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Cheap flights from Singapore to Chicago from S$ 755

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 8-5. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
27 May — 3 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 27 April 2026.

Wed 7-1006:15
SIN
-
ORD
1 stop21h 40m
ANA
Thu 22-1007:40
ORD
-
SIN
2 stops26h 40m
ANA
Deal found 23-4S$ 1,091
Sun 11-1022:00
SIN
-
ORD
1 stop24h 30m
Korean Air
Mon 26-1012:15
ORD
-
SIN
1 stop27h 45m
Korean Air
Deal found 27-4S$ 1,179
Mon 28-1222:30
SIN
-
ORD
1 stop24h 00m
Korean Air
Sun 10-111:25
ORD
-
SIN
1 stop43h 00m
Korean Air
Deal found 25-4S$ 1,221
Fri 9-1007:30
SIN
-
ORD
1 stop39h 00m
Multiple Airlines
Sat 24-1012:10
ORD
-
SIN
1 stop44h 45m
Multiple Airlines
Deal found 25-4S$ 1,341
Fri 9-1022:00
SIN
-
ORD
1 stop24h 30m
Delta
Sat 24-1007:10
ORD
-
SIN
2 stops32h 50m
Delta
Deal found 25-4S$ 1,356
Sun 11-1022:00
SIN
-
ORD
1 stop24h 30m
Delta
Mon 26-1007:00
ORD
-
SIN
2 stops28h 10m
Delta
Deal found 27-4S$ 1,357
Sun 27-1201:35
SIN
-
ORD
1 stop20h 55m
Delta
Tue 12-107:00
ORD
-
SIN
2 stops27h 10m
Delta
Deal found 25-4S$ 1,362
Wed 7-1001:25
SIN
-
ORD
2 stops31h 55m
Delta
Fri 23-1007:00
ORD
-
SIN
2 stops27h 55m
Delta
Deal found 24-4S$ 1,364
Wed 7-1022:00
SIN
-
ORD
2 stops29h 13m
Delta
Thu 22-1007:00
ORD
-
SIN
2 stops27h 55m
Delta
Deal found 23-4S$ 1,366
Mon 28-1222:30
SIN
-
ORD
1 stop24h 00m
Korean Air
Tue 12-111:25
ORD
-
SIN
1 stop22h 45m
Korean Air
Deal found 25-4S$ 1,417
Sun 10-501:25
SIN
-
ORD
2 stops33h 25m
Delta
Wed 27-518:20
ORD
-
SIN
2 stops40h 35m
Delta
Deal found 24-4S$ 1,420
Tue 15-1201:35
SIN
-
ORD
1 stop20h 55m
Korean Air
Sun 3-111:25
ORD
-
SIN
1 stop43h 00m
Korean Air
Deal found 23-4S$ 1,421

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 April 2026.

Round-trip from

S$ 1,091

One-way from

S$ 755

Popular in

January

Cheapest in

February

Average price

S$ 1,352
ANA
  • ANA
  • 7-10-22-10
  • 3 total stops
  • 48h 20m total
  • Singapore to Chicago
Search Deals
Delta
  • Delta
  • 8-5
  • 2 total stops
  • 33h 25m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (S$ 25 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 54 potential savings vs. average return price).
Search Deals
Average for round-trip flights in April 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 April 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

Mon 1-6

22:00-23:55

2 stops38h 55m

Chicago O'Hare Intl

Tue 13-10

09:30-05:00

2 stops30h 30m

S$ 1,426

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 8-6

13:45-06:20

2 stops29h 35m

Chicago O'Hare Intl

Sat 20-6

20:05-12:35

2 stops27h 30m

S$ 1,672

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 10-10

13:45-14:12

2 stops37h 27m

Chicago O'Hare Intl

Sun 25-10

15:09-13:05

2 stops32h 56m

S$ 1,699

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 9-5

02:00-06:40

2 stops41h 40m

Chicago O'Hare Intl

Sun 24-5

17:44-12:35

2 stops29h 51m

S$ 1,735

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 29-5

12:30-15:45

2 stops40h 15m

Chicago O'Hare Intl

Tue 13-10

20:35-11:30

2 stops25h 55m

S$ 1,744

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 9-6

21:15-16:50

2 stops32h 35m

Chicago O'Hare Intl

Tue 16-6

06:00-21:15

2 stops26h 15m

S$ 1,753

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 7-6

22:00-16:16

2 stops31h 16m

Chicago Midway

Sun 9-8

06:05-05:00

2 stops33h 55m

S$ 1,808

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 9-5

01:30-16:50

1 stop28h 20m

Chicago O'Hare Intl

Wed 13-5

15:57-16:15

2 stops35h 18m

S$ 1,832

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 7-6

13:45-05:55

2 stops29h 10m

Chicago Midway

Sun 9-8

20:35-12:35

2 stops27h 00m

S$ 1,833

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 4-6

08:45-22:59

1 stop27h 14m

Chicago O'Hare Intl

Tue 13-10

14:10-06:15

2 stops27h 05m

S$ 1,837

Flights are sorted by cheapest return flights first.

Deals found on 24-4

Showing 1-10 of 43 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$ 847). Flying from Singapore to Chicago in May is currently the most expensive (average of S$ 1,198). 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 27 April 2026.
Read reviews from past customers who have flown with EVA Air,ANA, 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
1,432 reviews
Check prices

Boarding

8.4

Overall

8.5

Crew

8.6

Food

8.1

Entertainment

8.0

Comfort

8.3

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
1,432 reviews
EVA Air
8.5
Very Good
1,432 reviews
Check prices

Boarding

8.4

Overall

8.5

Crew

8.6

Food

8.1

Entertainment

8.0

Comfort

8.3

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
8.4
Very Good
1,197 reviews
EVA Air
8.5
Very Good
1,432 reviews
Check prices

Boarding

8.4

Overall

8.5

Crew

8.6

Food

8.1

Entertainment

8.0

Comfort

8.3

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
9,664 reviews
EVA Air
8.5
Very Good
1,432 reviews
Check prices

Boarding

8.4

Overall

8.5

Crew

8.6

Food

8.1

Entertainment

8.0

Comfort

8.3

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?

    Delta and Emirates can get you from Singapore to Chicago in just under 38h 55m. Your travel time can differ by up to 1h 20m. 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$ 847). Flying from Singapore to Chicago in May is currently the most expensive (average of S$ 1,198). 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 4 airlines flying from Singapore to Chicago

Discover the top 4 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 April 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 880AverageS$ 1,373FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 886AverageS$ 1,485FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,049AverageS$ 2,590FlexibilityNo cancel feeOn-time80%
Search ANA flights
EVA AirCheapestS$ 1,322AverageS$ 1,695FlexibilityNo 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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