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Cheap flights from Singapore to Chicago Midway Airport from S$ 747

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 15-10. 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

Cheap 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 19 August 2025.

Round-trip from

S$ 1,252

One-way from

S$ 747

Popular in

January

Cheapest in

October

Average price

S$ 1,599
Delta
  • Delta
  • 9-9-14-9
  • 4 total stops
  • 69h 10m total
  • Singapore to Chicago
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15-10
  • 15-10
  • 3 total stops
  • 52h 21m total
  • Singapore to Chicago
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Highest demand for flights based on searches. 9% potential increase in price (S$ 184 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (S$ 51 potential savings vs. average return price).
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Average for round-trip flights in August 2025
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Find flight deals from Singapore to Midway

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 19 August 2025.

Tue 9-922:30SIN - MDW
2 stops26h 58mDelta
Sun 14-912:43MDW - SIN
2 stops42h 12mDelta
Deal found 17-8S$ 1,252
Tue 9-901:10SIN - MDW
2 stops24h 18mDelta
Thu 25-909:35MDW - SIN
2 stops25h 05mDelta
Deal found 17-8S$ 1,396
Thu 30-1001:30SIN - MDW
2 stops33h 44mDelta
Sat 8-1118:23MDW - SIN
2 stops39h 47mDelta
Deal found 18-8S$ 1,536
Sun 5-1022:30SIN - MDW
2 stops30h 39mDelta
Sun 19-1009:35MDW - SIN
2 stops30h 25mDelta
Deal found 19-8S$ 1,989
Sun 14-922:30SIN - MDW
2 stops32h 05mDelta
Sun 28-918:15MDW - SIN
2 stops40h 25mDelta
Deal found 17-8S$ 1,992
Wed 1-1001:10SIN - MDW
2 stops30h 25mDelta
Thu 9-1006:00MDW - SIN
2 stops34h 00mDelta
Deal found 18-8S$ 2,165
Mon 15-922:30SIN - MDW
2 stops26h 58mDelta
Tue 30-909:35MDW - SIN
2 stops25h 05mDelta
Deal found 19-8S$ 2,225
Fri 12-922:30SIN - MDW
2 stops35h 40mDelta
Sat 27-906:00MDW - SIN
2 stops34h 00mDelta
Deal found 17-8S$ 2,365
Sat 4-1001:10SIN - MDW
2 stops24h 18mMultiple Airlines
Sun 19-1009:35MDW - SIN
2 stops25h 05mMultiple Airlines
Deal found 19-8S$ 2,477
Sat 13-922:30SIN - MDW
2 stops32h 05mDelta
Sat 27-906:00MDW - SIN
2 stops34h 00mDelta
Deal found 17-8S$ 2,515
Sat 27-901:10SIN - MDW
2 stops24h 18mMultiple Airlines
Sat 30-509:30MDW - SIN
2 stops25h 10mMultiple Airlines
Deal found 19-8S$ 2,623

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 19 August 2025.
Use the filters below to find and compare flights from Singapore to Chicago Midway Airport that are best for you.

Fly from

Singapore

Fly to

Midway

Route

Depart

Return

Price

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 15-9

22:30-12:28

2 stops26h 58m

Chicago Midway

Fri 26-9

09:35-05:00

2 stops30h 25m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 16-9

01:10-12:28

2 stops24h 18m

Chicago Midway

Sun 28-9

18:30-23:40

2 stops40h 10m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 16-9

22:30-18:35

2 stops33h 05m

Chicago Midway

Fri 26-9

09:35-05:00

2 stops30h 25m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 15-9

01:10-12:28

2 stops24h 18m

Chicago Midway

Sun 28-9

18:30-23:40

2 stops40h 10m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 9-9

22:30-12:28

2 stops26h 58m

Chicago Midway

Sun 14-9

12:43-19:55

2 stops42h 12m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 17-9

07:30-21:36

2 stops27h 06m

Chicago Midway

Fri 26-9

09:35-05:00

2 stops30h 25m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 9-9

01:10-12:28

2 stops24h 18m

Chicago Midway

Mon 29-9

09:35-05:00

2 stops30h 25m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 15-9

01:10-12:28

2 stops24h 18m

Chicago Midway

Mon 29-9

09:20-23:40

2 stops25h 20m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 11-9

07:30-21:36

2 stops27h 06m

Chicago Midway

Mon 29-9

09:20-23:40

2 stops25h 20m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 10-9

01:10-12:28

2 stops24h 18m

Chicago Midway

Fri 26-9

09:35-05:00

2 stops30h 25m

S$ 1,252

Flights are sorted by cheapest return flights first.

Deals found on 18-8

Showing 1-10 of 19 results
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 26h 58m. 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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