S$ 758+ 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 12-5. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
22 May — 29 May1
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 22 April 2026.

Wed 7-1022:00
SIN
-
MDW
2 stops31h 25m
Delta
Fri 16-1009:55
MDW
-
SIN
2 stops30h 05m
Delta
Deal found 20-4S$ 1,368
Sun 7-622:00
SIN
-
MDW
2 stops27h 00m
Delta
Sun 9-806:05
MDW
-
SIN
2 stops33h 55m
Delta
Deal found 18-4S$ 1,566
Sun 7-615:20
SIN
-
MDW
2 stops27h 35m
Multiple Airlines
Sun 9-820:35
MDW
-
SIN
2 stops26h 20m
Multiple Airlines
Deal found 21-4S$ 1,745
Tue 29-1201:35
SIN
-
MDW
2 stops28h 50m
Delta
Tue 12-106:00
MDW
-
SIN
2 stops28h 10m
Delta
Deal found 22-4S$ 1,860
Mon 28-1210:40
SIN
-
MDW
2 stops25h 05m
Delta
Tue 12-117:25
MDW
-
SIN
2 stops40h 45m
Delta
Deal found 18-4S$ 1,891
Sun 27-1222:30
SIN
-
MDW
2 stops31h 52m
Delta
Tue 12-117:25
MDW
-
SIN
2 stops40h 45m
Delta
Deal found 18-4S$ 2,010
Thu 8-1013:45
SIN
-
MDW
2 stops29h 20m
Multiple Airlines
Fri 16-1015:55
MDW
-
SIN
3 stops31h 40m
Multiple Airlines
Deal found 20-4S$ 2,040
Wed 30-1201:35
SIN
-
MDW
2 stops28h 50m
Delta
Wed 13-117:35
MDW
-
SIN
2 stops40h 35m
Delta
Deal found 22-4S$ 2,056

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 22 April 2026.

Return from

S$ 1,042

One-way from

S$ 758

Popular in

January

Cheapest in

February

Average price

S$ 1,350
ANA
  • ANA
  • 5-10-20-10
  • 2 total stops
  • 47h 35m total
  • Singapore to Chicago
Search Deals
Delta
  • Delta
  • 12-5
  • 2 total stops
  • 32h 44m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (S$ 34 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 44 potential savings vs. average return price).
Search Deals
Average for return flights in April 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 22 April 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

Wed 7-10

22:00-16:25

2 stops31h 25m

Chicago Midway

Fri 16-10

09:55-05:00

2 stops30h 05m

S$ 1,368

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 7-6

22:00-12:00

2 stops27h 00m

Chicago Midway

Sun 9-8

06:05-05:00

2 stops33h 55m

S$ 1,566

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 19-5

13:45-12:00

2 stops35h 15m

Chicago Midway

Tue 26-5

15:55-12:35

2 stops31h 40m

S$ 2,179

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 17-6

22:00-16:16

2 stops31h 16m

Chicago Midway

Fri 26-6

09:54-05:00

2 stops30h 06m

S$ 2,296

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 1-6

22:00-16:12

2 stops31h 12m

Chicago Midway

Mon 8-6

06:05-05:00

2 stops33h 55m

S$ 2,325

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 6-5

07:30-22:28

2 stops27h 58m

Chicago Midway

Wed 13-5

06:23-05:00

2 stops33h 37m

S$ 2,328
Fastest return journey

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 4-6

13:45-05:00

2 stops28h 15m

Chicago Midway

Thu 11-6

18:40-12:35

3 stops28h 55m

S$ 2,419

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 4-6

01:25-21:09

2 stops32h 44m

Chicago Midway

Fri 12-6

06:05-05:00

2 stops33h 55m

S$ 2,446

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 23-9

01:25-12:30

2 stops24h 05m

Chicago Midway

Mon 28-9

09:30-19:15

2 stops44h 45m

S$ 2,521
Cheapest one-way

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 12-5

01:25-21:09

2 stops32h 44m

S$ 758

Flights are sorted by cheapest return flights first.

Deals found on 19-4

Showing 1-10 of 19 resultsSorted by cheapest first
1
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 35 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!

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.