Cheap flights from Chicago to Singapore from S$ 445
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 17-3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
20 Dec — 27 Dec1
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Chicago to Singapore Changi are usually found in February or September, booked 23 days in advance, depart on a Tuesday or Monday and return on a Tuesday
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Enter your travel dates to find the best prices.
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 20 November 2025.
Fri 21-1121:30ORD - SIN
2 stops32h 45mUnited Airlines
Fri 28-1122:20SIN - ORD
2 stops32h 48mUnited Airlines
Deal found 20-11S$ 1,641
Wed 26-1117:35ORD - SIN
1 stop33h 50mJapan Airlines
Thu 25-1202:20SIN - ORD
1 stop19h 10mJapan Airlines
Deal found 18-11S$ 1,643
Tue 2-1214:35ORD - SIN
1 stop25h 05mCathay Pacific
Thu 4-1201:25SIN - ORD
1 stop25h 30mCathay Pacific
Deal found 18-11S$ 1,653
Mon 1-1208:00ORD - SIN
3 stops35h 30mMultiple Airlines
Tue 9-1206:50SIN - ORD
3 stops37h 15mMultiple Airlines
Deal found 19-11S$ 1,655
Sun 30-1108:00ORD - SIN
3 stops33h 00mMultiple Airlines
Mon 8-1221:20SIN - ORD
3 stops46h 45mMultiple Airlines
Deal found 19-11S$ 1,662
Sat 6-1211:50ORD - SIN
1 stop32h 10mTurkish Airlines
Fri 12-1211:40SIN - ORD
1 stop36h 25mTurkish Airlines
Deal found 19-11S$ 1,667
Sat 29-1116:25ORD - SIN
1 stop24h 30mMultiple Airlines
Mon 8-1220:00SIN - ORD
2 stops38h 00mMultiple Airlines
Deal found 19-11S$ 1,668
Tue 9-1207:05ORD - SIN
3 stops31h 50mMultiple Airlines
Wed 17-1220:25SIN - ORD
3 stops47h 40mMultiple Airlines
Deal found 19-11S$ 1,670
Fri 5-1213:30ORD - SIN
1 stop27h 30mAir India
Thu 11-1220:00SIN - ORD
2 stops29h 30mAir India
Deal found 19-11S$ 1,679
Thu 4-1206:50ORD - SIN
2 stops34h 05mMultiple Airlines
Mon 8-1223:25SIN - ORD
1 stop24h 40mMultiple Airlines
Deal found 19-11S$ 1,681
Fri 21-1121:07ORD - SIN
1 stop33h 08mUnited Airlines
Mon 1-1222:20SIN - ORD
1 stop28h 04mUnited Airlines
Deal found 18-11S$ 1,683
Fri 28-1107:10ORD - SIN
2 stops27h 45mANA
Wed 10-1210:45SIN - ORD
2 stops33h 34mANA
Deal found 19-11S$ 1,685
Best flights from Chicago to Singapore
Discover carefully curated flight deals from Chicago to Singapore that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 20 November 2025.
Mon 26-110:35MDW - SIN
2 stops36h 30mMultiple Airlines
Wed 4-214:25SIN - MDW
2 stops36h 00mMultiple Airlines
Deal found 17-11S$ 1,640
Fri 20-307:10ORD - SIN
2 stops32h 50mDelta
Wed 25-301:35SIN - ORD
2 stops35h 09mDelta
Deal found 20-11S$ 1,697
Fri 6-218:50ORD - SIN
2 stops25h 30mQatar Airways
Thu 12-203:15SIN - ORD
2 stops32h 10mQatar Airways
Deal found 19-11S$ 1,705
Sun 11-110:35ORD - SIN
1 stop24h 15mJapan Airlines
Sat 17-108:15SIN - ORD
2 stops27h 08mJapan Airlines
Deal found 19-11S$ 1,774
Sat 3-122:00ORD - SIN
2 stops32h 15mUnited Airlines
Mon 12-110:10SIN - ORD
2 stops26h 49mUnited Airlines
Deal found 17-11S$ 1,814
Sat 7-313:15ORD - SIN
2 stops39h 25mFinnair
Wed 18-322:05SIN - ORD
2 stops43h 59mFinnair
Deal found 20-11S$ 1,869
Thu 22-111:10MDW - SIN
3 stops35h 55mMultiple Airlines
Mon 26-114:25SIN - MDW
2 stops36h 15mMultiple Airlines
Deal found 19-11S$ 1,690
Sun 30-1118:33ORD - SIN
2 stops44h 27mDelta
Wed 10-1201:35SIN - ORD
2 stops36h 24mDelta
Deal found 19-11S$ 1,724
Mon 9-215:40MDW - SIN
3 stops31h 25mMultiple Airlines
Sun 8-314:25SIN - MDW
2 stops33h 40mMultiple Airlines
Deal found 18-11S$ 1,705
Sat 14-205:25ORD - SIN
2 stops33h 35mDelta
Fri 20-201:35SIN - ORD
2 stops36h 20mDelta
Deal found 17-11S$ 1,762
Fri 20-310:20MDW - SIN
2 stops37h 45mMultiple Airlines
Tue 24-302:00SIN - MDW
2 stops31h 25mMultiple Airlines
Deal found 19-11S$ 1,761
Fri 20-306:00MDW - SIN
2 stops34h 00mDelta
Wed 25-301:35SIN - MDW
2 stops33h 11mDelta
Deal found 20-11S$ 1,822
Wed 4-314:15ORD - SIN
3 stops32h 50mMultiple Airlines
Mon 16-302:00SIN - ORD
2 stops45h 09mMultiple Airlines
Deal found 18-11S$ 1,761
Mon 1-1206:00MDW - SIN
2 stops33h 00mDelta
Tue 9-1222:30SIN - MDW
2 stops27h 25mDelta
Deal found 19-11S$ 1,907
Tue 3-213:00ORD - SIN
3 stops34h 05mMultiple Airlines
Wed 11-214:25SIN - ORD
2 stops57h 31mMultiple Airlines
Deal found 19-11S$ 1,769
Sun 5-400:30ORD - SIN
2 stops53h 20mMultiple Airlines
Fri 17-410:30SIN - ORD
2 stops47h 30mMultiple Airlines
Deal found 19-11S$ 1,792
Fri 24-400:30ORD - SIN
2 stops48h 10mMultiple Airlines
Sat 2-510:30SIN - ORD
2 stops47h 30mMultiple Airlines
Deal found 19-11S$ 1,843
Sun 1-215:40MDW - SIN
3 stops31h 25mMultiple Airlines
Tue 10-214:25SIN - MDW
2 stops36h 15mMultiple Airlines
Deal found 18-11S$ 1,861
Last-minute flights from Chicago to Singapore
Discover last-minute flight deals from Chicago to Singapore. Data last updated 20 November 2025 and is based on user searches.
Wed 26-1117:35ORD - SIN
1 stop33h 50mJapan Airlines
Thu 25-1202:20SIN - ORD
1 stop19h 10mJapan Airlines
Deal found 18-11S$ 1,643
Thu 27-1106:00MDW - SIN
2 stops28h 10mDelta
Mon 29-1210:40SIN - MDW
2 stops38h 26mDelta
Deal found 18-11S$ 1,701
Fri 28-1107:10ORD - SIN
2 stops27h 45mANA
Wed 10-1210:45SIN - ORD
2 stops33h 34mANA
Deal found 19-11S$ 1,685
Fri 28-1117:34MDW - SIN
2 stops45h 26mDelta
Mon 29-1210:40SIN - MDW
2 stops38h 26mDelta
Deal found 18-11S$ 1,693
Fri 28-1107:10ORD - SIN
1 stop23h 05mUnited Airlines
Wed 31-1210:10SIN - ORD
1 stop33h 17mUnited Airlines
Deal found 18-11S$ 1,700
Fri 28-1113:00ORD - SIN
2 stops50h 00mKorean Air
Sun 7-1201:35SIN - ORD
1 stop20h 55mKorean Air
Deal found 19-11S$ 1,736
Sat 29-1116:25ORD - SIN
1 stop24h 30mMultiple Airlines
Mon 8-1220:00SIN - ORD
2 stops38h 00mMultiple Airlines
Deal found 19-11S$ 1,668
Sat 29-1111:15ORD - SIN
1 stop27h 45mDelta
Sun 7-1210:40SIN - ORD
2 stops23h 15mDelta
Deal found 19-11S$ 1,709
Sat 29-1111:15ORD - SIN
1 stop27h 45mDelta
Tue 30-1222:30SIN - ORD
2 stops35h 08mDelta
Deal found 18-11S$ 1,774
Sun 30-1108:00ORD - SIN
3 stops33h 00mMultiple Airlines
Mon 8-1221:20SIN - ORD
3 stops46h 45mMultiple Airlines
Deal found 19-11S$ 1,662
Sun 30-1117:35ORD - SIN
1 stop23h 00mMultiple Airlines
Sat 6-1200:40SIN - ORD
2 stops26h 07mMultiple Airlines
Deal found 19-11S$ 1,683
Sun 30-1118:33ORD - SIN
2 stops44h 27mDelta
Wed 10-1201:35SIN - ORD
2 stops36h 24mDelta
Deal found 19-11S$ 1,724
One-way flights from Chicago to Singapore
Search for one-way flight options from Chicago to Singapore. Find affordable one-way fares based on user searches. Data last updated 20 November 2025.
Tue 17-317:29ORD - SIN
2 stops27h 06mMultiple Airlines
Deal found 18-11S$ 445
Wed 18-213:30ORD - SIN
1 stop39h 25mAir India
Deal found 19-11S$ 462
Mon 27-413:10ORD - SIN
1 stop41h 20mAir India
Deal found 19-11S$ 487
Fri 20-213:30ORD - SIN
1 stop39h 25mAir India
Deal found 18-11S$ 518
Fri 27-213:30ORD - SIN
1 stop27h 30mAir India
Deal found 18-11S$ 536
Sun 18-113:30ORD - SIN
1 stop42h 15mAir India
Deal found 19-11S$ 537
Tue 13-113:10ORD - SIN
3 stops31h 10mMultiple Airlines
Deal found 19-11S$ 540
Wed 14-114:35ORD - SIN
1 stop32h 30mCathay Pacific
Deal found 18-11S$ 545
Sat 21-213:52ORD - SIN
3 stops53h 43mMultiple Airlines
Deal found 18-11S$ 556
Wed 14-107:00ORD - SIN
2 stops27h 50mJapan Airlines
Deal found 18-11S$ 557
Thu 27-1108:00ORD - SIN
2 stops35h 35mMultiple Airlines
Deal found 18-11S$ 569
Wed 18-206:00MDW - SIN
2 stops33h 00mDelta
Deal found 18-11S$ 591
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 20 November 2025.
Customise 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 200,618 searches. Data last updated 20 November 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
Mon 26-1
10:35-13:05
2 stops36h 30m
Singapore Changi
Wed 4-2
14:25-12:25
2 stops36h 00m
S$ 1,640
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Thu 22-1
11:10-13:05
3 stops35h 55m
Singapore Changi
Mon 26-1
14:25-12:40
2 stops36h 15m
S$ 1,690
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Fri 20-3
07:10-05:00
2 stops32h 50m
Singapore Changi
Wed 25-3
01:35-23:44
2 stops35h 09m
S$ 1,697
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Fri 6-2
18:50-10:20
2 stops25h 30m
Singapore Changi
Thu 12-2
03:15-21:25
2 stops32h 10m
S$ 1,705
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Mon 9-2
15:40-13:05
3 stops31h 25m
Singapore Changi
Sun 8-3
14:25-10:05
2 stops33h 40m
S$ 1,705
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sun 30-11
18:33-05:00
2 stops44h 27m
Singapore Changi
Wed 10-12
01:35-23:59
2 stops36h 24m
S$ 1,724
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Fri 20-3
10:20-13:05
2 stops37h 45m
Singapore Changi
Tue 24-3
02:00-20:25
2 stops31h 25m
S$ 1,761
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Wed 4-3
14:15-13:05
3 stops32h 50m
Singapore Changi
Mon 16-3
02:00-10:09
2 stops45h 09m
S$ 1,761
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Sat 14-2
05:25-05:00
2 stops33h 35m
Singapore Changi
Fri 20-2
01:35-23:55
2 stops36h 20m
S$ 1,762
ChicagoSingapore
ORD - SIN
ORDSIN
Chicago O'Hare Intl
Tue 3-2
13:00-13:05
3 stops34h 05m
Singapore Changi
Wed 11-2
14:25-09:56
2 stops57h 31m
S$ 1,769
Flights are sorted by cheapest return flights first.
Deals found on 18-11
Showing 1-10 of 39 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 return 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 return flight from Chicago to Singapore. Price data was last updated on 14 November 2025.
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 S$ 862). Flying from Chicago to Singapore in December is currently the most expensive (average of S$ 1,714). 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 SIN?
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 20 November 2025.
Unlike at midday, when flights are generally more expensive, you can save up to 22% on flights from Chicago to Singapore by exploring options for tickets in the afternoon.
How much does it cost for a return flight from Chicago to Singapore?
What’s the top stopover airport for flights from Chicago to Singapore?
Share of one-stop return flights from Chicago to Singapore chosen by Cheapflights users in the past 12 months, using the same stopover each way.
Istanbul (IST) – chosen by Cheapflights users on 38% of one-stop itineraries from Chicago to Singapore on Cheapflights.
What’s the cheapest stopover airport for flights from Chicago to Singapore?
Average return fare for one-stop flights from Chicago to Singapore, chosen by Cheapflights users in the past 12 months, with the same stopover each way.
San Francisco (SFO) is the most affordable one-stop option, with an average return flight price of S$ 913.
What’s the fastest stopover option from Chicago to Singapore?
Shortest average travel time for one-stop one-way flights from Chicago to Singapore, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by stopover airport.
Flights via Vancouver (YVR) have the shortest average one-way travel time for one-stop routes: 22h 30m.
Which airport typically offers the quickest stopover for flights from Chicago to Singapore?
Average stopover duration for one-stop one-way flights from Chicago to Singapore, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via San Francisco (SFO) offer the fastest connection on this route, with an average stopover time of 1h 41m.
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?
For a flight from Chicago to Singapore, you will be flying into Changi. Singapore Changi (SIN) is just 16.9 km from the centre vof the city. Changi is the only Singapore airport and it handles 0 inbound flights from Chicago per day. 1 airline has flights to Singapore Changi from Chicago on a regular basis.
How long is the flight from Chicago to Singapore?
Delta and Qatar Airways can get you from Chicago to Singapore in just under 25h 30m. Your travel time can differ by up to 7h 20m. The distance from Chicago to Singapore is about 15039 km. Both multi-stop and direct flights can be found to your destination and back.
What is the cheapest airline to fly from Chicago to Singapore round-trip?
Cheapflights users have booked flights from Chicago to Singapore round-trip from S$ 930. You may be able to fly from Chicago to Singapore for 37% less than the average price by searching for this airline.
What are the cheapest airlines to fly from Chicago to Singapore one-way?
To fly one-way, consider booking your trip with Air India, which is currently one of the cheapest options available, starting at S$ 487. Japan Airlines flights start at S$ 569 while deals on Delta start at S$ 591 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 holiday 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 S$ 862). Flying from Chicago to Singapore in December is currently the most expensive (average of S$ 1,714). 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.
Explore flights to Singapore departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 20 November 2025.
Discover the top airline 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 200,618 searches. Data last updated 20 November 2025.
Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Chicago to Singapore?
900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Singapore from Chicago today with Cheapflights!
Why should you use Cheapflights to find cheap flight tickets from Chicago to Singapore?
Millions of users choose and trust Cheapflights to book the best flight deals from Chicago to Singapore for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.
Can Cheapflights find flights from Chicago to Singapore with no change fees?
Yes! Cheapflights helps users easily find flights from Chicago to Singapore with no change fees.
Can Cheapflights notify me if prices for flights from Chicago to Singapore become cheaper?
Of course! You can now track prices for flights from Chicago to Singapore and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.
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