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$373+ Cheap flights from Chicago (CHI) to Singapore

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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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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 October 14, 2025.

This lol.travel deal was found by Cheapflights users on 10/13. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/201:10 pmORD - SIN
1 stop41h 20mAir India
Sun 11/28:30 pmSIN - ORD
2 stops29h 00mAir India
Deal found 10/13$711
This CrystalTravel deal was found by Cheapflights users on 10/12. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/112:35 pmORD - SIN
1 stop32h 30mCathay Pacific
Tue 11/188:15 pmSIN - ORD
1 stop30h 40mCathay Pacific
Deal found 10/12$806
This CrystalTravel deal was found by Cheapflights users on 10/13. 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.
Mon 10/201:55 pmORD - SIN
1 stop30h 45mEtihad Airways
Mon 10/277:25 pmSIN - ORD
1 stop26h 10mEtihad Airways
Deal found 10/13$845
This Rumbo deal was found by Cheapflights users on 10/13. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/204:00 pmORD - SIN
1 stop30h 45mCathay Pacific
Sun 11/28:15 pmSIN - ORD
1 stop30h 40mCathay Pacific
Deal found 10/13$858
This Delta deal was found by Cheapflights users on 10/12. 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.
Wed 11/266:00 amMDW - SIN
2 stops28h 10mDelta
Tue 12/91:35 amSIN - MDW
2 stops36h 14mDelta
Deal found 10/12$1,139
This Delta deal was found by Cheapflights users on 10/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:00 amMDW - SIN
2 stops33h 00mDelta
Sun 11/2310:30 pmSIN - MDW
2 stops33h 38mDelta
Deal found 10/11$1,235
This Delta deal was found by Cheapflights users on 10/14. 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.
Thu 10/166:00 amMDW - SIN
2 stops28h 40mDelta
Sun 10/2610:30 pmSIN - MDW
2 stops36h 44mDelta
Deal found 10/14$1,289
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:00 amMDW - SIN
2 stops33h 00mDelta
Mon 11/2410:30 pmSIN - MDW
2 stops27h 22mDelta
Deal found 10/13$1,339
This Delta deal was found by Cheapflights users on 10/13. 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 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 stops27h 22mDelta
Deal found 10/13$1,385
This Delta deal was found by Cheapflights users on 10/12. 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.
Fri 11/286:00 amMDW - SIN
2 stops33h 00mDelta
Thu 12/1110:30 pmSIN - MDW
2 stops27h 25mDelta
Deal found 10/12$1,389
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:00 amMDW - SIN
2 stops33h 00mDelta
Mon 2/91:35 amSIN - MDW
2 stops34h 11mDelta
Deal found 10/13$1,460
This Delta deal was found by Cheapflights users on 10/14. 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.
Mon 11/175:34 pmMDW - SIN
2 stops45h 26mDelta
Mon 12/2910:40 amSIN - MDW
2 stops43h 44mDelta
Deal found 10/14$1,463

Cheap flight deals from Chicago to Singapore

Keep the following information in mind while searching for Chicago to Singapore flight deals. Data was last updated October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$806
(CrystalTravel)

One-way from

$373
(oojo)

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
Search Deals
One-way flight from Chicago (CHI) to Singapore
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($183 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($59 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 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

Tue 11/11

1:10 pm-9:35 am

1 stop30h 25m

Singapore Changi

Thu 12/4

7:25 pm-7:35 am

1 stop26h 10m

$921

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 4/12

11:25 am-5:55 pm

1 stop41h 30m

Singapore Changi

Wed 4/15

11:05 pm-6:15 pm

1 stop32h 10m

$1,011

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 11/25

3:40 pm-7:00 am

1 stop25h 20m

Singapore Changi

Tue 1/13

10:20 pm-7:30 pm

2 stops35h 10m

$1,012

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 11/9

6:30 am-1:00 pm

2 stops40h 30m

Singapore Changi

Wed 12/3

8:15 pm-12:55 pm

1 stop30h 40m

$1,117

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 2/8

6:50 pm-4:40 pm

2 stops31h 50m

Singapore Changi

Sun 2/22

3:15 am-2:30 pm

1 stop25h 15m

$1,119

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 2/11

6:50 pm-8:45 am

1 stop23h 55m

Singapore Changi

Fri 2/27

5:25 pm-2:30 pm

2 stops35h 05m

$1,119

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Thu 2/5

6:50 pm-8:45 am

1 stop23h 55m

Singapore Changi

Mon 2/23

7:30 pm-2:30 pm

2 stops33h 00m

$1,119

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 2/10

6:50 pm-8:45 am

1 stop23h 55m

Singapore Changi

Mon 2/23

5:25 pm-2:30 pm

2 stops35h 05m

$1,119

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 1/4

10:00 pm-8:15 pm

1 stop32h 15m

Singapore Changi

Wed 2/18

10:20 pm-6:19 am

1 stop21h 59m

$1,125

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sun 1/4

9:05 pm-8:15 pm

1 stop33h 10m

Singapore Changi

Wed 1/21

10:20 pm-6:25 am

1 stop22h 05m

$1,125

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 40 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

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 $1,202). 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 SG?

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 14, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 25% on flights from Chicago to Singapore by exploring options for tickets at noon.

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.

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 14, 2025.
Read reviews from past customers who have flown EVA Air, Cathay Pacific, and United Airlines from Chicago to Singapore. 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
8.4
Very good
1,250 reviews

Comfort

8.3

Boarding

8.4

Overall

8.4

Food

8.0

Crew

8.6

Entertainment

8.0

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
1,250 reviews
EVA Air
8.4
Very good
1,250 reviews

Comfort

8.3

Boarding

8.4

Overall

8.4

Food

8.0

Crew

8.6

Entertainment

8.0

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
1,023 reviews
EVA Air
8.4
Very good
1,250 reviews

Comfort

8.3

Boarding

8.4

Overall

8.4

Food

8.0

Crew

8.6

Entertainment

8.0

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
8,976 reviews
EVA Air
8.4
Very good
1,250 reviews

Comfort

8.3

Boarding

8.4

Overall

8.4

Food

8.0

Crew

8.6

Entertainment

8.0

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
4,010 reviews
EVA Air
8.4
Very good
1,250 reviews

Comfort

8.3

Boarding

8.4

Overall

8.4

Food

8.0

Crew

8.6

Entertainment

8.0

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
10,297 reviews
EVA Air
8.4
Very good
1,250 reviews

Comfort

8.3

Boarding

8.4

Overall

8.4

Food

8.0

Crew

8.6

Entertainment

8.0

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.

  • How long is the flight from Chicago to Singapore?

    There are many flights that can get you from Chicago to Singapore in 25h 20m. Fly via Etihad Airways, Turkish Airlines, or Air Canada 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.

  • 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 $1,202). 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.
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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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air IndiaCheapest$675Average$921FlexibilityNo cancel feeOn-timeN/A
Cathay PacificCheapest$701Average$882FlexibilityNo cancel feeOn-time72%
United AirlinesCheapest$709Average$1,297FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$744Average$902FlexibilityNo 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$1,466FlexibilityNo cancel feeOn-time74%

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