S$ 200+ 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 5-5. 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
9 May — 16 May1
1 adult
1 adult, Economy, 0 bags

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 9 April 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

Tue 1-9

09:20-05:00

2 stops30h 40m

Singapore Changi

Tue 29-9

07:30-21:46

2 stops27h 16m

S$ 1,564

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 25-8

09:20-23:55

2 stops25h 35m

Singapore Changi

Tue 1-9

07:30-21:46

2 stops27h 16m

S$ 1,660

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 7-5

06:23-23:55

2 stops28h 32m

Singapore Changi

Sun 10-5

22:00-16:12

2 stops31h 12m

S$ 1,660

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 23-4

09:27-05:00

2 stops30h 33m

Singapore Changi

Mon 4-5

07:30-22:28

2 stops27h 58m

S$ 1,715

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 6-10

20:40-12:35

2 stops26h 55m

Singapore Changi

Sun 11-10

13:45-05:45

2 stops29h 00m

S$ 1,722

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 12-8

20:30-11:55

2 stops26h 25m

Singapore Changi

Wed 19-8

15:20-05:50

2 stops27h 30m

S$ 1,799

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 9-7

06:05-23:55

2 stops28h 50m

Singapore Changi

Mon 10-8

22:00-11:54

2 stops26h 54m

S$ 1,985

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 11-8

06:00-23:55

2 stops28h 55m

Singapore Changi

Tue 18-8

22:00-16:27

2 stops31h 27m

S$ 2,001

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 13-8

06:00-23:55

2 stops28h 55m

Singapore Changi

Thu 20-8

22:00-11:54

2 stops26h 54m

S$ 2,010
Fastest return journey

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 1-7

09:54-23:55

2 stops25h 01m

Singapore Changi

Mon 6-7

01:25-12:33

2 stops24h 08m

S$ 2,041

Flights are sorted by cheapest return flights first.

Deals found on 8-4

Showing 1-10 of 22 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

Get recent, data-driven insights about flights from Midway including ideal travel times, pricing trends, and more.
No data available for this route at this time. Please check back soon.

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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 9 April 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 9 April 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 Los Angeles, Atlanta, Las Vegas. 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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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 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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