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Cheap flights from Singapore to Chicago from S$ 624

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 15-10. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
26 Aug — 2 Sep1
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 27 July 2026.

Thu 10-907:00
SIN
-
ORD
1 stop20h 43m
Air Canada
Thu 24-915:40
ORD
-
SIN
1 stop24h 35m
Air Canada
Deal found 22-7S$ 961
Tue 8-906:15
SIN
-
ORD
2 stops26h 57m
Air Canada
Tue 15-915:40
ORD
-
SIN
1 stop24h 35m
Air Canada
Deal found 25-7S$ 987
Sun 4-1007:00
SIN
-
ORD
1 stop20h 43m
Air Canada
Sun 11-1015:40
ORD
-
SIN
1 stop24h 35m
Air Canada
Deal found 23-7S$ 997
Thu 24-907:00
SIN
-
ORD
1 stop20h 43m
Air Canada
Sun 27-915:40
ORD
-
SIN
1 stop24h 35m
Air Canada
Deal found 26-7S$ 1,001
Tue 8-907:30
SIN
-
MDW
2 stops28h 14m
Delta
Tue 15-909:29
MDW
-
SIN
2 stops30h 31m
Delta
Deal found 25-7S$ 1,438
Wed 23-907:30
SIN
-
MDW
2 stops28h 14m
Delta
Sun 27-909:59
MDW
-
SIN
2 stops24h 56m
Delta
Deal found 26-7S$ 1,440
Mon 7-922:00
SIN
-
MDW
2 stops31h 57m
Delta
Mon 14-909:59
MDW
-
SIN
2 stops24h 56m
Delta
Deal found 24-7S$ 1,531
Thu 10-913:55
SIN
-
MDW
2 stops34h 20m
Multiple Airlines
Thu 24-915:55
MDW
-
SIN
2 stops31h 40m
Multiple Airlines
Deal found 27-7S$ 1,578
Thu 1-1002:00
SIN
-
MDW
3 stops35h 30m
Multiple Airlines
Sat 10-1019:05
MDW
-
SIN
2 stops28h 30m
Multiple Airlines
Deal found 22-7S$ 1,587
Tue 18-813:55
SIN
-
MDW
2 stops28h 50m
Multiple Airlines
Tue 25-821:00
MDW
-
SIN
2 stops26h 35m
Multiple Airlines
Deal found 22-7S$ 1,611

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 27 July 2026.

Round-trip from

S$ 961

One-way from

S$ 624

Popular in

August

Cheapest in

September

Average price

S$ 1,561
Air Canada
  • Air Canada
  • 10-9-24-9
  • 2 total stops
  • 45h 18m total
  • Singapore to Chicago
Search Deals
Air Canada
  • Air Canada
  • 15-10
  • 1 total stop
  • 20h 43m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (S$ 229 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (S$ 137 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 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 27 July 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

Sat 5-9

08:45-18:35

1 stop22h 50m

Chicago O'Hare Intl

Sat 5-9

21:40-18:35

1 stop31h 55m

S$ 1,414

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 2-10

08:45-00:59

1 stop29h 14m

Chicago O'Hare Intl

Sat 10-10

16:40-18:35

1 stop36h 55m

S$ 1,420
Fastest return journey

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 25-9

20:35-06:56

1 stop23h 21m

Chicago O'Hare Intl

Sun 27-9

18:25-06:15

1 stop22h 50m

S$ 1,421

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 18-8

08:45-20:26

1 stop24h 41m

Chicago O'Hare Intl

Tue 25-8

16:20-06:15

1 stop24h 55m

S$ 1,432

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 8-9

07:30-22:44

2 stops28h 14m

Chicago Midway

Tue 15-9

09:29-05:00

2 stops30h 31m

S$ 1,438

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 10-9

13:55-11:15

2 stops34h 20m

Chicago Midway

Thu 24-9

15:55-12:35

2 stops31h 40m

S$ 1,580

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 1-10

02:00-00:10

2 stops35h 10m

Chicago Midway

Sat 10-10

19:05-12:35

2 stops28h 30m

S$ 1,587

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 18-8

13:55-05:45

2 stops28h 50m

Chicago Midway

Tue 25-8

21:00-12:35

2 stops26h 35m

S$ 1,611

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 4-10

18:25-14:43

3 stops33h 18m

Chicago O'Hare Intl

Sun 11-10

14:00-09:40

3 stops30h 40m

S$ 1,632

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 22-12

02:00-01:15

3 stops37h 15m

Chicago Midway

Fri 8-1

15:50-13:05

2 stops31h 15m

S$ 1,658

Flights are sorted by cheapest return flights first.

Deals found on 22-7

Showing 1-10 of 31 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

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 27 July 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
1,504 reviews
Check prices

Entertainment

8.0

Overall

8.5

Food

8.1

Comfort

8.3

Boarding

8.4

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

TPE - SFO

Why when we’re about to board they suddenly announced the letters ABC to board first .. so what is the use us waiting at the door (with wheelchairs) ended up almost at the end to board and I can see people walking boarding first? Is this something new? You go by letters now?
EVA Air
8.5
Very Good
1,504 reviews
EVA Air
8.5
Very Good
1,504 reviews
Check prices

Entertainment

8.0

Overall

8.5

Food

8.1

Comfort

8.3

Boarding

8.4

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

TPE - SFO

Why when we’re about to board they suddenly announced the letters ABC to board first .. so what is the use us waiting at the door (with wheelchairs) ended up almost at the end to board and I can see people walking boarding first? Is this something new? You go by letters now?
Japan Airlines
8.3
Very Good
1,880 reviews
EVA Air
8.5
Very Good
1,504 reviews
Check prices

Entertainment

8.0

Overall

8.5

Food

8.1

Comfort

8.3

Boarding

8.4

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

TPE - SFO

Why when we’re about to board they suddenly announced the letters ABC to board first .. so what is the use us waiting at the door (with wheelchairs) ended up almost at the end to board and I can see people walking boarding first? Is this something new? You go by letters now?
United Airlines
7.4
Good
10,042 reviews
EVA Air
8.5
Very Good
1,504 reviews
Check prices

Entertainment

8.0

Overall

8.5

Food

8.1

Comfort

8.3

Boarding

8.4

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

TPE - SFO

Why when we’re about to board they suddenly announced the letters ABC to board first .. so what is the use us waiting at the door (with wheelchairs) ended up almost at the end to board and I can see people walking boarding first? Is this something new? You go by letters now?

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 and Delta can get you from Singapore to Chicago in just under 22h 50m. Your travel time can differ by up to 5h 24m. 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.

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 27 July 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 1,214AverageS$ 1,534FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
EVA AirCheapestS$ 1,337AverageS$ 1,714FlexibilityNo cancel feeOn-time74%
Search EVA Air flights
Japan AirlinesCheapestS$ 1,418AverageS$ 2,094FlexibilityNo cancel feeOn-time79%
Search Japan Airlines 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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