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S$ 172+ 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 8-4. 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
25 Feb — 4 Mar1
1 adult

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 20 February 2025.

Good round-trip deal

S$ 267 or less

Good one-way deal

S$ 159 or less
Price to beat on a round-trip flight from Chicago Midway.
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Price to beat on a one-way 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 20 February 2025.

Tue 18-306:00MDW - SIN
2 stops29h 10mDelta
Mon 24-301:30SIN - MDW
2 stops33h 53mDelta
Deal found 19-2S$ 1,485
Mon 7-410:25MDW - SIN
2 stops29h 35mKorean Air
Sun 13-401:10SIN - MDW
2 stops24h 25mKorean Air
Deal found 18-2S$ 2,077
Sat 29-319:13MDW - SIN
2 stops31h 17mKLM
Sun 13-400:40SIN - MDW
2 stops26h 42mKLM
Deal found 19-2S$ 2,414
Tue 4-314:08MDW - SIN
2 stops28h 52mMultiple Airlines
Tue 22-400:40SIN - MDW
2 stops26h 42mMultiple Airlines
Deal found 19-2S$ 2,427
Thu 24-409:52MDW - SIN
2 stops41h 38mAir France
Mon 28-422:30SIN - MDW
2 stops32h 50mAir France
Deal found 19-2S$ 2,490

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 20 February 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

Tue 18-3

12:51-20:25

2 stops42h 34m

Singapore Changi

Tue 25-3

11:00-22:23

2 stops24h 23m

S$ 1,485

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 7-4

10:25-05:00

2 stops29h 35m

Singapore Changi

Sun 13-4

01:10-12:35

2 stops24h 25m

S$ 2,077

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 29-3

19:13-15:30

2 stops31h 17m

Singapore Changi

Sun 13-4

00:40-14:22

2 stops26h 42m

S$ 2,414

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 4-3

14:08-09:00

2 stops28h 52m

Singapore Changi

Tue 22-4

00:40-14:22

2 stops26h 42m

S$ 2,427

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 24-4

09:52-16:30

2 stops41h 38m

Singapore Changi

Mon 28-4

22:30-18:20

2 stops32h 50m

S$ 2,490

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 13-5

09:34-13:20

3 stops38h 46m

S$ 788

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 15-4

16:59-23:40

2 stops41h 41m

S$ 834

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 10-4

10:25-05:00

2 stops29h 35m

S$ 938

Flights are sorted by cheapest return flights first.

Deals found on 19-2

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 (174 flights per day), Atlanta (172 flights per day) and Orlando (152 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$ 144. 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
8.4
Very Good
1,039 reviews
Check prices

Overall

8.4

Comfort

8.2

Entertainment

8.2

Crew

8.7

Food

8.1

Boarding

8.5

Reviews

1 / 20

6.0
Good

Anonymous,Feb 2025

ATL - SBN

Regional jets are small and uncomfortable. When flying in or out of South Bend airport, that's usually what I'm on. It's the price one pays for the great convenience of using a small airport (cheap parking, no lines). The CRJ900 has engines attached to the fuselage near the rear of the plane. So, very loud in the back of the plane, and I happened to have the far back corner that also had no window. Oh well, a short flight and pleasant neighbor and cheerful attendant.

Korean Air
8.4
Very Good
1,039 reviews
Korean Air
8.4
Very Good
1,039 reviews
Check prices

Overall

8.4

Comfort

8.2

Entertainment

8.2

Crew

8.7

Food

8.1

Boarding

8.5

Reviews

1 / 20

6.0
Good

Anonymous,Feb 2025

ATL - SBN

Regional jets are small and uncomfortable. When flying in or out of South Bend airport, that's usually what I'm on. It's the price one pays for the great convenience of using a small airport (cheap parking, no lines). The CRJ900 has engines attached to the fuselage near the rear of the plane. So, very loud in the back of the plane, and I happened to have the far back corner that also had no window. Oh well, a short flight and pleasant neighbor and cheerful attendant.

Delta
8.0
Very Good
8,236 reviews
Korean Air
8.4
Very Good
1,039 reviews
Check prices

Overall

8.4

Comfort

8.2

Entertainment

8.2

Crew

8.7

Food

8.1

Boarding

8.5

Reviews

1 / 20

6.0
Good

Anonymous,Feb 2025

ATL - SBN

Regional jets are small and uncomfortable. When flying in or out of South Bend airport, that's usually what I'm on. It's the price one pays for the great convenience of using a small airport (cheap parking, no lines). The CRJ900 has engines attached to the fuselage near the rear of the plane. So, very loud in the back of the plane, and I happened to have the far back corner that also had no window. Oh well, a short flight and pleasant neighbor and cheerful attendant.

KLM
7.8
Good
1,333 reviews
Korean Air
8.4
Very Good
1,039 reviews
Check prices

Overall

8.4

Comfort

8.2

Entertainment

8.2

Crew

8.7

Food

8.1

Boarding

8.5

Reviews

1 / 20

6.0
Good

Anonymous,Feb 2025

ATL - SBN

Regional jets are small and uncomfortable. When flying in or out of South Bend airport, that's usually what I'm on. It's the price one pays for the great convenience of using a small airport (cheap parking, no lines). The CRJ900 has engines attached to the fuselage near the rear of the plane. So, very loud in the back of the plane, and I happened to have the far back corner that also had no window. Oh well, a short flight and pleasant neighbor and cheerful attendant.

Air France
7.4
Good
1,451 reviews
Korean Air
8.4
Very Good
1,039 reviews
Check prices

Overall

8.4

Comfort

8.2

Entertainment

8.2

Crew

8.7

Food

8.1

Boarding

8.5

Reviews

1 / 20

6.0
Good

Anonymous,Feb 2025

ATL - SBN

Regional jets are small and uncomfortable. When flying in or out of South Bend airport, that's usually what I'm on. It's the price one pays for the great convenience of using a small airport (cheap parking, no lines). The CRJ900 has engines attached to the fuselage near the rear of the plane. So, very loud in the back of the plane, and I happened to have the far back corner that also had no window. Oh well, a short flight and pleasant neighbor and cheerful attendant.

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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 20 February 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 20 February 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, Miami. 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$ 144 to San Francisco (prices may vary depending on the airline and departure time). On average, users have booked flights for S$ 221 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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