Find flights
When to book
FAQs

Cheap flights from Singapore to Chicago Midway Airport from S$ 759

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 23-1. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
6 Dec — 13 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Singapore to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Singapore (SIN) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 6 November 2025.

Round-trip from

S$ 1,379

One-way from

S$ 759

Popular in

January

Cheapest in

October

Average price

S$ 1,261
Delta
  • Delta
  • 3-4-23-4
  • 4 total stops
  • 55h 55m total
  • Singapore to Chicago
Search Deals
23-1
  • 23-1
  • 3 total stops
  • 38h 05m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (S$ 236 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (S$ 59 potential savings vs. average return price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Find 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 6 November 2025.

Fri 7-1115:45SIN - MDW
2 stops27h 30mMultiple Airlines
Sun 23-1117:25MDW - SIN
2 stops28h 40mMultiple Airlines
Deal found 5-11S$ 1,592
Fri 14-1115:45SIN - MDW
2 stops27h 30mMultiple Airlines
Tue 17-216:40MDW - SIN
2 stops29h 25mMultiple Airlines
Deal found 5-11S$ 1,684
Wed 19-1113:15SIN - MDW
2 stops29h 45mMultiple Airlines
Sat 22-1119:00MDW - SIN
2 stops27h 05mMultiple Airlines
Deal found 5-11S$ 1,827
Sat 20-1215:45SIN - MDW
2 stops27h 30mMultiple Airlines
Sat 27-1219:00MDW - SIN
2 stops27h 05mMultiple Airlines
Deal found 5-11S$ 1,842
Mon 15-1201:40SIN - MDW
2 stops29h 04mMultiple Airlines
Wed 31-1218:08MDW - SIN
2 stops24h 52mMultiple Airlines
Deal found 3-11S$ 2,728
Tue 16-1222:30SIN - MDW
2 stops32h 04mDelta
Wed 31-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 3-11S$ 3,117
Thu 13-1101:40SIN - MDW
2 stops28h 58mMultiple Airlines
Mon 16-218:40MDW - SIN
2 stops32h 15mMultiple Airlines
Deal found 5-11S$ 3,268
Mon 22-1222:30SIN - MDW
2 stops27h 28mDelta
Mon 29-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 3-11S$ 4,170
Thu 6-1101:40SIN - MDW
2 stops28h 34mKLM
Sun 23-1113:05MDW - SIN
2 stops29h 55mKLM
Deal found 5-11S$ 4,734
Tue 18-1101:35SIN - MDW
2 stops36h 05mDelta
Sat 22-1119:02MDW - SIN
2 stops39h 08mDelta
Deal found 5-11S$ 10,757
Thu 18-1215:45SIN - MDW
2 stops27h 30mMultiple Airlines
Sat 3-119:00MDW - SIN
2 stops27h 05mMultiple Airlines
Deal found 5-11S$ 11,152
Thu 18-1222:30SIN - MDW
2 stops27h 25mDelta
Sat 3-106:00MDW - SIN
2 stops33h 00mDelta
Deal found 4-11S$ 12,434

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 6 November 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

Thu 16-4

07:30-13:07

2 stops42h 37m

Chicago Midway

Mon 20-4

09:20-23:40

2 stops25h 20m

S$ 1,414

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 19-11

13:15-05:00

2 stops29h 45m

Chicago Midway

Sat 22-11

19:00-12:05

2 stops27h 05m

S$ 1,592

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$ 1,772

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 20-12

15:45-05:15

2 stops27h 30m

Chicago Midway

Sat 27-12

19:00-12:05

2 stops27h 05m

S$ 1,842

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 25-1

10:30-23:25

3 stops50h 55m

S$ 795

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 16-11

19:25-20:31

2 stops39h 06m

S$ 816

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 14-4

07:30-09:51

2 stops39h 21m

S$ 823

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 7-2

01:35-22:26

2 stops34h 51m

S$ 825

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 6-2

22:30-22:26

2 stops37h 56m

S$ 825

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 25-1

22:30-22:26

2 stops37h 56m

S$ 826

Flights are sorted by cheapest return flights first.

Deals found on 4-11

Showing 1-10 of 13 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.

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.

  • What airport do you fly from for flights from Singapore to Chicago Midway?

    Singapore Changi (SIN) is the airport you will fly out of if you book a flight from Singapore to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Changi; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Singapore airport to Chicago Midway. It is only a 16.9 km journey to Changi (SIN) from Singapore’s city centre.

  • 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 42h 37m. 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

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 makes it easy to find Singapore to 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 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?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Singapore to Midway, users can toggle the no change fees filter when performing a flight search.

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

Not ready to book yet? You can track prices for flights from Singapore to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.

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.