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$322+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
Mar 31 — Apr 71
Tue 3/31
Tue 4/7
1 adult, Economy
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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 March 1, 2026.

This Jettzy deal was found by Cheapflights users on 2/28. 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.
Tue 4/145:45 pm
ORD
-
SIN
1 stop23h 55m
ANA
Tue 4/2111:05 am
SIN
-
ORD
1 stop34h 35m
ANA
Deal found 2/28$835
This United Airlines deal was found by Cheapflights users on 2/27. 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 5/166:20 am
ORD
-
SIN
1 stop23h 15m
United Airlines
Tue 6/28:45 am
SIN
-
ORD
1 stop24h 39m
United Airlines
Deal found 2/27$837
This United Airlines deal was found by Cheapflights users on 2/27. 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 4/36:25 am
ORD
-
SIN
1 stop23h 10m
United Airlines
Thu 4/99:00 am
SIN
-
ORD
1 stop21h 05m
United Airlines
Deal found 2/27$841
This United Airlines deal was found by Cheapflights users on 2/26. 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 3/89:15 pm
ORD
-
SIN
2 stops34h 00m
United Airlines
Fri 3/1310:10 am
SIN
-
ORD
1 stop27h 49m
United Airlines
Deal found 2/26$845
This United Airlines deal was found by Cheapflights users on 2/27. 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 8/219:30 pm
ORD
-
SIN
1 stop32h 05m
United Airlines
Tue 8/2511:05 am
SIN
-
ORD
2 stops24h 59m
United Airlines
Deal found 2/27$850
This FlightHub deal was found by Cheapflights users on 3/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/182:10 pm
ORD
-
SIN
1 stop42h 35m
Air India
Wed 7/111:00 pm
SIN
-
ORD
2 stops49h 10m
Air India
Deal found 3/1$851
This KAYAK deal was found by Cheapflights users on 2/28. 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 4/31:10 pm
ORD
-
SIN
1 stop31h 05m
Air India
Sun 5/38:55 am
SIN
-
ORD
2 stops39h 15m
Air India
Deal found 2/28$860
This oojo deal was found by Cheapflights users on 2/26. 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 4/68:10 pm
ORD
-
SIN
1 stop23h 35m
Turkish Airlines
Fri 4/1710:25 am
SIN
-
ORD
1 stop36h 15m
Turkish Airlines
Deal found 2/26$864
This United Airlines deal was found by Cheapflights users on 2/27. 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 3/159:15 pm
ORD
-
SIN
1 stop34h 00m
United Airlines
Thu 3/2610:20 pm
SIN
-
ORD
1 stop20h 59m
United Airlines
Deal found 2/27$866
This oojo deal was found by Cheapflights users on 2/27. 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 12/711:15 am
ORD
-
SIN
1 stop27h 45m
Korean Air
Mon 12/1410:40 am
SIN
-
ORD
1 stop35h 50m
Korean Air
Deal found 2/27$872
This Delta deal was found by Cheapflights users on 2/26. 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 9/116:00 am
MDW
-
SIN
2 stops34h 00m
Delta
Sat 9/2610:00 pm
SIN
-
MDW
2 stops31h 27m
Delta
Deal found 2/26$1,054
This Delta deal was found by Cheapflights users on 2/28. 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 9/206:00 am
MDW
-
SIN
2 stops28h 55m
Delta
Sat 9/261:25 am
SIN
-
MDW
2 stops33h 21m
Delta
Deal found 2/28$1,055

Find 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 March 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$835
(Jettzy)

One-way from

$322
(oojo)

Popular in

December

Cheapest in

September

Average price

$971
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 Changi
Search Deals
One-way flight from Chicago (CHI) to Singapore Changi
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($173 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($71 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 1, 2026.
Use the filters below to find and compare flights from Chicago to Singapore that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 3/16

9:15 pm-8:15 pm

1 stop34h 00m

Singapore Changi

Thu 3/26

10:10 am-6:51 pm

1 stop21h 41m

$866

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Fri 4/3

1:10 pm-9:15 am

1 stop31h 05m

Singapore Changi

Thu 4/9

1:10 pm-11:10 am

1 stop35h 00m

$890

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 6/30

7:40 am-12:45 am

2 stops28h 05m

Singapore Changi

Wed 7/8

11:05 am-5:58 am

2 stops31h 53m

$1,033

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 7/14

9:33 pm-6:35 pm

1 stop32h 02m

Singapore Changi

Tue 8/4

8:45 am-9:35 pm

1 stop25h 50m

$1,130

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 6/17

6:10 am-6:35 pm

1 stop23h 25m

Singapore Changi

Tue 7/7

6:15 am-9:35 pm

2 stops28h 20m

$1,142

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 6/9

3:45 pm-6:15 am

2 stops49h 30m

Singapore Changi

Wed 6/24

11:05 am-4:47 am

2 stops30h 42m

$1,160

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Sat 5/16

6:20 am-6:35 pm

1 stop23h 15m

Singapore Changi

Tue 6/2

8:35 pm-12:41 pm

1 stop29h 06m

$1,215

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Fri 6/12

10:45 pm-6:35 pm

1 stop30h 50m

Singapore Changi

Fri 7/10

6:15 am-11:07 pm

2 stops29h 52m

$1,249

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 4/24

6:00 am-5:00 am

2 stops34h 00m

Singapore Changi

Tue 4/28

1:25 am-4:26 pm

2 stops28h 01m

$1,254

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 4/12

6:00 am-5:00 am

2 stops34h 00m

Singapore Changi

Sun 4/19

10:00 pm-4:26 pm

2 stops31h 26m

$1,255

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/1

Showing 1-10 of 37 resultsSorted by cheapest first
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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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust Score*3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Singapore flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 February 27, 2026.

The best time to book flights from Chicago to Singapore is 6 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 $663). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,314). 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.

Incheon (ICN) – chosen by Cheapflights users on 25% 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 Incheon (ICN) offer the fastest connection on this route, with an average layover time of 1h 50m.

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 March 1, 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
1,362 reviews

Overall

8.4

Food

8.1

Boarding

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Jack,Feb 2026

TPE - SFO

Premium Economy for a.long-haul flight was worth it for the extra room. It is a 2-5-2 layout, so unless you have a family, get a seat in the 2-seat section. Nice slippers and goody bag. Food was tasty, although it seemed a bit repetitive (i.e., each meal used the same ingredients slightly re-configured). Staff were excellent.
EVA Air
8.4
Very good
1,362 reviews
EVA Air
8.4
Very good
1,362 reviews

Overall

8.4

Food

8.1

Boarding

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Jack,Feb 2026

TPE - SFO

Premium Economy for a.long-haul flight was worth it for the extra room. It is a 2-5-2 layout, so unless you have a family, get a seat in the 2-seat section. Nice slippers and goody bag. Food was tasty, although it seemed a bit repetitive (i.e., each meal used the same ingredients slightly re-configured). Staff were excellent.
Cathay Pacific
7.6
Good
1,180 reviews
EVA Air
8.4
Very good
1,362 reviews

Overall

8.4

Food

8.1

Boarding

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Jack,Feb 2026

TPE - SFO

Premium Economy for a.long-haul flight was worth it for the extra room. It is a 2-5-2 layout, so unless you have a family, get a seat in the 2-seat section. Nice slippers and goody bag. Food was tasty, although it seemed a bit repetitive (i.e., each meal used the same ingredients slightly re-configured). Staff were excellent.
United Airlines
7.4
Good
9,372 reviews
EVA Air
8.4
Very good
1,362 reviews

Overall

8.4

Food

8.1

Boarding

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Jack,Feb 2026

TPE - SFO

Premium Economy for a.long-haul flight was worth it for the extra room. It is a 2-5-2 layout, so unless you have a family, get a seat in the 2-seat section. Nice slippers and goody bag. Food was tasty, although it seemed a bit repetitive (i.e., each meal used the same ingredients slightly re-configured). Staff were excellent.
Turkish Airlines
7.3
Good
4,240 reviews
EVA Air
8.4
Very good
1,362 reviews

Overall

8.4

Food

8.1

Boarding

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Jack,Feb 2026

TPE - SFO

Premium Economy for a.long-haul flight was worth it for the extra room. It is a 2-5-2 layout, so unless you have a family, get a seat in the 2-seat section. Nice slippers and goody bag. Food was tasty, although it seemed a bit repetitive (i.e., each meal used the same ingredients slightly re-configured). Staff were excellent.
Air Canada
7.1
Good
10,762 reviews
EVA Air
8.4
Very good
1,362 reviews

Overall

8.4

Food

8.1

Boarding

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Jack,Feb 2026

TPE - SFO

Premium Economy for a.long-haul flight was worth it for the extra room. It is a 2-5-2 layout, so unless you have a family, get a seat in the 2-seat section. Nice slippers and goody bag. Food was tasty, although it seemed a bit repetitive (i.e., each meal used the same ingredients slightly re-configured). Staff were excellent.

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 11 different airlines.

  • How long is the flight from Chicago to Singapore?

    There are many flights that can get you from Chicago to Singapore in 31h 05m. Fly via United Airlines, Air India, 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, ANA ($698), Cathay Pacific ($698), and United Airlines ($705) offers the cheapest pricing from Chicago to Singapore. You may be able to fly from Chicago to Singapore for 38% 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 $663). Flying from Chicago to Singapore in December is currently the most expensive (average of $1,314). 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
St. Louis 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 March 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air IndiaCheapest$675Average$925FlexibilityNo cancel feeOn-timeN/A
ANACheapest$698Average$1,426FlexibilityNo cancel feeOn-time80%
Cathay PacificCheapest$698Average$882FlexibilityNo cancel feeOn-time72%
United AirlinesCheapest$705Average$1,180FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$799Average$1,103FlexibilityNo cancel feeOn-time77%
Etihad AirwaysCheapest$829Average$983FlexibilityNo cancel feeOn-time75%
Korean AirCheapest$858Average$1,153FlexibilityNo cancel feeOn-time81%
Air CanadaCheapest$872Average$1,340FlexibilityNo cancel feeOn-time67%
Japan AirlinesCheapest$981Average$1,081FlexibilityNo cancel feeOn-time79%
EVA AirCheapest$1,086Average$1,389FlexibilityNo cancel feeOn-time74%

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