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$337+ Cheap flights from Chicago (CHI) to Singapore (SIN)

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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Singapore Changi are usually found in February or September, booked 73 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from Chicago to Singapore

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Singapore (SIN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated agosto 14, 2025.

Round-trip from

$731
(FlightHub)

One-way from

$337
(CrystalTravel)

Popular in

December

Cheapest in

February

Average price

$1,153
From Chicago (CHI) to Singapore Changi
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One-way flight from Chicago (CHI) to Singapore Changi
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Highest demand for flights based on searches. 12% potential increase in price ($161 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($58 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Chicago to Singapore

Cheapest flights from Chicago to Singapore
Explore the most affordable flight options available from Chicago to Singapore. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 14, 2025.

This CrystalTravel deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/134:00 pmORD - SIN
1 stop24h 30mCathay Pacific
sáb. 9/208:05 pmSIN - ORD
1 stop31h 20mCathay Pacific
Deal found 8/14$730
This FlightHub deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/11:10 pmORD - SIN
1 stop29h 05mAir India
lun. 9/811:00 pmSIN - ORD
2 stops49h 10mAir India
Deal found 8/14$731
This Ovago deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/124:00 pmORD - SIN
1 stop31h 25mCathay Pacific
sáb. 10/181:25 pmSIN - ORD
1 stop38h 00mCathay Pacific
Deal found 8/13$732
This Surpr!ce deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Surpr!ce is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/278:05 pmORD - SIN
2 stops33h 20mUnited Airlines
sáb. 10/48:45 amSIN - ORD
1 stop21h 23mUnited Airlines
Deal found 8/13$733
This United Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/127:43 pmORD - SIN
1 stop33h 42mUnited Airlines
vie. 9/268:40 pmSIN - ORD
1 stop22h 18mUnited Airlines
Deal found 8/14$734
This Ovago deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/14:00 pmORD - SIN
1 stop24h 30mCathay Pacific
dom. 9/71:50 amSIN - ORD
1 stop25h 35mCathay Pacific
Deal found 8/11$742
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/126:15 amORD - SIN
1 stop23h 10mUnited Airlines
vie. 10/178:40 pmSIN - ORD
1 stop28h 06mUnited Airlines
Deal found 8/13$743
This CheapOair deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/297:19 amORD - SIN
2 stops28h 26mANA
lun. 9/810:10 pmSIN - ORD
1 stop30h 00mANA
Deal found 8/13$745
This CrystalTravel deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/124:00 pmORD - SIN
1 stop30h 45mCathay Pacific
jue. 9/181:50 amSIN - ORD
1 stop25h 35mCathay Pacific
Deal found 8/13$746
This Ovago deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/74:00 pmORD - SIN
1 stop24h 30mCathay Pacific
sáb. 9/131:50 amSIN - ORD
1 stop25h 35mCathay Pacific
Deal found 8/12$751
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/19:15 amMDW - SIN
2 stops25h 25mDelta
lun. 9/227:30 amSIN - MDW
2 stops27h 06mDelta
Deal found 8/14$904
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/196:42 pmMDW - SIN
2 stops39h 58mDelta
vie. 8/297:30 amSIN - MDW
2 stops39h 06mDelta
Deal found 8/12$909

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Singapore 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 2,558,603 searches. Data last updated agosto 14, 2025.
Use the filters below to find and compare flights from Chicago to Singapore that are best for you.

Fly from

Chicago

Fly to

Singapore

Route

Depart

Return

Price

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

mar. 2/3

2:40 pm-5:40 am

1 stop25h 00m

Singapore Changi

lun. 3/2

8:15 pm-1:00 pm

1 stop30h 45m

$720

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

lun. 2/2

2:40 pm-5:40 am

1 stop25h 00m

Singapore Changi

lun. 3/2

6:00 pm-1:00 pm

1 stop33h 00m

$720

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

lun. 9/1

1:10 pm-7:15 am

1 stop29h 05m

Singapore Changi

lun. 9/8

11:00 pm-11:10 am

2 stops49h 10m

$731

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

dom. 10/12

4:00 pm-12:25 pm

1 stop31h 25m

Singapore Changi

sáb. 10/18

1:25 pm-2:25 pm

1 stop38h 00m

$732

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

dom. 11/23

2:40 pm-5:40 am

1 stop25h 00m

Singapore Changi

mié. 11/26

1:25 am-1:00 pm

1 stop25h 35m

$732

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

sáb. 9/27

8:05 pm-6:25 pm

2 stops33h 20m

Singapore Changi

sáb. 10/4

8:45 am-8:18 pm

2 stops24h 33m

$733

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

sáb. 9/27

4:00 pm-5:30 am

1 stop24h 30m

Singapore Changi

vie. 10/3

1:50 am-2:25 pm

1 stop25h 35m

$733

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

vie. 9/19

4:00 pm-5:30 am

1 stop24h 30m

Singapore Changi

sáb. 9/27

8:05 pm-2:25 pm

1 stop31h 20m

$733

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

vie. 9/12

7:43 pm-6:25 pm

1 stop33h 42m

Singapore Changi

vie. 9/26

8:40 pm-5:58 am

1 stop22h 18m

$734

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

dom. 10/12

6:15 am-6:25 pm

1 stop23h 10m

Singapore Changi

vie. 10/17

8:40 pm-11:46 am

1 stop28h 06m

$743

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 41 results
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Best time to book a flight from Chicago to Singapore

Have a flexible travel schedule? Discover the best time to fly to Singapore from Chicago with our price prediction graph.
Estimated round-trip 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 Chicago to Singapore

How far ahead should I book a flight from Chicago to Singapore?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Singapore. Price data was last updated on August 8, 2025.

The best time to book flights from Chicago to Singapore is 73 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Singapore?

Currently, October is the cheapest month in which you can book a flight from Chicago to Singapore (average of $991). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,684). 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 CHI to SIN?

Find hourly flight availability from Chicago to Singapore. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated agosto 14, 2025.

It’s typically best to fly out from Chicago to Singapore at noon. Doing so could potentially save you 20% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago to Singapore?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Singapore. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Singapore flight should consider departing on Wednesday at noon when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

What’s the top layover airport for flights from Chicago to Singapore?

Share of 1-stop round-trip flights from Chicago to Singapore chosen by Cheapflights users in the past 12 months, using the same layover each way.

Istanbul (IST) – chosen by Cheapflights users on 38% of 1-stop itineraries from Chicago to Singapore on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Singapore?

Average round-trip fare for 1-stop flights from Chicago to Singapore, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Istanbul (IST) is the most affordable 1-stop option, with an average round-trip price of $915.

What’s the fastest layover option from Chicago to Singapore?

Shortest average travel time for 1-stop one-way flights from Chicago to Singapore, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Taipei City (TPE) have the shortest average one-way travel time for 1-stop routes: 22h 30m.

Which airport typically offers the quickest layover for flights from Chicago to Singapore?

Average layover duration for 1-stop one-way flights from Chicago to Singapore, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Taipei City (TPE) offer the fastest connection on this route, with an average layover time of 2h 30m.

Reviews of airlines servicing Singapore

Get insights into the airlines that provide service to Singapore. 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 Singapore. Reviews last updated agosto 14, 2025.
Get a feel of what it's like to fly with EVA Air, Cathay Pacific, and United Airlines from Chicago to Singapore by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
EVA Air
8.4
Very good
1,233 reviews

Overall

8.4

Entertainment

8.0

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

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
1,233 reviews
EVA Air
8.4
Very good
1,233 reviews

Overall

8.4

Entertainment

8.0

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

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
968 reviews
EVA Air
8.4
Very good
1,233 reviews

Overall

8.4

Entertainment

8.0

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

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
8,916 reviews
EVA Air
8.4
Very good
1,233 reviews

Overall

8.4

Entertainment

8.0

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

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
Turkish Airlines
7.3
Good
3,940 reviews
EVA Air
8.4
Very good
1,233 reviews

Overall

8.4

Entertainment

8.0

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

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
Air Canada
7.1
Good
9,949 reviews
EVA Air
8.4
Very good
1,233 reviews

Overall

8.4

Entertainment

8.0

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

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 Chicago to Singapore. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Singapore from Chicago?

    Located just 10.5 mi from the city center, Singapore Changi is the airport most travelers will use when flying to Singapore from Chicago. Booking flights from Chicago to Changi (SIN) should be relatively easy as there are 0 daily inbound flights from Chicago from 10 different airlines.

  • What are the cheapest airlines flying from Chicago to Singapore round-trip?

    According to our current data, Cathay Pacific ($717), Turkish Airlines ($729), and Japan Airlines ($783) offers the cheapest pricing from Chicago to Singapore. You may be able to fly from Chicago to Singapore for 36% less than the average price by searching for these airlines.

  • Where are the most common layover locations when flying from Chicago to Singapore?

    Of the flights from Chicago to Singapore that have layovers, most of them stop in Hong Kong.

  • What are some popular things to do or see while on a layover in Hong Kong?

    The majority of Hong Kong visitors spend their time at Hong Kong Disneyland, Shatin Baptist Church, and Fa Yeun Street Market. Travelers on a layover in Hong Kong can visit Hong Kong Disneyland, Shatin Baptist Church, and Fa Yeun Street Market, by traveling 7.8 mi, 18.3 mi, and 16.2 mi, respectively after landing at Hong Kong Intl.

  • Where are the least popular layover locations for Chicago to Singapore flights?

    Of the flights from Chicago to Singapore that have layovers, the fewest flights stop in Istanbul.

  • Can I find deals for flights from Chicago to Singapore that include hotel bookings?

    Yes. In addition to deals on Chicago to Singapore flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Singapore?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Singapore.

  • Can I find deals for business class flights from Chicago to Singapore?

    Yes. Cheapflights offers flight deals from Chicago to Singapore 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 Chicago to Singapore?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Singapore (average of $991). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,684). 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 Chicago to Singapore

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

Top 10 airlines flying from Chicago to Singapore

Discover the top 10 airlines that operate flights from Chicago to Singapore. 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 2,558,603 searches. Data last updated agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Cathay PacificCheapest$717Average$935FlexibilityNo cancel feeOn-time72%
Turkish AirlinesCheapest$729Average$847FlexibilityNo cancel feeOn-time77%
Japan AirlinesCheapest$783Average$1,047FlexibilityNo cancel feeOn-time79%
United AirlinesCheapest$840Average$1,189FlexibilityNo cancel feeOn-time69%
Qatar AirwaysCheapest$850Average$1,232FlexibilityNo cancel feeOn-time68%
Air CanadaCheapest$872Average$1,131FlexibilityNo cancel feeOn-time67%
Korean AirCheapest$940Average$1,364FlexibilityNo cancel feeOn-time81%
EVA AirCheapest$1,080Average$1,405FlexibilityNo cancel feeOn-time74%
ANACheapest$1,089Average$1,427FlexibilityNo cancel feeOn-time80%
FinnairCheapest$1,203Average$1,339FlexibilityNo cancel feeOn-time76%

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