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Cheap flights from Singapore to Chicago Midway Airport from S$ 836

SIN — MDW
5 Oct — 12 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

Sun 20-901:25 -
2 stops34h 19m
Tue 29-909:59 -
2 stops24h 56m
Deal found 4-9S$ 1,437
Tue 20-1022:00 -
2 stops33h 00m
Tue 27-1009:29 -
2 stops30h 31m
Deal found 5-9S$ 1,438
Mon 9-1122:30 -
2 stops27h 29m
Fri 27-1106:00 -
2 stops28h 10m
Deal found 4-9S$ 1,577
Sun 18-1013:55 -
2 stops29h 10m
Thu 29-1015:55 -
2 stops32h 10m
Deal found 2-9S$ 1,589
Fri 16-1013:55 -
2 stops28h 55m
Fri 23-1016:05 -
2 stops32h 00m
Deal found 1-9S$ 1,590
Thu 1-1013:55 -
2 stops29h 10m
Thu 15-1015:55 -
2 stops31h 35m
Deal found 31-8S$ 1,606
Thu 15-1013:55 -
2 stops29h 10m
Wed 28-1010:30 -
2 stops37h 35m
Deal found 4-9S$ 1,642
Sun 18-1013:55 -
2 stops29h 10m
Sun 25-1018:30 -
2 stops29h 35m
Deal found 3-9S$ 1,660
Tue 20-1013:55 -
2 stops29h 10m
Tue 27-1016:45 -
3 stops31h 20m
Deal found 5-9S$ 1,667
Fri 4-913:55 -
2 stops28h 50m
Thu 10-917:55 -
2 stops29h 35m
Deal found 3-9S$ 1,698
Sat 3-1013:55 -
2 stops34h 30m
Sun 18-1018:10 -
2 stops29h 20m
Deal found 1-9S$ 1,725

Find flight deals from Singapore to Midway

Round-trip from

S$ 1,437

One-way from

S$ 844

Popular in

August

Cheapest in

September

Average price

S$ 1,091
Delta
  • Delta
  • 20-9-29-9
  • 4 total stops
  • 59h 15m total
  • Singapore to Chicago
Search Deals
13-10-31-12
  • 13-10-31-12
  • 3 total stops
  • 51h 38m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (S$ 329 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (S$ 143 potential savings vs. average return price).
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Average for round-trip flights in September 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 13-10

09:05-23:43

3 stops51h 38m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 844

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sun 11-10

13:55-06:05

2 stops29h 10m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 917
Fastest return journey

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 22-9

13:55-05:05

2 stops28h 10m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 917

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sat 24-10

13:10-12:17

3 stops36h 07m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 926

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 2-3

02:00-05:45

2 stops41h 45m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 926

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Fri 16-10

13:55-05:50

2 stops28h 55m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 929

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 12-1

14:25-12:25

2 stops36h 00m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 939

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 20-10

13:55-06:05

2 stops29h 10m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 953

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Wed 14-10

22:00-09:23

2 stops48h 23m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 970

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Fri 29-1

01:35-22:10

2 stops34h 35m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 972

Flights are sorted by cheapest return flights first.

Deals found on 2-9

Showing 1-10 of 20 resultsSorted by cheapest first
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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

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 34h 19m. 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

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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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