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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 30-10. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
11 Aug — 18 Aug1
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 12 July 2026.

Thu 24-907:00
SIN
-
ORD
1 stop20h 43m
Air Canada
Sun 27-915:40
ORD
-
SIN
1 stop24h 35m
Air Canada
Deal found 9-7S$ 999
Sun 12-722:00
SIN
-
ORD
1 stop30h 25m
ANA
Sat 18-717:45
ORD
-
SIN
1 stop34h 30m
ANA
Deal found 9-7S$ 1,002
Sun 12-722:00
SIN
-
ORD
1 stop30h 25m
ANA
Sat 25-717:45
ORD
-
SIN
1 stop23h 55m
ANA
Deal found 9-7S$ 1,032
Tue 22-901:45
SIN
-
ORD
2 stops25h 58m
Multiple Airlines
Sun 27-915:40
ORD
-
SIN
1 stop24h 35m
Multiple Airlines
Deal found 9-7S$ 1,037
Thu 9-722:00
SIN
-
ORD
1 stop30h 25m
ANA
Wed 22-712:15
ORD
-
SIN
1 stop29h 25m
ANA
Deal found 7-7S$ 1,039
Thu 15-1007:00
SIN
-
ORD
1 stop26h 06m
Air Canada
Mon 19-1019:45
ORD
-
SIN
1 stop44h 30m
Air Canada
Deal found 9-7S$ 1,046
Thu 27-822:00
SIN
-
ORD
1 stop23h 40m
ANA
Sun 30-817:45
ORD
-
SIN
1 stop23h 55m
ANA
Deal found 9-7S$ 1,074
Wed 23-922:00
SIN
-
MDW
2 stops37h 45m
Delta
Mon 28-917:11
MDW
-
SIN
2 stops37h 04m
Delta
Deal found 9-7S$ 1,485
Wed 26-807:30
SIN
-
MDW
2 stops28h 06m
Delta
Wed 7-1009:29
MDW
-
SIN
2 stops30h 31m
Delta
Deal found 7-7S$ 1,486
Sun 23-813:45
SIN
-
MDW
2 stops29h 00m
Multiple Airlines
Mon 31-815:55
MDW
-
SIN
2 stops31h 40m
Multiple Airlines
Deal found 9-7S$ 1,589
Thu 27-813:45
SIN
-
MDW
2 stops29h 00m
Multiple Airlines
Sun 30-820:45
MDW
-
SIN
2 stops38h 50m
Multiple Airlines
Deal found 10-7S$ 1,593
Wed 26-801:25
SIN
-
MDW
2 stops27h 50m
Delta
Sun 30-809:59
MDW
-
SIN
2 stops24h 56m
Delta
Deal found 9-7S$ 1,625

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 12 July 2026.

Round-trip from

S$ 999

One-way from

S$ 661

Popular in

August

Cheapest in

September

Average price

S$ 1,508
Air Canada
  • Air Canada
  • 24-9-27-9
  • 2 total stops
  • 45h 18m total
  • Singapore to Chicago
Search Deals
Air Canada
  • Air Canada
  • 30-10
  • 2 total stops
  • 45h 30m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (S$ 225 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (S$ 140 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 12 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

Wed 23-9

20:35-05:23

1 stop21h 48m

Chicago O'Hare Intl

Sun 27-9

17:45-06:40

1 stop23h 55m

S$ 1,325

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 23-9

20:35-16:41

1 stop33h 06m

Chicago O'Hare Intl

Mon 28-9

17:45-06:40

1 stop23h 55m

S$ 1,325

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 22-12

10:10-20:22

1 stop24h 12m

Chicago O'Hare Intl

Wed 6-1

10:30-06:55

1 stop30h 25m

S$ 1,390

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 23-8

20:35-05:59

1 stop22h 24m

Chicago O'Hare Intl

Sun 30-8

15:35-18:35

1 stop38h 00m

S$ 1,421

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 6-12

20:45-16:55

1 stop34h 10m

Chicago O'Hare Intl

Wed 20-1

22:45-23:45

1 stop35h 00m

S$ 1,476

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 9-12

01:35-08:30

1 stop20h 55m

Chicago O'Hare Intl

Thu 21-1

11:25-00:10

1 stop22h 45m

S$ 1,483

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 24-9

07:30-13:20

2 stops42h 50m

Chicago Midway

Sun 27-9

09:59-19:15

2 stops44h 16m

S$ 1,485

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 10-12

01:35-21:53

2 stops34h 18m

Chicago O'Hare Intl

Mon 18-1

19:55-00:10

2 stops38h 15m

S$ 1,486

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 22-12

08:40-07:50

2 stops37h 10m

Chicago O'Hare Intl

Sun 3-1

12:50-07:00

2 stops28h 10m

S$ 1,523

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 5-8

08:45-00:59

1 stop29h 14m

Chicago O'Hare Intl

Fri 14-8

22:00-18:35

1 stop31h 35m

S$ 1,526

Flights are sorted by cheapest return flights first.

Deals found on 11-7

Showing 1-10 of 38 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 12 July 2026.
Read reviews from past customers who have flown with EVA Air,Japan Airlines, andANA 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
1,498 reviews
Check prices

Entertainment

8.0

Comfort

8.3

Crew

8.7

Boarding

8.4

Food

8.1

Overall

8.5

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
1,498 reviews
EVA Air
8.5
Very Good
1,498 reviews
Check prices

Entertainment

8.0

Comfort

8.3

Crew

8.7

Boarding

8.4

Food

8.1

Overall

8.5

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
1,869 reviews
EVA Air
8.5
Very Good
1,498 reviews
Check prices

Entertainment

8.0

Comfort

8.3

Crew

8.7

Boarding

8.4

Food

8.1

Overall

8.5

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?
ANA
8.3
Very Good
1,271 reviews
EVA Air
8.5
Very Good
1,498 reviews
Check prices

Entertainment

8.0

Comfort

8.3

Crew

8.7

Boarding

8.4

Food

8.1

Overall

8.5

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
9,980 reviews
EVA Air
8.5
Very Good
1,498 reviews
Check prices

Entertainment

8.0

Comfort

8.3

Crew

8.7

Boarding

8.4

Food

8.1

Overall

8.5

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, Philippine Airlines, and Delta can get you from Singapore to Chicago in just under 22h 24m. Your travel time can differ by up to 20h 26m. 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

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 12 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Japan AirlinesCheapestS$ 957AverageS$ 1,742FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
United AirlinesCheapestS$ 1,215AverageS$ 1,535FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
EVA AirCheapestS$ 1,338AverageS$ 1,716FlexibilityNo 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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