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Cheap flights from Singapore to Chicago Midway Airport from S$ 958

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 31-8. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
24 Aug — 31 Aug1
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 25 July 2026.

Tue 22-901:25
SIN
-
MDW
2 stops34h 19m
Delta
Sun 27-909:29
MDW
-
SIN
2 stops25h 26m
Delta
Deal found 20-7S$ 1,438
Wed 23-901:25
SIN
-
MDW
2 stops34h 19m
Delta
Sun 27-909:59
MDW
-
SIN
2 stops30h 01m
Delta
Deal found 23-7S$ 1,439
Mon 7-922:00
SIN
-
MDW
2 stops31h 57m
Delta
Mon 14-909:59
MDW
-
SIN
2 stops24h 56m
Delta
Deal found 24-7S$ 1,532
Tue 22-902:00
SIN
-
MDW
2 stops34h 20m
Multiple Airlines
Sun 27-920:35
MDW
-
SIN
2 stops27h 00m
Multiple Airlines
Deal found 20-7S$ 1,576
Thu 10-922:00
SIN
-
MDW
2 stops30h 24m
Delta
Thu 24-906:05
MDW
-
SIN
2 stops28h 50m
Delta
Deal found 21-7S$ 1,579
Thu 10-913:55
SIN
-
MDW
2 stops34h 20m
Multiple Airlines
Thu 24-915:55
MDW
-
SIN
2 stops31h 40m
Multiple Airlines
Deal found 22-7S$ 1,581
Thu 1-1002:00
SIN
-
MDW
2 stops35h 10m
Multiple Airlines
Sat 10-1019:05
MDW
-
SIN
2 stops28h 30m
Multiple Airlines
Deal found 22-7S$ 1,588
Tue 18-813:55
SIN
-
MDW
2 stops28h 50m
Multiple Airlines
Tue 25-821:00
MDW
-
SIN
2 stops26h 35m
Multiple Airlines
Deal found 22-7S$ 1,612
Tue 18-815:20
SIN
-
MDW
2 stops26h 45m
Multiple Airlines
Sun 23-820:35
MDW
-
SIN
2 stops26h 20m
Multiple Airlines
Deal found 20-7S$ 1,685
Fri 21-815:20
SIN
-
MDW
2 stops27h 30m
Multiple Airlines
Fri 28-821:20
MDW
-
SIN
2 stops25h 35m
Multiple Airlines
Deal found 23-7S$ 1,690

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 25 July 2026.

Round-trip from

S$ 1,438

One-way from

S$ 958

Popular in

August

Cheapest in

September

Average price

S$ 1,508
Delta
  • Delta
  • 22-9-27-9
  • 4 total stops
  • 59h 45m total
  • Singapore to Chicago
Search Deals
31-8
  • 31-8
  • 2 total stops
  • 47h 00m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (S$ 212 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (S$ 138 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 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 25 July 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

Tue 22-9

01:25-22:44

2 stops34h 19m

Chicago Midway

Sun 27-9

09:29-23:55

2 stops25h 26m

S$ 1,438

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 23-9

01:25-22:44

2 stops34h 19m

Chicago Midway

Sun 27-9

09:59-05:00

2 stops30h 01m

S$ 1,439

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 7-9

22:00-16:57

2 stops31h 57m

Chicago Midway

Mon 14-9

09:59-23:55

2 stops24h 56m

S$ 1,532

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 22-9

02:00-23:20

2 stops34h 20m

Chicago Midway

Sun 27-9

20:35-12:35

2 stops27h 00m

S$ 1,576

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 10-9

22:00-15:24

2 stops30h 24m

Chicago Midway

Thu 24-9

06:05-23:55

2 stops28h 50m

S$ 1,579

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 12-9

07:30-22:44

2 stops28h 14m

Chicago Midway

Fri 18-9

06:05-05:00

2 stops33h 55m

S$ 1,579

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 10-9

13:55-11:15

2 stops34h 20m

Chicago Midway

Thu 24-9

15:55-12:35

2 stops31h 40m

S$ 1,581

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 1-10

02:00-00:10

2 stops35h 10m

Chicago Midway

Sat 10-10

19:05-12:35

2 stops28h 30m

S$ 1,588
Fastest return journey

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 18-8

13:55-05:45

2 stops28h 50m

Chicago Midway

Tue 25-8

21:00-12:35

2 stops26h 35m

S$ 1,612

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 9-8

13:55-11:15

2 stops34h 20m

Chicago Midway

Sat 15-8

18:00-12:35

2 stops29h 35m

S$ 1,917

Flights are sorted by cheapest return flights first.

Deals found on 22-7

Showing 1-10 of 18 resultsSorted by cheapest first
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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.

  • 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 34h 19m. 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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