S$ 228+ 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 12-8. 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
7 Jul — 14 Jul1
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 7 June 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

Fri 9-10

06:00-05:00

2 stops34h 00m

Singapore Changi

Tue 13-10

01:25-16:25

2 stops28h 00m

S$ 1,495

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 8-11

06:00-05:00

2 stops33h 00m

Singapore Changi

Fri 13-11

22:30-11:56

2 stops27h 26m

S$ 1,558

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 21-7

06:00-23:55

2 stops28h 55m

Singapore Changi

Mon 27-7

01:25-16:15

2 stops27h 50m

S$ 1,617

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 22-7

06:00-23:55

2 stops28h 55m

Singapore Changi

Wed 29-7

22:00-11:56

2 stops26h 56m

S$ 1,617

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 2-8

13:18-23:55

2 stops45h 37m

Singapore Changi

Sat 15-8

22:00-22:36

2 stops37h 36m

S$ 1,624

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 31-7

06:00-05:00

2 stops34h 00m

Singapore Changi

Mon 10-8

01:25-16:15

2 stops27h 50m

S$ 1,669

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 18-7

18:35-19:15

2 stops59h 40m

Singapore Changi

Sat 25-7

22:00-18:18

2 stops57h 18m

S$ 1,807

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 28-7

09:54-23:55

2 stops25h 01m

Singapore Changi

Fri 14-8

22:00-15:38

2 stops30h 38m

S$ 1,812

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 26-7

19:06-23:55

2 stops39h 49m

Singapore Changi

Tue 11-8

22:00-11:51

2 stops26h 51m

S$ 1,852

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 12-11

06:00-05:00

2 stops33h 00m

Singapore Changi

Fri 27-11

01:35-21:45

2 stops34h 10m

S$ 1,927

Flights are sorted by cheapest return flights first.

Deals found on 4-6

Showing 1-10 of 20 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 7 June 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 7 June 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, 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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