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Cheap flights from Singapore to Chicago Midway Airport from S$ 755

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 17-3. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
4 Apr — 11 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 5 March 2026.

Wed 21-1022:00
SIN
-
MDW
2 stops27h 33m
Delta
Sun 8-1117:59
MDW
-
SIN
2 stops40h 11m
Delta
Deal found 4-3S$ 1,224
Wed 15-422:00
SIN
-
MDW
2 stops27h 07m
Delta
Wed 22-409:29
MDW
-
SIN
2 stops25h 26m
Delta
Deal found 1-3S$ 1,377
Fri 17-413:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Fri 24-411:00
MDW
-
SIN
2 stops36h 35m
Multiple Airlines
Deal found 3-3S$ 1,381
Wed 15-413:45
SIN
-
MDW
2 stops34h 20m
Multiple Airlines
Wed 22-411:00
MDW
-
SIN
2 stops36h 35m
Multiple Airlines
Deal found 3-3S$ 1,401
Wed 1-713:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Mon 31-817:55
MDW
-
SIN
2 stops29h 40m
Multiple Airlines
Deal found 3-3S$ 1,437
Wed 15-413:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Thu 30-418:10
MDW
-
SIN
2 stops29h 25m
Multiple Airlines
Deal found 4-3S$ 1,443
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$ 1,499
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$ 1,502
Tue 10-314:25
SIN
-
MDW
2 stops28h 15m
Multiple Airlines
Wed 29-411:00
MDW
-
SIN
2 stops36h 35m
Multiple Airlines
Deal found 2-3S$ 1,516
Tue 14-422:00
SIN
-
MDW
2 stops31h 29m
Delta
Tue 21-406:00
MDW
-
SIN
2 stops28h 55m
Delta
Deal found 4-3S$ 1,559

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 5 March 2026.

Round-trip from

S$ 1,377

One-way from

S$ 755

Popular in

January

Cheapest in

February

Average price

S$ 1,373
Delta
  • Delta
  • 15-4-22-4
  • 4 total stops
  • 52h 33m total
  • Singapore to Chicago
Search Deals
17-3
  • 17-3
  • 3 total stops
  • 53h 39m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (S$ 60 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 56 potential savings vs. average return price).
Search Deals
Average for round-trip flights in March 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 5 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

Fri 17-4

13:45-05:40

2 stops28h 55m

Chicago Midway

Fri 24-4

11:00-12:35

2 stops36h 35m

S$ 1,381

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$ 1,443

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 15-4

13:45-05:40

2 stops28h 55m

Chicago Midway

Thu 30-4

18:10-12:35

2 stops29h 25m

S$ 1,443

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$ 1,516

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 4-5

07:30-22:28

2 stops27h 58m

Chicago Midway

Sun 10-5

09:23-05:00

2 stops30h 37m

S$ 1,623

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 17-4

01:25-22:28

2 stops34h 03m

Chicago Midway

Sat 25-4

09:46-05:00

2 stops30h 14m

S$ 1,693

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 19-4

22:00-17:58

2 stops32h 58m

Chicago Midway

Sun 26-4

17:21-19:15

2 stops36h 54m

S$ 1,693

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 29-3

01:25-17:22

2 stops28h 57m

Chicago Midway

Wed 10-6

06:00-23:55

2 stops28h 55m

S$ 2,192

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$ 2,412

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 18-4

07:30-22:28

2 stops27h 58m

S$ 763

Flights are sorted by cheapest return flights first.

Deals found on 28-2

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.

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.

  • 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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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