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Cheap flights from Singapore to Chicago from S$ 618

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
1 Feb — 8 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Singapore to Chicago

Enter your travel dates to find the best prices.

Best flights from Singapore to Chicago
Discover carefully curated flight deals from Singapore to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 2 January 2026.

Thu 22-108:50SIN - ORD
1 stop19h 51mAir Canada
Wed 4-215:35ORD - SIN
1 stop25h 25mAir Canada
Deal found 1-1S$ 1,179
Tue 17-210:40SIN - ORD
2 stops24h 50mKorean Air
Wed 18-211:25ORD - SIN
1 stop43h 00mKorean Air
Deal found 30-12S$ 1,179
Tue 17-222:20SIN - ORD
1 stop21h 59mUnited Airlines
Wed 18-209:01ORD - SIN
1 stop32h 59mUnited Airlines
Deal found 30-12S$ 1,200
Wed 28-102:20SIN - ORD
1 stop19h 15mJapan Airlines
Thu 5-210:35ORD - SIN
1 stop24h 15mJapan Airlines
Deal found 30-12S$ 1,204
Sun 15-210:40SIN - MDW
2 stops25h 51mDelta
Sun 22-218:40MDW - SIN
2 stops39h 30mDelta
Deal found 1-1S$ 1,412
Thu 29-114:25SIN - MDW
2 stops36h 15mMultiple Airlines
Thu 5-208:15MDW - SIN
2 stops38h 50mMultiple Airlines
Deal found 30-12S$ 1,484
Sun 15-222:30SIN - ORD
1 stop24h 10mKorean Air
Sun 22-211:25ORD - SIN
1 stop43h 00mKorean Air
Deal found 1-1S$ 1,202
Wed 17-620:40SIN - ORD
1 stop21h 18mUnited Airlines
Thu 2-716:17ORD - SIN
1 stop37h 18mUnited Airlines
Deal found 1-1S$ 1,208
Tue 10-210:10SIN - ORD
1 stop27h 04mUnited Airlines
Fri 20-217:00ORD - SIN
1 stop25h 00mUnited Airlines
Deal found 1-1S$ 1,208
Tue 10-210:40SIN - MDW
2 stops37h 13mDelta
Fri 20-206:00MDW - SIN
2 stops33h 00mDelta
Deal found 1-1S$ 1,770
Tue 10-214:25SIN - MDW
2 stops36h 15mMultiple Airlines
Fri 20-216:55MDW - SIN
3 stops41h 45mMultiple Airlines
Deal found 1-1S$ 2,496
Sat 14-222:30SIN - MDW
2 stops38h 01mDelta
Sat 21-216:13MDW - SIN
2 stops38h 12mDelta
Deal found 31-12S$ 2,334
Sat 14-214:25SIN - MDW
3 stops38h 30mMultiple Airlines
Sat 21-211:10MDW - SIN
2 stops35h 55mMultiple Airlines
Deal found 31-12S$ 2,757
Sun 10-522:30SIN - MDW
2 stops30h 55mDelta
Mon 18-506:00MDW - SIN
2 stops28h 40mDelta
Deal found 1-1S$ 5,663
Sat 28-214:25SIN - MDW
2 stops35h 40mMultiple Airlines
Wed 11-307:05MDW - SIN
2 stops41h 00mMultiple Airlines
Deal found 1-1S$ 7,823
Sun 10-501:10SIN - MDW
2 stops24h 20mKorean Air
Mon 18-509:20MDW - SIN
2 stops25h 20mKorean Air
Deal found 1-1S$ 10,346

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 2 January 2026.

Round-trip from

S$ 1,128

One-way from

S$ 618

Popular in

January

Cheapest in

April

Average price

S$ 2,269
Korean Air
  • Korean Air
  • 13-2-20-2
  • 2 total stops
  • 63h 35m total
  • Singapore to Chicago
Search Deals
25-2
  • 25-2
  • 3 total stops
  • 50h 51m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (S$ 332 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (S$ 97 potential savings vs. average return price).
Search Deals
Average for round-trip flights in January 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 2 January 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 22-1

08:50-14:41

1 stop19h 51m

Chicago O'Hare Intl

Wed 4-2

15:35-07:00

1 stop25h 25m

S$ 1,179

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 17-2

10:40-21:30

2 stops24h 50m

Chicago O'Hare Intl

Wed 18-2

11:25-20:25

1 stop43h 00m

S$ 1,179

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 17-2

22:20-06:19

1 stop21h 59m

Chicago O'Hare Intl

Wed 18-2

09:01-08:00

1 stop32h 59m

S$ 1,200

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 15-2

22:30-08:40

1 stop24h 10m

Chicago O'Hare Intl

Sun 22-2

11:25-20:25

1 stop43h 00m

S$ 1,202

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 28-1

02:20-07:35

1 stop19h 15m

Chicago O'Hare Intl

Thu 5-2

10:35-00:50

1 stop24h 15m

S$ 1,204

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 17-6

20:40-04:58

1 stop21h 18m

Chicago O'Hare Intl

Thu 2-7

16:17-18:35

1 stop37h 18m

S$ 1,208

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 10-2

10:10-23:14

1 stop27h 04m

Chicago O'Hare Intl

Fri 20-2

17:00-08:00

1 stop25h 00m

S$ 1,208

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 15-2

10:40-22:31

2 stops25h 51m

Chicago Midway

Sun 22-2

18:40-00:10

2 stops39h 30m

S$ 1,412

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 29-1

14:25-12:40

2 stops36h 15m

Chicago Midway

Thu 5-2

08:15-13:05

2 stops38h 50m

S$ 1,484

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 10-2

10:40-09:53

2 stops37h 13m

Chicago Midway

Fri 20-2

06:00-05:00

2 stops33h 00m

S$ 1,770

Flights are sorted by cheapest return flights first.

Deals found on 30-12

Showing 1-10 of 33 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$ 893). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,324). 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 34% 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$ 1,278.

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 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 2 January 2026.
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
1,306 reviews
Check prices

Food

8.1

Comfort

8.3

Overall

8.4

Boarding

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

TPE - CRK

All was okay except for the medical emergency that happened before our boarding. I wish that the medical emergency response was more immediate.
EVA Air
8.4
Very Good
1,306 reviews
EVA Air
8.4
Very Good
1,306 reviews
Check prices

Food

8.1

Comfort

8.3

Overall

8.4

Boarding

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

TPE - CRK

All was okay except for the medical emergency that happened before our boarding. I wish that the medical emergency response was more immediate.
ANA
8.4
Very Good
1,055 reviews
EVA Air
8.4
Very Good
1,306 reviews
Check prices

Food

8.1

Comfort

8.3

Overall

8.4

Boarding

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

TPE - CRK

All was okay except for the medical emergency that happened before our boarding. I wish that the medical emergency response was more immediate.
Japan Airlines
8.3
Very Good
1,663 reviews
EVA Air
8.4
Very Good
1,306 reviews
Check prices

Food

8.1

Comfort

8.3

Overall

8.4

Boarding

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

TPE - CRK

All was okay except for the medical emergency that happened before our boarding. I wish that the medical emergency response was more immediate.
Cathay Pacific
7.6
Good
1,114 reviews
EVA Air
8.4
Very Good
1,306 reviews
Check prices

Food

8.1

Comfort

8.3

Overall

8.4

Boarding

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

TPE - CRK

All was okay except for the medical emergency that happened before our boarding. I wish that the medical emergency response was more immediate.
United Airlines
7.4
Good
9,129 reviews
EVA Air
8.4
Very Good
1,306 reviews
Check prices

Food

8.1

Comfort

8.3

Overall

8.4

Boarding

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

TPE - CRK

All was okay except for the medical emergency that happened before our boarding. I wish that the medical emergency response was more immediate.

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?

    Air Canada, Korean Air, and Delta can get you from Singapore to Chicago in just under 19h 51m. Your travel time can differ by up to 6h. 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$ 886, 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 38% 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$ 893). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,324). 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 2 January 2026.
EVA Air flights from Singapore Changi to Chicago
United Airlines flights from Singapore Changi to Chicago
Japan Airlines flights from Singapore Changi to Chicago
ANA 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 2 January 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 886AverageS$ 1,321FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 892AverageS$ 1,541FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,056AverageS$ 2,829FlexibilityNo cancel feeOn-time80%
Search ANA flights
EVA AirCheapestS$ 1,298AverageS$ 1,508FlexibilityNo 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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