Singapore

$354+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Jan 17 — Jan 241
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Cheap 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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:25 pmORD - SIN
1 stop23h 35mUnited Airlines
Thu 1/110:20 pmSIN - ORD
1 stop27h 05mUnited Airlines
Deal found 12/16$1,312
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Sat 12/2010:10 pmORD - SIN
1 stop32h 05mUnited Airlines
Sun 1/410:20 pmSIN - ORD
1 stop21h 07mUnited Airlines
Deal found 12/17$1,362
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2310:10 pmORD - SIN
1 stop32h 05mUnited Airlines
Mon 1/1210:10 amSIN - ORD
1 stop23h 55mUnited Airlines
Deal found 12/16$1,451
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:12 pmORD - SIN
2 stops44h 43mUnited Airlines
Tue 12/2310:20 pmSIN - ORD
1 stop21h 07mUnited Airlines
Deal found 12/15$1,473
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/221:30 pmORD - SIN
1 stop39h 25mMultiple Airlines
Wed 12/318:15 amSIN - ORD
2 stops39h 29mMultiple Airlines
Deal found 12/16$1,577
This Air Canada deal was found by Cheapflights users on 12/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/153:35 pmORD - SIN
2 stops49h 25mAir Canada
Mon 12/229:00 pmSIN - ORD
2 stops31h 41mAir Canada
Deal found 12/15$1,597
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2310:10 pmORD - SIN
1 stop32h 05mUnited Airlines
Thu 1/810:10 amSIN - ORD
1 stop25h 22mUnited Airlines
Deal found 12/16$1,601
This oojo deal was found by Cheapflights users on 12/17. 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 12/261:30 pmORD - SIN
1 stop39h 25mAir India
Sat 1/1011:00 pmSIN - ORD
2 stops50h 30mAir India
Deal found 12/17$1,629
This Air Canada deal was found by Cheapflights users on 12/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:45 amORD - SIN
2 stops32h 15mAir Canada
Tue 12/238:50 amSIN - ORD
1 stop19h 51mAir Canada
Deal found 12/15$1,632
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:45 amORD - SIN
2 stops33h 15mUnited Airlines
Wed 12/3110:10 amSIN - ORD
1 stop25h 22mUnited Airlines
Deal found 12/15$1,652
This Delta deal was found by Cheapflights users on 12/15. 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.
Thu 12/256:00 amMDW - SIN
2 stops33h 00mDelta
Wed 12/3110:30 pmSIN - MDW
2 stops30h 14mDelta
Deal found 12/15$1,836
This Delta deal was found by Cheapflights users on 12/17. 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 12/316:00 amMDW - SIN
2 stops33h 00mDelta
Tue 1/610:30 pmSIN - MDW
2 stops37h 37mDelta
Deal found 12/17$2,035

Find flight deals from Chicago to Singapore

Keep the following information in mind while searching for Chicago to Singapore flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,281
(China Airlines)

One-way from

$354
(oojo)

Popular in

December

Cheapest in

February

Average price

$1,913
Provider with most accurate pricing for Chicago (CHI)-Singapore Changi flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Singapore Changi flights.
From Chicago (CHI) to Singapore
One-way flight from Chicago (CHI) to Singapore
Highest demand for flights based on searches. 15% potential increase in price ($208 potential increase over avg. RT price).
Cheapest flight prices on average. 6% potential price decrease ($72 potential savings vs. average RT price).
Average for round-trip flights in December 2025

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 December 18, 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

MDW - SIN

MDWSIN

Chicago Midway

Tue 1/20

10:35 am-1:05 pm

2 stops36h 30m

Singapore Changi

Thu 1/22

2:00 am-10:50 pm

2 stops34h 50m

$1,281

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 1/29

2:10 pm-1:05 pm

2 stops32h 55m

Singapore Changi

Thu 2/5

2:25 pm-2:55 pm

3 stops38h 30m

$1,295

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 1/23

11:10 am-1:05 pm

3 stops35h 55m

Singapore Changi

Sat 1/31

2:25 pm-12:30 pm

2 stops36h 05m

$1,296

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 3/25

6:30 am-5:00 am

2 stops33h 30m

Singapore Changi

Fri 4/3

1:10 am-3:25 pm

2 stops27h 15m

$1,301

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 4/6

10:15 am-7:30 am

2 stops32h 15m

Singapore Changi

Fri 4/10

3:10 pm-8:15 am

3 stops54h 05m

$1,301

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 3/19

6:30 am-5:00 am

2 stops33h 30m

Singapore Changi

Sat 3/28

10:30 pm-4:53 pm

2 stops31h 23m

$1,301

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 3/27

6:30 am-5:00 am

2 stops33h 30m

Singapore Changi

Sat 4/4

1:10 am-10:29 pm

2 stops34h 19m

$1,314

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 3/26

9:32 am-12:10 am

2 stops25h 38m

Singapore Changi

Fri 4/3

1:10 am-12:29 pm

2 stops24h 19m

$1,314

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 4/4

6:30 am-11:40 pm

2 stops28h 10m

Singapore Changi

Fri 4/10

1:10 am-3:25 pm

2 stops27h 15m

$1,314

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 1/6

11:30 pm-12:05 pm

1 stop22h 35m

Singapore Changi

Sun 1/18

3:45 pm-7:35 pm

1 stop41h 50m

$1,318

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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 December is currently the most expensive (average of $1,361). 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 December 18, 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 December 18, 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.

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.5

Entertainment

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.5

Entertainment

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.5

Entertainment

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.5

Entertainment

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.5

Entertainment

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.

Comfort

8.3

Boarding

8.4

Food

8.1

Overall

8.5

Entertainment

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.

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 22h 35m. Fly via Delta, Ethiopian Air, or EVA Air 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 to fly from Chicago to Singapore one-way?

    To fly one-way, consider booking your trip with Cathay Pacific, which is currently one of the cheapest options available, starting at $370. United Airlines flights start at $446 while deals on Turkish Airlines start at $476 one-way.

  • 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 December is currently the most expensive (average of $1,361). 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

Browse thousands of different options on Cheapflights for your next trip

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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.

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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air IndiaCheapest$675Average$921FlexibilityNo cancel feeOn-timeN/A
Cathay PacificCheapest$701Average$880FlexibilityNo cancel feeOn-time72%
United AirlinesCheapest$709Average$1,244FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$747Average$957FlexibilityNo cancel feeOn-time77%
Japan AirlinesCheapest$791Average$1,081FlexibilityNo cancel feeOn-time79%
Etihad AirwaysCheapest$830Average$1,172FlexibilityNo cancel feeOn-time75%
Qatar AirwaysCheapest$850Average$1,204FlexibilityNo cancel feeOn-time68%
Air CanadaCheapest$884Average$1,340FlexibilityNo cancel feeOn-time67%
Korean AirCheapest$918Average$1,144FlexibilityNo cancel feeOn-time81%
ANACheapest$1,024Average$1,426FlexibilityNo cancel feeOn-time80%

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