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Cheap flights from Singapore to Chicago from S$ 659

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
17 Jan — 24 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 18 December 2025.

Sun 28-1210:10SIN - ORD
1 stop39h 15mUnited Airlines
Sun 11-119:58ORD - SIN
1 stop34h 17mUnited Airlines
Deal found 15-12S$ 1,209
Mon 29-1202:20SIN - ORD
1 stop19h 10mJapan Airlines
Thu 15-110:35ORD - SIN
1 stop24h 15mJapan Airlines
Deal found 15-12S$ 1,223
Sun 28-1213:15SIN - ORD
2 stops31h 14mEVA Air
Sun 11-118:06ORD - SIN
2 stops30h 24mEVA Air
Deal found 15-12S$ 1,375
Tue 30-1210:45SIN - ORD
2 stops26h 14mUnited Airlines
Thu 15-107:10ORD - SIN
2 stops33h 45mUnited Airlines
Deal found 15-12S$ 1,568
Thu 25-1207:40SIN - ORD
1 stop19h 15mCathay Pacific
Wed 31-1214:35ORD - SIN
1 stop32h 30mCathay Pacific
Deal found 16-12S$ 1,609
Tue 30-1213:15SIN - ORD
2 stops33h 16mMultiple Airlines
Thu 15-107:20ORD - SIN
3 stops35h 25mMultiple Airlines
Deal found 15-12S$ 1,919
Thu 25-1210:40SIN - ORD
2 stops36h 07mDelta
Wed 31-1206:00ORD - SIN
2 stops33h 00mDelta
Deal found 16-12S$ 2,016
Sun 28-1220:00SIN - ORD
2 stops29h 30mMultiple Airlines
Sun 11-108:00ORD - SIN
3 stops30h 55mMultiple Airlines
Deal found 15-12S$ 2,753
Tue 30-1210:25SIN - ORD
1 stop37h 40mTurkish Airlines
Sat 3-120:20ORD - SIN
1 stop22h 25mTurkish Airlines
Deal found 15-12S$ 6,176
Wed 17-1201:40SIN - MDW
2 stops28h 51mMultiple Airlines
Sat 3-118:08MDW - SIN
2 stops32h 47mMultiple Airlines
Deal found 16-12S$ 16,662

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 18 December 2025.

Round-trip from

S$ 1,108

One-way from

S$ 659

Popular in

January

Cheapest in

October

Average price

S$ 1,614
Korean Air
  • Korean Air
  • 20-3-25-3
  • 2 total stops
  • 51h 45m 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$ 342 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (S$ 99 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 18 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

Fri 20-3

22:30-09:40

1 stop24h 10m

Chicago O'Hare Intl

Wed 25-3

12:25-05:00

1 stop27h 35m

S$ 1,108

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 29-1

01:35-08:40

1 stop21h 05m

Chicago O'Hare Intl

Fri 6-2

11:25-00:10

1 stop22h 45m

S$ 1,130

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 22-3

01:35-09:40

1 stop21h 05m

Chicago O'Hare Intl

Thu 2-4

12:20-19:55

1 stop42h 35m

S$ 1,130

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 28-1

01:35-22:22

2 stops34h 47m

Chicago Midway

Thu 5-2

12:48-20:25

2 stops41h 37m

S$ 1,132

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 1-2

22:20-16:57

1 stop32h 37m

Chicago O'Hare Intl

Sun 8-2

18:29-08:00

1 stop23h 31m

S$ 1,207

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 29-1

10:00-20:05

1 stop24h 05m

Chicago O'Hare Intl

Mon 2-2

18:29-08:00

1 stop23h 31m

S$ 1,207

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 2-6

20:40-21:27

1 stop37h 47m

Chicago O'Hare Intl

Wed 17-6

06:02-18:35

1 stop23h 33m

S$ 1,209

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 31-1

10:45-18:48

1 stop22h 03m

Chicago O'Hare Intl

Sat 7-2

19:58-20:15

1 stop34h 17m

S$ 1,209

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 21-1

10:10-16:57

1 stop20h 47m

Chicago O'Hare Intl

Sat 24-1

19:58-20:15

1 stop34h 17m

S$ 1,209

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 14-1

22:20-06:25

1 stop22h 05m

Chicago O'Hare Intl

Wed 21-1

19:58-20:15

1 stop34h 17m

S$ 1,209

Flights are sorted by cheapest return flights first.

Deals found on 16-12

Showing 1-10 of 42 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$ 897). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,331). 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 18 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 18 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.
EVA Air
8.5
Very Good
1,297 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Overall

8.5

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.
EVA Air
8.5
Very Good
1,297 reviews
EVA Air
8.5
Very Good
1,297 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Overall

8.5

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.
ANA
8.4
Very Good
1,031 reviews
EVA Air
8.5
Very Good
1,297 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Overall

8.5

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.
Japan Airlines
8.3
Very Good
1,662 reviews
EVA Air
8.5
Very Good
1,297 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Overall

8.5

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.
Cathay Pacific
7.6
Good
1,095 reviews
EVA Air
8.5
Very Good
1,297 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Overall

8.5

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.
United Airlines
7.4
Good
9,092 reviews
EVA Air
8.5
Very Good
1,297 reviews
Check prices

Boarding

8.4

Comfort

8.3

Food

8.1

Overall

8.5

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, Delta, and United Airlines can get you from Singapore to Chicago in just under 24h 10m. Your travel time can differ by up to 10h 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$ 1,331). 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 18 December 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 891AverageS$ 1,328FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 897AverageS$ 1,472FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,061AverageS$ 2,844FlexibilityNo cancel feeOn-time80%
Search ANA flights
EVA AirCheapestS$ 1,305AverageS$ 1,516FlexibilityNo 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.

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