S$ 199+ Cheap flights from Chicago Midway Airport

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3-3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — SIN
26 Feb — 5 Mar1
1 adult
1 adult, Economy, 0 bags

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Enter your travel dates to find the best prices.

Cheapest flights from Midway
Explore the most affordable flight options available from Midway. Find the lowest fares based on data from user searches, with prices last updated on 27 January 2026.

Mon 9-218:35
MDW
-
SIN
2 stops39h 35m
Delta
Sun 8-322:30
SIN
-
MDW
2 stops37h 01m
Delta
Deal found 24-1S$ 1,142
Tue 17-309:35
MDW
-
SIN
2 stops25h 35m
Delta
Fri 27-310:40
SIN
-
MDW
2 stops36h 16m
Delta
Deal found 25-1S$ 1,331
Mon 16-318:34
MDW
-
SIN
2 stops40h 36m
Delta
Fri 27-310:40
SIN
-
MDW
2 stops36h 16m
Delta
Deal found 25-1S$ 1,339
Sat 28-217:00
MDW
-
SIN
2 stops41h 10m
Delta
Sun 8-322:30
SIN
-
MDW
2 stops57h 10m
Delta
Deal found 24-1S$ 1,342
Tue 3-318:40
MDW
-
SIN
2 stops35h 45m
Delta
Tue 10-310:40
SIN
-
MDW
2 stops24h 51m
Delta
Deal found 24-1S$ 1,387
Mon 16-318:34
MDW
-
SIN
2 stops40h 36m
Delta
Tue 31-322:30
SIN
-
MDW
2 stops26h 59m
Delta
Deal found 25-1S$ 1,394
Sat 28-217:00
MDW
-
SIN
2 stops41h 10m
Delta
Sat 7-310:40
SIN
-
MDW
2 stops25h 51m
Delta
Deal found 24-1S$ 1,397
Tue 17-309:35
MDW
-
SIN
2 stops25h 35m
Delta
Wed 25-310:40
SIN
-
MDW
2 stops35h 10m
Delta
Deal found 25-1S$ 1,420
Tue 17-309:35
MDW
-
SIN
2 stops30h 25m
Delta
Thu 26-322:30
SIN
-
MDW
2 stops37h 01m
Delta
Deal found 26-1S$ 1,517
Tue 10-312:47
MDW
-
SIN
2 stops42h 38m
Delta
Tue 17-322:30
SIN
-
MDW
2 stops37h 01m
Delta
Deal found 23-1S$ 1,578
Mon 20-406:00
MDW
-
SIN
2 stops34h 00m
Delta
Mon 4-522:30
SIN
-
MDW
2 stops26h 37m
Delta
Deal found 25-1S$ 1,580

Find flights from Midway within your budget

 
Find flights departing from Midway that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 27 January 2026. In the last 7 days, Cheapflights users made a total of 200,618 searches

Fly to

Singapore

Route

Depart

Return

Price

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 9-2

18:35-00:10

2 stops39h 35m

Singapore Changi

Sun 8-3

22:30-22:31

2 stops37h 01m

S$ 1,142

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 17-3

09:35-00:10

2 stops25h 35m

Singapore Changi

Fri 27-3

10:40-09:56

2 stops36h 16m

S$ 1,331

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 16-3

18:34-00:10

2 stops40h 36m

Singapore Changi

Fri 27-3

10:40-09:56

2 stops36h 16m

S$ 1,339

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 28-2

17:00-00:10

2 stops41h 10m

Singapore Changi

Sun 8-3

22:30-18:40

2 stops57h 10m

S$ 1,342

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 9-3

09:35-05:00

2 stops30h 25m

Singapore Changi

Mon 16-3

22:30-22:31

2 stops37h 01m

S$ 1,387

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 28-2

17:00-00:10

2 stops41h 10m

Singapore Changi

Sat 7-3

10:40-22:31

2 stops25h 51m

S$ 1,397

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 24-4

09:27-05:00

2 stops30h 33m

Singapore Changi

Sat 9-5

07:30-21:45

2 stops27h 15m

S$ 1,517

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 10-3

12:47-20:25

2 stops42h 38m

Singapore Changi

Tue 17-3

22:30-22:31

2 stops37h 01m

S$ 1,578

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 20-4

06:00-05:00

2 stops34h 00m

Singapore Changi

Mon 4-5

22:30-12:07

2 stops26h 37m

S$ 1,580

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 9-2

19:16-00:10

2 stops38h 54m

Singapore Changi

Mon 16-2

22:30-11:59

2 stops27h 29m

S$ 1,584

Flights are sorted by cheapest return flights first.

Deals found on 26-1

Showing 1-10 of 21 results
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Best time to book a flight from Midway

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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.

Travel insights for flights from Midway

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Alternate flight departure points to Midway

Consider leaving from one of these other departure points that are located a short distance from Midway. Flight origins were last updated on 27 January 2026.
Flights from St. Louis
Flights from O'Hare Intl
Flights from Belleville
Flights from Springfield
Flights from Paducah

Related info for your journey

Access useful and relevant information related to your journey from Midway. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 27 January 2026.

  • What are the most popular destinations to fly to from Chicago Midway Airport?

    This month, the top selected destinations from Chicago Midway Airport are Cancún, Atlanta, Miami. Throughout the year, Atlanta, Las Vegas, Orlando Airport are some of the top choices made by users flying from Chicago Midway Airport.

  • How does Cheapflights help users find flights from Midway?

    Cheapflights helps you search for flights from Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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

    Cheapflights helps you find that perfect flight from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

  • Can Cheapflights find flights from Midway with no change fees?

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

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

    Yes! Start tracking prices for flights from Midway today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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How does Cheapflights help users find flights from Midway?

Cheapflights helps you search for flights from Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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

Cheapflights helps you find that perfect flight from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Midway with no change fees?

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

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

Yes! Start tracking prices for flights from Midway today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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