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Cheap flights from Singapore to Chicago from S$ 627

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 20-10. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
2 marras — 9 marras1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Singapore Changi to Chicago are usually found in October or April, booked 6 days in advance, depart on a Tuesday or Monday and return on a Tuesday

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 3 lokakuu 2025.

Round-trip from

S$ 1,054

One-way from

S$ 627

Popular in

January

Cheapest in

October

Average price

S$ 1,167
Air Canada
  • Air Canada
  • 8-11-15-11
  • 4 total stops
  • 86h 35m total
  • Singapore to Chicago
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20-10
  • 20-10
  • 3 total stops
  • 48h 25m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (S$ 190 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (S$ 48 potential savings vs. average return price).
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Average for round-trip flights in October 2025
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Find 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 3 lokakuu 2025.

la 8-1108:50SIN - ORD
1 stop19h 51mAir Canada
la 15-1117:55ORD - SIN
2 stops47h 05mAir Canada
Deal found 1-10S$ 1,054
ti 28-1010:45SIN - ORD
2 stops31h 31mANA
ti 4-1116:25ORD - SIN
1 stop24h 30mANA
Deal found 30-9S$ 1,058
ti 4-1106:35SIN - ORD
1 stop21h 15mANA
su 9-1116:25ORD - SIN
1 stop24h 30mANA
Deal found 30-9S$ 1,067
ke 5-1106:35SIN - ORD
1 stop21h 15mANA
ma 10-1116:25ORD - SIN
1 stop35h 10mANA
Deal found 30-9S$ 1,071
la 15-1121:00SIN - ORD
2 stops31h 41mAir Canada
la 22-1117:55ORD - SIN
2 stops47h 05mAir Canada
Deal found 30-9S$ 1,083
ti 28-1006:35SIN - ORD
2 stops35h 41mANA
su 2-1116:25ORD - SIN
1 stop24h 30mANA
Deal found 1-10S$ 1,086
la 1-1108:50SIN - ORD
2 stops37h 10mAir Canada
la 8-1115:35ORD - SIN
2 stops49h 25mAir Canada
Deal found 1-10S$ 1,181
su 16-1108:50SIN - ORD
1 stop19h 51mAir Canada
su 23-1112:50ORD - SIN
2 stops28h 10mAir Canada
Deal found 2-10S$ 1,183
su 12-1009:10SIN - ORD
2 stops35h 48mAir Canada
to 30-1015:40ORD - SIN
1 stop26h 20mAir Canada
Deal found 30-9S$ 1,206
ke 26-1110:40SIN - MDW
2 stops27h 00mDelta
ma 8-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 29-9S$ 1,533
la 15-1115:45SIN - MDW
2 stops27h 30mMultiple Airlines
la 22-1119:00MDW - SIN
2 stops27h 05mMultiple Airlines
Deal found 30-9S$ 1,585
su 16-1115:45SIN - MDW
2 stops27h 30mMultiple Airlines
su 23-1117:25MDW - SIN
2 stops28h 40mMultiple Airlines
Deal found 1-10S$ 1,648

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 3 lokakuu 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

la 15-11

10:10-06:02

1 stop33h 52m

Chicago O'Hare Intl

la 22-11

21:10-20:15

1 stop33h 05m

S$ 1,233

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

ma 27-10

10:10-00:59

1 stop27h 49m

Chicago O'Hare Intl

to 13-11

07:10-20:15

1 stop23h 05m

S$ 1,234

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

la 13-12

22:20-05:00

1 stop20h 40m

Chicago O'Hare Intl

ma 5-1

22:00-20:15

1 stop32h 15m

S$ 1,244

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

ma 9-2

01:35-08:40

1 stop21h 05m

Chicago O'Hare Intl

pe 20-2

11:25-00:10

1 stop22h 45m

S$ 1,250

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

ti 10-2

10:40-21:46

2 stops25h 06m

Chicago Midway

pe 20-2

18:45-00:10

2 stops39h 25m

S$ 1,251

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

ma 9-2

01:35-21:55

2 stops34h 20m

Chicago O'Hare Intl

pe 20-2

19:35-00:10

2 stops38h 35m

S$ 1,251

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

ke 29-10

22:30-21:19

2 stops35h 49m

Chicago O'Hare Intl

ke 5-11

06:08-00:10

2 stops28h 02m

S$ 1,251

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

ti 17-3

22:20-14:44

1 stop29h 24m

Chicago O'Hare Intl

to 2-4

21:30-06:40

2 stops44h 10m

S$ 1,385

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

ma 16-3

01:35-23:44

2 stops35h 09m

Chicago O'Hare Intl

to 2-4

12:20-05:00

1 stop27h 40m

S$ 1,391

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

la 15-11

01:35-23:59

2 stops36h 24m

Chicago O'Hare Intl

su 23-11

06:45-05:00

2 stops32h 15m

S$ 1,395

Flights are sorted by cheapest return flights first.

Deals found on 2-10

Showing 1-10 of 35 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

How far ahead should I book a flight from Singapore to Chicago?

Use this chart to determine the optimal time to book a return flight from Singapore to Chicago. Price data was last updated on 26 September 2025.

The price you pay for your flight from Singapore to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 6 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 3 lokakuu 2025.

It’s typically best to fly out from Singapore to Chicago at midday. Doing so could potentially save you 14% on the flight price compared to flying in the morning, which is usually more expensive.

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 29% 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$ 1,303.

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 38m.

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 3 lokakuu 2025.
Check out reviews from past customers who have flown with EVA Air, ANA, andJapan Airlines 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
1,244 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Entertainment

8.0

Crew

8.6

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
1,244 reviews
EVA Air
8.4
Very Good
1,244 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Entertainment

8.0

Crew

8.6

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
ANA
8.4
Very Good
979 reviews
EVA Air
8.4
Very Good
1,244 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Entertainment

8.0

Crew

8.6

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
1,574 reviews
EVA Air
8.4
Very Good
1,244 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Entertainment

8.0

Crew

8.6

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
1,015 reviews
EVA Air
8.4
Very Good
1,244 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Entertainment

8.0

Crew

8.6

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
8,933 reviews
EVA Air
8.4
Very Good
1,244 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Entertainment

8.0

Crew

8.6

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?

    United Airlines, Korean Air, and Delta can get you from Singapore to Chicago in just under 21h 05m. Your travel time can differ by up to 12h 47m. 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$ 889, 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 37% 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.

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 3 lokakuu 2025.
EVA Air flights from Singapore Changi to Chicago
United Airlines flights from Singapore Changi to Chicago
ANA 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 3 lokakuu 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 889AverageS$ 1,299FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 895AverageS$ 1,532FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,059AverageS$ 2,616FlexibilityNo cancel feeOn-time80%
Search ANA flights
Cathay PacificCheapestS$ 1,198AverageS$ 1,474FlexibilityNo cancel feeOn-time72%
Search Cathay Pacific flights
Korean AirCheapestS$ 1,235AverageS$ 2,618FlexibilityNo cancel feeOn-time81%
Search Korean Air flights
EVA AirCheapestS$ 1,304AverageS$ 1,479FlexibilityNo cancel feeOn-time74%
Search EVA Air flights
Etihad AirwaysCheapestS$ 1,971AverageS$ 2,455FlexibilityNo 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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