S$ 143+ 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 21-4. 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
10 Apr — 17 Apr1
1 adult
1 adult, Economy, 0 bags

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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 11 March 2026.

Mon 4-506:00
MDW
-
SIN
2 stops34h 00m
Delta
Tue 19-522:00
SIN
-
MDW
2 stops31h 12m
Delta
Deal found 10-3S$ 1,214
Mon 6-418:07
MDW
-
SIN
2 stops40h 48m
Delta
Mon 13-422:00
SIN
-
MDW
2 stops31h 29m
Delta
Deal found 10-3S$ 1,221
Fri 24-406:00
MDW
-
SIN
2 stops34h 00m
Delta
Wed 29-422:00
SIN
-
MDW
2 stops31h 26m
Delta
Deal found 10-3S$ 1,278
Wed 22-409:29
MDW
-
SIN
2 stops25h 26m
Delta
Thu 30-401:25
SIN
-
MDW
2 stops28h 01m
Delta
Deal found 10-3S$ 1,469
Wed 8-418:07
MDW
-
SIN
2 stops36h 08m
Delta
Wed 13-507:30
SIN
-
MDW
2 stops26h 39m
Delta
Deal found 6-3S$ 1,578
Thu 23-409:29
MDW
-
SIN
2 stops25h 26m
Delta
Wed 29-401:25
SIN
-
MDW
2 stops34h 03m
Delta
Deal found 10-3S$ 1,596
Mon 7-909:30
MDW
-
SIN
2 stops30h 30m
Delta
Sat 12-922:00
SIN
-
MDW
2 stops27h 30m
Delta
Deal found 6-3S$ 1,642
Sun 29-306:00
MDW
-
SIN
2 stops34h 00m
Delta
Thu 9-422:00
SIN
-
MDW
2 stops32h 22m
Delta
Deal found 10-3S$ 1,660
Tue 18-821:00
MDW
-
SIN
2 stops26h 35m
Multiple Airlines
Mon 24-813:45
SIN
-
MDW
2 stops29h 05m
Multiple Airlines
Deal found 6-3S$ 1,662
Fri 24-411:00
MDW
-
SIN
2 stops36h 35m
Multiple Airlines
Wed 29-413:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Deal found 8-3S$ 1,664
Mon 13-410:35
MDW
-
SIN
2 stops37h 00m
Multiple Airlines
Tue 21-413:45
SIN
-
MDW
2 stops28h 55m
Multiple Airlines
Deal found 7-3S$ 1,676

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 11 March 2026. In the last 7 days, Cheapflights users made a total of 200,618 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 11-5

06:23-05:00

2 stops33h 37m

Singapore Changi

Sun 17-5

22:00-16:12

2 stops31h 12m

S$ 1,214
Fastest return journey

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 9-8

20:35-12:35

2 stops27h 00m

Singapore Changi

Mon 24-8

13:45-05:50

2 stops29h 05m

S$ 1,664

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 24-4

11:00-12:35

2 stops36h 35m

Singapore Changi

Wed 29-4

13:45-05:40

2 stops28h 55m

S$ 1,664

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 25-4

18:00-12:35

2 stops29h 35m

Singapore Changi

Sat 2-5

13:45-05:40

2 stops28h 55m

S$ 1,703

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 15-4

06:00-05:00

2 stops34h 00m

Singapore Changi

Sun 19-4

22:00-16:26

2 stops31h 26m

S$ 1,769

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 6-4

06:00-05:00

2 stops34h 00m

Singapore Changi

Mon 13-4

22:00-16:29

2 stops31h 29m

S$ 1,769

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 14-4

15:55-12:35

2 stops31h 40m

Singapore Changi

Tue 21-4

13:45-11:35

2 stops34h 50m

S$ 1,776

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 17-4

10:10-12:35

2 stops37h 25m

Singapore Changi

Fri 24-4

13:45-05:40

2 stops28h 55m

S$ 1,791

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 17-4

15:05-12:35

2 stops32h 30m

Singapore Changi

Sun 26-4

13:45-05:40

2 stops28h 55m

S$ 1,825

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 3-4

18:07-23:55

2 stops40h 48m

Singapore Changi

Wed 8-4

01:25-22:31

2 stops34h 06m

S$ 1,839

Flights are sorted by cheapest return flights first.

Deals found on 9-3

Showing 1-10 of 21 resultsSorted by cheapest first
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Best time to book a flight from Midway

Have a flexible travel schedule? Discover the best time to fly from Midway 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.

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 11 March 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 11 March 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 Orlando Airport, Las Vegas, Phoenix Sky Harbor Intl Airport. 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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