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$600+ Cheap flights from Singapore to Midway (MDW)

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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Singapore to Midway

Keep the following information in mind while searching for Singapore to Midway flight deals. Data was last updated August 14, 2025.

Round-trip from

$974
(Delta)

One-way from

$600
(Kiwi.com)

Popular in

January

Cheapest in

October

Average price

$1,246
From Singapore to Chicago Midway
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One-way flight from Singapore to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($111 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Singapore to Midway

Cheapest flights from Singapore to Midway
Explore the most affordable flight options available from Singapore to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Delta deal was found by Cheapflights users on 8/13. 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.
Tue 9/21:10 amSIN - MDW
2 stops33h 16mDelta
Sat 9/274:25 pmMDW - SIN
2 stops47h 35mDelta
Deal found 8/13$974
This Delta deal was found by Cheapflights users on 8/10. 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 9/810:30 pmSIN - MDW
2 stops26h 58mDelta
Sat 9/137:15 pmMDW - SIN
2 stops39h 25mDelta
Deal found 8/10$975
This Delta deal was found by Cheapflights users on 8/13. 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 9/110:30 pmSIN - MDW
2 stops35h 56mDelta
Sat 9/274:25 pmMDW - SIN
2 stops47h 35mDelta
Deal found 8/13$1,083
This Delta deal was found by Cheapflights users on 8/12. 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 9/211:10 amSIN - MDW
2 stops33h 26mDelta
Mon 9/299:35 amMDW - SIN
2 stops25h 05mDelta
Deal found 8/12$1,274
This Delta deal was found by Cheapflights users on 8/13. 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.
Tue 9/21:10 amSIN - MDW
2 stops33h 16mDelta
Tue 9/309:35 amMDW - SIN
2 stops25h 05mDelta
Deal found 8/13$1,275
This Delta deal was found by Cheapflights users on 8/10. 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.
Sat 10/410:30 pmSIN - MDW
2 stops32h 05mDelta
Mon 10/136:00 amMDW - SIN
2 stops28h 40mDelta
Deal found 8/10$1,306
This Delta deal was found by Cheapflights users on 8/13. 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 9/110:30 pmSIN - MDW
2 stops28h 06mDelta
Tue 9/309:20 amMDW - SIN
2 stops25h 20mDelta
Deal found 8/13$1,384
This Delta deal was found by Cheapflights users on 8/13. 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 9/221:10 amSIN - MDW
2 stops33h 26mDelta
Sat 9/276:00 amMDW - SIN
2 stops34h 00mDelta
Deal found 8/13$1,407
This Delta deal was found by Cheapflights users on 8/12. 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.
Sat 10/410:30 pmSIN - MDW
2 stops36h 06mDelta
Sun 10/199:35 amMDW - SIN
2 stops30h 25mDelta
Deal found 8/12$1,439
This Delta deal was found by Cheapflights users on 8/10. 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 10/67:30 amSIN - MDW
2 stops27h 44mDelta
Mon 10/136:00 amMDW - SIN
2 stops28h 40mDelta
Deal found 8/10$1,519
This Delta deal was found by Cheapflights users on 8/10. 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.
Tue 10/77:30 amSIN - MDW
2 stops38h 25mDelta
Tue 10/146:00 amMDW - SIN
2 stops34h 00mDelta
Deal found 8/10$1,635

Cheapflights Fare Finder

 
Customize your flight search to find flights from Singapore to Midway 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 August 14, 2025.
Use the filters below to find and compare flights from Singapore to Chicago Midway Airport that are best for you.

Fly from

Singapore

Fly to

Midway

Route

Depart

Return

Price

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 9/4

7:30 am-9:26 pm

2 stops26h 56m

Chicago Midway

Sat 9/27

4:25 pm-5:00 am

2 stops47h 35m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 9/2

10:30 pm-9:26 pm

2 stops35h 56m

Chicago Midway

Mon 9/29

9:20 am-5:00 am

2 stops30h 40m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 9/4

7:30 am-9:26 pm

2 stops26h 56m

Chicago Midway

Mon 9/29

9:35 am-5:00 am

2 stops30h 25m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 9/3

1:10 am-6:37 pm

2 stops30h 27m

Chicago Midway

Sun 9/28

9:35 am-5:00 am

2 stops30h 25m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 9/7

1:10 am-6:37 pm

2 stops30h 27m

Chicago Midway

Sun 9/14

9:35 am-11:40 pm

2 stops25h 05m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 9/2

1:10 am-9:26 pm

2 stops33h 16m

Chicago Midway

Sat 9/27

4:25 pm-5:00 am

2 stops47h 35m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 9/2

10:30 pm-9:26 pm

2 stops35h 56m

Chicago Midway

Sun 9/28

9:20 am-5:00 am

2 stops30h 40m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 9/8

1:10 am-6:37 pm

2 stops30h 27m

Chicago Midway

Tue 9/16

9:35 am-11:40 pm

2 stops25h 05m

$975

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 9/19

2:35 pm-11:17 pm

3 stops45h 42m

$600

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 1/27

10:30 pm-9:46 pm

2 stops37h 16m

$629

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

Showing 1-10 of 14 results
1
2

Best time to book a flight from Singapore to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Singapore 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 Singapore to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Singapore to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Singapore to Chicago Midway Airport (average of $160). Flying from Singapore to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Singapore to Midway

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