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S$ 162+ 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 15-5. 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
30 Mar — 6 Apr1
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 25 March 2025.

Good round-trip deal

S$ 266 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 25 March 2025.

Mon 15-918:50MDW - SIN
2 stops36h 05mDelta
Sun 21-922:30SIN - MDW
2 stops27h 00mDelta
Deal found 24-3S$ 1,480
Fri 9-518:25MDW - SIN
2 stops25h 00mMultiple Airlines
Thu 15-500:40SIN - MDW
2 stops27h 50mMultiple Airlines
Deal found 24-3S$ 2,403
Tue 6-517:59MDW - SIN
2 stops32h 31mKLM
Mon 12-500:40SIN - MDW
2 stops27h 50mKLM
Deal found 23-3S$ 2,404
Sat 5-717:53MDW - SIN
2 stops33h 37mAir France
Sun 13-722:30SIN - MDW
2 stops32h 58mAir France
Deal found 25-3S$ 2,851
Wed 17-909:30MDW - SIN
2 stops25h 10mKorean Air
Tue 30-901:10SIN - MDW
2 stops24h 20mKorean Air
Deal found 24-3S$ 2,926

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 25 March 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 15-9

18:50-19:55

2 stops36h 05m

Singapore Changi

Sun 21-9

22:30-12:30

2 stops27h 00m

S$ 1,480

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 9-5

18:25-08:25

2 stops25h 00m

Singapore Changi

Thu 15-5

00:40-15:30

2 stops27h 50m

S$ 2,403

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 6-5

17:59-15:30

2 stops32h 31m

Singapore Changi

Mon 12-5

00:40-15:30

2 stops27h 50m

S$ 2,404

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 5-7

17:53-16:30

2 stops33h 37m

Singapore Changi

Sun 13-7

22:30-18:28

2 stops32h 58m

S$ 2,851

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 17-9

09:30-23:40

2 stops25h 10m

Singapore Changi

Tue 30-9

01:10-12:30

2 stops24h 20m

S$ 2,926

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 8-5

06:00-05:00

2 stops34h 00m

S$ 931

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 10-4

09:23-23:40

2 stops25h 17m

S$ 934

Flights are sorted by cheapest return flights first.

Deals found on 24-3

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 (168 flights per day), Atlanta (151 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$ 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
1,047 reviews
Check prices

Food

8.1

Boarding

8.5

Crew

8.7

Overall

8.4

Entertainment

8.2

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.
Korean Air
8.4
Very Good
1,047 reviews
Korean Air
8.4
Very Good
1,047 reviews
Check prices

Food

8.1

Boarding

8.5

Crew

8.7

Overall

8.4

Entertainment

8.2

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.
Delta
8.0
Very Good
7,890 reviews
Korean Air
8.4
Very Good
1,047 reviews
Check prices

Food

8.1

Boarding

8.5

Crew

8.7

Overall

8.4

Entertainment

8.2

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.
KLM
7.8
Good
1,318 reviews
Korean Air
8.4
Very Good
1,047 reviews
Check prices

Food

8.1

Boarding

8.5

Crew

8.7

Overall

8.4

Entertainment

8.2

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.
Air France
7.4
Good
1,423 reviews
Korean Air
8.4
Very Good
1,047 reviews
Check prices

Food

8.1

Boarding

8.5

Crew

8.7

Overall

8.4

Entertainment

8.2

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.

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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 25 March 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 25 March 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 Orlando Airport, Las Vegas, Atlanta. 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$ 220 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

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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