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$584+ 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
1 adult, Economy
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Cheap 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 December 14, 2025.

This Delta deal was found by Cheapflights users on 12/13. 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.
Sat 12/2710:30 pmSIN - MDW
2 stops32h 56mDelta
Sun 1/45:59 pmMDW - SIN
2 stops40h 11mDelta
Deal found 12/13$1,932
This KLM deal was found by Cheapflights users on 12/14. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/171:40 amSIN - MDW
2 stops28h 51mKLM
Sat 1/105:31 pmMDW - SIN
2 stops32h 44mKLM
Deal found 12/14$2,408

Find flight deals from Singapore to Midway

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

Round-trip from

$877
(Delta)

One-way from

$584
(Delta)

Popular in

January

Cheapest in

October

Average price

$1,250
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. 15% potential increase in price ($206 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($59 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 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

Wed 1/21

1:35 am-10:22 pm

2 stops34h 47m

Chicago Midway

Wed 2/4

6:14 pm-8:25 pm

2 stops36h 11m

$877

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 5/26

10:30 pm-4:25 pm

2 stops30h 55m

Chicago Midway

Sat 6/27

6:00 am-11:40 pm

2 stops28h 40m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 5/27

10:30 pm-12:30 pm

2 stops27h 00m

Chicago Midway

Fri 6/26

6:00 am-5:00 am

2 stops34h 00m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 5/25

10:30 pm-4:25 pm

2 stops30h 55m

Chicago Midway

Sat 6/27

6:00 am-11:40 pm

2 stops28h 40m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 5/26

1:10 am-4:25 pm

2 stops28h 15m

Chicago Midway

Sat 6/27

6:00 am-5:00 am

2 stops34h 00m

$974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 1/28

10:30 pm-12:46 pm

2 stops28h 16m

Chicago Midway

Wed 2/4

6:00 am-12:10 am

2 stops28h 10m

$999

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 2/6

1:35 am-10:22 pm

2 stops34h 47m

Chicago Midway

Fri 2/27

6:17 pm-12:10 am

2 stops39h 53m

$999

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 1/27

2:25 pm-12:40 pm

2 stops36h 15m

Chicago Midway

Tue 2/3

10:35 am-1:05 pm

2 stops36h 30m

$1,145

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 1/22

2:25 pm-12:40 pm

2 stops36h 15m

Chicago Midway

Wed 2/4

11:10 am-1:05 pm

3 stops35h 55m

$1,201

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 2/9

1:35 am-10:22 pm

2 stops34h 47m

Chicago Midway

Fri 2/20

6:00 am-5:00 am

2 stops33h 00m

$1,248

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 21 results
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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.

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

    A quick flight from Singapore to Chicago Midway Airport can take about 34h 47m. Delta provides one of the quickest options available for as low as $877. There are 9360 mi between Singapore and Chicago Midway Airport.

  • 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Singapore to Midway

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