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Cheap flights from Singapore to Chicago Midway Airport from S$ 831

SIN — MDW
30 Sep — 7 Oct1
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 6-1010:12 -
2 stops29h 48m
Deal found 30-8S$ 1,439
Mon 14-901:25 -
2 stops24h 14m
Wed 2-1217:14 -
2 stops37h 11m
Deal found 27-8S$ 1,443
Mon 12-1001:25 -
2 stops29h 35m
Tue 20-1010:12 -
2 stops29h 48m
Deal found 30-8S$ 1,534
Mon 14-901:25 -
2 stops24h 14m
Sat 28-1118:44 -
2 stops39h 26m
Deal found 27-8S$ 1,538
Fri 16-1013:55 -
2 stops28h 55m
Thu 29-1015:55 -
2 stops32h 10m
Deal found 29-8S$ 1,547
Tue 6-1013:55 -
2 stops29h 10m
Fri 23-1016:05 -
2 stops32h 00m
Deal found 28-8S$ 1,548
Tue 13-1002:00 -
2 stops40h 50m
Wed 21-1016:45 -
3 stops42h 50m
Deal found 30-8S$ 1,569
Sat 10-1013:55 -
2 stops34h 30m
Sat 24-1019:05 -
2 stops29h 00m
Deal found 28-8S$ 1,570
Sun 11-1022:00 -
2 stops26h 54m
Sun 18-1006:04 -
2 stops28h 51m
Deal found 26-8S$ 1,583
Sat 14-1101:35 -
2 stops35h 19m
Thu 19-1106:00 -
2 stops33h 00m
Deal found 26-8S$ 1,584
Thu 15-1013:55 -
2 stops29h 10m
Tue 20-1016:45 -
3 stops30h 45m
Deal found 28-8S$ 1,630

Find flight deals from Singapore to Midway

Round-trip from

S$ 1,439

One-way from

S$ 831

Popular in

August

Cheapest in

September

Average price

S$ 2,618
Delta
  • Delta
  • 29-9-6-10
  • 4 total stops
  • 63h 21m total
  • Singapore to Chicago
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13-10
  • 13-10
  • 3 total stops
  • 51h 38m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (S$ 333 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

Thu 17-9

07:30-22:45

2 stops28h 15m

Chicago Midway

Mon 30-11

18:44-00:10

2 stops39h 26m

S$ 1,443

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sun 20-9

22:00-12:39

2 stops27h 39m

Chicago Midway

Mon 30-11

17:13-00:10

2 stops40h 57m

S$ 1,443

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Mon 14-9

01:25-12:39

2 stops24h 14m

Chicago Midway

Tue 1-12

17:14-20:25

2 stops37h 11m

S$ 1,443

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Mon 12-10

01:25-18:00

2 stops29h 35m

Chicago Midway

Tue 20-10

10:12-05:00

2 stops29h 48m

S$ 1,534

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Mon 14-9

01:25-12:39

2 stops24h 14m

Chicago Midway

Sat 28-11

18:44-00:10

2 stops39h 26m

S$ 1,538

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Fri 16-10

13:55-05:50

2 stops28h 55m

Chicago Midway

Thu 29-10

15:55-13:05

2 stops32h 10m

S$ 1,547

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Fri 16-10

13:55-05:50

2 stops28h 55m

Chicago Midway

Fri 30-10

15:55-13:05

2 stops32h 10m

S$ 1,547

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 13-10

02:00-23:55

2 stops34h 55m

Chicago Midway

Wed 21-10

15:35-12:30

2 stops31h 55m

S$ 1,565

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Wed 16-9

22:00-11:54

2 stops26h 54m

Chicago Midway

Sun 29-11

06:00-05:00

2 stops33h 00m

S$ 1,583

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sat 14-11

01:35-22:54

2 stops35h 19m

Chicago Midway

Thu 19-11

06:00-05:00

2 stops33h 00m

S$ 1,584

Flights are sorted by cheapest return flights first.

Deals found on 26-8

Showing 1-10 of 18 resultsSorted by cheapest first
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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

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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