Find flights
When to book
Airlines
FAQs

Cheap flights from Singapore to Chicago from S$ 673

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 21-4. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
11 Mar — 18 Mar1
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 9 February 2026.

Thu 24-907:30
SIN
-
ORD
1 stop39h 00m
Korean Air
Sun 27-912:10
ORD
-
SIN
1 stop27h 50m
Korean Air
Deal found 9-2S$ 1,190
Tue 17-210:10
SIN
-
ORD
1 stop33h 02m
United Airlines
Wed 18-209:01
ORD
-
SIN
1 stop32h 59m
United Airlines
Deal found 5-2S$ 1,196
Tue 10-222:20
SIN
-
ORD
1 stop22h 05m
United Airlines
Fri 20-206:25
ORD
-
SIN
1 stop23h 50m
United Airlines
Deal found 6-2S$ 1,204
Sat 21-222:20
SIN
-
ORD
1 stop30h 25m
United Airlines
Tue 24-218:17
ORD
-
SIN
1 stop23h 43m
United Airlines
Deal found 7-2S$ 1,205
Sun 8-310:10
SIN
-
ORD
1 stop21h 42m
United Airlines
Sun 15-321:15
ORD
-
SIN
1 stop34h 00m
United Airlines
Deal found 8-2S$ 1,208
Fri 6-310:10
SIN
-
ORD
1 stop27h 28m
United Airlines
Sat 14-321:15
ORD
-
SIN
1 stop34h 00m
United Airlines
Deal found 6-2S$ 1,217
Mon 23-301:35
SIN
-
ORD
2 stops36h 05m
Delta
Tue 31-308:55
ORD
-
SIN
2 stops31h 05m
Delta
Deal found 7-2S$ 1,222
Thu 24-907:30
SIN
-
ORD
2 stops29h 27m
Delta
Sun 27-908:55
ORD
-
SIN
2 stops25h 45m
Delta
Deal found 9-2S$ 1,224
Mon 23-314:25
SIN
-
MDW
2 stops28h 15m
Multiple Airlines
Mon 30-311:50
MDW
-
SIN
2 stops35h 45m
Multiple Airlines
Deal found 6-2S$ 1,377
Tue 24-322:30
SIN
-
MDW
2 stops37h 01m
Delta
Tue 31-309:30
MDW
-
SIN
2 stops30h 30m
Delta
Deal found 7-2S$ 1,417
Fri 26-613:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Mon 20-718:00
MDW
-
SIN
2 stops29h 35m
Multiple Airlines
Deal found 7-2S$ 1,516
Thu 11-613:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Fri 19-620:35
MDW
-
SIN
2 stops27h 00m
Multiple Airlines
Deal found 6-2S$ 1,671

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 9 February 2026.

Round-trip from

S$ 1,204

One-way from

S$ 673

Popular in

January

Cheapest in

February

Average price

S$ 983
United Airlines
  • United Airlines
  • 23-3-30-3
  • 2 total stops
  • 54h 52m total
  • Singapore to Chicago
Search Deals
21-4
  • 21-4
  • 2 total stops
  • 27h 35m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (S$ 60 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 55 potential savings vs. average return price).
Search Deals
Average for round-trip flights in February 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 9 February 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

Sat 21-2

22:20-14:45

1 stop30h 25m

Chicago O'Hare Intl

Tue 24-2

18:17-08:00

1 stop23h 43m

S$ 1,205

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 24-3

10:10-21:37

1 stop24h 27m

Chicago O'Hare Intl

Tue 31-3

21:20-18:35

1 stop32h 15m

S$ 1,205

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 26-6

08:45-00:59

1 stop29h 14m

Chicago O'Hare Intl

Mon 20-7

22:45-18:35

1 stop30h 50m

S$ 1,205

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 8-3

10:10-17:52

1 stop21h 42m

Chicago O'Hare Intl

Sun 15-3

21:15-20:15

1 stop34h 00m

S$ 1,208

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 26-3

22:20-21:36

1 stop36h 16m

Chicago O'Hare Intl

Thu 2-4

06:25-18:35

1 stop23h 10m

S$ 1,208

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 6-3

10:10-23:38

1 stop27h 28m

Chicago O'Hare Intl

Sat 14-3

21:15-20:15

1 stop34h 00m

S$ 1,217

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 23-3

01:35-00:40

2 stops36h 05m

Chicago O'Hare Intl

Tue 31-3

08:55-05:00

2 stops31h 05m

S$ 1,222

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 23-3

11:40-11:05

1 stop36h 25m

Chicago O'Hare Intl

Mon 30-3

20:10-09:30

1 stop24h 20m

S$ 1,226

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 20-2

11:40-10:05

1 stop36h 25m

Chicago O'Hare Intl

Mon 23-2

20:20-10:00

1 stop23h 40m

S$ 1,257

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 20-2

19:40-15:05

2 stops33h 25m

Chicago O'Hare Intl

Mon 23-2

13:10-09:35

1 stop30h 25m

S$ 1,299

Flights are sorted by cheapest return flights first.

Deals found on 6-2

Showing 1-10 of 37 results
1
2
3
4

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$ 883). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,524). 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 9 February 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
1,349 reviews
Check prices

Comfort

8.3

Overall

8.4

Crew

8.6

Food

8.1

Entertainment

8.0

Boarding

8.4

Reviews

1 / 20
8.0
Excellent

Jolene,Jan 2026

SGN - TPE

Everything was good. I asked for aisle seating as I must stretch my leg out because of back and pelvis issues. Sometimes I don't always get it. But I did for all 3 of my flights for my destination. It was very nice.
EVA Air
8.4
Very Good
1,349 reviews
EVA Air
8.4
Very Good
1,349 reviews
Check prices

Comfort

8.3

Overall

8.4

Crew

8.6

Food

8.1

Entertainment

8.0

Boarding

8.4

Reviews

1 / 20
8.0
Excellent

Jolene,Jan 2026

SGN - TPE

Everything was good. I asked for aisle seating as I must stretch my leg out because of back and pelvis issues. Sometimes I don't always get it. But I did for all 3 of my flights for my destination. It was very nice.
ANA
8.4
Very Good
1,092 reviews
EVA Air
8.4
Very Good
1,349 reviews
Check prices

Comfort

8.3

Overall

8.4

Crew

8.6

Food

8.1

Entertainment

8.0

Boarding

8.4

Reviews

1 / 20
8.0
Excellent

Jolene,Jan 2026

SGN - TPE

Everything was good. I asked for aisle seating as I must stretch my leg out because of back and pelvis issues. Sometimes I don't always get it. But I did for all 3 of my flights for my destination. It was very nice.
Cathay Pacific
7.6
Good
1,160 reviews
EVA Air
8.4
Very Good
1,349 reviews
Check prices

Comfort

8.3

Overall

8.4

Crew

8.6

Food

8.1

Entertainment

8.0

Boarding

8.4

Reviews

1 / 20
8.0
Excellent

Jolene,Jan 2026

SGN - TPE

Everything was good. I asked for aisle seating as I must stretch my leg out because of back and pelvis issues. Sometimes I don't always get it. But I did for all 3 of my flights for my destination. It was very nice.
United Airlines
7.4
Good
9,267 reviews
EVA Air
8.4
Very Good
1,349 reviews
Check prices

Comfort

8.3

Overall

8.4

Crew

8.6

Food

8.1

Entertainment

8.0

Boarding

8.4

Reviews

1 / 20
8.0
Excellent

Jolene,Jan 2026

SGN - TPE

Everything was good. I asked for aisle seating as I must stretch my leg out because of back and pelvis issues. Sometimes I don't always get it. But I did for all 3 of my flights for my destination. It was very nice.

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 30h 25m. Your travel time can differ by up to 6h 36m. 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, June is the cheapest month in which you can book a flight from Singapore to Chicago (average of S$ 883). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,524). 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 9 February 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 876AverageS$ 1,313FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 882AverageS$ 1,524FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,044AverageS$ 2,937FlexibilityNo cancel feeOn-time80%
Search ANA flights
EVA AirCheapestS$ 1,313AverageS$ 1,483FlexibilityNo 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book With Flexibility

Our users can plan ahead with confidence and find flights with no change fees.

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.