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Cheap flights from Singapore to Chicago Midway Airport from S$ 734

SIN — MDW
19 Sep — 26 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

Tue 29-922:00 -
2 stops33h 33m
Tue 6-1010:01 -
2 stops29h 59m
Deal found 15-8S$ 1,434
Mon 14-922:00 -
2 stops27h 39m
Tue 29-917:11 -
2 stops37h 04m
Deal found 16-8S$ 1,435
Tue 13-1022:00 -
2 stops27h 47m
Wed 28-1009:29 -
2 stops25h 41m
Deal found 18-8S$ 1,436
Thu 10-907:30 -
2 stops28h 14m
Wed 23-909:29 -
2 stops25h 26m
Deal found 15-8S$ 1,529
Thu 10-907:30 -
2 stops28h 14m
Thu 24-909:59 -
2 stops30h 01m
Deal found 19-8S$ 1,531
Sat 3-1013:55 -
2 stops34h 30m
Sat 10-1019:45 -
2 stops27h 45m
Deal found 19-8S$ 1,537
Tue 13-1013:55 -
2 stops29h 10m
Wed 28-1016:45 -
3 stops31h 20m
Deal found 18-8S$ 1,564
Sun 11-1001:25 -
2 stops27h 49m
Wed 28-1006:04 -
2 stops29h 06m
Deal found 18-8S$ 1,575
Thu 1-1013:55 -
2 stops29h 10m
Thu 8-1015:55 -
2 stops31h 35m
Deal found 16-8S$ 1,653
Fri 2-1013:55 -
2 stops28h 55m
Fri 9-1015:55 -
2 stops31h 35m
Deal found 18-8S$ 1,691
Sun 30-813:55 -
2 stops34h 45m
Wed 2-917:15 -
2 stops30h 15m
Deal found 16-8S$ 1,719

Find flight deals from Singapore to Midway

Round-trip from

S$ 1,434

One-way from

S$ 734

Popular in

August

Cheapest in

September

Average price

S$ 2,615
Delta
  • Delta
  • 29-9-6-10
  • 4 total stops
  • 63h 32m total
  • Singapore to Chicago
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23-10
  • 23-10
  • 2 total stops
  • 40h 12m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (S$ 320 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (S$ 144 potential savings vs. average return price).
Search Deals
Average for round-trip flights in August 2026
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Cheapflights Fare Finder

 
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

Tue 29-9

22:00-18:33

2 stops33h 33m

Chicago Midway

Tue 6-10

10:01-05:00

2 stops29h 59m

S$ 1,434

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Mon 14-9

22:00-12:39

2 stops27h 39m

Chicago Midway

Tue 29-9

17:11-19:15

2 stops37h 04m

S$ 1,435

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 22-9

07:30-22:44

2 stops28h 14m

Chicago Midway

Sun 27-9

09:29-05:00

2 stops30h 31m

S$ 1,435
Fastest return journey

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Thu 10-9

07:30-22:44

2 stops28h 14m

Chicago Midway

Wed 23-9

09:29-23:55

2 stops25h 26m

S$ 1,529

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$ 1,531

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 10-11

10:40-08:50

2 stops36h 10m

Chicago Midway

Sat 28-11

17:25-00:10

2 stops40h 45m

S$ 1,531

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Wed 30-9

07:30-22:44

2 stops28h 14m

Chicago Midway

Wed 7-10

09:29-23:55

2 stops25h 26m

S$ 1,531

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sat 3-10

13:55-11:25

2 stops34h 30m

Chicago Midway

Sat 10-10

19:45-12:30

2 stops27h 45m

S$ 1,537

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 13-10

13:55-06:05

2 stops29h 10m

Chicago Midway

Wed 28-10

16:45-13:05

3 stops31h 20m

S$ 1,564

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sun 11-10

01:25-16:14

2 stops27h 49m

Chicago Midway

Wed 28-10

06:04-00:10

2 stops29h 06m

S$ 1,575

Flights are sorted by cheapest return flights first.

Deals found on 18-8

Showing 1-10 of 20 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

Related info for your journey

  • 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

Alternative routes for Singapore to Midway

Singapore to O'Hare Intl flights

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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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