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Cheap flights from Singapore to Chicago from S$ 650

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 4-2. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
19 Dec — 26 Dec1
1 adult
1 adult, Economy, 0 bags

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 19 November 2025.

Round-trip from

S$ 1,201

One-way from

S$ 650

Popular in

January

Cheapest in

October

Average price

S$ 1,257
United Airlines
  • United Airlines
  • 25-1-25-1
  • 2 total stops
  • 55h 04m total
  • Singapore to Chicago
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4-2
  • 4-2
  • 2 total stops
  • 47h 16m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (S$ 288 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 70 potential savings vs. average return price).
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Average for round-trip flights in November 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 19 November 2025.

Sat 13-1210:10SIN - ORD
1 stop24h 57mUnited Airlines
Mon 5-106:15ORD - SIN
1 stop24h 00mUnited Airlines
Deal found 17-11S$ 1,417
Sat 13-1223:00SIN - ORD
2 stops50h 30mAir India
Mon 5-113:30ORD - SIN
1 stop42h 15mAir India
Deal found 17-11S$ 1,620
Sat 13-1208:50SIN - ORD
2 stops37h 10mAir Canada
Mon 5-115:35ORD - SIN
2 stops49h 25mAir Canada
Deal found 17-11S$ 1,644
Thu 27-1108:50SIN - ORD
1 stop21h 54mAir Canada
Mon 8-1217:55ORD - SIN
2 stops47h 05mAir Canada
Deal found 18-11S$ 1,654
Sat 6-1208:50SIN - ORD
1 stop19h 51mAir Canada
Thu 11-1215:40ORD - SIN
2 stops29h 35mAir Canada
Deal found 17-11S$ 1,681
Thu 18-1201:25SIN - ORD
1 stop25h 30mCathay Pacific
Sat 3-114:35ORD - SIN
1 stop32h 30mCathay Pacific
Deal found 17-11S$ 1,832
Fri 19-1207:40SIN - ORD
1 stop19h 15mMultiple Airlines
Sat 3-111:50ORD - SIN
2 stops39h 55mMultiple Airlines
Deal found 17-11S$ 2,056
Tue 16-1201:40SIN - MDW
2 stops28h 54mKLM
Thu 8-117:31MDW - SIN
2 stops32h 44mKLM
Deal found 16-11S$ 2,915
Wed 17-1201:40SIN - MDW
2 stops28h 51mKLM
Thu 8-117:31MDW - SIN
2 stops32h 44mKLM
Deal found 16-11S$ 3,033
Thu 18-1201:40SIN - MDW
2 stops28h 51mKLM
Thu 8-117:31MDW - SIN
2 stops32h 44mKLM
Deal found 16-11S$ 3,321
Fri 19-1222:30SIN - MDW
2 stops37h 52mDelta
Fri 9-106:45MDW - SIN
2 stops32h 15mDelta
Deal found 16-11S$ 3,664
Thu 18-1222:30SIN - MDW
2 stops32h 01mDelta
Thu 8-106:45MDW - SIN
2 stops32h 15mDelta
Deal found 16-11S$ 3,924

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 19 November 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

Wed 28-1

22:20-06:25

1 stop22h 05m

Chicago O'Hare Intl

Sun 1-2

12:45-08:00

1 stop29h 15m

S$ 1,209

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 25-1

22:20-14:53

1 stop30h 33m

Chicago O'Hare Intl

Fri 30-1

06:47-20:15

1 stop23h 28m

S$ 1,213

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 20-12

10:10-01:09

1 stop28h 59m

Chicago O'Hare Intl

Wed 7-1

06:47-20:15

1 stop23h 28m

S$ 1,213

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 16-4

20:40-07:12

1 stop23h 32m

Chicago O'Hare Intl

Mon 20-4

06:25-18:25

1 stop23h 00m

S$ 1,213

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 16-12

22:20-05:00

1 stop20h 40m

Chicago O'Hare Intl

Sun 11-1

06:47-20:15

1 stop23h 28m

S$ 1,213

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 15-12

22:20-06:02

1 stop21h 42m

Chicago O'Hare Intl

Sun 11-1

16:16-08:00

1 stop25h 44m

S$ 1,213

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 10-2

10:10-18:48

1 stop22h 38m

Chicago O'Hare Intl

Fri 20-2

06:25-20:15

1 stop23h 50m

S$ 1,214

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 4-5

06:15-08:05

2 stops38h 50m

Chicago O'Hare Intl

Tue 19-5

08:40-07:05

2 stops33h 25m

S$ 1,218

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 27-1

01:35-08:40

1 stop21h 05m

Chicago O'Hare Intl

Sun 1-2

11:25-00:10

1 stop22h 45m

S$ 1,236

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 25-1

08:50-20:10

2 stops25h 20m

Chicago O'Hare Intl

Fri 30-1

07:15-07:00

2 stops33h 45m

S$ 1,262

Flights are sorted by cheapest return flights first.

Deals found on 18-11

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$ 905). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,343). 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 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 19 November 2025.

It’s typically best to fly out from Singapore to Chicago in the morning. Doing so could potentially save you 23% on the flight price compared to flying in the afternoon, 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 33% 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$ 1,289.

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 Taipei City (TPE) have the shortest average one-way travel time for one-stop routes: 20h 39m.

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 19 November 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
1,277 reviews
Check prices

Crew

8.6

Boarding

8.4

Food

8.1

Comfort

8.3

Entertainment

8.0

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.
EVA Air
8.4
Very Good
1,277 reviews
EVA Air
8.4
Very Good
1,277 reviews
Check prices

Crew

8.6

Boarding

8.4

Food

8.1

Comfort

8.3

Entertainment

8.0

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.
ANA
8.4
Very Good
1,007 reviews
EVA Air
8.4
Very Good
1,277 reviews
Check prices

Crew

8.6

Boarding

8.4

Food

8.1

Comfort

8.3

Entertainment

8.0

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.
Japan Airlines
8.3
Very Good
1,623 reviews
EVA Air
8.4
Very Good
1,277 reviews
Check prices

Crew

8.6

Boarding

8.4

Food

8.1

Comfort

8.3

Entertainment

8.0

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.
Cathay Pacific
7.6
Good
1,061 reviews
EVA Air
8.4
Very Good
1,277 reviews
Check prices

Crew

8.6

Boarding

8.4

Food

8.1

Comfort

8.3

Entertainment

8.0

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.
United Airlines
7.4
Good
9,019 reviews
EVA Air
8.4
Very Good
1,277 reviews
Check prices

Crew

8.6

Boarding

8.4

Food

8.1

Comfort

8.3

Entertainment

8.0

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.

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 4 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 05m. Your travel time can differ by up to 31h 50m. 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$ 898, 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.

  • 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$ 905). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,343). 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 19 November 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 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 19 November 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 898AverageS$ 1,313FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 905AverageS$ 1,516FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,071AverageS$ 2,645FlexibilityNo cancel feeOn-time80%
Search ANA flights
EVA AirCheapestS$ 1,318AverageS$ 1,520FlexibilityNo 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?

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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