Cheap flights from Singapore to Chicago from S$ 727

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 18-4. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
10 Jan — 17 Jan1
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 11 December 2025.

Thu 11-1210:10SIN - ORD
1 stop20h 50mUnited Airlines
Thu 11-1219:35ORD - SIN
1 stop34h 40mUnited Airlines
Deal found 9-12S$ 1,206
Fri 12-1222:20SIN - ORD
1 stop30h 28mUnited Airlines
Sun 14-1218:35ORD - SIN
1 stop23h 25mUnited Airlines
Deal found 9-12S$ 1,505
Sat 13-1222:20SIN - ORD
1 stop20h 40mUnited Airlines
Mon 5-106:15ORD - SIN
1 stop24h 00mUnited Airlines
Deal found 10-12S$ 1,636
Wed 24-1201:35SIN - ORD
2 stops36h 27mDelta
Wed 31-1206:00ORD - SIN
2 stops33h 00mDelta
Deal found 10-12S$ 1,772
Sat 13-1220:00SIN - ORD
2 stops29h 30mAir India
Mon 5-113:30ORD - SIN
1 stop27h 30mAir India
Deal found 9-12S$ 1,860
Thu 25-1215:45SIN - ORD
2 stops28h 44mMultiple Airlines
Sun 28-1213:30ORD - SIN
1 stop27h 30mMultiple Airlines
Deal found 10-12S$ 1,918
Wed 17-1201:40SIN - MDW
2 stops28h 51mMultiple Airlines
Sat 3-118:08MDW - SIN
2 stops32h 47mMultiple Airlines
Deal found 10-12S$ 12,705

Find flight deals from Singapore to Chicago

Keep the following information in mind while searching for Singapore to Chicago flight deals. Data was last updated 11 December 2025.

Round-trip from

S$ 1,087

One-way from

S$ 727

Popular in

January

Cheapest in

October

Average price

S$ 1,622
Korean Air
  • Korean Air
  • 22-1-4-2
  • 2 total stops
  • 46h 55m total
  • Singapore to Chicago
18-4
  • 18-4
  • 2 total stops
  • 28h 25m total
  • Singapore to Chicago
Highest demand for flights based on searches. 15% potential increase in price (S$ 345 potential increase over avg. return price).
Cheapest flight prices on average. 5% potential price decrease (S$ 99 potential savings vs. average return price).
Average for round-trip flights in December 2025

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 11 December 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

10:40-08:40

1 stop36h 00m

Chicago O'Hare Intl

Fri 20-2

11:25-00:10

1 stop22h 45m

S$ 1,128

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 22-1

01:35-08:40

1 stop21h 05m

Chicago O'Hare Intl

Fri 30-1

11:25-20:25

1 stop43h 00m

S$ 1,128

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 26-2

22:30-08:40

1 stop24h 10m

Chicago O'Hare Intl

Sun 1-3

11:25-00:10

1 stop22h 45m

S$ 1,128

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 10-3

10:40-13:23

2 stops39h 43m

Chicago Midway

Tue 24-3

09:32-00:10

2 stops25h 38m

S$ 1,131

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 21-1

01:35-22:22

2 stops34h 47m

Chicago Midway

Wed 4-2

12:48-20:25

2 stops41h 37m

S$ 1,131

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 10-3

10:40-23:53

2 stops26h 13m

Chicago O'Hare Intl

Tue 24-3

07:20-05:00

2 stops32h 40m

S$ 1,131

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 21-1

01:35-23:53

2 stops36h 18m

Chicago O'Hare Intl

Wed 4-2

17:59-20:25

2 stops36h 26m

S$ 1,131

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 21-1

01:35-22:22

2 stops34h 47m

Chicago Midway

Thu 29-1

06:00-00:10

2 stops28h 10m

S$ 1,132

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 20-1

01:35-22:22

2 stops34h 47m

Chicago Midway

Wed 28-1

06:00-00:10

2 stops28h 10m

S$ 1,132

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 25-1

10:10-16:57

1 stop20h 47m

Chicago O'Hare Intl

Sun 1-2

18:29-20:15

1 stop35h 46m

S$ 1,207

Flights are sorted by cheapest return flights first.

Deals found on 9-12

Showing 1-10 of 35 results
1
2
3
4

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$ 900). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,336). 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 11 December 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 11 December 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.

Food

8.1

Boarding

8.4

Overall

8.5

Comfort

8.3

Entertainment

8.0

Crew

8.6

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.

Food

8.1

Boarding

8.4

Overall

8.5

Comfort

8.3

Entertainment

8.0

Crew

8.6

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.
8.4
Very Good

Food

8.1

Boarding

8.4

Overall

8.5

Comfort

8.3

Entertainment

8.0

Crew

8.6

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.

Food

8.1

Boarding

8.4

Overall

8.5

Comfort

8.3

Entertainment

8.0

Crew

8.6

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.

Food

8.1

Boarding

8.4

Overall

8.5

Comfort

8.3

Entertainment

8.0

Crew

8.6

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.

Food

8.1

Boarding

8.4

Overall

8.5

Comfort

8.3

Entertainment

8.0

Crew

8.6

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.
  • How long is the flight from Singapore to Chicago?

    Korean Air and Delta can get you from Singapore to Chicago in just under 36h. Your travel time can differ by up to 3h 43m. 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$ 900). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,336). 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.

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 11 December 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 894AverageS$ 1,332FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 900AverageS$ 1,465FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,065AverageS$ 2,853FlexibilityNo cancel feeOn-time80%
Search ANA flights
EVA AirCheapestS$ 1,309AverageS$ 1,521FlexibilityNo 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?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Singapore today with Cheapflights!

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book With Flexibility

Our users can plan ahead with confidence and find flights with no change fees.

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.