S$ 150+ 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 22-10. 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
12 Oct — 19 Oct1
1 adult
1 adult, Economy

What to know about flights from Midway

Discover essential information about flights departing from Midway, including flight schedules, destinations, airlines operating at the Midway airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 12 September 2025.

Good round-trip deal

S$ 255 or less
Price to beat on a round-trip flight from Chicago Midway.
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Find flights from Midway

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 12 September 2025.

Mon 3-1106:00MDW - SIN
2 stops33h 00mDelta
Tue 11-1122:30SIN - MDW
2 stops32h 09mDelta
Deal found 11-9S$ 1,134
Sun 2-1105:00MDW - SIN
2 stops33h 00mDelta
Tue 11-1122:30SIN - MDW
2 stops27h 22mDelta
Deal found 9-9S$ 1,149
Tue 21-1009:20MDW - SIN
2 stops30h 40mDelta
Tue 11-1110:40SIN - MDW
2 stops26h 52mDelta
Deal found 10-9S$ 1,202
Wed 29-1009:35MDW - SIN
2 stops25h 35mDelta
Wed 12-1110:40SIN - MDW
2 stops36h 21mDelta
Deal found 12-9S$ 1,208
Wed 26-1106:00MDW - SIN
2 stops33h 00mDelta
Fri 19-1210:40SIN - MDW
2 stops38h 26mDelta
Deal found 10-9S$ 1,224
Mon 23-206:00MDW - SIN
2 stops28h 10mDelta
Thu 26-210:40SIN - MDW
2 stops25h 06mDelta
Deal found 11-9S$ 1,461
Mon 2-206:00MDW - SIN
2 stops28h 10mDelta
Fri 13-201:35SIN - MDW
2 stops34h 11mDelta
Deal found 10-9S$ 1,525
Mon 27-1009:35MDW - SIN
2 stops25h 35mDelta
Sun 9-1122:30SIN - MDW
2 stops33h 38mDelta
Deal found 12-9S$ 1,551
Mon 19-108:15MDW - SIN
2 stops38h 50mMultiple Airlines
Tue 27-102:00SIN - MDW
2 stops26h 45mMultiple Airlines
Deal found 10-9S$ 1,558

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 12 September 2025. 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 3-11

06:00-05:00

2 stops33h 00m

Singapore Changi

Tue 11-11

22:30-16:39

2 stops32h 09m

S$ 1,134

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 2-11

05:00-04:00

2 stops33h 00m

Singapore Changi

Tue 11-11

22:30-11:52

2 stops27h 22m

S$ 1,149

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 21-10

09:20-05:00

2 stops30h 40m

Singapore Changi

Tue 11-11

10:40-23:32

2 stops26h 52m

S$ 1,202

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 29-10

09:35-00:10

2 stops25h 35m

Singapore Changi

Wed 12-11

10:40-09:01

2 stops36h 21m

S$ 1,208

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 26-11

06:00-05:00

2 stops33h 00m

Singapore Changi

Fri 19-12

10:40-11:06

2 stops38h 26m

S$ 1,224

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 23-2

06:00-00:10

2 stops28h 10m

Singapore Changi

Thu 26-2

10:40-21:46

2 stops25h 06m

S$ 1,461

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 2-2

06:00-00:10

2 stops28h 10m

Singapore Changi

Fri 13-2

01:35-21:46

2 stops34h 11m

S$ 1,525

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 9-2

06:00-05:00

2 stops33h 00m

Singapore Changi

Sun 8-3

10:40-08:56

2 stops36h 16m

S$ 1,531

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 19-10

12:09-23:20

3 stops46h 11m

S$ 552

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 25-9

08:15-18:55

3 stops45h 40m

S$ 553

Flights are sorted by cheapest return flights first.

Deals found on 11-9

Showing 1-10 of 15 results
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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.

What are popular destinations to fly to from Chicago Midway Airport?

From Chicago Midway Airport you can expect to find greater availability for the following destinations: Detroit (232 flights per day), Atlanta (125 flights per day) and Minneapolis (89 flights per day).

Buffalo
Buffalo
From S$ 199

What is the cheapest place to fly to from Chicago Midway Airport?

The cheapest city to fly to from Chicago Midway Airport is Buffalo, with prices starting at S$ 255. Explore other affordable destinations below.

Buffalo
Buffalo
From S$ 199

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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 12 September 2025.
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 12 September 2025.

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

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

  • What is the cheapest flight from Chicago Midway Airport to anywhere?

    Users have flown out of Chicago Midway Airport for as low as S$ 255 to Buffalo (prices may vary depending on the airline and departure time). On average, users have booked flights for S$ 255 to fly 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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