Cheap flights from Singapore to Chicago from S$ 661

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 29-1. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
23 Nov — 30 Nov1
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 24 October 2025.

Thu 20-1108:50SIN - ORD
2 stops25h 10mAir Canada
Thu 27-1110:38ORD - SIN
2 stops30h 22mAir Canada
Deal found 23-10S$ 1,055
Thu 27-1108:50SIN - ORD
1 stop19h 51mAir Canada
Sun 30-1115:40ORD - SIN
1 stop25h 20mAir Canada
Deal found 22-10S$ 1,139
Thu 20-1108:50SIN - ORD
2 stops37h 10mAir Canada
Wed 25-215:40ORD - SIN
1 stop25h 20mAir Canada
Deal found 22-10S$ 1,143
Mon 24-1121:00SIN - ORD
2 stops33h 44mAir Canada
Wed 25-208:45ORD - SIN
2 stops32h 15mAir Canada
Deal found 22-10S$ 1,146
Mon 27-1021:00SIN - ORD
2 stops30h 41mAir Canada
Thu 13-1115:40ORD - SIN
1 stop25h 20mAir Canada
Deal found 23-10S$ 1,156
Sun 23-1108:50SIN - ORD
1 stop19h 51mAir Canada
Sat 6-1215:35ORD - SIN
2 stops49h 25mAir Canada
Deal found 22-10S$ 1,185
Mon 27-1010:10SIN - ORD
1 stop32h 52mUnited Airlines
Thu 13-1107:10ORD - SIN
1 stop23h 05mUnited Airlines
Deal found 23-10S$ 1,207
Tue 25-1122:20SIN - ORD
1 stop21h 42mUnited Airlines
Wed 25-206:25ORD - SIN
1 stop23h 50mUnited Airlines
Deal found 22-10S$ 1,211
Tue 28-1010:10SIN - ORD
1 stop26h 00mUnited Airlines
Fri 31-1006:15ORD - SIN
1 stop25h 00mUnited Airlines
Deal found 21-10S$ 1,212
Mon 24-1110:40SIN - MDW
2 stops27h 00mDelta
Wed 25-217:25MDW - SIN
2 stops37h 00mDelta
Deal found 22-10S$ 1,634
Sun 7-1222:30SIN - MDW
2 stops32h 04mDelta
Sun 14-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 23-10S$ 3,050
Sat 6-1222:30SIN - MDW
2 stops27h 25mDelta
Sat 13-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 21-10S$ 3,358

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 24 October 2025.

Round-trip from

S$ 1,055

One-way from

S$ 661

Popular in

January

Cheapest in

October

Average price

S$ 1,194
Air Canada
  • Air Canada
  • 20-11-27-11
  • 3 total stops
  • 50h 30m total
  • Singapore to Chicago
IndiGo
  • IndiGo
  • 29-1
  • 2 total stops
  • 36h 45m total
  • Singapore to Chicago
Highest demand for flights based on searches. 11% potential increase in price (S$ 233 potential increase over avg. return price).
Cheapest flight prices on average. 3% potential price decrease (S$ 59 potential savings vs. average return price).
Average for round-trip flights in October 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 24 October 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

Wed 25-3

22:20-13:06

1 stop27h 46m

Chicago O'Hare Intl

Thu 9-4

06:15-18:25

1 stop23h 10m

S$ 1,208

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 16-4

09:00-01:11

1 stop29h 11m

Chicago O'Hare Intl

Mon 20-4

06:15-18:25

1 stop23h 10m

S$ 1,208

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 15-4

01:10-09:40

1 stop21h 30m

Chicago O'Hare Intl

Mon 20-4

12:20-05:00

1 stop27h 40m

S$ 1,235

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 15-4

07:30-23:50

2 stops29h 20m

Chicago O'Hare Intl

Thu 23-4

09:30-05:00

2 stops30h 30m

S$ 1,238

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 16-4

07:30-23:50

2 stops29h 20m

Chicago O'Hare Intl

Mon 20-4

06:00-23:40

2 stops28h 40m

S$ 1,240

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 27-3

22:20-06:19

1 stop20h 59m

Chicago O'Hare Intl

Thu 9-4

07:15-00:45

2 stops28h 30m

S$ 1,365

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 24-3

01:25-13:55

1 stop25h 30m

Chicago O'Hare Intl

Thu 9-4

16:00-20:35

1 stop39h 35m

S$ 1,374

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 9-2

01:25-12:55

1 stop25h 30m

Chicago O'Hare Intl

Fri 20-2

14:35-11:55

1 stop31h 20m

S$ 1,376

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 23-11

01:35-23:59

2 stops36h 24m

Chicago O'Hare Intl

Wed 25-2

11:25-00:10

1 stop22h 45m

S$ 1,381

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 15-4

01:10-13:07

2 stops48h 57m

Chicago Midway

Mon 20-4

09:20-05:00

2 stops30h 40m

S$ 1,413

Flights are sorted by cheapest return flights first.

Deals found on 23-10

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$ 903). Flying from Singapore to Chicago in May is currently the most expensive (average of S$ 1,491). 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 24 October 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 24 October 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.

Boarding

8.4

Food

8.1

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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

Boarding

8.4

Food

8.1

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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
8.4
Very Good

Boarding

8.4

Food

8.1

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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

Boarding

8.4

Food

8.1

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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

Boarding

8.4

Food

8.1

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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

Boarding

8.4

Food

8.1

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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, Korean Air, and Delta can get you from Singapore to Chicago in just under 21h 30m. Your travel time can differ by up to 7h 50m. The distance between Singapore and Chicago is about 15039 km. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Singapore to Chicago one-way?

    One-way options have recently been found by users for as low as S$ 665 on Air Canada. Other airlines that offer cheap prices include United Airlines from S$ 748 and Delta from S$ 824 one-way.

  • 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$ 903). Flying from Singapore to Chicago in May is currently the most expensive (average of S$ 1,491). 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

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Alternative routes for Singapore to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 7 airlines flying from Singapore to Chicago

Discover the top 7 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 24 October 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 896AverageS$ 1,310FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 902AverageS$ 1,544FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,068AverageS$ 2,637FlexibilityNo cancel feeOn-time80%
Search ANA flights
Cathay PacificCheapestS$ 1,208AverageS$ 1,486FlexibilityNo cancel feeOn-time72%
Search Cathay Pacific flights
Korean AirCheapestS$ 1,246AverageS$ 2,641FlexibilityNo cancel feeOn-time81%
Search Korean Air flights
EVA AirCheapestS$ 1,312AverageS$ 1,492FlexibilityNo cancel feeOn-time74%
Search EVA Air flights
Etihad AirwaysCheapestS$ 1,987AverageS$ 2,476FlexibilityNo cancel feeOn-time75%
Search Etihad Airways flights

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