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S$ 108+ 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 27-2. 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
19 Jan — 26 Jan1
1 adult

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 14 January 2025.

Wed 12-206:00MDW - SIN
2 stops28h 10mDelta
Wed 19-211:00SIN - MDW
2 stops25h 20mDelta
Deal found 13-1S$ 1,516
Tue 18-309:25MDW - SIN
2 stops30h 35mKorean Air
Sun 23-322:30SIN - MDW
2 stops27h 06mKorean Air
Deal found 13-1S$ 1,950
Tue 1-709:30MDW - SIN
2 stops25h 10mMultiple Airlines
Tue 15-701:10SIN - MDW
2 stops24h 20mMultiple Airlines
Deal found 13-1S$ 2,249
Wed 12-217:07MDW - SIN
2 stops33h 08mKLM
Tue 18-201:40SIN - MDW
2 stops28h 41mKLM
Deal found 13-1S$ 2,465

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 14 January 2025. In the last 7 days, Cheapflights users made a total of 200,618 searches

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 12-2

06:00-05:00

2 stops33h 00m

Singapore Changi

Tue 18-2

01:30-22:20

2 stops34h 50m

S$ 1,516

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 16-4

09:30-23:40

2 stops25h 10m

Singapore Changi

Wed 23-4

01:10-12:30

2 stops24h 20m

S$ 2,122

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 1-7

09:30-23:40

2 stops25h 10m

Singapore Changi

Tue 15-7

01:10-12:30

2 stops24h 20m

S$ 2,249

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 26-2

17:07-16:15

2 stops33h 08m

Singapore Changi

Tue 4-3

01:40-16:20

2 stops28h 40m

S$ 2,435

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 24-1

13:26-09:00

2 stops29h 34m

Singapore Changi

Sun 2-2

22:55-16:20

2 stops31h 25m

S$ 2,539

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 27-2

06:40-19:05

2 stops46h 25m

S$ 733

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 26-2

06:00-00:10

2 stops28h 10m

S$ 852

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 25-6

09:30-05:00

2 stops30h 30m

S$ 1,710

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 25-2

14:08-09:00

2 stops28h 52m

S$ 8,266

Flights are sorted by cheapest return flights first.

Deals found on 12-1

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 (180 flights per day), Atlanta (149 flights per day) and Orlando (104 flights per day).

San Francisco

San Francisco

From S$ 107

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 San Francisco, with prices starting at S$ 147. Explore other affordable destinations below.

San Francisco

San Francisco

From S$ 107

Buffalo

Buffalo

From S$ 199

Airline reviews for flights from Midway

Get insights into the airlines that provide service from Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Midway. In the last 7 days, Cheapflights users made a total of 200,618 searches.
Korean Air
8.5
Very Good
1,032 reviews
Check prices

Entertainment

8.2

Comfort

8.3

Overall

8.5

Boarding

8.5

Crew

8.7

Food

8.1

Reviews

1 / 10

Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.

Korean Air
8.5
Very Good
1,032 reviews
Korean Air
8.5
Very Good
1,032 reviews
Check prices

Entertainment

8.2

Comfort

8.3

Overall

8.5

Boarding

8.5

Crew

8.7

Food

8.1

Reviews

1 / 10

Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.

Delta
8.0
Very Good
8,505 reviews
Korean Air
8.5
Very Good
1,032 reviews
Check prices

Entertainment

8.2

Comfort

8.3

Overall

8.5

Boarding

8.5

Crew

8.7

Food

8.1

Reviews

1 / 10

Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.

KLM
7.8
Good
1,336 reviews
Korean Air
8.5
Very Good
1,032 reviews
Check prices

Entertainment

8.2

Comfort

8.3

Overall

8.5

Boarding

8.5

Crew

8.7

Food

8.1

Reviews

1 / 10

Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.

Air France
7.4
Good
1,486 reviews
Korean Air
8.5
Very Good
1,032 reviews
Check prices

Entertainment

8.2

Comfort

8.3

Overall

8.5

Boarding

8.5

Crew

8.7

Food

8.1

Reviews

1 / 10

Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.

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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 14 January 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 14 January 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 Cancún, Atlanta, Las Vegas. Throughout the year, Las Vegas, Atlanta, Orlando Airport 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$ 147 to San Francisco (prices may vary depending on the airline and departure time). On average, users have booked flights for S$ 226 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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Fly with Cheapflights

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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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