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$416+ Cheap flights from Midway (MDW) 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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SIN
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Midway to Singapore

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) 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 September 11, 2025.

Round-trip from

$884
(Delta)

One-way from

$416
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$885
From Chicago Midway to Singapore Changi
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One-way flight from Chicago Midway to Singapore Changi
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Highest demand for flights based on searches. 14% potential increase in price ($198 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($64 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Singapore

Cheapest flights from Midway to Singapore
Explore the most affordable flight options available from Midway to Singapore. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 9/179:20 amMDW - SIN
2 stops25h 20mDelta
Tue 9/231:10 amSIN - MDW
2 stops33h 26mDelta
Deal found 9/10$734
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:00 amMDW - SIN
2 stops33h 00mDelta
Tue 11/1110:30 pmSIN - MDW
2 stops32h 09mDelta
Deal found 9/11$884
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/25:00 amMDW - SIN
2 stops33h 00mDelta
Tue 11/1110:30 pmSIN - MDW
2 stops27h 22mDelta
Deal found 9/9$896
This Delta deal was found by Cheapflights users on 9/10. 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.
Sun 9/146:30 pmMDW - SIN
2 stops40h 10mDelta
Tue 9/231:10 amSIN - MDW
2 stops30h 25mDelta
Deal found 9/10$937
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 11/266:00 amMDW - SIN
2 stops33h 00mDelta
Fri 12/1910:40 amSIN - MDW
2 stops38h 26mDelta
Deal found 9/10$954
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:00 amMDW - SIN
2 stops34h 00mDelta
Wed 9/171:10 amSIN - MDW
2 stops33h 26mDelta
Deal found 9/11$1,232
This Delta deal was found by Cheapflights users on 9/10. 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.
Sun 10/199:35 amMDW - SIN
2 stops30h 25mDelta
Sun 11/210:30 pmSIN - MDW
2 stops33h 55mDelta
Deal found 9/10$1,259
This Delta deal was found by Cheapflights users on 9/10. 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 10/206:00 amMDW - SIN
2 stops28h 40mDelta
Mon 11/310:30 pmSIN - MDW
2 stops31h 44mDelta
Deal found 9/10$1,289
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/246:00 amMDW - SIN
2 stops34h 00mDelta
Sat 9/2710:30 pmSIN - MDW
2 stops32h 05mDelta
Deal found 9/11$1,301
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:00 amMDW - SIN
2 stops33h 00mDelta
Mon 11/1710:40 amSIN - MDW
2 stops36h 21mDelta
Deal found 9/11$1,309

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 September 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Singapore that are best for you.

Fly from

Midway

Fly to

Singapore

Route

Depart

Return

Price

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 11/3

6:00 am-5:00 am

2 stops33h 00m

Singapore Changi

Tue 11/11

10:30 pm-4:39 pm

2 stops32h 09m

$884

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 11/2

5:00 am-4:00 am

2 stops33h 00m

Singapore Changi

Tue 11/11

10:30 pm-11:52 am

2 stops27h 22m

$896

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 10/21

9:20 am-5:00 am

2 stops30h 40m

Singapore Changi

Tue 11/11

10:40 am-11:32 pm

2 stops26h 52m

$937

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 11/26

6:00 am-5:00 am

2 stops33h 00m

Singapore Changi

Fri 12/19

10:40 am-11:06 am

2 stops38h 26m

$954

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 2/23

6:00 am-12:10 am

2 stops28h 10m

Singapore Changi

Wed 2/25

1:35 am-9:46 pm

2 stops34h 11m

$1,139

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 2/2

6:00 am-12:10 am

2 stops28h 10m

Singapore Changi

Fri 2/13

1:35 am-9:46 pm

2 stops34h 11m

$1,189

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 2/1

5:59 pm-12:10 am

2 stops40h 11m

Singapore Changi

Sat 2/7

1:35 am-9:46 pm

2 stops34h 11m

$1,194

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 1/19

8:15 am-1:05 pm

2 stops38h 50m

Singapore Changi

Tue 1/27

2:00 am-2:45 pm

2 stops26h 45m

$1,215

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 1/31

4:30 pm-8:25 pm

2 stops37h 55m

Singapore Changi

Sat 2/7

1:35 am-9:46 pm

2 stops34h 11m

$1,239

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 2/7

4:30 pm-12:10 am

2 stops41h 40m

Singapore Changi

Thu 2/12

1:35 am-9:46 pm

2 stops34h 11m

$1,239

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 17 results
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Best time to book a flight from Midway to Singapore

Have a flexible travel schedule? Discover the best time to fly to Singapore from Midway 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 Midway Airport to Singapore

What is the cheapest time of day to fly from MDW to SIN?

Find hourly flight availability from Midway 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 September 11, 2025.

When flying from Chicago Midway Airport to Singapore, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Midway?

    If you book a flight to Singapore from Chicago Midway, you will be flying to Changi, which is the city’s only airport. Singapore Changi (SIN) is located 10.5 mi from the center of Singapore. There are 0 flights from Chicago Midway to Changi per day from 0 different airlines.

  • How long is the flight from Chicago Midway Airport to Singapore?

    Airlines like Delta fly from Chicago Midway Airport to Singapore in about 33h. The time it takes to get you to your destination can typically vary by up to . The distance between Chicago Midway Airport and Singapore is about 9360 mi.

  • Can I find deals for flights from Midway to Singapore that include hotel bookings?

    Yes. In addition to deals on Midway to Singapore flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Singapore?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Singapore.

  • Can I find deals for business class flights from Midway to Singapore?

    Yes. Cheapflights offers flight deals from Midway 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 Midway Airport to Singapore?

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Singapore (average of $1,002). Flying from Chicago Midway Airport to Singapore in December is currently the most expensive (average of $1,665). 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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