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Cheap flights from Singapore to Chicago from S$ 606

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 25-9. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
25 Aug — 1 Sep1
1 adult

Cheap 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 August 2025.

Round-trip from

S$ 1,021

One-way from

S$ 606

Popular in

January

Cheapest in

October

Average price

S$ 1,600
Air Canada
  • Air Canada
  • 2-2-18-2
  • 3 total stops
  • 82h 28m total
  • Singapore to Chicago
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25-9
  • 25-9
  • 2 total stops
  • 35h 23m total
  • Singapore to Chicago
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Highest demand for flights based on searches. 9% potential increase in price (S$ 184 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (S$ 51 potential savings vs. average return price).
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Average for round-trip flights in August 2025
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Find flight deals from Singapore to Chicago

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 August 2025.

Fri 17-1000:20SIN - ORD
2 stops36h 39mMultiple Airlines
Sun 26-1007:25ORD - SIN
2 stops46h 45mMultiple Airlines
Deal found 20-8S$ 1,045
Tue 18-1121:00SIN - ORD
2 stops31h 41mAir Canada
Wed 3-1208:00ORD - SIN
2 stops32h 55mAir Canada
Deal found 18-8S$ 1,049
Sat 18-1009:10SIN - ORD
1 stop20h 32mAir Canada
Sun 26-1013:10ORD - SIN
1 stop28h 50mAir Canada
Deal found 20-8S$ 1,053
Thu 13-1121:00SIN - ORD
2 stops31h 41mAir Canada
Sun 30-1115:40ORD - SIN
1 stop25h 20mAir Canada
Deal found 19-8S$ 1,057
Thu 28-806:15SIN - ORD
1 stop21h 40mANA
Sun 7-917:45ORD - SIN
1 stop23h 55mANA
Deal found 19-8S$ 1,059
Thu 28-806:15SIN - ORD
1 stop21h 40mANA
Mon 8-912:40ORD - SIN
1 stop29h 00mANA
Deal found 19-8S$ 1,061
Wed 17-906:15SIN - ORD
1 stop21h 40mANA
Wed 24-917:45ORD - SIN
1 stop34h 30mANA
Deal found 19-8S$ 1,072
Mon 27-1021:00SIN - ORD
2 stops32h 44mAir Canada
Thu 13-1112:50ORD - SIN
2 stops28h 10mAir Canada
Deal found 18-8S$ 1,076
Sun 5-1009:10SIN - ORD
1 stop20h 32mAir Canada
Sun 19-1015:45ORD - SIN
1 stop26h 20mAir Canada
Deal found 19-8S$ 1,080
Sun 5-1009:10SIN - ORD
1 stop20h 32mAir Canada
Sun 12-1015:45ORD - SIN
1 stop26h 20mAir Canada
Deal found 19-8S$ 1,084
Tue 9-922:10SIN - ORD
1 stop30h 00mANA
Sun 14-912:40ORD - SIN
1 stop39h 35mANA
Deal found 17-8S$ 1,085
Tue 2-901:10SIN - MDW
2 stops33h 16mDelta
Sat 6-909:31MDW - SIN
2 stops30h 29mDelta
Deal found 20-8S$ 1,252

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 August 2025.
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

Tue 18-11

21:00-14:41

2 stops31h 41m

Chicago O'Hare Intl

Wed 3-12

08:00-06:55

2 stops32h 55m

S$ 1,049

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 4-10

09:10-17:10

2 stops45h 00m

Chicago O'Hare Intl

Sat 11-10

15:35-07:05

2 stops50h 30m

S$ 1,053

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 14-11

08:50-14:41

1 stop19h 51m

Chicago O'Hare Intl

Sun 30-11

08:45-07:00

2 stops32h 15m

S$ 1,054

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 18-10

09:10-12:32

2 stops40h 22m

Chicago O'Hare Intl

Sun 26-10

15:40-07:00

1 stop26h 20m

S$ 1,054

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 31-10

08:50-17:10

2 stops45h 20m

Chicago O'Hare Intl

Sat 8-11

08:45-07:00

2 stops56h 15m

S$ 1,054

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 13-11

21:00-14:41

2 stops31h 41m

Chicago O'Hare Intl

Sun 30-11

08:45-07:00

2 stops32h 15m

S$ 1,057

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 17-9

07:30-21:36

2 stops27h 06m

Chicago Midway

Wed 24-9

09:35-23:40

2 stops25h 05m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 2-9

01:10-21:26

2 stops33h 16m

Chicago Midway

Sat 6-9

09:31-05:00

2 stops30h 29m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 9-9

22:30-12:28

2 stops26h 58m

Chicago Midway

Sun 14-9

12:43-19:55

2 stops42h 12m

S$ 1,253

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 30-10

01:30-22:14

2 stops33h 44m

Chicago Midway

Sat 8-11

18:23-00:10

2 stops39h 47m

S$ 1,537

Flights are sorted by cheapest return flights first.

Deals found on 19-8

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 time of day to fly from SIN to CHI?

Find hourly flight availability from Singapore to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 20 August 2025.

It’s typically best to fly out from Singapore to Chicago at midday. Doing so could potentially save you 15% on the flight price compared to flying in the morning, which is usually more expensive.

How much does it cost for a return flight from Singapore to Chicago?

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 28% 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.

Istanbul (IST) is the most affordable one-stop option, with an average return flight price of S$ 1,242.

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: 20h 30m.

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 Incheon (ICN) offer the fastest connection on this route, with an average stopover time of 1h 53m.

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 August 2025.
Check out reviews from past customers who have flown with EVA Air, Japan Airlines, 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
1,232 reviews
Check prices

Comfort

8.3

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
EVA Air
8.4
Very Good
1,232 reviews
EVA Air
8.4
Very Good
1,232 reviews
Check prices

Comfort

8.3

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Japan Airlines
8.3
Very Good
1,550 reviews
EVA Air
8.4
Very Good
1,232 reviews
Check prices

Comfort

8.3

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Cathay Pacific
7.6
Good
972 reviews
EVA Air
8.4
Very Good
1,232 reviews
Check prices

Comfort

8.3

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
United Airlines
7.4
Good
8,928 reviews
EVA Air
8.4
Very Good
1,232 reviews
Check prices

Comfort

8.3

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Air Canada
7.1
Good
10,000 reviews
EVA Air
8.4
Very Good
1,232 reviews
Check prices

Comfort

8.3

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak

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 7 different airlines.

  • How long is the flight from Singapore to Chicago?

    Air Canada and Delta can get you from Singapore to Chicago in just under 27h 06m. Your travel time can differ by up to 4h 35m. The distance between Singapore and Chicago is about 15063 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$ 886, was found to be the cheapest airline from Singapore to Chicago.Alternate airlines to your destination round-trip include Japan Airlines and Cathay Pacific. You may be able to fly from Singapore to Chicago for 37% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Singapore to Chicago one-way?

    One-way options have recently been found by users for as low as S$ 661 on IndiGo. Other airlines that offer cheap prices include Air Canada from S$ 672 and Delta from S$ 809 one-way.

  • 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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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 August 2025.
EVA Air flights from Singapore Changi to Chicago
United Airlines flights from Singapore Changi to Chicago
Japan Airlines flights from Singapore Changi to Chicago

Top 7 airlines flying from Singapore to Chicago

Discover the top 7 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 August 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 886AverageS$ 1,320FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 892AverageS$ 1,563FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
Cathay PacificCheapestS$ 1,194AverageS$ 1,407FlexibilityNo cancel feeOn-time72%
Search Cathay Pacific flights
Korean AirCheapestS$ 1,231AverageS$ 2,609FlexibilityNo cancel feeOn-time81%
Search Korean Air flights
EVA AirCheapestS$ 1,299AverageS$ 1,508FlexibilityNo cancel feeOn-time74%
Search EVA Air flights
ANACheapestS$ 1,378AverageS$ 2,646FlexibilityNo cancel feeOn-time80%
Search ANA flights
Etihad AirwaysCheapestS$ 1,964AverageS$ 2,447FlexibilityNo cancel feeOn-time75%
Search Etihad Airways 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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