S$ 750+ Cheap flights to Midway

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 27-10. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
12 Oct — 19 Oct1
1 adult
1 adult, Economy

Flights to Midway in 2025

Find the latest flights to Midway in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 200,618 searches and data was last updated on 12 September 2025.

Return from

S$ 1,053

One-way from

S$ 750

Popular in

January

Cheapest in

October

Average price

S$ 1,248
Air Canada
  • Air Canada
  • 18-10-26-10
  • 3 total stops
  • 57h 09m total
  • Singapore to Chicago
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27-10
  • 27-10
  • 2 total stops
  • 39h 23m total
  • Singapore to Chicago
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Highest demand for flights based on searches. 9% potential increase in price (S$ 183 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (S$ 53 potential savings vs. average return price).
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Average for return flights in September 2025
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Find flight deals to Midway Airport

Cheapest flights to Midway Airport
Explore the most affordable flight options available to Midway Airport. Find the lowest fares based on data from user searches, with prices last updated on 12 September 2025.

Wed 1-1001:10SIN - MDW
2 stops30h 25mDelta
Mon 6-1009:20MDW - SIN
2 stops30h 40mDelta
Deal found 10-9S$ 1,252
Wed 1-1022:30SIN - MDW
2 stops36h 06mDelta
Sun 5-1006:00MDW - SIN
2 stops34h 00mDelta
Deal found 10-9S$ 1,392
Sun 26-1022:30SIN - MDW
2 stops30h 40mDelta
Sun 2-1105:00MDW - SIN
2 stops33h 00mDelta
Deal found 11-9S$ 1,535
Sun 14-1201:35SIN - MDW
2 stops35h 57mDelta
Tue 13-106:00MDW - SIN
2 stops48h 25mDelta
Deal found 9-9S$ 1,553
Sat 25-1007:30SIN - MDW
2 stops38h 25mDelta
Sun 9-1106:00MDW - SIN
2 stops33h 00mDelta
Deal found 11-9S$ 1,707
Thu 18-1210:40SIN - MDW
2 stops26h 52mDelta
Sun 11-117:59MDW - SIN
2 stops40h 11mDelta
Deal found 9-9S$ 1,720
Fri 19-1210:40SIN - MDW
2 stops38h 26mDelta
Sun 11-118:45MDW - SIN
2 stops39h 25mDelta
Deal found 11-9S$ 1,887
Sat 25-1007:30SIN - MDW
2 stops27h 44mDelta
Sat 1-1106:00MDW - SIN
2 stops34h 00mDelta
Deal found 10-9S$ 1,991
Wed 17-1210:40SIN - MDW
2 stops36h 39mDelta
Sat 10-117:25MDW - SIN
2 stops40h 45mDelta
Deal found 9-9S$ 2,028
Sun 14-901:10SIN - MDW
2 stops30h 25mDelta
Tue 30-906:00MDW - SIN
2 stops28h 40mDelta
Deal found 11-9S$ 2,225

Cheapflights Fare Finder

 
Locate flights to Midway that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 200,618 searches and data was last updated on 12 September 2025.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Singapore

Route

Depart

Return

Price

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 10-2

10:40-08:54

2 stops36h 14m

Chicago Midway

Fri 20-2

18:45-00:10

2 stops39h 25m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 1-10

01:10-18:35

2 stops30h 25m

Chicago Midway

Mon 6-10

09:20-05:00

2 stops30h 40m

S$ 1,252

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 16-12

01:35-23:32

2 stops35h 57m

Chicago Midway

Tue 13-1

17:25-20:25

2 stops37h 00m

S$ 1,553

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 14-12

01:35-23:32

2 stops35h 57m

Chicago Midway

Tue 13-1

06:00-20:25

2 stops48h 25m

S$ 1,553

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 13-2

13:15-05:15

2 stops30h 00m

Chicago Midway

Fri 3-4

17:40-12:00

2 stops29h 20m

S$ 1,678

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 25-10

07:30-08:55

2 stops38h 25m

Chicago Midway

Sun 9-11

06:00-05:00

2 stops33h 00m

S$ 1,707

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 12-2

01:35-12:01

2 stops24h 26m

Chicago Midway

Fri 3-4

09:20-05:00

2 stops30h 40m

S$ 1,878

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 1-10

22:35-20:46

3 stops59h 11m

S$ 793

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 27-10

10:00-11:38

3 stops38h 38m

S$ 811

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 6-10

07:30-22:14

2 stops27h 44m

S$ 818

Flights are sorted by cheapest return flights first.

Deals found on 10-9

Showing 1-10 of 15 results
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2

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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals 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

Plan your trip to Midway by taking into account the average temperature totals 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 27 hours 6 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 Kitch is the closest property to Chicago Midway (0.0 km away from Chicago Midway).

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How does Cheapflights help users find flights to Midway?

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Why should you use Cheapflights to find cheap flight tickets to Midway?

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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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