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Cheap flights from Singapore to Chicago Midway Airport from S$ 839

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 7-10. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
11 Aug — 18 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 12 July 2026.

Wed 23-922:00
SIN
-
MDW
2 stops37h 45m
Delta
Mon 28-917:11
MDW
-
SIN
2 stops37h 04m
Delta
Deal found 9-7S$ 1,485
Sun 23-813:45
SIN
-
MDW
2 stops29h 00m
Multiple Airlines
Mon 31-815:55
MDW
-
SIN
2 stops31h 40m
Multiple Airlines
Deal found 9-7S$ 1,589
Thu 27-813:45
SIN
-
MDW
2 stops29h 00m
Multiple Airlines
Sun 30-820:45
MDW
-
SIN
2 stops38h 50m
Multiple Airlines
Deal found 12-7S$ 1,591
Wed 26-801:25
SIN
-
MDW
2 stops27h 50m
Delta
Sun 30-809:59
MDW
-
SIN
2 stops24h 56m
Delta
Deal found 9-7S$ 1,625
Mon 24-813:45
SIN
-
MDW
2 stops43h 15m
Multiple Airlines
Mon 31-821:20
MDW
-
SIN
2 stops38h 15m
Multiple Airlines
Deal found 10-7S$ 1,629
Sat 22-813:45
SIN
-
MDW
2 stops34h 25m
Multiple Airlines
Sat 29-820:45
MDW
-
SIN
2 stops26h 50m
Multiple Airlines
Deal found 8-7S$ 1,633
Thu 20-802:00
SIN
-
MDW
2 stops40h 45m
Multiple Airlines
Fri 28-814:00
MDW
-
SIN
2 stops33h 35m
Multiple Airlines
Deal found 7-7S$ 1,636
Thu 20-813:45
SIN
-
MDW
2 stops29h 00m
Multiple Airlines
Thu 27-820:45
MDW
-
SIN
2 stops26h 50m
Multiple Airlines
Deal found 9-7S$ 1,640
Sat 22-813:45
SIN
-
MDW
2 stops29h 00m
Multiple Airlines
Sun 6-920:30
MDW
-
SIN
2 stops27h 05m
Multiple Airlines
Deal found 10-7S$ 1,655
Sun 23-815:20
SIN
-
MDW
2 stops26h 45m
Multiple Airlines
Sun 30-820:35
MDW
-
SIN
2 stops26h 20m
Multiple Airlines
Deal found 9-7S$ 1,686

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 July 2026.

Round-trip from

S$ 1,485

One-way from

S$ 839

Popular in

August

Cheapest in

September

Average price

S$ 1,508
Delta
  • Delta
  • 23-9-28-9
  • 4 total stops
  • 74h 49m total
  • Singapore to Chicago
Search Deals
7-10
  • 7-10
  • 2 total stops
  • 27h 13m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (S$ 225 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (S$ 140 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 2026
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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 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

Wed 23-9

22:00-22:45

2 stops37h 45m

Chicago Midway

Mon 28-9

17:11-19:15

2 stops37h 04m

S$ 1,485

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 24-9

07:30-13:20

2 stops42h 50m

Chicago Midway

Sun 27-9

09:59-19:15

2 stops44h 16m

S$ 1,485

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 23-8

13:45-05:45

2 stops29h 00m

Chicago Midway

Sun 30-8

20:45-00:35

2 stops38h 50m

S$ 1,589

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 27-8

13:45-05:45

2 stops29h 00m

Chicago Midway

Sun 30-8

20:45-00:35

2 stops38h 50m

S$ 1,593

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 24-8

13:45-20:00

2 stops43h 15m

Chicago Midway

Mon 31-8

13:50-12:35

3 stops33h 45m

S$ 1,629
Fastest return journey

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 22-8

13:45-11:10

2 stops34h 25m

Chicago Midway

Sat 29-8

20:45-12:35

2 stops26h 50m

S$ 1,633

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 23-9

02:00-05:45

2 stops40h 45m

Chicago Midway

Sun 27-9

12:35-12:35

3 stops35h 00m

S$ 1,633

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 20-8

02:00-05:45

2 stops40h 45m

Chicago Midway

Fri 28-8

14:00-12:35

2 stops33h 35m

S$ 1,636
Cheapest one-way

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 25-9

09:05-12:07

2 stops40h 02m

S$ 860

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 8-9

01:25-22:45

2 stops34h 20m

S$ 933

Flights are sorted by cheapest return flights first.

Deals found on 11-7

Showing 1-10 of 18 resultsSorted by cheapest first
1
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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.

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 45m. 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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