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Cheap flights from Chicago to Singapore from S$ 457

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 27-4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIN
19 Jan — 26 Jan1
1 adult
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

Cheap flight deals from Chicago to Singapore

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 December 2025.

Tue 23-1206:15ORD - SIN
1 stop24h 00mUnited Airlines
Thu 25-1222:20SIN - ORD
1 stop29h 06mUnited Airlines
Deal found 19-12S$ 1,681
Fri 26-1221:23ORD - SIN
2 stops32h 52mUnited Airlines
Thu 8-122:20SIN - ORD
2 stops30h 20mUnited Airlines
Deal found 19-12S$ 1,699
Thu 25-1221:23ORD - SIN
2 stops32h 52mUnited Airlines
Tue 30-1210:10SIN - ORD
2 stops26h 49mUnited Airlines
Deal found 19-12S$ 1,707
Mon 22-1222:10ORD - SIN
1 stop32h 05mUnited Airlines
Thu 25-1222:20SIN - ORD
1 stop29h 06mUnited Airlines
Deal found 19-12S$ 1,723
Sun 28-1222:10ORD - SIN
1 stop32h 05mUnited Airlines
Wed 31-1222:20SIN - ORD
1 stop21h 07mUnited Airlines
Deal found 19-12S$ 1,734
Mon 29-1208:54ORD - SIN
2 stops33h 06mUnited Airlines
Wed 31-1222:20SIN - ORD
1 stop21h 07mUnited Airlines
Deal found 19-12S$ 1,739
Mon 22-1222:10ORD - SIN
1 stop32h 05mUnited Airlines
Sat 27-1222:20SIN - ORD
1 stop29h 06mUnited Airlines
Deal found 19-12S$ 1,788
Sat 27-1222:10ORD - SIN
1 stop32h 05mUnited Airlines
Wed 31-1222:20SIN - ORD
1 stop21h 07mUnited Airlines
Deal found 19-12S$ 1,798
Mon 22-1213:30ORD - SIN
1 stop39h 25mAir India
Sat 27-1220:00SIN - ORD
2 stops29h 30mAir India
Deal found 19-12S$ 1,810
Tue 23-1213:00ORD - SIN
2 stops29h 00mUnited Airlines
Tue 13-122:20SIN - ORD
2 stops30h 20mUnited Airlines
Deal found 19-12S$ 1,829
Wed 31-1206:00MDW - SIN
2 stops33h 00mDelta
Wed 7-122:30SIN - MDW
2 stops37h 37mDelta
Deal found 19-12S$ 2,372
Sun 28-1206:00MDW - SIN
2 stops33h 00mDelta
Mon 5-122:30SIN - MDW
2 stops31h 59mDelta
Deal found 20-12S$ 2,566

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 20 December 2025.

Round-trip from

S$ 1,681

One-way from

S$ 457

Popular in

December

Cheapest in

February

Average price

S$ 2,471
Delta
  • Delta
  • 12-3-28-3
  • 4 total stops
  • 61h 55m total
  • Chicago to Singapore
Search Deals
Air India
  • Air India
  • 27-4
  • 1 total stop
  • 29h 20m total
  • Chicago to Singapore
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (S$ 348 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (S$ 120 potential savings vs. average return price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
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 December 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

Thu 26-3

06:30-05:00

2 stops33h 30m

Singapore Changi

Fri 3-4

01:10-15:25

2 stops27h 15m

S$ 1,681

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 1-2

15:40-15:30

3 stops33h 50m

Singapore Changi

Sun 15-2

14:25-11:55

2 stops35h 30m

S$ 1,708

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 3-2

11:10-13:05

3 stops35h 55m

Singapore Changi

Tue 10-2

14:25-12:40

2 stops36h 15m

S$ 1,725

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 1-2

15:40-15:30

3 stops33h 50m

Singapore Changi

Tue 10-2

14:25-12:35

2 stops36h 10m

S$ 1,744

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 22-5

06:00-05:00

2 stops34h 00m

Singapore Changi

Fri 5-6

01:10-15:25

2 stops27h 15m

S$ 1,784

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Mon 6-4

15:05-00:35

3 stops44h 30m

Singapore Changi

Thu 16-4

02:00-23:55

2 stops34h 55m

S$ 1,785

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 23-1

11:10-13:05

3 stops35h 55m

Singapore Changi

Sat 31-1

14:25-05:00

2 stops28h 35m

S$ 1,816

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Tue 6-1

07:30-05:00

2 stops31h 30m

Singapore Changi

Sun 18-1

22:30-23:53

2 stops39h 23m

S$ 1,869

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Fri 23-1

13:00-13:05

3 stops34h 05m

Singapore Changi

Sat 31-1

14:25-14:38

2 stops38h 13m

S$ 1,872

ChicagoSingapore

ORD - SIN

ORDSIN

Chicago O'Hare Intl

Wed 4-3

13:00-13:05

3 stops34h 05m

Singapore Changi

Sat 28-3

02:00-23:55

2 stops34h 55m

S$ 1,873

Flights are sorted by cheapest return flights first.

Deals found on 19-12

Showing 1-10 of 43 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 12 December 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$ 854). Flying from Chicago to Singapore in December is currently the most expensive (average of S$ 1,758). 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 December 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 43% 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$ 905.

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.

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 20 December 2025.
Check out reviews from past customers who have flown with United Airlines from Chicago to Singapore to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,099 reviews
Check prices

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,099 reviews
United Airlines
7.4
Good
9,099 reviews
Check prices

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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. 2 airlines have flights to Singapore Changi from Chicago on a regular basis.

  • How long is the flight from Chicago to Singapore?

    Delta and United Airlines can get you from Chicago to Singapore in just under 32h 05m. Your travel time can differ by up to 1h 25m. 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 are the cheapest airlines flying from Chicago to Singapore round-trip?

    Cheapflights users have booked flights from Chicago to Singapore round-trip from S$ 2,070. Another airline that can offer you cheap pricing is JetBlue.

  • 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$ 854). Flying from Chicago to Singapore in December is currently the most expensive (average of S$ 1,758). 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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Fly from Chicago to Singapore on these airlines

Choose from the following airlines for your flight from Chicago to Singapore. Flights are based on user searches made on Cheapflights and were last updated on 20 December 2025.
United Airlines flights from Chicago to Singapore Changi

Top 2 airlines flying from Chicago to Singapore

Discover the top 2 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 200,618 searches. Data last updated 20 December 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 2,070AverageS$ 2,083FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
JetBlueCheapestS$ 2,844AverageS$ 2,844FlexibilityNo cancel feeOn-time62%
Search JetBlue flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Chicago to Singapore?

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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.

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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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