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Cheap flights from Singapore to Chicago Midway Airport from S$ 983

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 4-9. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
11 Jul — 18 Jul1
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 11 June 2026.

Fri 18-907:30
SIN
-
MDW
2 stops38h 20m
Delta
Sun 20-918:51
MDW
-
SIN
2 stops40h 04m
Delta
Deal found 6-6S$ 1,487
Sat 21-1122:30
SIN
-
MDW
2 stops28h 03m
Delta
Mon 23-1117:35
MDW
-
SIN
2 stops45h 25m
Delta
Deal found 6-6S$ 1,583
Sat 4-715:20
SIN
-
MDW
2 stops26h 40m
Multiple Airlines
Sat 11-721:00
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 6-6S$ 1,685
Tue 16-615:20
SIN
-
MDW
2 stops27h 35m
Multiple Airlines
Sat 27-621:00
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 7-6S$ 1,689
Wed 15-715:20
SIN
-
MDW
2 stops26h 40m
Multiple Airlines
Thu 24-920:55
MDW
-
SIN
2 stops26h 00m
Multiple Airlines
Deal found 7-6S$ 1,702
Sun 7-615:20
SIN
-
MDW
2 stops26h 40m
Multiple Airlines
Sun 9-820:35
MDW
-
SIN
2 stops26h 20m
Multiple Airlines
Deal found 6-6S$ 1,709
Sat 27-607:30
SIN
-
MDW
2 stops27h 47m
Delta
Sun 12-717:10
MDW
-
SIN
2 stops41h 45m
Delta
Deal found 8-6S$ 1,715
Sat 20-615:20
SIN
-
MDW
2 stops27h 35m
Multiple Airlines
Sat 27-621:00
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 10-6S$ 1,717
Sun 21-615:20
SIN
-
MDW
2 stops27h 35m
Multiple Airlines
Sat 27-621:00
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 7-6S$ 1,720
Thu 16-715:20
SIN
-
MDW
2 stops26h 40m
Multiple Airlines
Wed 19-821:00
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 10-6S$ 1,734
Mon 6-701:25
SIN
-
MDW
2 stops33h 50m
Delta
Wed 22-709:54
MDW
-
SIN
2 stops25h 01m
Delta
Deal found 10-6S$ 1,743
Mon 6-713:45
SIN
-
MDW
2 stops34h 20m
Multiple Airlines
Tue 21-715:50
MDW
-
SIN
2 stops31h 45m
Multiple Airlines
Deal found 6-6S$ 1,789

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 11 June 2026.

Round-trip from

S$ 1,487

One-way from

S$ 983

Popular in

August

Cheapest in

February

Average price

S$ 1,604
Delta
  • Delta
  • 18-9-20-9
  • 4 total stops
  • 78h 24m total
  • Singapore to Chicago
Search Deals
4-9
  • 4-9
  • 3 total stops
  • 54h 57m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (S$ 351 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (S$ 139 potential savings vs. average return price).
Search Deals
Average for round-trip flights in June 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 11 June 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

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 18-9

07:30-08:50

2 stops38h 20m

Chicago Midway

Sun 20-9

18:51-23:55

2 stops40h 04m

S$ 1,487

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 27-6

07:30-22:17

2 stops27h 47m

Chicago Midway

Sun 12-7

17:10-23:55

2 stops41h 45m

S$ 1,715

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 21-6

15:20-05:55

2 stops27h 35m

Chicago Midway

Sat 27-6

21:00-11:55

2 stops25h 55m

S$ 1,720
Fastest return journey

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 16-7

15:20-05:00

2 stops26h 40m

Chicago Midway

Wed 19-8

21:00-11:55

2 stops25h 55m

S$ 1,734

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 18-9

01:25-18:33

2 stops30h 08m

Chicago Midway

Mon 21-9

09:49-23:55

2 stops25h 06m

S$ 1,887

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 10-9

07:30-12:30

2 stops42h 00m

Chicago Midway

Mon 14-9

09:30-05:00

2 stops30h 30m

S$ 2,236

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 1-7

13:45-05:55

2 stops29h 10m

Chicago Midway

Wed 22-7

13:10-12:35

3 stops34h 25m

S$ 2,299

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 19-8

15:20-05:50

2 stops27h 30m

Chicago Midway

Fri 18-12

18:05-12:05

2 stops28h 00m

S$ 2,506
Cheapest one-way
Fastest single journey

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 18-6

15:20-05:00

2 stops26h 40m

S$ 1,009

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 31-8

13:45-16:35

2 stops39h 50m

S$ 1,010

Flights are sorted by cheapest return flights first.

Deals found on 9-6

Showing 1-10 of 17 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 38h 20m. 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

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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