S$ 927+ 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 22-8. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
22 Aug — 29 Aug1
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 23 July 2026.

Tue 22-901:25
SIN
-
MDW
2 stops34h 19m
Delta
Sun 27-909:29
MDW
-
SIN
2 stops25h 26m
Delta
Deal found 20-7S$ 1,438
Tue 1-907:30
SIN
-
MDW
2 stops28h 06m
Delta
Thu 24-909:29
MDW
-
SIN
2 stops25h 26m
Delta
Deal found 21-7S$ 1,440
Mon 31-807:30
SIN
-
MDW
2 stops28h 06m
Delta
Mon 7-918:42
MDW
-
SIN
2 stops40h 13m
Delta
Deal found 17-7S$ 1,441
Tue 18-813:45
SIN
-
MDW
2 stops29h 00m
Multiple Airlines
Tue 25-820:45
MDW
-
SIN
2 stops26h 50m
Multiple Airlines
Deal found 19-7S$ 1,565
Tue 22-902:00
SIN
-
MDW
2 stops34h 20m
Multiple Airlines
Sun 27-920:35
MDW
-
SIN
2 stops27h 00m
Multiple Airlines
Deal found 20-7S$ 1,576
Thu 10-922:00
SIN
-
MDW
2 stops30h 24m
Delta
Thu 24-906:05
MDW
-
SIN
2 stops28h 50m
Delta
Deal found 21-7S$ 1,579
Thu 10-913:55
SIN
-
MDW
2 stops34h 20m
Multiple Airlines
Thu 24-915:55
MDW
-
SIN
2 stops31h 40m
Multiple Airlines
Deal found 22-7S$ 1,583
Thu 1-1002:00
SIN
-
MDW
3 stops35h 30m
Multiple Airlines
Sat 10-1019:05
MDW
-
SIN
2 stops28h 30m
Multiple Airlines
Deal found 22-7S$ 1,588
Tue 18-815:20
SIN
-
MDW
2 stops26h 45m
Multiple Airlines
Sun 23-820:35
MDW
-
SIN
2 stops26h 20m
Multiple Airlines
Deal found 20-7S$ 1,685
Thu 3-913:55
SIN
-
MDW
2 stops34h 20m
Multiple Airlines
Tue 15-917:15
MDW
-
SIN
2 stops30h 20m
Multiple Airlines
Deal found 21-7S$ 1,751

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 23 July 2026.

Return from

S$ 964

One-way from

S$ 853

Popular in

August

Cheapest in

September

Average price

S$ 1,508
Air Canada
  • Air Canada
  • 10-9-24-9
  • 2 total stops
  • 45h 18m total
  • Singapore to Chicago
Search Deals
29-9
  • 29-9
  • 3 total stops
  • 32h 43m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (S$ 165 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (S$ 107 potential savings vs. average return price).
Search Deals
Average for return flights in July 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 23 July 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

Tue 22-9

01:25-22:44

2 stops34h 19m

Chicago Midway

Sun 27-9

09:29-23:55

2 stops25h 26m

S$ 1,438

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 1-9

07:30-22:36

2 stops28h 06m

Chicago Midway

Tue 8-9

19:13-23:55

2 stops39h 42m

S$ 1,440
Fastest return journey

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 1-9

07:30-22:36

2 stops28h 06m

Chicago Midway

Mon 14-9

09:59-23:55

2 stops24h 56m

S$ 1,440

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 23-9

01:25-22:44

2 stops34h 19m

Chicago Midway

Sun 27-9

09:59-05:00

2 stops30h 01m

S$ 1,440

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 31-8

07:30-22:36

2 stops28h 06m

Chicago Midway

Mon 7-9

18:42-23:55

2 stops40h 13m

S$ 1,441

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 22-9

02:00-23:20

2 stops34h 20m

Chicago Midway

Sun 27-9

20:35-12:35

2 stops27h 00m

S$ 1,576

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 12-9

07:30-22:44

2 stops28h 14m

Chicago Midway

Fri 18-9

06:05-05:00

2 stops33h 55m

S$ 1,579

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 1-10

02:00-00:10

2 stops35h 10m

Chicago Midway

Sat 10-10

19:05-12:35

2 stops28h 30m

S$ 1,588

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 18-8

13:55-05:45

2 stops28h 50m

Chicago Midway

Tue 25-8

21:00-12:35

2 stops26h 35m

S$ 1,613

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 2-8

22:00-16:15

2 stops31h 15m

Chicago Midway

Mon 17-8

06:05-05:00

2 stops33h 55m

S$ 1,916

Flights are sorted by cheapest return flights first.

Deals found on 18-7

Showing 1-10 of 21 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 28 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 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 flights to Chicago Midway Airport
Business Class flights to Chicago Midway Airport
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Economy Class flights to Chicago Midway Airport

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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