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Cheap flights from Singapore to Chicago from S$ 757

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 13-9. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
27 Apr — 4 May1
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 28 March 2026.

Tue 5-520:35
SIN
-
ORD
1 stop28h 20m
United Airlines
Mon 11-523:00
ORD
-
SIN
1 stop30h 35m
United Airlines
Deal found 28-3S$ 1,031
Mon 4-520:35
SIN
-
ORD
1 stop22h 05m
United Airlines
Sun 10-506:20
ORD
-
SIN
1 stop23h 15m
United Airlines
Deal found 23-3S$ 1,046
Tue 20-1006:15
SIN
-
ORD
1 stop21h 40m
ANA
Tue 20-1020:00
ORD
-
SIN
2 stops38h 20m
ANA
Deal found 27-3S$ 1,103
Thu 24-920:35
SIN
-
ORD
1 stop21h 23m
United Airlines
Mon 28-921:39
ORD
-
SIN
1 stop31h 56m
United Airlines
Deal found 25-3S$ 1,215
Tue 27-1001:35
SIN
-
ORD
1 stop20h 55m
Korean Air
Sun 1-1111:15
ORD
-
SIN
1 stop27h 45m
Korean Air
Deal found 27-3S$ 1,222
Sun 7-620:35
SIN
-
ORD
1 stop22h 22m
United Airlines
Sun 9-821:35
ORD
-
SIN
1 stop32h 00m
United Airlines
Deal found 24-3S$ 1,224
Thu 10-901:25
SIN
-
ORD
2 stops35h 32m
Delta
Sat 26-917:45
ORD
-
SIN
2 stops41h 10m
Delta
Deal found 28-3S$ 1,225
Thu 10-907:30
SIN
-
ORD
2 stops29h 17m
Delta
Fri 25-909:30
ORD
-
SIN
2 stops30h 30m
Delta
Deal found 27-3S$ 1,228
Mon 19-1001:25
SIN
-
ORD
1 stop21h 05m
Korean Air
Tue 20-1012:10
ORD
-
SIN
1 stop22h 45m
Korean Air
Deal found 27-3S$ 1,229
Wed 9-907:30
SIN
-
ORD
2 stops29h 17m
Delta
Thu 24-909:30
ORD
-
SIN
2 stops25h 25m
Delta
Deal found 26-3S$ 1,231
Mon 7-901:25
SIN
-
ORD
2 stops35h 22m
Delta
Wed 23-917:45
ORD
-
SIN
2 stops41h 10m
Delta
Deal found 25-3S$ 1,233
Sun 7-613:45
SIN
-
MDW
2 stops29h 10m
Multiple Airlines
Sun 9-820:35
MDW
-
SIN
2 stops27h 00m
Multiple Airlines
Deal found 26-3S$ 1,482

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 28 March 2026.

Round-trip from

S$ 1,031

One-way from

S$ 757

Popular in

January

Cheapest in

February

Average price

S$ 1,426
United Airlines
  • United Airlines
  • 5-5-11-5
  • 2 total stops
  • 58h 55m total
  • Singapore to Chicago
Search Deals
United Airlines
  • United Airlines
  • 14-9
  • 1 total stop
  • 31h 15m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (S$ 41 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 57 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 28 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

Mon 7-9

20:35-07:16

1 stop23h 41m

Chicago O'Hare Intl

Tue 22-9

18:20-18:35

1 stop35h 15m

S$ 1,215

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 7-6

20:35-05:57

1 stop22h 22m

Chicago O'Hare Intl

Sun 9-8

21:35-18:35

1 stop32h 00m

S$ 1,224

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 9-9

07:30-23:47

2 stops29h 17m

Chicago O'Hare Intl

Thu 24-9

09:30-23:55

2 stops25h 25m

S$ 1,231

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 7-9

01:25-23:47

2 stops35h 22m

Chicago O'Hare Intl

Wed 23-9

17:45-23:55

2 stops41h 10m

S$ 1,233
Fastest return journey

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 4-5

20:35-13:15

2 stops29h 40m

Chicago O'Hare Intl

Sun 10-5

06:20-18:35

1 stop23h 15m

S$ 1,338

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 11-5

20:35-23:29

1 stop39h 54m

Chicago O'Hare Intl

Mon 18-5

21:35-18:35

2 stops32h 00m

S$ 1,408

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$ 1,482

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$ 1,556

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 24-9

08:05-21:25

2 stops26h 20m

Chicago O'Hare Intl

Mon 28-9

14:10-06:10

1 stop27h 00m

S$ 1,615

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 27-6

13:45-05:40

2 stops28h 55m

Chicago Midway

Fri 10-7

11:45-12:35

2 stops35h 50m

S$ 1,695

Flights are sorted by cheapest return flights first.

Deals found on 28-3

Showing 1-10 of 36 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 28 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
8.5
Very Good
1,389 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Overall

8.5

Crew

8.7

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
1,389 reviews
EVA Air
8.5
Very Good
1,389 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Overall

8.5

Crew

8.7

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?
ANA
8.4
Very Good
1,154 reviews
EVA Air
8.5
Very Good
1,389 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Overall

8.5

Crew

8.7

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?
Cathay Pacific
7.6
Good
1,232 reviews
EVA Air
8.5
Very Good
1,389 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Overall

8.5

Crew

8.7

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
9,507 reviews
EVA Air
8.5
Very Good
1,389 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Overall

8.5

Crew

8.7

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?

    United Airlines, Korean Air, and Delta can get you from Singapore to Chicago in just under 21h 23m. Your travel time can differ by up to 17h 37m. 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 28 March 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 888AverageS$ 1,385FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 894AverageS$ 1,497FlexibilityNo 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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