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$342+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
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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 January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,145
(Mytrip)

One-way from

$342
(Expedia)

Popular in

December

Cheapest in

February

Average price

$1,035
Provider with most accurate pricing for Chicago (CHI)-Singapore Changi flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Singapore Changi flights.
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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 ($187 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($72 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 6, 2026.

This Mytrip deal was found by Cheapflights users on 1/6. 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.
Fri 2/202:20 pmORD - SIN
2 stops26h 40mMultiple Airlines
Fri 2/2710:30 amSIN - ORD
3 stops35h 05mMultiple Airlines
Deal found 1/6$1,145
This Mytrip deal was found by Cheapflights users on 1/6. 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.
Tue 1/208:00 amORD - SIN
3 stops33h 00mMultiple Airlines
Fri 1/239:55 amSIN - ORD
3 stops35h 40mMultiple Airlines
Deal found 1/6$1,162
This Mytrip deal was found by Cheapflights users on 1/5. 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.
Fri 1/307:20 amORD - SIN
3 stops33h 40mMultiple Airlines
Sun 2/12:20 pmSIN - ORD
3 stops31h 15mMultiple Airlines
Deal found 1/5$1,182
This KAYAK deal was found by Cheapflights users on 1/5. 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.
Fri 2/201:30 pmORD - SIN
1 stop39h 25mAir India
Mon 3/1611:00 pmSIN - ORD
2 stops50h 30mAir India
Deal found 1/5$1,187
This Delta deal was found by Cheapflights users on 1/5. 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 4/105:40 pmMDW - SIN
2 stops46h 20mDelta
Sun 4/1910:30 pmSIN - MDW
2 stops32h 24mDelta
Deal found 1/5$1,190
This Trip.com deal was found by Cheapflights users on 1/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/122:35 pmORD - SIN
1 stop25h 05mMultiple Airlines
Mon 1/1910:25 pmSIN - ORD
1 stop29h 20mMultiple Airlines
Deal found 1/5$1,190
This Delta deal was found by Cheapflights users on 1/5. 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 10/255:59 pmMDW - SIN
2 stops41h 11mDelta
Sat 10/3110:30 pmSIN - MDW
2 stops37h 15mDelta
Deal found 1/5$1,195
This KAYAK deal was found by Cheapflights users on 1/5. 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 4/127:00 amORD - SIN
2 stops34h 40mANA
Thu 4/306:15 amSIN - ORD
2 stops26h 51mANA
Deal found 1/5$1,196
This Mytrip deal was found by Cheapflights users on 1/5. 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.
Mon 1/192:20 pmORD - SIN
3 stops33h 40mMultiple Airlines
Thu 1/223:15 pmSIN - ORD
3 stops31h 58mMultiple Airlines
Deal found 1/5$1,199
This Gurufare deal was found by Cheapflights users on 1/6. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/274:00 pmORD - SIN
1 stop30h 45mCathay Pacific
Sat 7/118:05 pmSIN - ORD
1 stop31h 20mCathay Pacific
Deal found 1/6$1,200
This Justfly.com deal was found by Cheapflights users on 1/5. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:10 pmORD - SIN
1 stop29h 20mAir India
Fri 5/111:00 pmSIN - ORD
2 stops49h 10mAir India
Deal found 1/5$1,201
This KAYAK deal was found by Cheapflights users on 1/5. 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 1/196:00 amORD - SIN
2 stops34h 35mAmerican Airlines
Wed 1/282:20 amSIN - ORD
2 stops28h 29mAmerican Airlines
Deal found 1/5$1,202

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 January 6, 2026.
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

Sun 4/12

9:30 am-11:40 pm

2 stops25h 10m

Singapore Changi

Sun 4/19

10:30 pm-5:54 pm

2 stops32h 24m

$1,190

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 4/11

9:30 am-5:00 am

2 stops30h 30m

Singapore Changi

Thu 4/16

7:30 am-10:29 pm

2 stops27h 59m

$1,190

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sat 2/21

6:30 am-8:25 pm

2 stops47h 55m

Singapore Changi

Sun 3/15

10:40 am-9:40 am

1 stop36h 00m

$1,200

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 4/9

9:30 am-11:40 pm

2 stops25h 10m

Singapore Changi

Sun 4/19

10:30 pm-5:54 pm

2 stops32h 24m

$1,203

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 4/10

5:40 pm-5:00 am

2 stops46h 20m

Singapore Changi

Fri 4/17

7:30 am-10:29 pm

2 stops27h 59m

$1,203

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 4/12

9:30 am-11:40 pm

2 stops25h 10m

Singapore Changi

Fri 4/17

7:30 am-10:29 pm

2 stops27h 59m

$1,203

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 4/14

9:26 am-5:00 am

2 stops30h 34m

Singapore Changi

Sun 4/19

10:30 pm-5:54 pm

2 stops32h 24m

$1,203

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 4/13

9:26 am-11:40 pm

2 stops25h 14m

Singapore Changi

Thu 4/16

7:30 am-10:29 pm

2 stops27h 59m

$1,203

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 4/13

9:26 am-11:40 pm

2 stops25h 14m

Singapore Changi

Sun 4/19

10:30 pm-5:54 pm

2 stops32h 24m

$1,203

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 4/11

9:30 am-5:00 am

2 stops30h 30m

Singapore Changi

Fri 4/17

7:30 am-10:29 pm

2 stops27h 59m

$1,203

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 45 results
1
2
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5

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 $1,312). 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.

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 January 6, 2026.
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
1,313 reviews

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Comfort

8.3

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.
EVA Air
8.4
Very good
1,313 reviews
EVA Air
8.4
Very good
1,313 reviews

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Comfort

8.3

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.
Cathay Pacific
7.6
Good
1,121 reviews
EVA Air
8.4
Very good
1,313 reviews

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Comfort

8.3

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.
United Airlines
7.4
Good
9,134 reviews
EVA Air
8.4
Very good
1,313 reviews

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Comfort

8.3

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.
Turkish Airlines
7.3
Good
4,152 reviews
EVA Air
8.4
Very good
1,313 reviews

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Comfort

8.3

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.
Air Canada
7.1
Good
10,597 reviews
EVA Air
8.4
Very good
1,313 reviews

Entertainment

8.0

Food

8.1

Crew

8.6

Boarding

8.4

Overall

8.4

Comfort

8.3

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.

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 10m. Fly via Delta, Korean Air, or Qatar Airways to get the fastest option. Airlines will cover a distance of 9360 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 $1,312). 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.
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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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air IndiaCheapest$675Average$921FlexibilityNo cancel feeOn-timeN/A
Cathay PacificCheapest$698Average$879FlexibilityNo cancel feeOn-time72%
United AirlinesCheapest$709Average$1,200FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$770Average$980FlexibilityNo cancel feeOn-time77%
Japan AirlinesCheapest$818Average$1,081FlexibilityNo cancel feeOn-time79%
Etihad AirwaysCheapest$830Average$1,172FlexibilityNo cancel feeOn-time75%
Qatar AirwaysCheapest$850Average$1,204FlexibilityNo cancel feeOn-time68%
Korean AirCheapest$858Average$1,132FlexibilityNo cancel feeOn-time81%
Air CanadaCheapest$884Average$1,340FlexibilityNo cancel feeOn-time67%
ANACheapest$1,024Average$1,426FlexibilityNo cancel feeOn-time80%

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