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Cheap flights from Singapore to Chicago Midway Airport from S$ 753

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 25-3. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
13 Mar — 20 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Singapore to Midway

Enter your travel dates to find the best prices.

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 11 February 2026.

Tue 17-314:25
SIN
-
MDW
2 stops28h 30m
Multiple Airlines
Tue 24-310:55
MDW
-
SIN
2 stops37h 10m
Multiple Airlines
Deal found 10-2S$ 1,681
Sun 22-314:25
SIN
-
MDW
2 stops28h 15m
Multiple Airlines
Mon 6-411:50
MDW
-
SIN
2 stops35h 45m
Multiple Airlines
Deal found 11-2S$ 1,703
Wed 1-407:30
SIN
-
MDW
2 stops28h 01m
Delta
Thu 16-406:00
MDW
-
SIN
2 stops34h 00m
Delta
Deal found 10-2S$ 1,789
Fri 27-314:25
SIN
-
MDW
2 stops28h 15m
Multiple Airlines
Fri 3-411:50
MDW
-
SIN
2 stops35h 45m
Multiple Airlines
Deal found 10-2S$ 1,899
Thu 26-310:40
SIN
-
MDW
2 stops24h 51m
Delta
Thu 2-406:00
MDW
-
SIN
2 stops34h 00m
Delta
Deal found 9-2S$ 2,015
Thu 12-214:25
SIN
-
MDW
2 stops37h 05m
Multiple Airlines
Wed 25-208:10
MDW
-
SIN
3 stops38h 55m
Multiple Airlines
Deal found 8-2S$ 2,244
Tue 10-214:25
SIN
-
MDW
2 stops28h 30m
Multiple Airlines
Fri 20-208:05
MDW
-
SIN
2 stops39h 00m
Multiple Airlines
Deal found 9-2S$ 2,328
Sat 28-322:30
SIN
-
MDW
2 stops31h 52m
Delta
Sat 4-416:30
MDW
-
SIN
2 stops42h 10m
Delta
Deal found 10-2S$ 2,362

Find flight deals from Singapore to Midway

Keep the following information in mind while searching for Singapore to Midway flight deals. Data was last updated 11 February 2026.

Round-trip from

S$ 1,681

One-way from

S$ 753

Popular in

January

Cheapest in

February

Average price

S$ 979
17-3-24-3
  • 17-3-24-3
  • 4 total stops
  • 65h 40m total
  • Singapore to Chicago
Search Deals
Delta
  • Delta
  • 25-3
  • 2 total stops
  • 24h 51m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (S$ 61 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 55 potential savings vs. average return price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 11 February 2026.
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 17-3

14:25-05:55

2 stops28h 30m

Chicago Midway

Tue 24-3

10:55-13:05

2 stops37h 10m

S$ 1,681

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 22-3

14:25-05:40

2 stops28h 15m

Chicago Midway

Mon 6-4

11:50-12:35

2 stops35h 45m

S$ 1,703

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 1-4

07:30-22:31

2 stops28h 01m

Chicago Midway

Thu 16-4

06:00-05:00

2 stops34h 00m

S$ 1,789

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 26-3

10:40-22:31

2 stops24h 51m

Chicago Midway

Thu 2-4

06:00-05:00

2 stops34h 00m

S$ 2,015

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 28-3

22:30-17:22

2 stops31h 52m

Chicago Midway

Sat 4-4

16:30-23:40

2 stops42h 10m

S$ 2,362

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 9-4

13:45-05:55

2 stops29h 10m

Chicago Midway

Mon 20-4

10:35-12:35

2 stops37h 00m

S$ 5,692

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 5-4

13:45-11:10

2 stops34h 25m

Chicago Midway

Thu 16-4

18:10-12:35

2 stops29h 25m

S$ 5,956

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 10-4

13:45-14:40

3 stops37h 55m

Chicago Midway

Tue 21-4

15:55-12:35

2 stops31h 40m

S$ 7,290

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 27-3

14:25-05:55

2 stops28h 30m

Chicago Midway

Fri 3-4

11:50-12:35

2 stops35h 45m

S$ 7,290

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 25-3

10:40-22:31

2 stops24h 51m

S$ 753

Flights are sorted by cheapest return flights first.

Deals found on 7-2

Showing 1-10 of 17 results
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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 28h 01m. 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

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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.

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