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Cheap flights from Singapore to Chicago from S$ 582

SIN — CHI
20 Sep — 27 Sep1
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

Thu 10-907:00 -
1 stop20h 43m
Thu 24-915:40 -
1 stop24h 35m
Deal found 18-8S$ 950
Sat 3-1007:00 -
1 stop20h 43m
Sat 10-1019:45 -
1 stop44h 30m
Deal found 19-8S$ 978
Sun 15-1108:40 -
1 stop19h 57m
Sun 6-1215:30 -
1 stop25h 30m
Deal found 18-8S$ 985
Tue 22-920:50 -
2 stops30h 53m
Sun 27-909:55 -
2 stops30h 20m
Deal found 19-8S$ 1,008
Mon 14-922:00 -
2 stops27h 39m
Tue 29-917:11 -
2 stops37h 04m
Deal found 16-8S$ 1,432
Tue 13-1022:00 -
2 stops27h 47m
Wed 28-1009:29 -
2 stops25h 41m
Deal found 18-8S$ 1,433
Sun 20-1201:35 -
2 stops34h 35m
Tue 26-117:25 -
2 stops37h 00m
Deal found 20-8S$ 1,436
Thu 10-907:30 -
2 stops28h 14m
Thu 24-909:59 -
2 stops30h 01m
Deal found 19-8S$ 1,527
Sat 3-1013:55 -
2 stops34h 30m
Sat 10-1019:45 -
2 stops27h 45m
Deal found 19-8S$ 1,534
Fri 18-1214:25 -
2 stops29h 30m
Mon 11-110:25 -
2 stops36h 40m
Deal found 20-8S$ 1,559
Tue 13-1013:55 -
2 stops29h 10m
Wed 28-1016:45 -
3 stops31h 20m
Deal found 18-8S$ 1,560
Sun 11-1001:25 -
2 stops27h 49m
Wed 28-1006:04 -
2 stops29h 06m
Deal found 18-8S$ 1,572

Find flight deals from Singapore to Chicago

Round-trip from

S$ 949

One-way from

S$ 582

Popular in

August

Cheapest in

September

Average price

S$ 2,609
Air Canada
  • Air Canada
  • 30-1-14-2
  • 2 total stops
  • 45h 17m total
  • Singapore to Chicago
Search Deals
Air Canada
  • Air Canada
  • 29-1
  • 1 total stop
  • 19h 52m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (S$ 319 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (S$ 143 potential savings vs. average return price).
Search Deals
Average for round-trip flights in August 2026
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Cheapflights Fare Finder

 
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
Fastest return journey

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Thu 1-10

07:00-16:35

2 stops22h 35m

Chicago O'Hare Intl

Thu 8-10

10:15-00:20

1 stop25h 05m

S$ 1,389

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Sun 30-8

08:45-18:32

1 stop22h 47m

Chicago O'Hare Intl

Wed 2-9

21:28-18:35

1 stop32h 07m

S$ 1,414

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Sun 30-8

20:35-12:29

1 stop28h 54m

Chicago O'Hare Intl

Wed 9-9

16:00-06:15

1 stop25h 15m

S$ 1,414

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Fri 25-9

08:45-00:59

1 stop29h 14m

Chicago O'Hare Intl

Sun 27-9

16:40-06:15

1 stop24h 35m

S$ 1,417

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Mon 14-9

22:00-12:39

2 stops27h 39m

Chicago Midway

Tue 29-9

17:11-19:15

2 stops37h 04m

S$ 1,432

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Sat 29-8

01:25-21:33

2 stops33h 08m

Chicago O'Hare Intl

Wed 9-9

07:00-05:00

2 stops33h 00m

S$ 1,433

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Wed 23-12

01:35-22:10

2 stops34h 35m

Chicago Midway

Sun 24-1

17:25-20:25

2 stops37h 00m

S$ 1,436

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Wed 9-9

01:25-16:57

2 stops28h 32m

Chicago Midway

Thu 24-9

09:59-05:00

2 stops30h 01m

S$ 1,436

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Fri 25-9

07:30-08:38

2 stops38h 08m

Chicago O'Hare Intl

Sun 27-9

18:25-19:15

2 stops35h 50m

S$ 1,436

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 10-11

10:40-08:50

2 stops36h 10m

Chicago Midway

Sat 28-11

17:25-00:10

2 stops40h 45m

S$ 1,527

Flights are sorted by cheapest return flights first.

Deals found on 18-8

Showing 1-10 of 42 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

Cheapflights Insights

Everything you need to know about your flight from Singapore to Chicago

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

Airfare is below average for this route at the moment.
Singapore to Chicago flights typically cost between S$ 1,676 and S$ 1,859 in February.
The cheapest return price found within the last 5 days was S$ 872 on Air Canada (4 Feb–19 Feb).

What’s the top stopover airport for flights from Singapore to Chicago?

San Francisco (SFO) – chosen by Cheapflights users on 38% of one-stop itineraries from Singapore to Chicago on Cheapflights.

What’s the cheapest stopover airport for flights from Singapore to Chicago?

Vancouver (YVR) is the most affordable one-stop option, with an average return flight price of S$ 1,059.

What’s the fastest stopover option from Singapore to Chicago?

Flights via Vancouver (YVR) have the shortest average one-way travel time for one-stop routes: 19h 57m.

Which airport typically offers the quickest stopover for flights from Singapore to Chicago?

Flights via Incheon (ICN) offer the fastest connection on this route, with an average stopover time of 1h 33m.

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 1,095 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

Check out reviews from past customers who have flown with EVA Air,Korean Air, 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
8.5
Very Good
1,518 reviews
Check prices

Boarding

8.4

Food

8.1

Comfort

8.3

Crew

8.7

Entertainment

8.0

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking
EVA Air
8.5
Very Good
1,518 reviews
EVA Air
8.5
Very Good
1,518 reviews
Check prices

Boarding

8.4

Food

8.1

Comfort

8.3

Crew

8.7

Entertainment

8.0

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking
Korean Air
8.4
Very Good
1,221 reviews
EVA Air
8.5
Very Good
1,518 reviews
Check prices

Boarding

8.4

Food

8.1

Comfort

8.3

Crew

8.7

Entertainment

8.0

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking
Japan Airlines
8.3
Very Good
1,908 reviews
EVA Air
8.5
Very Good
1,518 reviews
Check prices

Boarding

8.4

Food

8.1

Comfort

8.3

Crew

8.7

Entertainment

8.0

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking
United Airlines
7.4
Good
10,104 reviews
EVA Air
8.5
Very Good
1,518 reviews
Check prices

Boarding

8.4

Food

8.1

Comfort

8.3

Crew

8.7

Entertainment

8.0

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking

Related info for your journey

  • 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 2 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 47m. Your travel time can differ by up to 4h 52m. 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$ 1,206, was found to be the cheapest airline from Singapore to Chicago. An alternate airline flying to your destination would be EVA Air. You may be able to fly from Singapore to Chicago for 19% 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

Fly from Singapore to Chicago on these airlines

Japan Airlines flights from Singapore Changi to Chicago
United Airlines flights from Singapore Changi to Chicago
EVA Air flights from Singapore Changi to Chicago

Top 2 airlines flying from Singapore to Chicago

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 1,206AverageS$ 1,512FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
EVA AirCheapestS$ 1,318AverageS$ 1,690FlexibilityNo cancel feeOn-time74%
Search EVA Air flights

Fly with Cheapflights

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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