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Cheap flights from Singapore to Chicago Midway Airport from S$ 738

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 8-5. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
1 Apr — 8 Apr1
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 2 March 2026.

Wed 15-422:00
SIN
-
MDW
2 stops27h 07m
Delta
Wed 22-409:29
MDW
-
SIN
2 stops25h 26m
Delta
Deal found 1-3S$ 1,364
Thu 16-413:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Thu 23-418:10
MDW
-
SIN
2 stops29h 25m
Multiple Airlines
Deal found 1-3S$ 1,430
Tue 14-413:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Thu 16-411:00
MDW
-
SIN
2 stops36h 35m
Multiple Airlines
Deal found 27-2S$ 1,462
Fri 6-314:25
SIN
-
MDW
2 stops29h 30m
Multiple Airlines
Sun 22-310:45
MDW
-
SIN
2 stops37h 20m
Multiple Airlines
Deal found 28-2S$ 1,485
Mon 9-314:25
SIN
-
MDW
2 stops34h 15m
Multiple Airlines
Sun 22-310:45
MDW
-
SIN
2 stops37h 20m
Multiple Airlines
Deal found 1-3S$ 1,488
Mon 30-322:00
SIN
-
MDW
2 stops37h 31m
Delta
Mon 6-409:30
MDW
-
SIN
2 stops30h 30m
Delta
Deal found 2-3S$ 1,623
Tue 10-322:30
SIN
-
MDW
2 stops37h 01m
Delta
Tue 17-306:00
MDW
-
SIN
2 stops34h 00m
Delta
Deal found 27-2S$ 1,762
Sun 8-314:25
SIN
-
MDW
2 stops28h 30m
Multiple Airlines
Sat 14-318:20
MDW
-
SIN
2 stops29h 45m
Multiple Airlines
Deal found 27-2S$ 2,137

Find flight deals from Singapore to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Singapore (SIN) to Midway (MDW). 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 2 March 2026.

Round-trip from

S$ 1,364

One-way from

S$ 738

Popular in

January

Cheapest in

February

Average price

S$ 1,360
Delta
  • Delta
  • 20-4-26-4
  • 4 total stops
  • 58h 34m total
  • Singapore to Chicago
Search Deals
8-5
  • 8-5
  • 3 total stops
  • 53h 39m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (S$ 58 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 55 potential savings vs. average return price).
Search Deals
Average for round-trip flights in March 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 2 March 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

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 20-4

01:25-16:26

2 stops28h 01m

Chicago Midway

Sun 26-4

09:27-05:00

2 stops30h 33m

S$ 1,364

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 16-4

13:45-05:40

2 stops28h 55m

Chicago Midway

Thu 23-4

18:10-12:35

2 stops29h 25m

S$ 1,430

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 14-4

13:45-05:40

2 stops28h 55m

Chicago Midway

Thu 16-4

11:00-12:35

2 stops36h 35m

S$ 1,462

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 1-4

01:25-12:29

2 stops24h 04m

Chicago Midway

Mon 6-4

09:30-05:00

2 stops30h 30m

S$ 2,389

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 13-5

22:00-11:56

2 stops26h 56m

Chicago Midway

Wed 28-10

06:00-05:00

2 stops34h 00m

S$ 5,660

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 11-5

13:45-12:00

2 stops35h 15m

Chicago Midway

Fri 22-5

18:10-12:35

2 stops29h 25m

S$ 6,287

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 1-7

13:45-05:40

2 stops28h 55m

Chicago Midway

Sat 11-7

20:35-12:35

2 stops27h 00m

S$ 6,289

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 26-4

13:45-05:40

2 stops28h 55m

Chicago Midway

Thu 7-5

18:10-12:35

2 stops29h 25m

S$ 6,289

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 18-4

07:30-22:28

2 stops27h 58m

S$ 756

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 8-5

07:30-21:09

2 stops26h 39m

S$ 756

Flights are sorted by cheapest return flights first.

Deals found on 28-2

Showing 1-10 of 19 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.

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.

  • What airport do you fly from for flights from Singapore to Chicago Midway?

    Singapore Changi (SIN) is the airport you will fly out of if you book a flight from Singapore to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Changi; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Singapore airport to Chicago Midway. It is only a 16.9 km journey to Changi (SIN) from Singapore’s city centre.

  • 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 24h 04m. Fly via Delta or Korean Air to get the fastest option. There are 15063 km between Singapore and Chicago Midway Airport. Both multi-stop and direct flights can be found to your destination and back.

  • 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

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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

Cheapflights makes it easy to find Singapore to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Singapore to Midway, users can toggle the no change fees filter when performing a flight search.

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

Not ready to book yet? You can track prices for flights from Singapore to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.

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