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Cheap flights from Singapore to Chicago from S$ 651

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
20 Dec — 27 Dec1
1 adult
1 adult, Economy, 0 bags

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 20 November 2025.

Sat 13-1210:10SIN - ORD
1 stop23h 32mUnited Airlines
Mon 5-106:15ORD - SIN
1 stop24h 00mUnited Airlines
Deal found 19-11S$ 1,418
Tue 16-1221:00SIN - ORD
2 stops31h 41mAir Canada
Tue 30-1207:05ORD - SIN
2 stops33h 55mAir Canada
Deal found 19-11S$ 1,435
Tue 16-1222:20SIN - ORD
1 stop20h 40mUnited Airlines
Tue 30-1214:40ORD - SIN
1 stop27h 20mUnited Airlines
Deal found 19-11S$ 1,518
Sat 13-1208:50SIN - ORD
2 stops37h 10mAir Canada
Mon 5-115:35ORD - SIN
2 stops49h 25mAir Canada
Deal found 19-11S$ 1,623
Sat 13-1223:00SIN - ORD
2 stops50h 30mAir India
Mon 5-113:30ORD - SIN
1 stop39h 25mAir India
Deal found 18-11S$ 1,625
Thu 27-1108:50SIN - ORD
1 stop19h 51mAir Canada
Mon 8-1215:35ORD - SIN
2 stops49h 25mAir Canada
Deal found 20-11S$ 1,655
Sat 6-1208:50SIN - ORD
2 stops22h 20mAir Canada
Thu 11-1213:10ORD - SIN
1 stop27h 50mAir Canada
Deal found 19-11S$ 1,681
Mon 15-1201:40SIN - MDW
2 stops29h 04mMultiple Airlines
Tue 30-1218:08MDW - SIN
2 stops32h 47mMultiple Airlines
Deal found 19-11S$ 2,812
Tue 16-1210:40SIN - MDW
2 stops27h 07mDelta
Tue 30-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 19-11S$ 3,082
Wed 31-1201:35SIN - MDW
2 stops34h 47mDelta
Thu 8-106:45MDW - SIN
2 stops32h 15mDelta
Deal found 17-11S$ 10,809
Thu 18-1215:45SIN - MDW
2 stops27h 30mMultiple Airlines
Sat 3-119:00MDW - SIN
2 stops27h 05mMultiple Airlines
Deal found 19-11S$ 13,214
Thu 18-1222:30SIN - MDW
2 stops27h 25mDelta
Sat 3-106:00MDW - SIN
2 stops28h 10mDelta
Deal found 18-11S$ 13,524

Cheap flight deals from Singapore to Chicago

Keep the following information in mind while searching for Singapore to Chicago flight deals. Data was last updated 20 November 2025.

Round-trip from

S$ 1,203

One-way from

S$ 651

Popular in

January

Cheapest in

October

Average price

S$ 1,259
United Airlines
  • United Airlines
  • 25-1-25-1
  • 2 total stops
  • 55h 04m total
  • Singapore to Chicago
Search Deals
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$ 71 potential savings vs. average return price).
Search Deals
Average for round-trip flights in November 2025
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 20 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

Tue 10-2

22:20-06:25

1 stop22h 05m

Chicago O'Hare Intl

Fri 20-2

06:25-20:15

1 stop23h 50m

S$ 1,210

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$ 1,210

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 5-5

09:10-08:05

2 stops35h 55m

Chicago O'Hare Intl

Wed 20-5

08:40-00:45

2 stops27h 05m

S$ 1,220

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$ 1,220

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$ 1,238

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 3-5

01:50-14:25

1 stop25h 35m

Chicago O'Hare Intl

Tue 19-5

16:00-05:30

1 stop24h 30m

S$ 1,333

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 4-5

01:50-14:25

1 stop25h 35m

Chicago O'Hare Intl

Wed 20-5

16:00-15:05

1 stop34h 05m

S$ 1,333

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 9-2

01:25-12:55

1 stop25h 30m

Chicago O'Hare Intl

Fri 20-2

14:35-19:15

1 stop38h 40m

S$ 1,334

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 25-1

10:10-16:57

1 stop20h 47m

Chicago O'Hare Intl

Sun 25-1

19:58-06:55

2 stops44h 57m

S$ 1,355

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 27-1

01:25-12:55

1 stop25h 30m

Chicago O'Hare Intl

Sun 1-2

14:35-11:55

1 stop31h 20m

S$ 1,377

Flights are sorted by cheapest return flights first.

Deals found on 18-11

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$ 906). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,345). 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 SG 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 20 November 2025.

One of the essential ways to save on airfare from Singapore to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 23% on airfare.

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 20 November 2025.
Read reviews from past customers who have flown with EVA Air, ANA, andJapan Airlines from Singapore to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
EVA Air
8.4
Very Good
1,279 reviews
Check prices

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
EVA Air
8.4
Very Good
1,279 reviews
EVA Air
8.4
Very Good
1,279 reviews
Check prices

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
ANA
8.4
Very Good
1,007 reviews
EVA Air
8.4
Very Good
1,279 reviews
Check prices

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Japan Airlines
8.3
Very Good
1,623 reviews
EVA Air
8.4
Very Good
1,279 reviews
Check prices

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Cathay Pacific
7.6
Good
1,061 reviews
EVA Air
8.4
Very Good
1,279 reviews
Check prices

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
United Airlines
7.4
Good
9,027 reviews
EVA Air
8.4
Very Good
1,279 reviews
Check prices

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.4

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak

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.

  • How long is the flight from Singapore to Chicago?

    United Airlines, Air Canada, 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.

  • 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$ 906). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,345). 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.

Alternative routes for Singapore to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Singapore to O'Hare Intl flights
Singapore to Midway flights

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 20 November 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 900AverageS$ 1,315FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 906AverageS$ 1,518FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,072AverageS$ 2,648FlexibilityNo cancel feeOn-time80%
Search ANA flights
EVA AirCheapestS$ 1,320AverageS$ 1,523FlexibilityNo cancel feeOn-time74%
Search EVA Air flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Singapore to Chicago?

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Why should you use Cheapflights to find cheap flight tickets from Singapore to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Singapore to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Singapore to Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from Singapore to Chicago with no change fees.

Can Cheapflights notify me if prices for flights from Singapore to Chicago become cheaper?

Not ready to book yet? You can track prices for flights from Singapore to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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