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Cheap flights from Singapore to Chicago from S$ 692

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 25-2. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
22 Mar — 29 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 20 February 2026.

Fri 1-518:40
SIN
-
ORD
1 stop25h 20m
Multiple Airlines
Wed 26-806:00
ORD
-
SIN
2 stops50h 30m
Multiple Airlines
Deal found 17-2S$ 1,183
Fri 1-518:40
SIN
-
ORD
1 stop25h 20m
Multiple Airlines
Tue 25-812:44
ORD
-
SIN
2 stops43h 46m
Multiple Airlines
Deal found 17-2S$ 1,197
Tue 8-922:00
SIN
-
ORD
1 stop24h 30m
Korean Air
Fri 18-912:10
ORD
-
SIN
1 stop27h 50m
Korean Air
Deal found 17-2S$ 1,203
Mon 23-210:10
SIN
-
ORD
1 stop27h 16m
United Airlines
Sun 8-314:26
ORD
-
SIN
1 stop27h 34m
United Airlines
Deal found 20-2S$ 1,204
Fri 13-322:20
SIN
-
ORD
1 stop39h 39m
United Airlines
Sun 22-319:50
ORD
-
SIN
1 stop35h 25m
United Airlines
Deal found 19-2S$ 1,210
Tue 28-409:00
SIN
-
ORD
1 stop22h 43m
United Airlines
Sat 9-506:20
ORD
-
SIN
1 stop23h 15m
United Airlines
Deal found 17-2S$ 1,211
Sun 6-920:35
SIN
-
ORD
1 stop23h 41m
United Airlines
Sun 20-914:25
ORD
-
SIN
1 stop26h 50m
United Airlines
Deal found 17-2S$ 1,212
Wed 4-310:10
SIN
-
ORD
1 stop20h 52m
United Airlines
Tue 7-418:20
ORD
-
SIN
1 stop23h 25m
United Airlines
Deal found 16-2S$ 1,223
Mon 7-922:00
SIN
-
ORD
1 stop24h 30m
Korean Air
Fri 18-912:10
ORD
-
SIN
1 stop27h 50m
Korean Air
Deal found 17-2S$ 1,227
Tue 28-407:30
SIN
-
ORD
2 stops29h 28m
Delta
Wed 26-815:35
ORD
-
SIN
2 stops38h 40m
Delta
Deal found 17-2S$ 1,229
Mon 7-922:00
SIN
-
MDW
2 stops27h 30m
Delta
Wed 16-909:30
MDW
-
SIN
2 stops25h 25m
Delta
Deal found 17-2S$ 1,230
Mon 7-907:30
SIN
-
ORD
2 stops29h 17m
Delta
Wed 16-908:55
ORD
-
SIN
2 stops26h 00m
Delta
Deal found 17-2S$ 1,230

Find flight deals from Singapore to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Singapore (SIN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 20 February 2026.

Round-trip from

S$ 1,183

One-way from

S$ 663

Popular in

January

Cheapest in

February

Average price

S$ 981
1-5-26-8
  • 1-5-26-8
  • 3 total stops
  • 75h 50m total
  • Singapore to Chicago
Search Deals
6-5
  • 6-5
  • 1 total stop
  • 22h 05m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (S$ 61 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 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 20 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

Thu 30-4

20:35-06:20

1 stop22h 45m

Chicago O'Hare Intl

Sat 9-5

06:20-18:35

1 stop23h 15m

S$ 1,211

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 29-4

20:35-07:07

1 stop23h 32m

Chicago O'Hare Intl

Sun 10-5

18:20-06:45

1 stop23h 25m

S$ 1,211

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 28-4

20:35-05:27

1 stop21h 52m

Chicago O'Hare Intl

Mon 11-5

06:20-18:35

1 stop23h 15m

S$ 1,211

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 5-3

10:10-21:37

1 stop25h 27m

Chicago O'Hare Intl

Mon 6-4

14:15-06:45

1 stop27h 30m

S$ 1,212

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 4-3

10:10-17:02

1 stop20h 52m

Chicago O'Hare Intl

Tue 7-4

18:20-06:45

1 stop23h 25m

S$ 1,223

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 5-3

10:10-17:02

1 stop20h 52m

Chicago O'Hare Intl

Tue 7-4

06:25-18:35

1 stop23h 10m

S$ 1,223

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 4-3

10:10-17:02

1 stop20h 52m

Chicago O'Hare Intl

Mon 6-4

06:25-18:35

1 stop23h 10m

S$ 1,223

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 28-4

07:30-23:58

2 stops29h 28m

Chicago O'Hare Intl

Wed 26-8

15:35-19:15

2 stops38h 40m

S$ 1,229

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 5-3

14:25-12:01

2 stops35h 36m

Chicago O'Hare Intl

Mon 6-4

15:05-12:35

3 stops32h 30m

S$ 1,343

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 18-4

13:45-06:39

2 stops29h 54m

Chicago O'Hare Intl

Sun 26-4

19:15-12:35

2 stops28h 20m

S$ 1,343

Flights are sorted by cheapest return flights first.

Deals found on 16-2

Showing 1-10 of 43 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$ 881). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,521). 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.

What’s the top stopover airport for flights from Singapore to Chicago?

Share of one-stop return flights from Singapore to Chicago chosen by Cheapflights users in the past 12 months, using the same stopover each way.

Taipei City (TPE) – chosen by Cheapflights users on 25% of one-stop itineraries from Singapore to Chicago on Cheapflights.

What’s the cheapest stopover airport for flights from Singapore to Chicago?

Average return fare for one-stop flights from Singapore to Chicago, chosen by Cheapflights users in the past 12 months, with the same stopover each way.

San Francisco (SFO) is the most affordable one-stop option, with an average return flight price of S$ 1,259.

What’s the fastest stopover option from Singapore to Chicago?

Shortest average travel time for one-stop one-way flights from Singapore to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by stopover airport.

Flights via Tokyo (HND) have the shortest average one-way travel time for one-stop routes: 19h 08m.

Which airport typically offers the quickest stopover for flights from Singapore to Chicago?

Average stopover duration for one-stop one-way flights from Singapore to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Vancouver (YVR) offer the fastest connection on this route, with an average stopover time of 1h 44m.

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 20 February 2026.
Check out reviews from past customers who have flown with EVA Air, ANA, andCathay Pacific from Singapore to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
EVA Air
8.4
Very Good
1,357 reviews
Check prices

Overall

8.4

Crew

8.6

Comfort

8.3

Entertainment

8.0

Food

8.1

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
1,357 reviews
EVA Air
8.4
Very Good
1,357 reviews
Check prices

Overall

8.4

Crew

8.6

Comfort

8.3

Entertainment

8.0

Food

8.1

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
1,097 reviews
EVA Air
8.4
Very Good
1,357 reviews
Check prices

Overall

8.4

Crew

8.6

Comfort

8.3

Entertainment

8.0

Food

8.1

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
1,174 reviews
EVA Air
8.4
Very Good
1,357 reviews
Check prices

Overall

8.4

Crew

8.6

Comfort

8.3

Entertainment

8.0

Food

8.1

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
9,331 reviews
EVA Air
8.4
Very Good
1,357 reviews
Check prices

Overall

8.4

Crew

8.6

Comfort

8.3

Entertainment

8.0

Food

8.1

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.

  • What airport do you fly from for flights from Singapore to Chicago?

    Located just 16.9 km from the city centre, Singapore Changi is the airport most travellers will use when flying to Chicago from Singapore. Booking flights from Changi (SIN) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 3 different airlines.

  • How long is the flight from Singapore to Chicago?

    United Airlines and Delta can get you from Singapore to Chicago in just under 22h 45m. Your travel time can differ by up to 12h 11m. The distance between Singapore and Chicago is about 15039 km. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Singapore to Chicago round-trip?

    United Airlines, at S$ 870, was found to be the cheapest airline from Singapore to Chicago.Alternate airlines to your destination round-trip include Japan Airlines and ANA. You may be able to fly from Singapore to Chicago for 35% less than the average price by searching for these airlines.

  • 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$ 881). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,521). 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.

Fly from Singapore to Chicago on these airlines

Choose from the following airlines for your flight from Singapore to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 20 February 2026.
United Airlines flights from Singapore Changi to Chicago
EVA Air flights from Singapore Changi to Chicago
ANA flights from Singapore Changi to Chicago

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 20 February 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 870AverageS$ 1,339FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 881AverageS$ 1,521FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,042AverageS$ 2,932FlexibilityNo cancel feeOn-time80%
Search ANA 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?

Cheapflights makes it easy to find Singapore to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Singapore to Chicago?

Millions of users choose and trust Cheapflights to book the best flight deals from Singapore to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Singapore to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Singapore to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Singapore to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Singapore to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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