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Cheap flights from Singapore to Chicago Midway Airport from S$ 826

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 14-5. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
3 May — 10 May1
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 3 April 2026.

Thu 20-813:45
SIN
-
MDW
2 stops29h 00m
Multiple Airlines
Thu 27-817:55
MDW
-
SIN
2 stops29h 40m
Multiple Airlines
Deal found 29-3S$ 1,436
Sun 7-613:45
SIN
-
MDW
2 stops29h 10m
Multiple Airlines
Sun 9-820:35
MDW
-
SIN
2 stops27h 00m
Multiple Airlines
Deal found 31-3S$ 1,533
Sun 7-622:00
SIN
-
MDW
2 stops31h 16m
Delta
Sun 9-806:05
MDW
-
SIN
2 stops33h 55m
Delta
Deal found 1-4S$ 1,544
Mon 18-513:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Mon 25-511:00
MDW
-
SIN
2 stops36h 35m
Multiple Airlines
Deal found 31-3S$ 1,616
Thu 14-513:45
SIN
-
MDW
2 stops29h 05m
Multiple Airlines
Thu 21-518:10
MDW
-
SIN
2 stops29h 25m
Multiple Airlines
Deal found 30-3S$ 1,644
Sat 16-513:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Sat 23-518:10
MDW
-
SIN
2 stops29h 25m
Multiple Airlines
Deal found 1-4S$ 1,694
Fri 15-513:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Fri 22-510:10
MDW
-
SIN
2 stops37h 25m
Multiple Airlines
Deal found 30-3S$ 1,894
Sun 14-601:25
SIN
-
MDW
2 stops33h 52m
Delta
Wed 8-717:10
MDW
-
SIN
2 stops37h 05m
Delta
Deal found 28-3S$ 1,955

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 3 April 2026.

Round-trip from

S$ 1,436

One-way from

S$ 826

Popular in

January

Cheapest in

February

Average price

S$ 1,222
20-8-27-8
  • 20-8-27-8
  • 4 total stops
  • 58h 40m total
  • Singapore to Chicago
Search Deals
Delta
  • Delta
  • 14-5
  • 2 total stops
  • 26h 56m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (S$ 41 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 57 potential savings vs. average return price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 3 April 2026.
Use the filters below to find and compare flights from Singapore to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 7-6

13:45-05:55

2 stops29h 10m

Chicago Midway

Sun 9-8

20:35-12:35

2 stops27h 00m

S$ 1,533

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 7-6

22:00-16:16

2 stops31h 16m

Chicago Midway

Sun 9-8

06:05-05:00

2 stops33h 55m

S$ 1,544

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 16-5

13:45-05:40

2 stops28h 55m

Chicago Midway

Sat 23-5

18:10-12:35

2 stops29h 25m

S$ 1,694

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 15-5

13:45-05:40

2 stops28h 55m

Chicago Midway

Fri 22-5

10:10-12:35

2 stops37h 25m

S$ 1,894

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 13-5

22:00-11:56

2 stops26h 56m

Chicago Midway

Wed 20-5

06:23-05:00

2 stops33h 37m

S$ 2,052

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 14-4

02:00-23:20

2 stops34h 20m

Chicago Midway

Sat 18-4

18:10-12:35

2 stops29h 25m

S$ 2,352

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 18-4

13:45-05:50

2 stops29h 05m

Chicago Midway

Sat 25-4

15:20-12:35

2 stops32h 15m

S$ 2,533
Cheapest one-way

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 14-5

22:00-11:56

2 stops26h 56m

S$ 826

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 20-5

22:00-11:56

2 stops26h 56m

S$ 828

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 28-8

02:00-05:45

2 stops40h 45m

S$ 869

Flights are sorted by cheapest return flights first.

Deals found on 30-3

Showing 1-10 of 18 resultsSorted by cheapest first
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 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.

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

    There are many flights that can get you from Singapore to Chicago Midway Airport in 31h 16m. Fly via Delta to get the fastest option. There are 15063 km 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 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.

See more FAQs

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?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Singapore to Midway. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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.

Can Cheapflights notify me if prices for flights from Singapore to Midway become cheaper?

Of course! You can now track prices for flights from Singapore to Midway 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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