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Cheap flights from Singapore to Chicago Midway Airport from S$ 1,302

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 30-12. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
14 Dec — 21 Dec1
1 adult
1 adult, Economy, 0 bags

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 14 November 2025.

Round-trip from

S$ 1,411

One-way from

S$ 1,302

Popular in

January

Cheapest in

October

Average price

S$ 1,255
Delta
  • Delta
  • 15-4-20-4
  • 4 total stops
  • 90h 03m total
  • Singapore to Chicago
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30-12
  • 30-12
  • 3 total stops
  • 46h 06m total
  • Singapore to Chicago
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Highest demand for flights based on searches. 13% potential increase in price (S$ 286 potential increase over avg. return price).
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Cheapest flight prices on average. 3% potential price decrease (S$ 70 potential savings vs. average return price).
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Average for round-trip flights in November 2025
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Find 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 14 November 2025.

Tue 30-1210:40SIN - MDW
2 stops38h 26mDelta
Fri 16-117:31MDW - SIN
2 stops40h 39mDelta
Deal found 13-11S$ 2,341
Sat 27-1215:45SIN - MDW
2 stops27h 30mMultiple Airlines
Sat 3-119:00MDW - SIN
2 stops27h 05mMultiple Airlines
Deal found 12-11S$ 2,479
Mon 22-1201:40SIN - MDW
2 stops28h 40mMultiple Airlines
Tue 30-1218:08MDW - SIN
2 stops32h 47mMultiple Airlines
Deal found 13-11S$ 2,796
Tue 23-1222:30SIN - MDW
2 stops37h 52mDelta
Tue 30-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 13-11S$ 2,878
Sat 27-1222:30SIN - MDW
2 stops31h 50mDelta
Sat 3-106:00MDW - SIN
2 stops33h 00mDelta
Deal found 12-11S$ 3,198
Wed 31-1201:35SIN - MDW
2 stops34h 47mDelta
Thu 15-118:14MDW - SIN
2 stops39h 56mDelta
Deal found 13-11S$ 9,935
Sun 16-1115:45SIN - MDW
2 stops27h 30mMultiple Airlines
Sat 22-1119:00MDW - SIN
2 stops27h 05mMultiple Airlines
Deal found 12-11S$ 10,290
Wed 31-1222:30SIN - MDW
2 stops30h 14mDelta
Wed 14-119:16MDW - SIN
2 stops38h 54mDelta
Deal found 13-11S$ 10,733
Wed 17-1201:35SIN - MDW
2 stops36h 12mDelta
Sat 3-106:00MDW - SIN
2 stops33h 00mDelta
Deal found 13-11S$ 12,381

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 14 November 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

Wed 15-4

01:10-08:38

2 stops44h 28m

Chicago Midway

Mon 20-4

09:20-19:55

2 stops45h 35m

S$ 1,411

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 10-2

10:40-12:48

2 stops40h 08m

Chicago Midway

Fri 20-2

06:00-05:00

2 stops33h 00m

S$ 1,769

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 30-12

10:40-11:06

2 stops38h 26m

Chicago Midway

Thu 15-1

13:28-00:10

2 stops44h 42m

S$ 2,341

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 30-12

10:40-11:06

2 stops38h 26m

Chicago Midway

Fri 16-1

17:31-00:10

2 stops40h 39m

S$ 2,341

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 27-12

15:45-05:15

2 stops27h 30m

Chicago Midway

Sat 3-1

19:00-12:05

2 stops27h 05m

S$ 2,479

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 30-12

05:15-13:21

3 stops46h 06m

S$ 1,302

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 25-11

10:40-12:34

2 stops39h 54m

S$ 1,553

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 10-1

22:30-22:09

2 stops37h 39m

S$ 1,765

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 28-11

15:45-05:15

2 stops27h 30m

S$ 1,994

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 27-11

12:55-09:52

3 stops58h 57m

S$ 2,197

Flights are sorted by cheapest return flights first.

Deals found on 11-11

Showing 1-10 of 12 results
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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 44h 28m. 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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