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Cheap flights from Singapore to Chicago from S$ 661

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 20-8. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
18 Jun — 25 Jun1
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 19 May 2026.

Fri 30-1008:50
SIN
-
ORD
2 stops24h 20m
Air Canada
Sat 14-1115:55
ORD
-
SIN
2 stops49h 05m
Air Canada
Deal found 16-5S$ 1,050
Tue 18-807:00
SIN
-
ORD
2 stops28h 46m
Air Canada
Sun 6-907:00
ORD
-
SIN
2 stops33h 15m
Air Canada
Deal found 15-5S$ 1,053
Tue 18-807:00
SIN
-
ORD
2 stops29h 59m
Air Canada
Mon 7-921:22
ORD
-
SIN
2 stops42h 53m
Air Canada
Deal found 15-5S$ 1,063
Tue 18-807:00
SIN
-
ORD
2 stops29h 59m
Air Canada
Wed 9-907:09
ORD
-
SIN
2 stops34h 31m
Air Canada
Deal found 15-5S$ 1,075
Sun 1-1122:30
SIN
-
ORD
1 stop24h 00m
Korean Air
Mon 16-1111:15
ORD
-
SIN
1 stop43h 10m
Korean Air
Deal found 18-5S$ 1,185
Thu 29-1022:30
SIN
-
ORD
1 stop24h 00m
Korean Air
Fri 13-1111:15
ORD
-
SIN
1 stop22h 55m
Korean Air
Deal found 15-5S$ 1,190
Thu 22-1001:25
SIN
-
ORD
1 stop21h 05m
Korean Air
Sun 25-1012:15
ORD
-
SIN
1 stop43h 10m
Korean Air
Deal found 17-5S$ 1,222
Wed 28-1010:40
SIN
-
ORD
2 stops36h 27m
Delta
Thu 12-1107:05
ORD
-
SIN
2 stops31h 55m
Delta
Deal found 14-5S$ 1,231
Fri 30-1010:40
SIN
-
ORD
1 stop35h 50m
Multiple Airlines
Sat 14-1111:15
ORD
-
SIN
1 stop44h 40m
Multiple Airlines
Deal found 16-5S$ 1,346
Wed 28-1010:40
SIN
-
ORD
1 stop35h 50m
Multiple Airlines
Thu 12-1111:15
ORD
-
SIN
1 stop44h 40m
Multiple Airlines
Deal found 14-5S$ 1,352
Sun 1-1110:40
SIN
-
ORD
1 stop35h 50m
Delta
Mon 16-1107:00
ORD
-
SIN
2 stops32h 00m
Delta
Deal found 18-5S$ 1,356
Wed 23-1201:35
SIN
-
MDW
2 stops34h 10m
Delta
Sat 9-117:35
MDW
-
SIN
2 stops40h 35m
Delta
Deal found 14-5S$ 1,529

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 19 May 2026.

Round-trip from

S$ 1,050

One-way from

S$ 661

Popular in

August

Cheapest in

February

Average price

S$ 1,369
Air Canada
  • Air Canada
  • 30-10-14-11
  • 4 total stops
  • 73h 25m total
  • Singapore to Chicago
Search Deals
Air Canada
  • Air Canada
  • 20-8
  • 1 total stop
  • 20h 36m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (S$ 348 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (S$ 139 potential savings vs. average return price).
Search Deals
Average for round-trip flights in May 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 19 May 2026.
Use the filters below to find and compare flights from Singapore to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 22-10

01:25-09:30

1 stop21h 05m

Chicago O'Hare Intl

Sun 25-10

12:15-05:00

1 stop27h 45m

S$ 1,222

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 18-8

07:30-23:28

2 stops28h 58m

Chicago O'Hare Intl

Wed 9-9

07:30-05:00

2 stops32h 30m

S$ 1,618

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 19-8

13:45-05:45

2 stops29h 00m

Chicago Midway

Thu 10-9

17:55-12:35

2 stops29h 40m

S$ 1,636

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 21-8

15:35-07:45

2 stops29h 10m

Chicago O'Hare Intl

Sat 26-9

10:15-11:25

2 stops36h 10m

S$ 1,657

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 20-8

16:35-07:45

2 stops28h 10m

Chicago O'Hare Intl

Sun 20-9

10:15-09:05

2 stops33h 50m

S$ 1,657

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 7-6

13:45-11:25

2 stops34h 40m

Chicago Midway

Sun 9-8

20:35-12:35

2 stops27h 00m

S$ 1,681

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 4-8

15:20-05:50

2 stops27h 30m

Chicago Midway

Thu 27-8

20:55-11:55

2 stops26h 00m

S$ 1,725

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 3-8

13:45-05:00

2 stops28h 15m

Chicago Midway

Sat 29-8

18:00-12:35

2 stops29h 35m

S$ 1,726

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 28-6

03:15-18:58

2 stops28h 43m

Chicago O'Hare Intl

Mon 6-7

19:20-15:45

1 stop31h 25m

S$ 1,743

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 20-8

22:00-12:36

2 stops27h 36m

Chicago O'Hare Intl

Fri 11-9

12:10-05:00

1 stop27h 50m

S$ 1,769

Flights are sorted by cheapest return flights first.

Deals found on 18-5

Showing 1-10 of 36 resultsSorted by cheapest first
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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, October is the cheapest month in which you can book a flight from Singapore to Chicago (average of S$ 850). Flying from Singapore to Chicago in December is currently the most expensive (average of S$ 1,228). 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.

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.

San Francisco (SFO) – chosen by Cheapflights users on 35% 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$ 1,311.

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 10m.

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 Tokyo (HND) offer the fastest connection on this route, with an average stopover time of 1h 30m.

How often are flights from Singapore to Chicago delayed?

About 100% of weekly flights between Singapore and Chicago have experienced delays in the past year, with the average delay time being 1,189 minutes.

What is the most punctual flight time for Singapore to Chicago flights?

Historically, flights departing in the evening are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.

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 May 2026.
Check out reviews from past customers who have flown with EVA Air and United 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
8.5
Very Good
1,453 reviews
Check prices

Boarding

8.4

Food

8.1

Crew

8.7

Entertainment

8.0

Comfort

8.3

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

TPE - SFO

Why when we’re about to board they suddenly announced the letters ABC to board first .. so what is the use us waiting at the door (with wheelchairs) ended up almost at the end to board and I can see people walking boarding first? Is this something new? You go by letters now?
EVA Air
8.5
Very Good
1,453 reviews
EVA Air
8.5
Very Good
1,453 reviews
Check prices

Boarding

8.4

Food

8.1

Crew

8.7

Entertainment

8.0

Comfort

8.3

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

TPE - SFO

Why when we’re about to board they suddenly announced the letters ABC to board first .. so what is the use us waiting at the door (with wheelchairs) ended up almost at the end to board and I can see people walking boarding first? Is this something new? You go by letters now?
United Airlines
7.4
Good
9,736 reviews
EVA Air
8.5
Very Good
1,453 reviews
Check prices

Boarding

8.4

Food

8.1

Crew

8.7

Entertainment

8.0

Comfort

8.3

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

TPE - SFO

Why when we’re about to board they suddenly announced the letters ABC to board first .. so what is the use us waiting at the door (with wheelchairs) ended up almost at the end to board and I can see people walking boarding first? Is this something new? You go by letters now?

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?

    Korean Air, Delta, and Malaysia Airlines can get you from Singapore to Chicago in just under 21h 05m. Your travel time can differ by up to 8h 05m. 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$ 883, was found to be the cheapest airline from Singapore to Chicago.Alternate airlines to your destination round-trip include Japan Airlines and EVA Air. You may be able to fly from Singapore to Chicago for 39% 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, October is the cheapest month in which you can book a flight from Singapore to Chicago (average of S$ 850). Flying from Singapore to Chicago in December is currently the most expensive (average of S$ 1,228). 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

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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 19 May 2026.
United Airlines flights from Singapore Changi to Chicago
EVA Air 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 19 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 883AverageS$ 1,377FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 889AverageS$ 1,489FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
EVA AirCheapestS$ 1,326AverageS$ 1,700FlexibilityNo 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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