Find flights
When to book
FAQs

Cheap flights from Singapore to Chicago Midway Airport from S$ 783

SIN — MDW
7 Oct — 14 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$ 1,436
Tue 20-1022:00 -
2 stops33h 00m
Tue 27-1009:29 -
2 stops30h 31m
Deal found 5-9S$ 1,437
Tue 6-1007:30 -
2 stops28h 03m
Tue 13-1017:31 -
2 stops41h 24m
Deal found 7-9S$ 1,438
Mon 9-1122:30 -
2 stops27h 29m
Fri 27-1106:00 -
2 stops28h 10m
Deal found 4-9S$ 1,577
Thu 22-1007:30 -
2 stops41h 24m
Thu 29-1017:09 -
2 stops42h 06m
Deal found 7-9S$ 1,578
Sun 18-1013:55 -
2 stops29h 10m
Thu 29-1015:55 -
2 stops32h 10m
Deal found 3-9S$ 1,588
Thu 15-1013:55 -
2 stops29h 10m
Wed 28-1010:30 -
2 stops37h 35m
Deal found 4-9S$ 1,641
Mon 5-1013:55 -
2 stops29h 10m
Thu 29-1015:55 -
2 stops32h 10m
Deal found 7-9S$ 1,642
Sun 18-1013:55 -
2 stops29h 10m
Sun 25-1018:30 -
2 stops29h 35m
Deal found 3-9S$ 1,659
Tue 20-1013:55 -
2 stops29h 10m
Tue 27-1016:45 -
3 stops31h 20m
Deal found 5-9S$ 1,666
Sat 3-1022:00 -
2 stops31h 15m
Sun 18-1009:29 -
2 stops30h 31m
Deal found 5-9S$ 1,673

Find flight deals from Singapore to Midway

Round-trip from

S$ 1,436

One-way from

S$ 783

Popular in

August

Cheapest in

September

Average price

S$ 1,090
Delta
  • Delta
  • 20-9-29-9
  • 4 total stops
  • 59h 15m total
  • Singapore to Chicago
Search Deals
11-11-31-12
  • 11-11-31-12
  • 2 total stops
  • 40h 20m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (S$ 324 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).
Search Deals
Average for round-trip flights in September 2026
Search Deals

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

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

Tue 20-10

13:55-06:05

2 stops29h 10m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 952

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Mon 21-9

13:55-05:05

2 stops28h 10m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 954

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 9-2

02:00-22:10

2 stops34h 10m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 966

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$ 975

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$ 976

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sun 20-9

01:25-22:44

2 stops34h 19m

Chicago Midway

Tue 29-9

09:59-23:55

2 stops24h 56m

S$ 1,436

Flights are sorted by cheapest return flights first.

Deals found on 3-9

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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

Cheapflights Insights

Everything you need to know about your flight from Singapore to Chicago Midway Airport

No data available for this route at this time. Please check back soon.

Related info for your journey

  • 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Singapore to Midway

Singapore to O'Hare Intl flights
Singapore to Midway flights

Fly with Cheapflights

How does Cheapflights help users find flights from Singapore to Midway?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Singapore to Midway. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Singapore to Midway flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Singapore to Midway become cheaper?

Of course! You can now track prices for flights from Singapore to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book With Flexibility

Our users can plan ahead with confidence and find flights with no change fees.

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.