Find flights
When to book
Airlines
FAQs

Cheap flights from Singapore to Chicago from S$ 655

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 21-2. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
22 gen — 29 gen1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Singapore to Chicago

Enter your travel dates to find the best prices.

Best flights from Singapore to Chicago
Discover carefully curated flight deals from Singapore to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 23 dicembre 2025.

mar 3-201:35SIN - ORD
1 stop21h 05mKorean Air
mer 11-211:25ORD - SIN
1 stop27h 35mKorean Air
Deal found 21-12S$ 1,099
lun 19-101:35SIN - ORD
2 stops34h 17mDelta
mar 17-206:30ORD - SIN
2 stops32h 30mDelta
Deal found 21-12S$ 1,130
mar 3-208:50SIN - ORD
2 stops25h 20mAir Canada
mar 10-215:35ORD - SIN
2 stops33h 15mAir Canada
Deal found 20-12S$ 1,139
lun 2-214:25SIN - MDW
2 stops36h 15mMultiple Airlines
dom 15-208:15MDW - SIN
2 stops38h 50mMultiple Airlines
Deal found 22-12S$ 1,485
mar 3-222:30SIN - ORD
1 stop24h 10mKorean Air
mar 10-211:25ORD - SIN
1 stop22h 45mKorean Air
Deal found 20-12S$ 1,108
dom 18-101:35SIN - ORD
2 stops36h 18mDelta
lun 26-107:30ORD - SIN
2 stops26h 40mDelta
Deal found 20-12S$ 1,130
mar 20-108:50SIN - ORD
1 stop19h 51mAir Canada
mar 17-214:00ORD - SIN
2 stops27h 00mAir Canada
Deal found 21-12S$ 1,143
lun 2-222:30SIN - ORD
1 stop24h 10mKorean Air
dom 15-211:25ORD - SIN
1 stop27h 35mKorean Air
Deal found 22-12S$ 1,128
mar 10-201:35SIN - ORD
2 stops36h 21mDelta
mer 18-206:15ORD - SIN
2 stops27h 55mDelta
Deal found 22-12S$ 1,130
mar 10-222:30SIN - ORD
1 stop24h 10mKorean Air
ven 20-211:25ORD - SIN
1 stop27h 35mKorean Air
Deal found 20-12S$ 1,129
mer 11-210:40SIN - MDW
2 stops25h 42mDelta
mer 18-212:45MDW - SIN
2 stops41h 40mDelta
Deal found 22-12S$ 1,288
mar 3-201:35SIN - MDW
2 stops34h 47mDelta
mer 11-206:00MDW - SIN
2 stops28h 10mDelta
Deal found 21-12S$ 1,288
mer 11-214:25SIN - MDW
2 stops35h 30mMultiple Airlines
mer 18-208:10MDW - SIN
3 stops38h 55mMultiple Airlines
Deal found 22-12S$ 1,739
mer 4-214:25SIN - MDW
2 stops36h 00mMultiple Airlines
mer 11-211:10MDW - SIN
3 stops35h 55mMultiple Airlines
Deal found 21-12S$ 2,138
mar 10-210:40SIN - MDW
2 stops25h 42mDelta
ven 20-206:00MDW - SIN
2 stops33h 00mDelta
Deal found 21-12S$ 1,609
mer 4-201:35SIN - MDW
2 stops34h 47mDelta
gio 12-206:00MDW - SIN
2 stops33h 00mDelta
Deal found 22-12S$ 1,768
mar 10-214:25SIN - MDW
2 stops36h 15mMultiple Airlines
ven 20-216:55MDW - SIN
3 stops41h 45mMultiple Airlines
Deal found 22-12S$ 2,498

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 23 dicembre 2025.

Round-trip from

S$ 1,099

One-way from

S$ 655

Popular in

January

Cheapest in

April

Average price

S$ 1,613
Korean Air
  • Korean Air
  • 3-2-11-2
  • 2 total stops
  • 48h 40m total
  • Singapore to Chicago
Search Deals
21-2
  • 21-2
  • 2 total stops
  • 34h 49m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (S$ 335 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (S$ 98 potential savings vs. average return price).
Search Deals
Average for round-trip flights in December 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 23 dicembre 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

mar 3-2

01:35-08:40

1 stop21h 05m

Chicago O'Hare Intl

mer 11-2

11:25-05:00

1 stop27h 35m

S$ 1,099

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

mar 3-2

22:30-08:40

1 stop24h 10m

Chicago O'Hare Intl

mar 10-2

11:25-00:10

1 stop22h 45m

S$ 1,108

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

lun 2-2

22:30-08:40

1 stop24h 10m

Chicago O'Hare Intl

dom 15-2

11:25-05:00

1 stop27h 35m

S$ 1,128

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

mar 10-2

22:30-08:40

1 stop24h 10m

Chicago O'Hare Intl

ven 20-2

11:25-05:00

1 stop27h 35m

S$ 1,129

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

lun 19-1

01:35-21:52

2 stops34h 17m

Chicago O'Hare Intl

mar 17-2

06:30-05:00

2 stops32h 30m

S$ 1,130

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

dom 18-1

01:35-23:53

2 stops36h 18m

Chicago O'Hare Intl

lun 26-1

07:30-00:10

2 stops26h 40m

S$ 1,130

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

mar 10-2

01:35-23:56

2 stops36h 21m

Chicago O'Hare Intl

mer 18-2

06:15-00:10

2 stops27h 55m

S$ 1,130

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

mar 3-2

08:50-20:10

2 stops25h 20m

Chicago O'Hare Intl

mar 10-2

15:35-14:50

2 stops33h 15m

S$ 1,139

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

mar 20-1

08:50-14:41

1 stop19h 51m

Chicago O'Hare Intl

mar 17-2

14:00-07:00

2 stops27h 00m

S$ 1,143

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

mer 11-2

10:40-22:22

2 stops25h 42m

Chicago Midway

mer 18-2

12:45-20:25

2 stops41h 40m

S$ 1,288

Flights are sorted by cheapest return flights first.

Deals found on 21-12

Showing 1-10 of 37 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$ 897). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,330). 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 23 dicembre 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 23 dicembre 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
8.5
Very Good
1,298 reviews
Check prices

Boarding

8.4

Crew

8.6

Comfort

8.3

Food

8.1

Overall

8.5

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.
EVA Air
8.5
Very Good
1,298 reviews
EVA Air
8.5
Very Good
1,298 reviews
Check prices

Boarding

8.4

Crew

8.6

Comfort

8.3

Food

8.1

Overall

8.5

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.
ANA
8.4
Very Good
1,040 reviews
EVA Air
8.5
Very Good
1,298 reviews
Check prices

Boarding

8.4

Crew

8.6

Comfort

8.3

Food

8.1

Overall

8.5

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.
Japan Airlines
8.3
Very Good
1,660 reviews
EVA Air
8.5
Very Good
1,298 reviews
Check prices

Boarding

8.4

Crew

8.6

Comfort

8.3

Food

8.1

Overall

8.5

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.
Cathay Pacific
7.6
Good
1,103 reviews
EVA Air
8.5
Very Good
1,298 reviews
Check prices

Boarding

8.4

Crew

8.6

Comfort

8.3

Food

8.1

Overall

8.5

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.
United Airlines
7.4
Good
9,106 reviews
EVA Air
8.5
Very Good
1,298 reviews
Check prices

Boarding

8.4

Crew

8.6

Comfort

8.3

Food

8.1

Overall

8.5

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.

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 21h 05m. Your travel time can differ by up to 4h 37m. 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$ 897). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,330). 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 23 dicembre 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 890AverageS$ 1,326FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 896AverageS$ 1,548FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,061AverageS$ 2,841FlexibilityNo cancel feeOn-time80%
Search ANA flights
EVA AirCheapestS$ 1,304AverageS$ 1,515FlexibilityNo 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.