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Cheap flights from Singapore to Chicago from S$ 749

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 4-5. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
9 Apr — 16 Apr1
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 10 March 2026.

Thu 4-608:45
SIN
-
ORD
1 stop24h 39m
United Airlines
Mon 10-806:10
ORD
-
SIN
1 stop23h 25m
United Airlines
Deal found 7-3S$ 1,208
Thu 23-409:00
SIN
-
ORD
1 stop21h 05m
United Airlines
Thu 30-416:35
ORD
-
SIN
1 stop37h 00m
United Airlines
Deal found 9-3S$ 1,209
Thu 4-620:35
SIN
-
ORD
1 stop22h 22m
United Airlines
Sun 9-814:29
ORD
-
SIN
1 stop26h 46m
United Airlines
Deal found 8-3S$ 1,210
Mon 20-401:25
SIN
-
ORD
2 stops32h 53m
Delta
Tue 28-408:52
ORD
-
SIN
2 stops26h 03m
Delta
Deal found 6-3S$ 1,226
Wed 22-407:30
SIN
-
ORD
2 stops29h 28m
Delta
Sun 26-407:15
ORD
-
SIN
2 stops27h 40m
Delta
Deal found 5-3S$ 1,228
Tue 21-410:25
SIN
-
ORD
1 stop36h 15m
Turkish Airlines
Tue 28-420:10
ORD
-
SIN
1 stop23h 35m
Turkish Airlines
Deal found 7-3S$ 1,240
Thu 23-410:25
SIN
-
ORD
1 stop44h 50m
Turkish Airlines
Thu 30-411:25
ORD
-
SIN
1 stop33h 05m
Turkish Airlines
Deal found 8-3S$ 1,264
Sun 19-410:20
SIN
-
ORD
2 stops37h 50m
Air India
Sun 26-413:10
ORD
-
SIN
1 stop43h 35m
Air India
Deal found 5-3S$ 1,304
Sun 19-410:20
SIN
-
ORD
2 stops37h 50m
Multiple Airlines
Sun 26-416:20
ORD
-
SIN
2 stops36h 20m
Multiple Airlines
Deal found 5-3S$ 1,322
Wed 8-410:30
SIN
-
ORD
3 stops35h 05m
Multiple Airlines
Sun 12-414:00
ORD
-
SIN
3 stops34h 35m
Multiple Airlines
Deal found 10-3S$ 1,349
Tue 21-422:00
SIN
-
MDW
2 stops31h 26m
Delta
Tue 28-409:27
MDW
-
SIN
2 stops25h 28m
Delta
Deal found 7-3S$ 1,365
Wed 22-422:00
SIN
-
MDW
2 stops31h 26m
Delta
Sun 26-409:27
MDW
-
SIN
2 stops25h 28m
Delta
Deal found 5-3S$ 1,368

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 10 March 2026.

Round-trip from

S$ 1,208

One-way from

S$ 749

Popular in

January

Cheapest in

February

Average price

S$ 1,418
United Airlines
  • United Airlines
  • 4-6-12-8
  • 2 total stops
  • 48h 14m total
  • Singapore to Chicago
Search Deals
United Airlines
  • United Airlines
  • 4-5
  • 1 total stop
  • 41h 24m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (S$ 37 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 56 potential savings vs. average return price).
Search Deals
Average for round-trip flights in March 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 10 March 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

Thu 16-4

09:00-23:29

1 stop27h 29m

Chicago O'Hare Intl

Mon 20-4

06:25-18:35

1 stop23h 10m

S$ 1,208

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 6-4

09:00-05:27

1 stop33h 27m

Chicago O'Hare Intl

Sun 19-4

06:25-18:35

1 stop23h 10m

S$ 1,208

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 22-4

20:35-06:20

1 stop22h 45m

Chicago O'Hare Intl

Sun 26-4

21:40-18:35

1 stop31h 55m

S$ 1,210

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 22-4

07:30-23:58

2 stops29h 28m

Chicago O'Hare Intl

Sun 26-4

07:15-23:55

2 stops27h 40m

S$ 1,228

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 21-4

22:00-21:25

2 stops36h 25m

Chicago O'Hare Intl

Tue 28-4

12:20-05:00

1 stop27h 40m

S$ 1,365

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 22-4

22:00-16:26

2 stops31h 26m

Chicago Midway

Sun 26-4

09:27-23:55

2 stops25h 28m

S$ 1,368

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 20-4

13:45-05:40

2 stops28h 55m

Chicago Midway

Mon 27-4

11:00-12:35

2 stops36h 35m

S$ 1,422

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 16-4

02:00-22:20

2 stops33h 20m

Chicago Midway

Fri 24-4

11:00-12:35

2 stops36h 35m

S$ 1,432

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 23-4

13:45-05:40

2 stops28h 55m

Chicago Midway

Thu 30-4

18:10-12:35

2 stops29h 25m

S$ 1,434

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 17-4

20:35-09:38

2 stops26h 03m

Chicago O'Hare Intl

Fri 24-4

16:40-06:45

1 stop25h 05m

S$ 1,455

Flights are sorted by cheapest return flights first.

Deals found on 5-3

Showing 1-10 of 41 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
No data available for this route at this time. Please check back soon.

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 10 March 2026.
Read reviews from past customers who have flown with EVA Air,ANA, andCathay Pacific 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
8.4
Very Good
1,370 reviews
Check prices

Food

8.1

Boarding

8.4

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
8.0
Excellent

Jack,Feb 2026

TPE - SFO

Premium Economy for a.long-haul flight was worth it for the extra room. It is a 2-5-2 layout, so unless you have a family, get a seat in the 2-seat section. Nice slippers and goody bag. Food was tasty, although it seemed a bit repetitive (i.e., each meal used the same ingredients slightly re-configured). Staff were excellent.
EVA Air
8.4
Very Good
1,370 reviews
EVA Air
8.4
Very Good
1,370 reviews
Check prices

Food

8.1

Boarding

8.4

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
8.0
Excellent

Jack,Feb 2026

TPE - SFO

Premium Economy for a.long-haul flight was worth it for the extra room. It is a 2-5-2 layout, so unless you have a family, get a seat in the 2-seat section. Nice slippers and goody bag. Food was tasty, although it seemed a bit repetitive (i.e., each meal used the same ingredients slightly re-configured). Staff were excellent.
ANA
8.4
Very Good
1,119 reviews
EVA Air
8.4
Very Good
1,370 reviews
Check prices

Food

8.1

Boarding

8.4

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
8.0
Excellent

Jack,Feb 2026

TPE - SFO

Premium Economy for a.long-haul flight was worth it for the extra room. It is a 2-5-2 layout, so unless you have a family, get a seat in the 2-seat section. Nice slippers and goody bag. Food was tasty, although it seemed a bit repetitive (i.e., each meal used the same ingredients slightly re-configured). Staff were excellent.
Cathay Pacific
7.6
Good
1,202 reviews
EVA Air
8.4
Very Good
1,370 reviews
Check prices

Food

8.1

Boarding

8.4

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
8.0
Excellent

Jack,Feb 2026

TPE - SFO

Premium Economy for a.long-haul flight was worth it for the extra room. It is a 2-5-2 layout, so unless you have a family, get a seat in the 2-seat section. Nice slippers and goody bag. Food was tasty, although it seemed a bit repetitive (i.e., each meal used the same ingredients slightly re-configured). Staff were excellent.
United Airlines
7.4
Good
9,409 reviews
EVA Air
8.4
Very Good
1,370 reviews
Check prices

Food

8.1

Boarding

8.4

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
8.0
Excellent

Jack,Feb 2026

TPE - SFO

Premium Economy for a.long-haul flight was worth it for the extra room. It is a 2-5-2 layout, so unless you have a family, get a seat in the 2-seat section. Nice slippers and goody bag. Food was tasty, although it seemed a bit repetitive (i.e., each meal used the same ingredients slightly re-configured). Staff were excellent.

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 27h 29m. Your travel time can differ by up to 1h 59m. 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 2 airlines flying from Singapore to Chicago

Discover the top 2 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 10 March 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 878AverageS$ 1,502FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 889AverageS$ 1,489FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Singapore to Chicago?

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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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