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Cheap flights from Singapore to Chicago Midway Airport from S$ 705

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 23-10. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
17 Oct — 24 Oct1
1 adult
1 adult, Economy

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 17 September 2025.

Round-trip from

S$ 1,248

One-way from

S$ 705

Popular in

January

Cheapest in

October

Average price

S$ 1,243
Delta
  • Delta
  • 5-10-19-10
  • 4 total stops
  • 67h 24m total
  • Singapore to Chicago
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23-10
  • 23-10
  • 3 total stops
  • 45h 05m total
  • Singapore to Chicago
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Highest demand for flights based on searches. 9% potential increase in price (S$ 186 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (S$ 48 potential savings vs. average return price).
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Average for round-trip flights in September 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 17 September 2025.

Sun 5-1022:30SIN - MDW
2 stops36h 44mDelta
Sun 19-1009:20MDW - SIN
2 stops30h 40mDelta
Deal found 15-9S$ 1,248
Sun 28-922:30SIN - MDW
2 stops32h 05mDelta
Sun 19-1006:00MDW - SIN
2 stops34h 00mDelta
Deal found 15-9S$ 1,387
Fri 24-1001:10SIN - MDW
2 stops34h 04mDelta
Thu 30-1009:35MDW - SIN
2 stops25h 35mDelta
Deal found 16-9S$ 1,395
Tue 11-1101:35SIN - MDW
2 stops24h 17mDelta
Wed 19-1106:00MDW - SIN
2 stops33h 00mDelta
Deal found 15-9S$ 1,531
Thu 30-1001:35SIN - MDW
2 stops26h 51mDelta
Fri 7-1106:00MDW - SIN
2 stops33h 00mDelta
Deal found 15-9S$ 1,672
Sat 18-1001:10SIN - MDW
2 stops34h 04mDelta
Mon 27-1018:23MDW - SIN
2 stops40h 47mDelta
Deal found 16-9S$ 1,703
Sun 28-901:10SIN - MDW
2 stops24h 18mKorean Air
Mon 6-1009:35MDW - SIN
2 stops30h 25mKorean Air
Deal found 15-9S$ 2,231
Fri 31-1013:15SIN - MDW
2 stops28h 45mMultiple Airlines
Fri 7-1117:25MDW - SIN
2 stops28h 40mMultiple Airlines
Deal found 15-9S$ 2,275
Sat 4-1001:10SIN - MDW
2 stops24h 18mMultiple Airlines
Sun 19-1009:35MDW - SIN
2 stops25h 05mMultiple Airlines
Deal found 15-9S$ 2,441

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 17 September 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

Tue 10-2

10:40-09:56

2 stops37h 16m

Chicago Midway

Fri 20-2

17:59-00:10

2 stops40h 11m

S$ 1,248

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 5-10

22:30-22:14

2 stops36h 44m

Chicago Midway

Sun 19-10

09:20-05:00

2 stops30h 40m

S$ 1,248

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 12-11

10:40-09:01

2 stops36h 21m

Chicago Midway

Wed 19-11

06:00-05:00

2 stops33h 00m

S$ 1,387

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 24-10

01:10-22:14

2 stops34h 04m

Chicago Midway

Thu 30-10

09:35-00:10

2 stops25h 35m

S$ 1,395

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 23-10

15:15-23:20

3 stops45h 05m

S$ 705

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 6-10

03:40-13:38

3 stops46h 58m

S$ 732

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 29-10

09:15-16:53

2 stops44h 38m

S$ 779

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 31-10

09:15-14:57

2 stops42h 42m

S$ 801

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 10-10

20:05-11:39

3 stops52h 34m

S$ 806

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 1-11

01:25-13:37

3 stops49h 12m

S$ 809

Flights are sorted by cheapest return flights first.

Deals found on 15-9

Showing 1-10 of 13 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 37h 16m. 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

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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