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$342+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Singapore Changi are usually found in September or February, booked 4 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 September 17, 2025.

Round-trip from

$693
(lastminute.com)

One-way from

$342
(Expedia)

Popular in

December

Cheapest in

September

Average price

$805
From Chicago (CHI) to Singapore Changi
Search Deals
One-way flight from Chicago (CHI) to Singapore Changi
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Highest demand for flights based on searches. 13% potential increase in price ($177 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($66 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This lastminute.com deal was found by Cheapflights users on 9/16. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2712:15 pmORD - SIN
1 stop22h 55mKorean Air
Sun 11/910:30 pmSIN - ORD
1 stop24h 00mKorean Air
Deal found 9/16$693
This Jettzy deal was found by Cheapflights users on 9/15. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:15 pmORD - SIN
1 stop22h 55mKorean Air
Wed 11/51:35 amSIN - ORD
1 stop20h 55mKorean Air
Deal found 9/15$702
This Bravofly deal was found by Cheapflights users on 9/16. 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/294:00 pmORD - SIN
1 stop24h 30mCathay Pacific
Sun 10/51:25 pmSIN - ORD
1 stop38h 00mCathay Pacific
Deal found 9/16$710
This oojo deal was found by Cheapflights users on 9/16. 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 10/224:00 pmORD - SIN
1 stop39h 35mCathay Pacific
Sun 11/28:15 pmSIN - ORD
1 stop30h 40mCathay Pacific
Deal found 9/16$721
This oojo deal was found by Cheapflights users on 9/15. 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 10/224:00 pmORD - SIN
1 stop34h 25mCathay Pacific
Mon 10/2710:00 amSIN - ORD
1 stop40h 55mCathay Pacific
Deal found 9/15$722
This oojo deal was found by Cheapflights users on 9/16. 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
Mon 11/101:25 amSIN - ORD
1 stop25h 30mCathay Pacific
Deal found 9/16$723
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/224:00 pmORD - SIN
1 stop24h 30mCathay Pacific
Wed 10/294:45 pmSIN - ORD
1 stop34h 10mCathay Pacific
Deal found 9/16$730
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/304:00 pmORD - SIN
1 stop24h 30mCathay Pacific
Sun 10/512:45 pmSIN - ORD
1 stop38h 40mCathay Pacific
Deal found 9/16$731
This Delta deal was found by Cheapflights users on 9/15. 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.
Wed 9/179:35 amMDW - SIN
2 stops25h 05mDelta
Mon 9/221:10 amSIN - MDW
2 stops24h 18mDelta
Deal found 9/15$734
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 11/36:00 amMDW - SIN
2 stops33h 00mDelta
Tue 11/1110:30 pmSIN - MDW
2 stops32h 09mDelta
Deal found 9/15$884
This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 11/154:28 pmMDW - SIN
2 stops41h 42mDelta
Mon 11/2410:30 pmSIN - MDW
2 stops32h 08mDelta
Deal found 9/15$901
This Delta deal was found by Cheapflights users on 9/15. 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.
Sun 11/165:34 pmMDW - SIN
2 stops40h 36mDelta
Sat 11/2210:30 pmSIN - MDW
2 stops32h 08mDelta
Deal found 9/15$902

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 September 17, 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

Wed 11/19

11:15 am-8:25 pm

1 stop43h 10m

Singapore Changi

Tue 11/25

1:35 am-8:30 am

1 stop20h 55m

$723

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 11/16

11:15 am-12:10 am

1 stop22h 55m

Singapore Changi

Sun 11/23

1:35 am-8:30 am

1 stop20h 55m

$735

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 2/11

2:35 pm-5:40 am

1 stop25h 05m

Singapore Changi

Sun 3/8

1:25 am-1:55 pm

1 stop25h 30m

$749

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 2/9

2:35 pm-1:05 pm

1 stop32h 30m

Singapore Changi

Wed 3/11

1:25 am-1:55 pm

1 stop25h 30m

$749

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Thu 2/12

2:35 pm-11:55 am

1 stop31h 20m

Singapore Changi

Tue 3/10

4:45 pm-1:55 pm

1 stop34h 10m

$749

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 2/10

2:35 pm-11:55 am

1 stop31h 20m

Singapore Changi

Tue 3/10

12:55 pm-1:55 pm

1 stop38h 00m

$749

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 2/8

2:35 pm-7:15 pm

1 stop38h 40m

Singapore Changi

Sun 3/8

8:15 pm-1:55 pm

1 stop30h 40m

$799

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Thu 2/12

2:35 pm-1:05 pm

1 stop32h 30m

Singapore Changi

Thu 3/5

1:25 am-12:55 pm

1 stop25h 30m

$799

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 2/8

2:35 pm-5:40 am

1 stop25h 05m

Singapore Changi

Wed 3/11

1:25 am-1:55 pm

1 stop25h 30m

$799

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sat 2/21

2:35 pm-1:05 pm

1 stop32h 30m

Singapore Changi

Sat 3/14

1:25 am-1:55 pm

1 stop25h 30m

$849

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 44 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 September 12, 2025.

The best time to book flights from Chicago to Singapore is 4 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 $994). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,665). 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 September 17, 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 September 17, 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
1,237 reviews

Entertainment

8.0

Food

8.1

Overall

8.4

Comfort

8.3

Crew

8.6

Boarding

8.4

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
1,237 reviews
EVA Air
8.4
Very good
1,237 reviews

Entertainment

8.0

Food

8.1

Overall

8.4

Comfort

8.3

Crew

8.6

Boarding

8.4

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
998 reviews
EVA Air
8.4
Very good
1,237 reviews

Entertainment

8.0

Food

8.1

Overall

8.4

Comfort

8.3

Crew

8.6

Boarding

8.4

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
8,926 reviews
EVA Air
8.4
Very good
1,237 reviews

Entertainment

8.0

Food

8.1

Overall

8.4

Comfort

8.3

Crew

8.6

Boarding

8.4

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
3,965 reviews
EVA Air
8.4
Very good
1,237 reviews

Entertainment

8.0

Food

8.1

Overall

8.4

Comfort

8.3

Crew

8.6

Boarding

8.4

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
10,000 reviews
EVA Air
8.4
Very good
1,237 reviews

Entertainment

8.0

Food

8.1

Overall

8.4

Comfort

8.3

Crew

8.6

Boarding

8.4

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 12 different airlines.

  • How long is the flight from Chicago to Singapore?

    There are many flights that can get you from Chicago to Singapore in 25h 05m. Fly via Korean Air, Cathay Pacific, 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 40% 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 $994). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,665). 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air IndiaCheapest$675Average$921FlexibilityNo cancel feeOn-timeN/A
Cathay PacificCheapest$701Average$888FlexibilityNo cancel feeOn-time72%
United AirlinesCheapest$709Average$1,295FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$729Average$844FlexibilityNo 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%
Korean AirCheapest$940Average$1,400FlexibilityNo cancel feeOn-time81%
ANACheapest$1,024Average$1,427FlexibilityNo cancel feeOn-time80%
EVA AirCheapest$1,080Average$1,459FlexibilityNo cancel feeOn-time74%

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