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Cheap flights from Singapore to Chicago from S$ 701

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 28-1. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
21 Feb — 28 Feb1
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 22 January 2026.

Mon 1-613:45
SIN
-
ORD
2 stops29h 55m
Multiple Airlines
Tue 30-618:53
ORD
-
SIN
2 stops28h 42m
Multiple Airlines
Deal found 21-1S$ 1,158
Tue 17-222:20
SIN
-
ORD
1 stop20h 52m
United Airlines
Wed 18-209:01
ORD
-
SIN
1 stop32h 59m
United Airlines
Deal found 18-1S$ 1,196
Tue 30-608:45
SIN
-
ORD
1 stop27h 49m
United Airlines
Mon 3-821:39
ORD
-
SIN
1 stop31h 56m
United Airlines
Deal found 18-1S$ 1,204
Tue 10-222:20
SIN
-
ORD
1 stop21h 24m
United Airlines
Fri 20-206:25
ORD
-
SIN
1 stop23h 50m
United Airlines
Deal found 19-1S$ 1,205
Thu 22-110:10
SIN
-
ORD
1 stop25h 22m
United Airlines
Wed 4-219:58
ORD
-
SIN
1 stop34h 17m
United Airlines
Deal found 20-1S$ 1,208
Sun 28-601:55
SIN
-
ORD
1 stop20h 20m
Japan Airlines
Mon 3-801:30
ORD
-
SIN
1 stop27h 00m
Japan Airlines
Deal found 18-1S$ 1,210
Thu 5-314:25
SIN
-
ORD
2 stops35h 36m
Multiple Airlines
Thu 12-317:29
ORD
-
SIN
2 stops30h 36m
Multiple Airlines
Deal found 19-1S$ 1,212
Sun 28-601:55
SIN
-
ORD
1 stop20h 20m
Japan Airlines
Wed 5-812:30
ORD
-
SIN
1 stop22h 50m
Japan Airlines
Deal found 18-1S$ 1,214
Fri 6-310:40
SIN
-
ORD
2 stops24h 50m
Delta
Tue 17-307:10
ORD
-
SIN
2 stops28h 00m
Delta
Deal found 18-1S$ 1,234
Mon 1-613:45
SIN
-
MDW
2 stops35h 15m
Multiple Airlines
Tue 30-617:05
MDW
-
SIN
2 stops30h 30m
Multiple Airlines
Deal found 21-1S$ 1,377
Sun 28-613:45
SIN
-
MDW
2 stops34h 40m
Multiple Airlines
Mon 3-817:15
MDW
-
SIN
2 stops30h 20m
Multiple Airlines
Deal found 20-1S$ 1,409
Tue 2-613:45
SIN
-
MDW
2 stops35h 15m
Multiple Airlines
Thu 2-718:00
MDW
-
SIN
2 stops29h 35m
Multiple Airlines
Deal found 21-1S$ 1,418

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 22 January 2026.

Round-trip from

S$ 1,158

One-way from

S$ 701

Popular in

January

Cheapest in

September

Average price

S$ 2,029
1-6-30-6
  • 1-6-30-6
  • 4 total stops
  • 58h 37m total
  • Singapore to Chicago
Search Deals
28-1
  • 28-1
  • 3 total stops
  • 48h 17m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (S$ 213 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (S$ 75 potential savings vs. average return price).
Search Deals
Average for round-trip flights in January 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 22 January 2026.
Use the filters below to find and compare flights from Singapore to Chicago that are best for you.

Fly from

Singapore

Fly to

Chicago

Route

Depart

Return

Price

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 6-3

10:10-00:59

1 stop28h 49m

Chicago O'Hare Intl

Tue 17-3

12:52-07:00

1 stop29h 08m

S$ 1,204

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 1-7

20:35-11:45

1 stop28h 10m

Chicago O'Hare Intl

Sun 2-8

21:39-18:35

1 stop31h 56m

S$ 1,204

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 1-7

20:35-11:45

1 stop28h 10m

Chicago O'Hare Intl

Sat 8-8

18:25-18:35

1 stop35h 10m

S$ 1,204

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 5-6

08:45-20:17

1 stop24h 32m

Chicago O'Hare Intl

Sun 21-6

21:39-18:35

1 stop31h 56m

S$ 1,204

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 10-2

22:20-06:25

1 stop22h 05m

Chicago O'Hare Intl

Fri 20-2

06:25-20:15

1 stop23h 50m

S$ 1,207

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 6-7

20:35-22:55

1 stop39h 20m

Chicago O'Hare Intl

Tue 21-7

18:25-18:35

1 stop35h 10m

S$ 1,207

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 19-3

22:20-13:06

1 stop27h 46m

Chicago O'Hare Intl

Wed 25-3

14:26-07:00

1 stop27h 34m

S$ 1,207

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 7-3

22:20-06:19

1 stop21h 59m

Chicago O'Hare Intl

Sat 14-3

14:26-20:15

1 stop40h 49m

S$ 1,208

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 6-7

13:45-14:45

2 stops38h 00m

Chicago O'Hare Intl

Tue 21-7

18:53-12:35

2 stops28h 42m

S$ 1,263

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 19-3

15:10-12:30

3 stops34h 20m

Chicago O'Hare Intl

Wed 25-3

14:10-09:35

1 stop30h 25m

S$ 1,320

Flights are sorted by cheapest return flights first.

Deals found on 21-1

Showing 1-10 of 32 results
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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, June is the cheapest month in which you can book a flight from Singapore to Chicago (average of S$ 892). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,472). 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.

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 22 January 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
1,328 reviews
Check prices

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Food

8.1

Boarding

8.4

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.
EVA Air
8.4
Very Good
1,328 reviews
EVA Air
8.4
Very Good
1,328 reviews
Check prices

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Food

8.1

Boarding

8.4

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.
ANA
8.4
Very Good
1,077 reviews
EVA Air
8.4
Very Good
1,328 reviews
Check prices

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Food

8.1

Boarding

8.4

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.
Cathay Pacific
7.6
Good
1,140 reviews
EVA Air
8.4
Very Good
1,328 reviews
Check prices

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Food

8.1

Boarding

8.4

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.
United Airlines
7.4
Good
9,193 reviews
EVA Air
8.4
Very Good
1,328 reviews
Check prices

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Food

8.1

Boarding

8.4

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.

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 can get you from Singapore to Chicago in just under 28h 49m. Your travel time can differ by up to . The distance between Singapore and Chicago is about 15039 km.

  • 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, June is the cheapest month in which you can book a flight from Singapore to Chicago (average of S$ 892). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,472). 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 22 January 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 881AverageS$ 1,320FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 892AverageS$ 1,540FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,055AverageS$ 2,969FlexibilityNo cancel feeOn-time80%
Search ANA flights
EVA AirCheapestS$ 1,327AverageS$ 1,499FlexibilityNo 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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