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Cheap flights from Singapore to Chicago Midway Airport from S$ 744

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 16-5. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
8 Mar — 15 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Singapore to Midway

Enter your travel dates to find the best prices.

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 6 February 2026.

Thu 7-513:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Thu 14-518:10
MDW
-
SIN
2 stops29h 25m
Multiple Airlines
Deal found 5-2S$ 1,356
Mon 23-314:25
SIN
-
MDW
2 stops28h 15m
Multiple Airlines
Mon 30-311:50
MDW
-
SIN
2 stops35h 45m
Multiple Airlines
Deal found 6-2S$ 1,381
Wed 18-314:25
SIN
-
MDW
2 stops28h 15m
Multiple Airlines
Tue 31-310:55
MDW
-
SIN
2 stops36h 40m
Multiple Airlines
Deal found 4-2S$ 1,438
Sat 6-615:20
SIN
-
MDW
2 stops26h 40m
Multiple Airlines
Sat 13-621:00
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 3-2S$ 1,532
Thu 8-1007:30
SIN
-
MDW
2 stops27h 15m
Delta
Sun 18-1009:30
MDW
-
SIN
2 stops25h 10m
Delta
Deal found 4-2S$ 1,620
Wed 1-713:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Sun 2-820:40
MDW
-
SIN
2 stops26h 55m
Multiple Airlines
Deal found 3-2S$ 1,739
Sun 22-314:25
SIN
-
MDW
2 stops28h 15m
Multiple Airlines
Sun 29-316:10
MDW
-
SIN
2 stops31h 25m
Multiple Airlines
Deal found 5-2S$ 1,897
Tue 24-214:25
SIN
-
MDW
2 stops36h 15m
Multiple Airlines
Wed 20-511:00
MDW
-
SIN
2 stops36h 35m
Multiple Airlines
Deal found 3-2S$ 1,907
Sat 16-522:30
SIN
-
MDW
2 stops30h 47m
Delta
Wed 17-609:20
MDW
-
SIN
2 stops30h 40m
Delta
Deal found 4-2S$ 1,925
Thu 19-202:00
SIN
-
MDW
2 stops34h 15m
Multiple Airlines
Mon 23-208:10
MDW
-
SIN
2 stops38h 55m
Multiple Airlines
Deal found 6-2S$ 1,964
Sat 21-322:30
SIN
-
MDW
2 stops37h 01m
Delta
Sat 28-314:05
MDW
-
SIN
2 stops44h 35m
Delta
Deal found 4-2S$ 2,116

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 6 February 2026.

Round-trip from

S$ 1,356

One-way from

S$ 744

Popular in

January

Cheapest in

September

Average price

S$ 1,201
7-5-14-5
  • 7-5-14-5
  • 4 total stops
  • 58h 20m total
  • Singapore to Chicago
Search Deals
16-5
  • 16-5
  • 3 total stops
  • 53h 30m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (S$ 70 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (S$ 28 potential savings vs. average return price).
Search Deals
Average for round-trip flights in February 2026
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Cheapflights Fare Finder

 
Customise 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 200,618 searches. Data last updated 6 February 2026.
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

Mon 23-3

14:25-05:40

2 stops28h 15m

Chicago Midway

Mon 30-3

11:50-12:35

2 stops35h 45m

S$ 1,381

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 18-3

14:25-05:40

2 stops28h 15m

Chicago Midway

Tue 31-3

10:55-12:35

2 stops36h 40m

S$ 1,438

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 6-6

15:20-05:00

2 stops26h 40m

Chicago Midway

Sat 13-6

21:00-11:55

2 stops25h 55m

S$ 1,532

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 1-7

13:45-05:40

2 stops28h 55m

Chicago Midway

Sun 2-8

20:40-12:35

2 stops26h 55m

S$ 1,739

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 22-3

14:25-05:40

2 stops28h 15m

Chicago Midway

Sun 29-3

16:10-12:35

2 stops31h 25m

S$ 1,897

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 24-2

14:25-12:40

2 stops36h 15m

Chicago Midway

Wed 20-5

11:00-12:35

2 stops36h 35m

S$ 1,907

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 16-5

22:30-16:17

2 stops30h 47m

Chicago Midway

Wed 17-6

09:20-05:00

2 stops30h 40m

S$ 1,925

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 19-2

02:00-22:15

2 stops34h 15m

Chicago Midway

Mon 23-2

08:10-13:05

2 stops38h 55m

S$ 1,964

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 17-2

22:30-22:31

2 stops38h 01m

Chicago Midway

Fri 20-2

06:00-05:00

2 stops33h 00m

S$ 2,196

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 18-2

14:25-12:30

2 stops36h 05m

Chicago Midway

Sat 21-2

08:05-13:05

2 stops39h 00m

S$ 2,247

Flights are sorted by cheapest return flights first.

Deals found on 5-2

Showing 1-10 of 17 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 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 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 holiday 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.

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Singapore to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Singapore to O'Hare Intl flights
Singapore to Midway flights

Fly with Cheapflights

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

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Why should you use Cheapflights to find cheap flight tickets from Singapore to Midway?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Singapore.

Can Cheapflights find flights from Singapore to Midway with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Singapore to Midway flexibly with Cheapflights today.

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