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$341+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find cheap flights from Chicago to Singapore with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to Singapore Changi are usually found in February or September, booked 23 days in advance, depart on a Tuesday or Monday and return on a Monday

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 October 30, 2025.

This oojo deal was found by Cheapflights users on 10/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/511:50 amORD - SIN
1 stop39h 45mTurkish Airlines
Tue 11/185:15 amSIN - ORD
1 stop27h 10mTurkish Airlines
Deal found 10/28$860
This oojo deal was found by Cheapflights users on 10/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/32:35 pmORD - SIN
1 stop25h 05mCathay Pacific
Sun 11/91:25 amSIN - ORD
1 stop25h 30mCathay Pacific
Deal found 10/28$865
This oojo deal was found by Cheapflights users on 10/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/52:35 pmORD - SIN
1 stop35h 10mCathay Pacific
Mon 11/171:25 amSIN - ORD
1 stop25h 30mCathay Pacific
Deal found 10/28$866
This IEagle deal was found by Cheapflights users on 10/28. 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 IEagle is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/31:30 pmORD - SIN
1 stop27h 30mAir India
Tue 2/178:20 amSIN - ORD
2 stops41h 10mAir India
Deal found 10/28$873
This oojo deal was found by Cheapflights users on 10/29. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2811:50 amORD - SIN
1 stop39h 45mTurkish Airlines
Fri 12/511:40 amSIN - ORD
1 stop36h 25mTurkish Airlines
Deal found 10/29$898
This FlightHub deal was found by Cheapflights users on 10/28. 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.
Wed 12/31:30 pmORD - SIN
1 stop27h 30mAir India
Mon 2/1611:00 pmSIN - ORD
2 stops50h 30mAir India
Deal found 10/28$900
This CrystalTravel deal was found by Cheapflights users on 10/28. 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.
Sun 11/302:35 pmORD - SIN
1 stop25h 05mCathay Pacific
Thu 12/41:25 amSIN - ORD
1 stop25h 30mCathay Pacific
Deal found 10/28$902
This oojo deal was found by Cheapflights users on 10/29. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2611:50 amORD - SIN
1 stop30h 55mTurkish Airlines
Wed 12/311:25 pmSIN - ORD
1 stop24h 40mTurkish Airlines
Deal found 10/29$906
This KAYAK deal was found by Cheapflights users on 10/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/111:50 amORD - SIN
1 stop30h 55mTurkish Airlines
Wed 2/1811:25 pmSIN - ORD
1 stop33h 00mTurkish Airlines
Deal found 10/28$918
This KAYAK deal was found by Cheapflights users on 10/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/301:10 pmORD - SIN
1 stop30h 25mEtihad Airways
Sun 2/157:25 pmSIN - ORD
1 stop26h 10mEtihad Airways
Deal found 10/28$923
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1811:50 amORD - SIN
1 stop30h 55mTurkish Airlines
Sun 11/2310:25 amSIN - ORD
1 stop37h 40mTurkish Airlines
Deal found 10/29$933
This KAYAK deal was found by Cheapflights users on 10/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/302:35 pmORD - SIN
1 stop25h 05mCathay Pacific
Sun 2/158:15 pmSIN - ORD
1 stop30h 40mCathay Pacific
Deal found 10/28$939

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$851
(FlightHub)

One-way from

$341
(Expedia)

Popular in

December

Cheapest in

February

Average price

$902
Provider with most accurate pricing for Chicago (CHI)-Singapore Changi flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Singapore Changi flights.
Search Deals
From Chicago (CHI) to Singapore Changi
Search Deals
One-way flight from Chicago (CHI) to Singapore Changi
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($184 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($58 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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

Sun 11/9

11:50 am-8:45 am

1 stop30h 55m

Singapore Changi

Sat 11/22

12:10 pm-12:00 pm

3 stops37h 50m

$1,049

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 1/4

6:50 pm-9:15 pm

1 stop36h 25m

Singapore Changi

Sat 2/14

10:15 am-2:30 pm

1 stop42h 15m

$1,094

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Thu 2/12

6:50 pm-8:45 am

1 stop23h 55m

Singapore Changi

Wed 2/25

7:30 pm-2:30 pm

2 stops33h 00m

$1,119

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Thu 2/12

6:50 pm-8:45 am

1 stop23h 55m

Singapore Changi

Tue 2/24

5:25 pm-2:30 pm

2 stops35h 05m

$1,119

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 2/10

6:50 pm-8:45 am

1 stop23h 55m

Singapore Changi

Thu 2/26

1:40 pm-2:30 pm

2 stops38h 50m

$1,119

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 2/10

6:50 pm-8:45 am

1 stop23h 55m

Singapore Changi

Wed 2/25

5:25 pm-2:30 pm

2 stops35h 05m

$1,119

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 3/30

12:20 pm-5:00 am

1 stop27h 40m

Singapore Changi

Wed 4/15

1:10 am-9:40 am

1 stop21h 30m

$1,128

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 4/1

9:30 am-5:00 am

2 stops30h 30m

Singapore Changi

Tue 4/21

7:30 am-9:16 pm

2 stops26h 46m

$1,139

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 3/31

9:30 am-5:00 am

2 stops30h 30m

Singapore Changi

Tue 4/21

7:30 am-9:16 pm

2 stops26h 46m

$1,139

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 3/1

5:59 pm-12:10 am

2 stops40h 11m

Singapore Changi

Tue 3/10

10:40 am-12:35 pm

2 stops38h 55m

$1,144

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 39 results
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Compare providers for flights from Chicago to Singapore

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Singapore in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Singapore flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Singapore flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Singapore flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Singapore flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Singapore flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 24, 2025.

The best time to book flights from Chicago to Singapore is 23 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, September is the cheapest month in which you can book a flight from Chicago to Singapore (average of $661). Flying from Chicago to Singapore in June is currently the most expensive (average of $1,199). 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 October 30, 2025.

It’s typically best to fly out from Chicago to Singapore at noon. Doing so could potentially save you 25% 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 Monday 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 43% 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 October 30, 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
1,267 reviews

Overall

8.4

Boarding

8.4

Entertainment

8.0

Crew

8.6

Comfort

8.3

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
1,267 reviews
EVA Air
8.4
Very good
1,267 reviews

Overall

8.4

Boarding

8.4

Entertainment

8.0

Crew

8.6

Comfort

8.3

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
1,044 reviews
EVA Air
8.4
Very good
1,267 reviews

Overall

8.4

Boarding

8.4

Entertainment

8.0

Crew

8.6

Comfort

8.3

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
8,998 reviews
EVA Air
8.4
Very good
1,267 reviews

Overall

8.4

Boarding

8.4

Entertainment

8.0

Crew

8.6

Comfort

8.3

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
4,031 reviews
EVA Air
8.4
Very good
1,267 reviews

Overall

8.4

Boarding

8.4

Entertainment

8.0

Crew

8.6

Comfort

8.3

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
10,378 reviews
EVA Air
8.4
Very good
1,267 reviews

Overall

8.4

Boarding

8.4

Entertainment

8.0

Crew

8.6

Comfort

8.3

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 14 different airlines.

  • How long is the flight from Chicago to Singapore?

    There are many flights that can get you from Chicago to Singapore in 36h 25m. Fly via Qatar Airways or Delta to get the fastest option. Airlines will cover a distance of 9345 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, Air India ($675), Cathay Pacific ($701), and United Airlines ($709) offers the cheapest pricing from Chicago to Singapore. You may be able to fly from Chicago to Singapore for 39% less than the average price by searching for these airlines.

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

    To fly one-way, consider booking your trip with Etihad Airways, which is currently one of the cheapest options available, starting at $446. Cathay Pacific flights start at $466 while deals on Delta start at $645 one-way.

  • 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, September is the cheapest month in which you can book a flight from Chicago to Singapore (average of $661). Flying from Chicago to Singapore in June is currently the most expensive (average of $1,199). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air IndiaCheapest$675Average$921FlexibilityNo cancel feeOn-timeN/A
Cathay PacificCheapest$701Average$882FlexibilityNo cancel feeOn-time72%
United AirlinesCheapest$709Average$1,284FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$744Average$914FlexibilityNo cancel feeOn-time77%
Japan AirlinesCheapest$791Average$1,081FlexibilityNo cancel feeOn-time79%
Qatar AirwaysCheapest$850Average$1,204FlexibilityNo cancel feeOn-time68%
Air CanadaCheapest$884Average$1,340FlexibilityNo cancel feeOn-time67%
Etihad AirwaysCheapest$909Average$1,236FlexibilityNo cancel feeOn-time75%
Korean AirCheapest$940Average$1,400FlexibilityNo cancel feeOn-time81%
ANACheapest$1,024Average$1,427FlexibilityNo cancel feeOn-time80%

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