S$ 822+ 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 25-12. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals to Midway Airport

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 28 October 2025.

Tue 25-1110:40SIN - MDW
2 stops27h 00mDelta
Mon 1-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 27-10S$ 1,377
Mon 24-1110:40SIN - MDW
2 stops27h 00mDelta
Mon 1-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 27-10S$ 1,769
Mon 17-1122:30SIN - MDW
2 stops27h 22mDelta
Mon 1-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 26-10S$ 1,949
Mon 17-1101:35SIN - MDW
2 stops36h 05mDelta
Tue 2-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 26-10S$ 1,974
Fri 21-1110:40SIN - MDW
2 stops27h 00mDelta
Fri 28-1106:00MDW - SIN
2 stops33h 00mDelta
Deal found 26-10S$ 2,014
Fri 14-1115:45SIN - MDW
2 stops27h 30mMultiple Airlines
Sun 16-1118:05MDW - SIN
2 stops28h 00mMultiple Airlines
Deal found 26-10S$ 2,236
Thu 13-1122:30SIN - MDW
2 stops27h 22mDelta
Thu 27-1106:00MDW - SIN
2 stops28h 10mDelta
Deal found 26-10S$ 2,342
Tue 23-1210:40SIN - MDW
2 stops25h 42mDelta
Tue 13-117:31MDW - SIN
2 stops36h 54mDelta
Deal found 26-10S$ 2,356
Sun 16-1101:40SIN - MDW
2 stops28h 59mKLM
Mon 1-1217:34MDW - SIN
2 stops32h 41mKLM
Deal found 26-10S$ 2,709
Mon 22-1201:40SIN - MDW
2 stops28h 44mKLM
Tue 13-117:31MDW - SIN
2 stops32h 44mKLM
Deal found 26-10S$ 2,800
Wed 12-1101:40SIN - MDW
2 stops28h 58mMultiple Airlines
Thu 27-1117:34MDW - SIN
2 stops33h 21mMultiple Airlines
Deal found 26-10S$ 2,892

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 28 October 2025.

Return from

S$ 987

One-way from

S$ 766

Popular in

January

Cheapest in

October

Average price

S$ 1,192
Air Canada
  • Air Canada
  • 13-11-27-11
  • 2 total stops
  • 45h 11m total
  • Singapore to Chicago
Search Deals
14-1
  • 14-1
  • 3 total stops
  • 51h 47m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (S$ 180 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 45 potential savings vs. average return price).
Search Deals
Average for return flights in October 2025
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 28 October 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

Wed 15-4

01:10-08:38

2 stops44h 28m

Chicago Midway

Mon 20-4

09:20-05:00

2 stops30h 40m

S$ 1,412

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 10-2

10:40-22:26

2 stops25h 46m

Chicago Midway

Fri 20-2

06:00-05:00

2 stops33h 00m

S$ 1,551

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 24-11

10:40-23:40

2 stops27h 00m

Chicago Midway

Mon 1-12

06:00-05:00

2 stops33h 00m

S$ 1,769

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 17-11

22:30-11:52

2 stops27h 22m

Chicago Midway

Mon 1-12

06:00-05:00

2 stops33h 00m

S$ 1,949

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 17-11

01:35-23:40

2 stops36h 05m

Chicago Midway

Tue 2-12

06:00-05:00

2 stops33h 00m

S$ 1,974

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 8-1

09:30-20:02

3 stops48h 32m

S$ 875

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 6-12

15:45-11:08

3 stops57h 23m

S$ 917

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 5-12

23:00-18:12

3 stops57h 12m

S$ 951

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 26-12

01:35-22:22

2 stops34h 47m

S$ 1,135

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 8-2

13:15-05:00

2 stops29h 45m

S$ 1,611

Flights are sorted by cheapest return flights first.

Deals found on 26-10

Showing 1-10 of 13 results
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 25 hours 42 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).

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
Business Class
Prem Econ Class
Economy class

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.