S$ 152+ 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 8-1. 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
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

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Enter your travel dates to find the best prices.

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 28 October 2025.

Mon 2-317:25MDW - SIN
2 stops40h 45mDelta
Tue 10-310:40SIN - MDW
2 stops38h 55mDelta
Deal found 26-10S$ 1,476
Mon 9-206:00MDW - SIN
2 stops28h 10mDelta
Sat 7-301:35SIN - MDW
2 stops33h 11mDelta
Deal found 27-10S$ 1,541
Sun 12-409:20MDW - SIN
2 stops25h 20mDelta
Wed 15-422:30SIN - MDW
2 stops47h 08mDelta
Deal found 27-10S$ 1,550
Mon 9-208:15MDW - SIN
2 stops38h 50mMultiple Airlines
Wed 18-214:25SIN - MDW
2 stops36h 00mMultiple Airlines
Deal found 27-10S$ 1,560
Mon 9-208:15MDW - SIN
2 stops38h 50mMultiple Airlines
Sun 8-314:25SIN - MDW
2 stops28h 05mMultiple Airlines
Deal found 26-10S$ 1,593
Sat 11-418:10MDW - SIN
2 stops29h 25mMultiple Airlines
Mon 20-413:45SIN - MDW
2 stops28h 55mMultiple Airlines
Deal found 27-10S$ 1,617
Sat 28-318:20MDW - SIN
2 stops29h 15mMultiple Airlines
Sun 5-413:45SIN - MDW
2 stops34h 25mMultiple Airlines
Deal found 27-10S$ 1,629
Wed 14-117:31MDW - SIN
2 stops40h 39mDelta
Sat 31-122:30SIN - MDW
2 stops37h 56mDelta
Deal found 27-10S$ 1,665
Sat 31-115:00MDW - SIN
2 stops32h 05mMultiple Airlines
Sat 21-314:25SIN - MDW
2 stops33h 45mMultiple Airlines
Deal found 27-10S$ 1,666

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 28 October 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 2-3

17:25-00:10

2 stops40h 45m

Singapore Changi

Tue 10-3

10:40-12:35

2 stops38h 55m

S$ 1,476

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 9-2

06:00-00:10

2 stops28h 10m

Singapore Changi

Sat 7-3

01:35-20:46

2 stops33h 11m

S$ 1,541

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 12-4

09:20-05:00

2 stops30h 40m

Singapore Changi

Wed 15-4

22:30-18:05

2 stops56h 35m

S$ 1,550

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 9-2

08:15-13:05

2 stops38h 50m

Singapore Changi

Sun 8-3

14:25-04:30

2 stops28h 05m

S$ 1,593

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 9-2

15:40-13:05

3 stops31h 25m

Singapore Changi

Wed 18-2

14:25-12:25

2 stops36h 00m

S$ 1,596

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 11-4

18:10-12:35

2 stops29h 25m

Singapore Changi

Mon 20-4

13:45-05:40

2 stops28h 55m

S$ 1,617

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 28-3

18:20-12:35

2 stops29h 15m

Singapore Changi

Sun 5-4

13:45-11:10

2 stops34h 25m

S$ 1,629

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 4-4

18:20-12:35

2 stops29h 15m

Singapore Changi

Sat 11-4

13:45-11:30

2 stops34h 45m

S$ 1,629

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 19-11

13:56-14:00

3 stops58h 04m

S$ 573

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Thu 8-1

21:07-17:45

2 stops54h 38m

S$ 616

Flights are sorted by cheapest return flights first.

Deals found on 27-10

Showing 1-10 of 19 results
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Best time to book a flight from Midway

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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

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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 28 October 2025.
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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 28 October 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 Atlanta, Las Vegas, Dallas/Fort Worth Airport. Throughout the year, Atlanta, Las Vegas, Cancún are some of the top choices made by users flying 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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