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Cheap flights from Singapore to Chicago from S$ 630

SIN — CHI
4 Nov — 11 Nov1
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 19-1108:40 -
1 stop19h 57m
Thu 26-1115:30 -
1 stop25h 30m
Deal found 4-10S$ 984
Sun 1-1108:40 -
1 stop19h 57m
Sun 15-1115:30 -
1 stop25h 30m
Deal found 2-10S$ 1,039
Sun 15-1108:40 -
1 stop25h 19m
Sun 22-1121:21 -
2 stops43h 34m
Deal found 1-10S$ 1,066
Thu 19-1108:30 -
2 stops25h 29m
Thu 26-1113:30 -
2 stops27h 30m
Deal found 4-10S$ 1,084
Fri 30-1008:40 -
1 stop24h 21m
Tue 24-1115:30 -
1 stop25h 30m
Deal found 2-10S$ 1,092
Tue 27-1008:40 -
1 stop24h 21m
Mon 2-1115:50 -
2 stops49h 10m
Deal found 30-9S$ 1,098

Find flight deals from Singapore to Chicago

Round-trip from

S$ 984

One-way from

S$ 630

Popular in

August

Cheapest in

September

Average price

S$ 1,349
Air Canada
  • Air Canada
  • 19-11-26-11
  • 2 total stops
  • 45h 27m total
  • Singapore to Chicago
Search Deals
Air Canada
  • Air Canada
  • 11-10-31-12
  • 1 total stop
  • 20h 43m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (S$ 365 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (S$ 144 potential savings vs. average return price).
Search Deals
Average for round-trip flights in October 2026
Search Deals

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

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Thu 10-12

08:40-08:00

2 stops37h 20m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 665

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Fri 19-3

10:30-09:30

1 stop36h 00m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 721

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Thu 11-2

10:30-21:37

2 stops25h 07m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 725

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Thu 18-3

01:40-23:46

2 stops35h 06m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 797

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Mon 18-1

12:55-12:30

1 stop37h 35m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 884
Fastest return journey

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Mon 11-1

01:40-08:30

1 stop20h 50m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 968

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Sun 1-11

22:30-16:58

2 stops32h 28m

Chicago O'Hare Intl

Thu 5-11

17:30-00:15

2 stops40h 45m

S$ 1,257

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Wed 28-10

01:40-23:34

2 stops34h 54m

Chicago O'Hare Intl

Thu 5-11

17:00-00:15

2 stops41h 15m

S$ 1,259

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Thu 18-3

01:40-23:46

2 stops35h 06m

Chicago O'Hare Intl

Sat 3-4

17:55-23:55

2 stops41h 00m

S$ 1,261

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Wed 23-12

19:25-07:35

1 stop26h 10m

Chicago O'Hare Intl

Thu 7-1

13:15-09:35

1 stop30h 20m

S$ 1,339

Flights are sorted by cheapest return flights first.

Deals found on 5-10

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

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

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

San Francisco (SFO) – chosen by Cheapflights users on 41% 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$ 1,065.

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

Flights via Hong Kong (HKG) have the shortest average one-way travel time for one-stop routes: 19h 15m.

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.

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
1,544 reviews
Check prices

Comfort

8.3

Overall

8.5

Crew

8.7

Boarding

8.5

Entertainment

8.0

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2026

SEA - TPE

The food on EVA suits my Asian palate and is always of a high standard. The flight was comfortable and the crew very helpful. I lost an ear bud while I slept and they helped me find it at the end of the flight. I was very grateful!
EVA Air
8.5
Very Good
1,544 reviews
EVA Air
8.5
Very Good
1,544 reviews
Check prices

Comfort

8.3

Overall

8.5

Crew

8.7

Boarding

8.5

Entertainment

8.0

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2026

SEA - TPE

The food on EVA suits my Asian palate and is always of a high standard. The flight was comfortable and the crew very helpful. I lost an ear bud while I slept and they helped me find it at the end of the flight. I was very grateful!
Korean Air
8.4
Very Good
1,218 reviews
EVA Air
8.5
Very Good
1,544 reviews
Check prices

Comfort

8.3

Overall

8.5

Crew

8.7

Boarding

8.5

Entertainment

8.0

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2026

SEA - TPE

The food on EVA suits my Asian palate and is always of a high standard. The flight was comfortable and the crew very helpful. I lost an ear bud while I slept and they helped me find it at the end of the flight. I was very grateful!
Japan Airlines
8.3
Very Good
1,932 reviews
EVA Air
8.5
Very Good
1,544 reviews
Check prices

Comfort

8.3

Overall

8.5

Crew

8.7

Boarding

8.5

Entertainment

8.0

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2026

SEA - TPE

The food on EVA suits my Asian palate and is always of a high standard. The flight was comfortable and the crew very helpful. I lost an ear bud while I slept and they helped me find it at the end of the flight. I was very grateful!
United Airlines
7.4
Good
10,289 reviews
EVA Air
8.5
Very Good
1,544 reviews
Check prices

Comfort

8.3

Overall

8.5

Crew

8.7

Boarding

8.5

Entertainment

8.0

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2026

SEA - TPE

The food on EVA suits my Asian palate and is always of a high standard. The flight was comfortable and the crew very helpful. I lost an ear bud while I slept and they helped me find it at the end of the flight. I was very grateful!

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?

    Delta, Etihad Airways, and Japan Airlines can get you from Singapore to Chicago in just under 26h 10m. Your travel time can differ by up to 11h 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$ 1,203, 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 20% 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$ 1,203AverageS$ 1,521FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
EVA AirCheapestS$ 1,491AverageS$ 1,699FlexibilityNo 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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