Find flights
When to book
FAQs

Cheap flights from Singapore to Chicago Midway Airport from S$ 779

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 29-10. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
18 Oct — 25 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Singapore to Midway

Keep the following information in mind while searching for Singapore to Midway flight deals. Data was last updated 18 September 2025.

Round-trip from

S$ 1,247

One-way from

S$ 779

Popular in

January

Cheapest in

October

Average price

S$ 1,242
Delta
  • Delta
  • 5-10-19-10
  • 4 total stops
  • 57h 46m total
  • Singapore to Chicago
Search Deals
29-10
  • 29-10
  • 2 total stops
  • 44h 38m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (S$ 185 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (S$ 47 potential savings vs. average return price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Singapore to Midway

Cheapest flights from Singapore to Midway
Explore the most affordable flight options available from Singapore to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 18 September 2025.

Sun 5-1007:30SIN - MDW
2 stops27h 06mDelta
Sun 19-1009:20MDW - SIN
2 stops30h 40mDelta
Deal found 16-9S$ 1,247
Sun 28-922:30SIN - MDW
2 stops32h 05mDelta
Sun 19-1006:00MDW - SIN
2 stops34h 00mDelta
Deal found 15-9S$ 1,386
Fri 24-1001:10SIN - MDW
2 stops34h 04mDelta
Thu 30-1009:35MDW - SIN
2 stops25h 35mDelta
Deal found 16-9S$ 1,394
Tue 11-1101:35SIN - MDW
2 stops24h 17mDelta
Wed 19-1106:00MDW - SIN
2 stops33h 00mDelta
Deal found 15-9S$ 1,529
Sun 2-1115:45SIN - MDW
2 stops27h 30mMultiple Airlines
Sun 9-1118:05MDW - SIN
2 stops28h 00mMultiple Airlines
Deal found 17-9S$ 1,617
Thu 30-1001:35SIN - MDW
2 stops26h 51mDelta
Fri 7-1106:00MDW - SIN
2 stops33h 00mDelta
Deal found 15-9S$ 1,671
Sat 18-1001:10SIN - MDW
2 stops34h 04mDelta
Mon 27-1018:23MDW - SIN
2 stops40h 47mDelta
Deal found 16-9S$ 1,701
Fri 31-1013:15SIN - MDW
2 stops28h 45mMultiple Airlines
Fri 7-1117:25MDW - SIN
2 stops28h 40mMultiple Airlines
Deal found 15-9S$ 2,273
Sat 4-1001:10SIN - MDW
2 stops24h 18mMultiple Airlines
Sun 19-1009:35MDW - SIN
2 stops25h 05mMultiple Airlines
Deal found 16-9S$ 2,470
Mon 29-901:10SIN - MDW
2 stops24h 18mKorean Air
Tue 7-1009:20MDW - SIN
2 stops30h 40mKorean Air
Deal found 16-9S$ 2,659

Cheapflights Fare Finder

 
Customise your flight search to find flights from Singapore to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 200,618 searches. Data last updated 18 September 2025.
Use the filters below to find and compare flights from Singapore to Chicago Midway Airport that are best for you.

Fly from

Singapore

Fly to

Midway

Route

Depart

Return

Price

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 10-2

10:40-08:54

2 stops36h 14m

Chicago Midway

Fri 20-2

17:59-00:10

2 stops40h 11m

S$ 1,247

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 5-10

22:30-22:14

2 stops36h 44m

Chicago Midway

Sun 19-10

09:20-05:00

2 stops30h 40m

S$ 1,247

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 12-11

10:40-09:01

2 stops36h 21m

Chicago Midway

Wed 19-11

06:00-05:00

2 stops33h 00m

S$ 1,386

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 28-9

22:30-17:35

2 stops32h 05m

Chicago Midway

Sun 19-10

06:00-05:00

2 stops34h 00m

S$ 1,386

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 24-10

01:10-22:14

2 stops34h 04m

Chicago Midway

Thu 30-10

09:35-00:10

2 stops25h 35m

S$ 1,394

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 2-11

15:45-05:15

2 stops27h 30m

Chicago Midway

Sun 9-11

18:05-12:05

2 stops28h 00m

S$ 1,617

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 29-10

09:15-16:53

2 stops44h 38m

S$ 779

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 7-11

09:15-13:57

2 stops42h 42m

S$ 784

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 31-10

23:20-12:30

3 stops50h 10m

S$ 799

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 1-11

01:25-13:37

3 stops49h 12m

S$ 808

Flights are sorted by cheapest return flights first.

Deals found on 17-9

Showing 1-10 of 17 results
1
2

Best time to book a flight from Singapore to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Singapore 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 from Singapore to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Singapore to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Singapore to Chicago Midway Airport?

    There are many flights that can get you from Singapore to Chicago Midway Airport in 36h 14m. Fly via Delta to get the fastest option. There are 15063 km between Singapore and Chicago Midway Airport.

  • Can I find deals for flights from Singapore to Midway that include hotel bookings?

    Yes. In addition to deals on Singapore to Midway flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Singapore to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Singapore to Midway.

  • Can I find deals for business class flights from Singapore to Midway?

    Yes. Cheapflights offers flight deals from Singapore to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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.

Alternative routes for Singapore to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Singapore to O'Hare Intl flights
Singapore to Midway flights

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 from Singapore to Midway?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Singapore to Midway. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Singapore to Midway?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Singapore.

Can Cheapflights find flights from Singapore to Midway with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Singapore to Midway flexibly with Cheapflights today.

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

Of course! You can now track prices for flights from Singapore to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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.