S$ 782+ Cheap flights to Midway

— MDW
9 Oct — 16 Oct1
1 adult
1 adult, Economy, 0 bags

Flights to Midway in 2026

Enter your travel dates to find the best prices.

Cheapest flights to Midway Airport

Tue 20-1022:00 -
2 stops33h 00m
Tue 27-1009:29 -
2 stops30h 31m
Deal found 5-9S$ 1,436
Tue 6-1007:30 -
2 stops28h 03m
Tue 13-1017:31 -
2 stops41h 24m
Deal found 7-9S$ 1,437
Mon 9-1122:30 -
2 stops27h 29m
Fri 27-1106:00 -
2 stops28h 10m
Deal found 4-9S$ 1,575
Thu 22-1007:30 -
2 stops41h 24m
Thu 29-1017:09 -
2 stops42h 06m
Deal found 7-9S$ 1,576
Thu 15-1013:55 -
2 stops29h 10m
Wed 28-1010:30 -
2 stops37h 35m
Deal found 4-9S$ 1,639
Mon 5-1013:55 -
2 stops29h 10m
Thu 29-1015:55 -
2 stops32h 10m
Deal found 7-9S$ 1,641
Sun 18-1013:55 -
2 stops34h 20m
Thu 29-1015:55 -
2 stops32h 10m
Deal found 8-9S$ 1,647
Fri 23-1013:55 -
2 stops28h 55m
Fri 30-1018:15 -
2 stops29h 50m
Deal found 8-9S$ 1,655
Tue 20-1013:55 -
2 stops29h 10m
Tue 27-1016:45 -
3 stops31h 20m
Deal found 5-9S$ 1,665
Sat 3-1022:00 -
2 stops31h 15m
Sun 18-1009:29 -
2 stops30h 31m
Deal found 5-9S$ 1,671
Sun 11-1001:25 -
2 stops27h 49m
Tue 13-1017:09 -
2 stops37h 06m
Deal found 6-9S$ 1,717

Find flight deals to Midway Airport

Return from

S$ 950

One-way from

S$ 782

Popular in

August

Cheapest in

September

Average price

S$ 1,089
Air Canada
  • Air Canada
  • 15-10-28-10
  • 3 total stops
  • 59h 26m 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$ 257 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (S$ 112 potential savings vs. average return price).
Search Deals
Average for return flights in September 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest return flight
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$ 916

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$ 925

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$ 951

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$ 953

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$ 965

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$ 974

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$ 975

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sat 28-11

14:25-11:05

2 stops34h 40m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 975

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 20-10

22:00-18:00

2 stops33h 00m

Chicago Midway

Tue 27-10

09:29-05:00

2 stops30h 31m

S$ 1,436

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 6-10

07:30-22:33

2 stops28h 03m

Chicago Midway

Tue 13-10

17:31-23:55

2 stops41h 24m

S$ 1,437

Flights are sorted by cheapest return flights first.

Deals found on 4-9

Showing 1-10 of 19 resultsSorted by cheapest first
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Best time to book a flight to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway with our price prediction graph.
Estimated return price

Cheapflights Insights

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

Rainfall in Midway by month

In terms of precipitation, rainfall in Midway ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Midway when rainfall is around 43.0 mm.

Temperature in Midway by month

If weather is an important factor for your trip to Midway, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

How long is the flight to Midway?

On average, a flight from Singapore to Midway takes 28 hours 3 minutes. Flights to Midway from other popular cities in Singapore will vary in length. Below are a few examples of popular routes and their flight times.

FAQs about flying to Midway

  • Can I find cheaper flights to Midway if I am willing to have stopovers?

    Yes, flights with stopovers are often cheaper than direct flights. Keep an eye out for flight deals to Midway on Cheapflights that require 1 or 2 stops for potential cost savings.

  • Does Chicago Midway have rental cars?

    Yes. Those touching down at Chicago Midway can take advantage of the car hire services offered upon their arrival.

  • Are there hotels close to Chicago Midway?

    Yes. Chicago Midway has hotels nearby for those requiring accommodations. Midway Airport 2 Bedroom With Full Kitchen is the closest property to Chicago Midway (0.0 km away from Chicago Midway).

Browse thousands of different options on Cheapflights for your next trip

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How does Cheapflights help users find flights to Midway?

Cheapflights makes it easy to find 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 to Midway?

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Can Cheapflights find flights to Midway with no change fees?

Need flexible booking options for your flight to Midway ? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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Yes, and it’s super simple to set up Price Alerts. Click the bell icon next to the flight deals above and provide your email address. That’s it!

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