
MDW
-
SIN
2 stops30h 11m
Delta
Deal found 31-5S$ 1,226
Tue 9-601:25
SIN
-
MDW
2 stops33h 52m
Delta
Thu 9-709:49
MDW
-
SIN
2 stops25h 06m
Delta
Deal found 29-5S$ 1,423

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 3 June 2026.

Round-trip from

S$ 1,018

One-way from

S$ 595

Popular in

August

Cheapest in

February

Average price

S$ 1,591
Air Canada
  • Air Canada
  • 13-11-28-11
  • 3 total stops
  • 66h 21m total
  • Singapore to Chicago
Search Deals
Air Canada
  • Air Canada
  • 14-9
  • 2 total stops
  • 38h 36m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (S$ 362 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (S$ 135 potential savings vs. average return price).
Search Deals
Average for round-trip flights in June 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 3 June 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 14-6

08:45-00:59

1 stop29h 14m

Chicago O'Hare Intl

Fri 3-7

21:35-06:15

1 stop43h 40m

S$ 1,031

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 13-6

01:25-22:17

2 stops33h 52m

Chicago Midway

Wed 8-7

06:00-19:15

2 stops48h 15m

S$ 1,423

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 24-9

13:45-12:07

2 stops35h 22m

Chicago O'Hare Intl

Sat 26-9

13:03-12:35

2 stops34h 32m

S$ 1,449

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 14-6

08:45-00:59

1 stop29h 14m

Chicago O'Hare Intl

Mon 6-7

18:20-18:35

1 stop35h 15m

S$ 1,486

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 3-11

22:30-16:25

2 stops31h 55m

Chicago Midway

Sat 7-11

06:00-00:10

2 stops28h 10m

S$ 1,563

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 21-6

18:15-07:45

2 stops26h 30m

Chicago O'Hare Intl

Fri 26-6

10:40-10:15

2 stops34h 35m

S$ 1,569

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 1-9

01:25-22:36

2 stops34h 11m

Chicago Midway

Sat 12-9

18:45-23:55

2 stops40h 10m

S$ 1,616

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 1-8

13:45-12:03

2 stops35h 18m

Chicago O'Hare Intl

Sun 16-8

20:20-12:35

2 stops27h 15m

S$ 1,625

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 13-6

20:35-05:53

1 stop22h 18m

Chicago O'Hare Intl

Sat 4-7

08:50-06:15

1 stop32h 25m

S$ 1,638

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 16-6

20:35-05:53

1 stop22h 18m

Chicago O'Hare Intl

Sat 27-6

10:00-18:35

2 stops43h 35m

S$ 1,641

Flights are sorted by cheapest return flights first.

Deals found on 30-5

Showing 1-10 of 40 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 April is currently the most expensive (average of S$ 1,207). 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 3 June 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
1,465 reviews
Check prices

Overall

8.5

Crew

8.7

Boarding

8.4

Comfort

8.3

Food

8.1

Entertainment

8.0

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
1,465 reviews
EVA Air
8.5
Very Good
1,465 reviews
Check prices

Overall

8.5

Crew

8.7

Boarding

8.4

Comfort

8.3

Food

8.1

Entertainment

8.0

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
1,835 reviews
EVA Air
8.5
Very Good
1,465 reviews
Check prices

Overall

8.5

Crew

8.7

Boarding

8.4

Comfort

8.3

Food

8.1

Entertainment

8.0

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
9,771 reviews
EVA Air
8.5
Very Good
1,465 reviews
Check prices

Overall

8.5

Crew

8.7

Boarding

8.4

Comfort

8.3

Food

8.1

Entertainment

8.0

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?

    United Airlines, Delta, and Malaysia Airlines can get you from Singapore to Chicago in just under 26h 30m. Your travel time can differ by up to 7h 22m. 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 April is currently the most expensive (average of S$ 1,207). 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 3 June 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 882AverageS$ 1,376FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 888AverageS$ 1,488FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
EVA AirCheapestS$ 1,325AverageS$ 1,699FlexibilityNo 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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