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$266+ 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
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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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 January 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$888
(Kissandfly.com)

One-way from

$266
(Trip.com)

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 Changi
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One-way flight from Chicago (CHI) to Singapore Changi
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Highest demand for flights based on searches. 14% potential increase in price ($186 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 12, 2026.

This United Airlines deal was found by Cheapflights users on 1/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:15 am
ORD
-
SIN
2 stops24h 20m
United Airlines
Fri 10/3010:10 am
SIN
-
ORD
1 stop23h 15m
United Airlines
Deal found 1/12$957
This Delta deal was found by Cheapflights users on 1/12. 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.
Mon 4/66:25 am
MDW
-
SIN
2 stops33h 35m
Delta
Mon 4/131:10 am
SIN
-
MDW
2 stops28h 26m
Delta
Deal found 1/12$1,021
This Delta deal was found by Cheapflights users on 1/12. 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.
Thu 2/56:00 am
MDW
-
SIN
2 stops28h 10m
Delta
Thu 2/1910:30 pm
SIN
-
MDW
2 stops28h 16m
Delta
Deal found 1/12$1,056
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Fri 3/202:30 pm
ORD
-
SIN
1 stop38h 15m
Multiple Airlines
Sun 3/298:45 am
SIN
-
ORD
2 stops37h 00m
Multiple Airlines
Deal found 1/10$1,064
This United Airlines deal was found by Cheapflights users on 1/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/19:45 pm
ORD
-
SIN
2 stops31h 50m
United Airlines
Sat 8/88:40 pm
SIN
-
ORD
2 stops25h 59m
United Airlines
Deal found 1/11$1,066
This Delta deal was found by Cheapflights users on 1/10. 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 1/266:00 am
MDW
-
SIN
2 stops28h 10m
Delta
Mon 2/1610:30 pm
SIN
-
MDW
2 stops33h 07m
Delta
Deal found 1/10$1,069
This Delta deal was found by Cheapflights users on 1/12. 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.
Sun 4/126:25 am
MDW
-
SIN
2 stops28h 15m
Delta
Mon 4/2010:30 pm
SIN
-
MDW
2 stops26h 37m
Delta
Deal found 1/12$1,071
This United Airlines deal was found by Cheapflights users on 1/9. 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.
Fri 7/39:39 pm
ORD
-
SIN
1 stop31h 56m
United Airlines
Fri 7/2411:05 am
SIN
-
ORD
2 stops32h 15m
United Airlines
Deal found 1/9$1,071
This Expedia deal was found by Cheapflights users on 1/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/212:10 pm
ORD
-
SIN
2 stops32h 20m
Multiple Airlines
Sat 4/119:10 pm
SIN
-
ORD
1 stop24h 35m
Multiple Airlines
Deal found 1/11$1,075
This United Airlines deal was found by Cheapflights users on 1/9. 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.
Fri 7/39:35 pm
ORD
-
SIN
2 stops32h 00m
United Airlines
Sun 7/1911:05 am
SIN
-
ORD
2 stops31h 42m
United Airlines
Deal found 1/9$1,076
This CheapOair deal was found by Cheapflights users on 1/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/63:40 pm
ORD
-
SIN
2 stops33h 50m
Air Canada
Fri 4/178:10 am
SIN
-
ORD
2 stops38h 00m
Air Canada
Deal found 1/12$1,078
This KAYAK deal was found by Cheapflights users on 1/10. 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 2/271:30 pm
ORD
-
SIN
1 stop42h 15m
Air India
Fri 3/611:00 pm
SIN
-
ORD
2 stops50h 30m
Air India
Deal found 1/10$1,080

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 12, 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

Mon 3/2

6:00 am-5:00 am

2 stops33h 00m

Singapore Changi

Wed 3/18

10:40 am-12:29 pm

2 stops38h 49m

$1,069

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sat 7/4

5:15 am-6:35 pm

2 stops24h 20m

Singapore Changi

Fri 7/24

11:05 am-11:20 pm

2 stops25h 15m

$1,076

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sat 6/13

9:39 pm-6:35 pm

1 stop31h 56m

Singapore Changi

Tue 7/7

8:45 am-11:34 pm

1 stop27h 49m

$1,087

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 6/17

6:02 am-6:35 pm

1 stop23h 33m

Singapore Changi

Sun 7/5

8:40 pm-5:57 am

1 stop22h 17m

$1,087

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 6/16

9:39 pm-6:35 pm

1 stop31h 56m

Singapore Changi

Fri 7/3

8:45 am-12:58 am

1 stop29h 13m

$1,087

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 7/1

6:02 am-6:35 pm

1 stop23h 33m

Singapore Changi

Sun 7/19

8:40 pm-4:58 am

1 stop21h 18m

$1,087

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 2/3

5:15 am-7:00 am

3 stops35h 45m

Singapore Changi

Mon 2/9

5:20 am-2:41 pm

3 stops47h 21m

$1,090

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 6/17

5:15 am-6:35 pm

2 stops24h 20m

Singapore Changi

Fri 7/3

8:45 am-12:58 am

1 stop29h 13m

$1,091

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 6/15

9:39 pm-6:35 pm

1 stop31h 56m

Singapore Changi

Fri 7/3

8:45 am-12:58 am

2 stops29h 13m

$1,091

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 6/3

5:15 am-6:35 pm

2 stops24h 20m

Singapore Changi

Sat 6/13

8:40 pm-9:39 am

2 stops25h 59m

$1,091

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

Showing 1-10 of 42 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*2 stars

*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 January 9, 2026.

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 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.

How much does it cost to fly round-trip from Chicago to Singapore?

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.

Hong Kong (HKG) – chosen by Cheapflights users on 33% 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.

Hong Kong (HKG) is the most affordable 1-stop option, with an average round-trip price of $882.

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 January 12, 2026.
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
1,316 reviews

Food

8.1

Comfort

8.3

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

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
1,316 reviews
EVA Air
8.4
Very good
1,316 reviews

Food

8.1

Comfort

8.3

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

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
1,126 reviews
EVA Air
8.4
Very good
1,316 reviews

Food

8.1

Comfort

8.3

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

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
9,144 reviews
EVA Air
8.4
Very good
1,316 reviews

Food

8.1

Comfort

8.3

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

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
4,154 reviews
EVA Air
8.4
Very good
1,316 reviews

Food

8.1

Comfort

8.3

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

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
10,616 reviews
EVA Air
8.4
Very good
1,316 reviews

Food

8.1

Comfort

8.3

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

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.

  • 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 13 different airlines.

  • How long is the flight from Chicago to Singapore?

    There are many flights that can get you from Chicago to Singapore in 24h 20m. Fly via Delta or United Airlines 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 ($698), 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.

  • 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. Turkish Airlines flights start at $444 while deals on United Airlines start at $446 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 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.
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 January 12, 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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