S$ 732+ 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 30-3. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
26 Feb — 5 Mar1
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 27 January 2026.

Wed 11-314:25
SIN
-
MDW
2 stops33h 45m
Multiple Airlines
Wed 18-310:05
MDW
-
SIN
2 stops38h 00m
Multiple Airlines
Deal found 24-1S$ 1,372
Mon 26-114:25
SIN
-
MDW
2 stops36h 15m
Multiple Airlines
Sun 8-210:35
MDW
-
SIN
2 stops36h 30m
Multiple Airlines
Deal found 25-1S$ 1,434
Tue 21-713:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Mon 27-718:00
MDW
-
SIN
2 stops29h 35m
Multiple Airlines
Deal found 25-1S$ 1,471
Tue 31-302:00
SIN
-
MDW
2 stops35h 10m
Multiple Airlines
Tue 30-617:05
MDW
-
SIN
2 stops30h 30m
Multiple Airlines
Deal found 27-1S$ 1,486
Thu 26-210:40
SIN
-
MDW
2 stops36h 26m
Delta
Thu 5-306:00
MDW
-
SIN
2 stops33h 00m
Delta
Deal found 27-1S$ 1,561
Thu 12-314:25
SIN
-
MDW
2 stops28h 05m
Multiple Airlines
Fri 13-311:50
MDW
-
SIN
2 stops36h 15m
Multiple Airlines
Deal found 25-1S$ 1,583
Thu 12-314:25
SIN
-
MDW
2 stops28h 30m
Multiple Airlines
Thu 19-317:40
MDW
-
SIN
2 stops30h 25m
Multiple Airlines
Deal found 25-1S$ 1,592
Sun 15-314:25
SIN
-
MDW
2 stops28h 30m
Multiple Airlines
Wed 25-312:05
MDW
-
SIN
2 stops36h 00m
Multiple Airlines
Deal found 26-1S$ 2,167
Sun 15-310:40
SIN
-
MDW
2 stops36h 16m
Delta
Wed 25-309:35
MDW
-
SIN
2 stops25h 35m
Delta
Deal found 26-1S$ 2,332

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 27 January 2026.

Return from

S$ 1,206

One-way from

S$ 755

Popular in

January

Cheapest in

September

Average price

S$ 1,576
United Airlines
  • United Airlines
  • 23-2-2-3
  • 2 total stops
  • 52h 51m total
  • Singapore to Chicago
Search Deals
Delta
  • Delta
  • 3-5
  • 2 total stops
  • 27h 58m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (S$ 55 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (S$ 22 potential savings vs. average return price).
Search Deals
Average for return flights in January 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 27 January 2026.
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

Wed 11-3

14:25-11:10

2 stops33h 45m

Chicago Midway

Wed 18-3

10:05-13:05

2 stops38h 00m

S$ 1,372

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 21-7

13:45-05:40

2 stops28h 55m

Chicago Midway

Mon 27-7

18:00-12:35

2 stops29h 35m

S$ 1,471

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 27-3

14:25-05:40

2 stops28h 15m

Chicago Midway

Sun 12-4

15:55-12:35

2 stops31h 40m

S$ 1,583

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 12-3

14:25-05:30

2 stops28h 05m

Chicago Midway

Fri 13-3

11:50-13:05

2 stops36h 15m

S$ 1,583

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 12-3

14:25-05:55

2 stops28h 30m

Chicago Midway

Thu 19-3

17:40-13:05

2 stops30h 25m

S$ 1,592

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 15-3

14:25-05:55

2 stops28h 30m

Chicago Midway

Wed 25-3

12:05-13:05

2 stops36h 00m

S$ 2,167

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 10-2

14:25-12:40

2 stops36h 15m

Chicago Midway

Fri 20-2

05:10-13:05

2 stops41h 55m

S$ 2,404

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 30-3

09:00-15:02

3 stops43h 02m

S$ 732

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 24-5

07:30-08:38

2 stops38h 08m

S$ 749

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 14-4

22:30-22:28

2 stops36h 58m

S$ 751

Flights are sorted by cheapest return flights first.

Deals found on 24-1

Showing 1-10 of 19 results
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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 28 hours 5 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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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
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Economy class

Fly with Cheapflights

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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?

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.

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