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Cheap flights from Singapore to Chicago Midway Airport from S$ 655

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 21-2. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
22 gen — 29 gen1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Singapore to Midway

Enter your travel dates to find the best prices.

Best flights from Singapore to Midway
Discover carefully curated flight deals from Singapore to Midway that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 23 dicembre 2025.

mer 11-210:40SIN - MDW
2 stops25h 42mDelta
mer 18-212:45MDW - SIN
2 stops41h 40mDelta
Deal found 22-12S$ 1,288
lun 2-214:25SIN - MDW
2 stops36h 15mMultiple Airlines
dom 15-208:15MDW - SIN
2 stops38h 50mMultiple Airlines
Deal found 22-12S$ 1,485
mar 3-201:35SIN - MDW
2 stops34h 47mDelta
mer 11-206:00MDW - SIN
2 stops28h 10mDelta
Deal found 21-12S$ 1,288
mer 11-214:25SIN - MDW
2 stops35h 30mMultiple Airlines
mer 18-208:10MDW - SIN
3 stops38h 55mMultiple Airlines
Deal found 22-12S$ 1,739
mar 10-210:40SIN - MDW
2 stops25h 42mDelta
ven 20-206:00MDW - SIN
2 stops33h 00mDelta
Deal found 21-12S$ 1,609
mer 4-201:35SIN - MDW
2 stops34h 47mDelta
gio 12-206:00MDW - SIN
2 stops33h 00mDelta
Deal found 22-12S$ 1,768
mer 4-214:25SIN - MDW
2 stops36h 00mMultiple Airlines
mer 11-211:10MDW - SIN
3 stops35h 55mMultiple Airlines
Deal found 21-12S$ 2,138
mar 10-214:25SIN - MDW
2 stops36h 15mMultiple Airlines
ven 20-216:55MDW - SIN
3 stops41h 45mMultiple Airlines
Deal found 22-12S$ 2,498

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 23 dicembre 2025.

Round-trip from

S$ 1,288

One-way from

S$ 655

Popular in

January

Cheapest in

April

Average price

S$ 1,613
Delta
  • Delta
  • 3-2-11-2
  • 4 total stops
  • 62h 57m total
  • Singapore to Chicago
Search Deals
21-2
  • 21-2
  • 2 total stops
  • 34h 49m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (S$ 335 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (S$ 98 potential savings vs. average return price).
Search Deals
Average for round-trip flights in December 2025
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 23 dicembre 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

mer 11-2

10:40-22:22

2 stops25h 42m

Chicago Midway

mer 18-2

12:45-20:25

2 stops41h 40m

S$ 1,288

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

mar 3-2

01:35-22:22

2 stops34h 47m

Chicago Midway

mer 11-2

06:00-00:10

2 stops28h 10m

S$ 1,288

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

lun 2-2

14:25-12:40

2 stops36h 15m

Chicago Midway

dom 15-2

08:15-13:05

2 stops38h 50m

S$ 1,485

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

mar 10-2

10:40-22:22

2 stops25h 42m

Chicago Midway

ven 20-2

06:00-05:00

2 stops33h 00m

S$ 1,609

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

mer 11-2

14:25-11:55

2 stops35h 30m

Chicago Midway

mer 18-2

08:10-13:05

3 stops38h 55m

S$ 1,739

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

mer 4-2

01:35-22:22

2 stops34h 47m

Chicago Midway

gio 12-2

06:00-05:00

2 stops33h 00m

S$ 1,768

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

mer 4-2

14:25-12:25

2 stops36h 00m

Chicago Midway

mer 11-2

11:10-13:05

3 stops35h 55m

S$ 2,138

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

mar 10-2

14:25-12:40

2 stops36h 15m

Chicago Midway

ven 20-2

16:55-00:40

3 stops41h 45m

S$ 2,498

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

sab 21-2

00:40-21:29

2 stops34h 49m

S$ 655

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

ven 6-2

01:35-22:22

2 stops34h 47m

S$ 755

Flights are sorted by cheapest return flights first.

Deals found on 21-12

Showing 1-10 of 18 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 25h 42m. 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

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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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