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Cheap flights from Singapore to Chicago Midway Airport from S$ 826

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
11 Sep — 18 Sep1
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 12 August 2026.

Mon 21-922:00 -
2 stops33h 33m
Mon 28-909:59 -
2 stops24h 56m
Deal found 7-8S$ 1,436
Wed 9-907:30 -
2 stops28h 14m
Thu 24-909:29 -
2 stops30h 31m
Deal found 11-8S$ 1,439
Wed 23-922:00 -
2 stops37h 44m
Wed 30-909:29 -
2 stops44h 46m
Deal found 9-8S$ 1,442
Thu 10-907:30 -
2 stops28h 14m
Thu 24-909:59 -
2 stops30h 01m
Deal found 7-8S$ 1,532
Thu 10-907:30 -
2 stops28h 14m
Fri 25-909:29 -
2 stops25h 26m
Deal found 11-8S$ 1,535
Sun 11-1001:25 -
2 stops27h 54m
Wed 28-1006:04 -
2 stops29h 06m
Deal found 12-8S$ 1,578
Wed 9-901:25 -
2 stops34h 19m
Thu 17-906:05 -
2 stops28h 50m
Deal found 10-8S$ 1,581
Sat 12-913:55 -
2 stops28h 10m
Sun 27-920:35 -
2 stops27h 00m
Deal found 11-8S$ 1,582
Tue 25-802:00 -
2 stops34h 20m
Sat 29-820:45 -
2 stops26h 50m
Deal found 12-8S$ 1,596
Sat 26-913:55 -
2 stops34h 35m
Sat 3-1019:45 -
2 stops27h 50m
Deal found 11-8S$ 1,600
Sat 22-802:00 -
2 stops35h 25m
Wed 26-817:15 -
2 stops30h 20m
Deal found 9-8S$ 1,709

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 12 August 2026.

Round-trip from

S$ 1,436

One-way from

S$ 826

Popular in

August

Cheapest in

September

Average price

S$ 2,627
Delta
  • Delta
  • 21-9-28-9
  • 4 total stops
  • 58h 29m total
  • Singapore to Chicago
Search Deals
15-10
  • 15-10
  • 2 total stops
  • 38h 53m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (S$ 302 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (S$ 143 potential savings vs. average return price).
Search Deals
Average for round-trip flights in August 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 12 August 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 Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Mon 21-9

22:00-18:33

2 stops33h 33m

Chicago Midway

Mon 28-9

09:59-23:55

2 stops24h 56m

S$ 1,436
Fastest return journey

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Thu 17-9

07:30-22:45

2 stops28h 15m

Chicago Midway

Mon 28-9

09:59-23:55

2 stops24h 56m

S$ 1,439

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sun 20-9

22:00-18:33

2 stops33h 33m

Chicago Midway

Thu 24-9

09:59-05:00

2 stops30h 01m

S$ 1,439

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Wed 9-9

07:30-22:44

2 stops28h 14m

Chicago Midway

Thu 24-9

09:29-05:00

2 stops30h 31m

S$ 1,439

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 3-11

22:30-12:47

2 stops28h 17m

Chicago Midway

Tue 17-11

18:44-00:10

2 stops39h 26m

S$ 1,442

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 22-9

01:25-18:33

2 stops30h 08m

Chicago Midway

Wed 30-9

09:29-23:55

2 stops25h 26m

S$ 1,442

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Wed 11-11

10:40-22:56

2 stops26h 16m

Chicago Midway

Tue 17-11

18:44-00:10

2 stops39h 26m

S$ 1,442

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Thu 10-9

07:30-22:44

2 stops28h 14m

Chicago Midway

Thu 24-9

09:59-05:00

2 stops30h 01m

S$ 1,442

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Thu 10-9

07:30-22:44

2 stops28h 14m

Chicago Midway

Fri 25-9

09:29-23:55

2 stops25h 26m

S$ 1,535

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Wed 23-12

10:40-09:52

2 stops37h 12m

Chicago Midway

Tue 29-12

06:00-05:00

2 stops33h 00m

S$ 1,581

Flights are sorted by cheapest return flights first.

Deals found on 10-8

Showing 1-10 of 16 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 33h 33m. 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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