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S$ 179+ 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 14-5. 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
5 May — 12 May1
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 30 April 2025.

Good round-trip deal

S$ 260 or less

Good one-way deal

S$ 155 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 30 April 2025.

Sun 7-918:45MDW - SIN
2 stops39h 55mDelta
Sun 21-922:30SIN - MDW
2 stops33h 06mDelta
Deal found 29-4S$ 1,456
Sun 7-909:30MDW - SIN
2 stops25h 10mMultiple Airlines
Sat 20-901:10SIN - MDW
2 stops24h 22mMultiple Airlines
Deal found 29-4S$ 1,781
Sun 22-619:21MDW - SIN
2 stops31h 09mKLM
Wed 2-700:40SIN - MDW
2 stops28h 01mKLM
Deal found 29-4S$ 2,381
Fri 27-609:21MDW - SIN
2 stops25h 19mKorean Air
Sun 13-707:30SIN - MDW
2 stops41h 59mKorean Air
Deal found 28-4S$ 2,895

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 30 April 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

Sun 7-9

18:45-23:40

2 stops39h 55m

Singapore Changi

Sun 21-9

22:30-18:36

2 stops33h 06m

S$ 1,456

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 7-9

09:30-23:40

2 stops25h 10m

Singapore Changi

Sat 20-9

01:10-12:32

2 stops24h 22m

S$ 1,781

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 22-6

19:21-15:30

2 stops31h 09m

Singapore Changi

Wed 2-7

00:40-15:41

2 stops28h 01m

S$ 2,381

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 27-6

09:21-23:40

2 stops25h 19m

Singapore Changi

Sun 13-7

07:30-12:29

2 stops41h 59m

S$ 2,895

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 18-5

06:15-05:00

2 stops57h 45m

S$ 822

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 14-6

06:00-23:40

2 stops28h 40m

S$ 1,251

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 3-6

09:20-23:40

2 stops25h 20m

S$ 1,596

Flights are sorted by cheapest return flights first.

Deals found on 29-4

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 (202 flights per day), Atlanta (190 flights per day) and Minneapolis (107 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$ 141. 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
1,066 reviews
Check prices

Comfort

8.3

Food

8.1

Overall

8.4

Boarding

8.5

Crew

8.7

Entertainment

8.2

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
1,066 reviews
Korean Air
8.4
Very Good
1,066 reviews
Check prices

Comfort

8.3

Food

8.1

Overall

8.4

Boarding

8.5

Crew

8.7

Entertainment

8.2

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
7,936 reviews
Korean Air
8.4
Very Good
1,066 reviews
Check prices

Comfort

8.3

Food

8.1

Overall

8.4

Boarding

8.5

Crew

8.7

Entertainment

8.2

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
1,333 reviews
Korean Air
8.4
Very Good
1,066 reviews
Check prices

Comfort

8.3

Food

8.1

Overall

8.4

Boarding

8.5

Crew

8.7

Entertainment

8.2

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 30 April 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 30 April 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, Los Angeles. 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$ 141 to San Francisco (prices may vary depending on the airline and departure time). On average, users have booked flights for S$ 216 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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