S$ 983+ 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 4-9. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
10 Jul — 17 Jul1
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
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 10 June 2026.

Fri 18-907:30
SIN
-
MDW
2 stops38h 20m
Delta
Sun 20-918:51
MDW
-
SIN
2 stops40h 04m
Delta
Deal found 6-6S$ 1,486
Sat 21-1122:30
SIN
-
MDW
2 stops28h 03m
Delta
Mon 23-1117:35
MDW
-
SIN
2 stops45h 25m
Delta
Deal found 6-6S$ 1,582
Sat 4-715:20
SIN
-
MDW
2 stops26h 40m
Multiple Airlines
Sat 11-721:00
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 6-6S$ 1,684
Tue 16-615:20
SIN
-
MDW
2 stops27h 35m
Multiple Airlines
Sat 27-621:00
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 7-6S$ 1,688
Wed 15-715:20
SIN
-
MDW
2 stops26h 40m
Multiple Airlines
Thu 24-920:55
MDW
-
SIN
2 stops26h 00m
Multiple Airlines
Deal found 7-6S$ 1,701
Sun 7-615:20
SIN
-
MDW
2 stops26h 40m
Multiple Airlines
Sun 9-820:35
MDW
-
SIN
2 stops26h 20m
Multiple Airlines
Deal found 6-6S$ 1,708
Sat 27-607:30
SIN
-
MDW
2 stops27h 47m
Delta
Sun 12-717:10
MDW
-
SIN
2 stops41h 45m
Delta
Deal found 8-6S$ 1,714
Sat 20-615:20
SIN
-
MDW
2 stops27h 35m
Multiple Airlines
Sat 27-621:00
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 10-6S$ 1,716
Sun 21-615:20
SIN
-
MDW
2 stops27h 35m
Multiple Airlines
Sat 27-621:00
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 7-6S$ 1,719
Thu 16-715:20
SIN
-
MDW
2 stops26h 40m
Multiple Airlines
Wed 19-821:00
MDW
-
SIN
2 stops25h 55m
Multiple Airlines
Deal found 10-6S$ 1,733
Mon 6-701:25
SIN
-
MDW
2 stops33h 50m
Delta
Wed 22-709:54
MDW
-
SIN
2 stops25h 01m
Delta
Deal found 10-6S$ 1,742
Mon 6-713:45
SIN
-
MDW
2 stops34h 20m
Multiple Airlines
Tue 21-715:50
MDW
-
SIN
2 stops31h 45m
Multiple Airlines
Deal found 6-6S$ 1,788

Find flight deals to Midway Airport

Find the latest flights to Midway in 2026, 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 10 June 2026.

Return from

S$ 1,023

One-way from

S$ 983

Popular in

August

Cheapest in

February

Average price

S$ 1,603
ANA
  • ANA
  • 4-11-10-11
  • 2 total stops
  • 59h 05m total
  • Singapore to Chicago
Search Deals
4-9
  • 4-9
  • 3 total stops
  • 54h 57m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (S$ 272 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (S$ 108 potential savings vs. average return price).
Search Deals
Average for return flights in June 2026
Search Deals

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 10 June 2026.
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

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 18-9

07:30-08:50

2 stops38h 20m

Chicago Midway

Sun 20-9

18:51-23:55

2 stops40h 04m

S$ 1,486

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 27-6

07:30-22:17

2 stops27h 47m

Chicago Midway

Sun 12-7

17:10-23:55

2 stops41h 45m

S$ 1,714

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 21-6

15:20-05:55

2 stops27h 35m

Chicago Midway

Sat 27-6

21:00-11:55

2 stops25h 55m

S$ 1,719
Fastest return journey

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 16-7

15:20-05:00

2 stops26h 40m

Chicago Midway

Wed 19-8

21:00-11:55

2 stops25h 55m

S$ 1,733

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 18-9

01:25-18:33

2 stops30h 08m

Chicago Midway

Mon 21-9

09:49-23:55

2 stops25h 06m

S$ 1,886

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 10-9

07:30-12:30

2 stops42h 00m

Chicago Midway

Mon 14-9

09:30-05:00

2 stops30h 30m

S$ 2,235

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 1-7

13:45-05:55

2 stops29h 10m

Chicago Midway

Wed 22-7

13:10-12:35

3 stops34h 25m

S$ 2,298

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 19-8

15:20-05:50

2 stops27h 30m

Chicago Midway

Fri 18-12

18:05-12:05

2 stops28h 00m

S$ 2,505
Cheapest one-way

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 31-8

13:45-16:35

2 stops39h 50m

S$ 1,010

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 28-7

13:10-05:00

2 stops28h 50m

S$ 1,041

Flights are sorted by cheapest return flights first.

Deals found on 9-6

Showing 1-10 of 16 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
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 25 hours 20 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Search flights to Midway by cabin class

Find flights to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class flights to Chicago Midway Airport
Business Class flights to Chicago Midway Airport
Prem Economy Class flights to Chicago Midway Airport
Economy Class flights to Chicago Midway Airport

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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?

Cheapflights simply makes it quick and affordable to book flights to Midway by bringing together all flight options from hundreds of airlines and agencies online — and we put them in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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.

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

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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