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Cheap flights from Singapore to Chicago from S$ 752

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 24-9. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
5 Jun — 12 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 6 May 2026.

Sun 18-1000:50
SIN
-
ORD
1 stop27h 05m
ANA
Tue 3-1116:25
ORD
-
SIN
1 stop24h 30m
ANA
Deal found 5-5S$ 1,040
Tue 8-922:00
SIN
-
ORD
1 stop23h 40m
ANA
Wed 23-917:45
ORD
-
SIN
1 stop23h 55m
ANA
Deal found 1-5S$ 1,050
Wed 9-900:50
SIN
-
ORD
1 stop27h 05m
ANA
Wed 23-917:45
ORD
-
SIN
1 stop23h 55m
ANA
Deal found 1-5S$ 1,054
Mon 19-1011:05
SIN
-
ORD
2 stops25h 15m
Multiple Airlines
Tue 3-1116:25
ORD
-
SIN
1 stop35h 10m
Multiple Airlines
Deal found 5-5S$ 1,090
Wed 9-911:05
SIN
-
ORD
2 stops30h 40m
ANA
Wed 23-917:45
ORD
-
SIN
1 stop23h 55m
ANA
Deal found 1-5S$ 1,092
Wed 9-911:05
SIN
-
ORD
2 stops24h 59m
Multiple Airlines
Wed 23-917:45
ORD
-
SIN
1 stop23h 55m
Multiple Airlines
Deal found 2-5S$ 1,094
Sun 18-1022:00
SIN
-
ORD
1 stop24h 30m
Korean Air
Mon 2-1111:15
ORD
-
SIN
1 stop43h 10m
Korean Air
Deal found 4-5S$ 1,184
Mon 12-1001:25
SIN
-
ORD
1 stop21h 05m
Korean Air
Wed 28-1012:15
ORD
-
SIN
1 stop22h 55m
Korean Air
Deal found 1-5S$ 1,186
Mon 28-1201:35
SIN
-
ORD
1 stop20h 55m
Korean Air
Wed 13-111:25
ORD
-
SIN
1 stop22h 45m
Korean Air
Deal found 1-5S$ 1,220
Wed 23-1210:40
SIN
-
ORD
1 stop35h 50m
Korean Air
Sun 3-111:25
ORD
-
SIN
1 stop43h 00m
Korean Air
Deal found 2-5S$ 1,221
Thu 15-1007:30
SIN
-
MDW
2 stops27h 15m
Delta
Thu 29-1006:00
MDW
-
SIN
2 stops29h 10m
Delta
Deal found 1-5S$ 1,424
Wed 30-922:00
SIN
-
MDW
2 stops27h 30m
Delta
Thu 8-1006:00
MDW
-
SIN
2 stops28h 55m
Delta
Deal found 2-5S$ 1,565

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 6 May 2026.

Round-trip from

S$ 1,040

One-way from

S$ 752

Popular in

January

Cheapest in

February

Average price

S$ 1,358
ANA
  • ANA
  • 18-10-3-11
  • 2 total stops
  • 51h 35m total
  • Singapore to Chicago
Search Deals
Korean Air
  • Korean Air
  • 24-9
  • 1 total stop
  • 21h 05m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (S$ 23 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 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 6 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

Mon 19-10

07:30-21:34

2 stops27h 04m

Chicago O'Hare Intl

Tue 3-11

19:55-20:25

2 stops34h 30m

S$ 1,225

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 12-10

01:25-09:30

1 stop21h 05m

Chicago O'Hare Intl

Wed 28-10

06:00-05:00

2 stops34h 00m

S$ 1,357

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 9-9

07:30-20:17

2 stops25h 47m

Chicago O'Hare Intl

Wed 23-9

12:15-23:55

2 stops46h 40m

S$ 1,425

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 30-9

22:00-12:30

2 stops27h 30m

Chicago Midway

Thu 8-10

06:00-23:55

2 stops28h 55m

S$ 1,565

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 19-10

15:20-20:45

1 stop42h 25m

Chicago O'Hare Intl

Tue 20-10

00:30-13:55

1 stop24h 25m

S$ 1,603

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 19-10

19:40-15:05

1 stop32h 25m

Chicago O'Hare Intl

Wed 21-10

16:50-15:45

2 stops33h 55m

S$ 1,662

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 8-9

08:45-00:55

1 stop29h 10m

Chicago O'Hare Intl

Wed 23-9

12:45-06:15

2 stops28h 30m

S$ 1,672

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 9-9

07:30-21:46

2 stops27h 16m

Chicago Midway

Wed 23-9

17:25-19:15

2 stops36h 50m

S$ 1,693
Fastest return journey

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 14-10

20:35-11:04

2 stops27h 29m

Chicago O'Hare Intl

Thu 29-10

07:45-20:15

1 stop23h 30m

S$ 1,719

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$ 1,738

Flights are sorted by cheapest return flights first.

Deals found on 6-5

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

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 6 May 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
1,445 reviews
Check prices

Crew

8.6

Overall

8.5

Comfort

8.3

Food

8.1

Boarding

8.4

Entertainment

8.0

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
1,445 reviews
EVA Air
8.5
Very Good
1,445 reviews
Check prices

Crew

8.6

Overall

8.5

Comfort

8.3

Food

8.1

Boarding

8.4

Entertainment

8.0

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
1,806 reviews
EVA Air
8.5
Very Good
1,445 reviews
Check prices

Crew

8.6

Overall

8.5

Comfort

8.3

Food

8.1

Boarding

8.4

Entertainment

8.0

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
9,684 reviews
EVA Air
8.5
Very Good
1,445 reviews
Check prices

Crew

8.6

Overall

8.5

Comfort

8.3

Food

8.1

Boarding

8.4

Entertainment

8.0

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 EVA Air can get you from Singapore to Chicago in just under 27h 04m. Your travel time can differ by up to 15h 21m. 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 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 6 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 880AverageS$ 1,374FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 886AverageS$ 1,485FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
EVA AirCheapestS$ 1,323AverageS$ 1,696FlexibilityNo 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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