S$ 169+ 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 18-2. 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
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

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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 12 December 2025.

Mon 26-111:10MDW - SIN
3 stops35h 55mMultiple Airlines
Mon 2-214:25SIN - MDW
2 stops28h 35mMultiple Airlines
Deal found 12-12S$ 1,652
Fri 23-118:14MDW - SIN
2 stops39h 56mDelta
Thu 29-101:35SIN - MDW
2 stops34h 47mDelta
Deal found 10-12S$ 1,682
Mon 26-110:35MDW - SIN
2 stops36h 30mMultiple Airlines
Mon 9-214:25SIN - MDW
2 stops36h 15mMultiple Airlines
Deal found 10-12S$ 1,706
Fri 23-107:45MDW - SIN
2 stops39h 20mMultiple Airlines
Sat 31-114:25SIN - MDW
2 stops35h 50mMultiple Airlines
Deal found 11-12S$ 1,721
Sat 24-108:25MDW - SIN
2 stops38h 40mMultiple Airlines
Sat 31-114:25SIN - MDW
2 stops36h 05mMultiple Airlines
Deal found 10-12S$ 1,749
Fri 22-506:00MDW - SIN
2 stops34h 00mDelta
Fri 5-601:10SIN - MDW
2 stops27h 15mDelta
Deal found 11-12S$ 1,794
Sun 25-115:40MDW - SIN
3 stops31h 25mMultiple Airlines
Wed 4-214:25SIN - MDW
3 stops38h 30mMultiple Airlines
Deal found 12-12S$ 1,838
Mon 9-215:40MDW - SIN
3 stops31h 25mMultiple Airlines
Sun 8-314:25SIN - MDW
2 stops33h 45mMultiple Airlines
Deal found 10-12S$ 1,852

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 12 December 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 26-1

11:10-13:05

3 stops35h 55m

Singapore Changi

Mon 2-2

14:25-05:00

2 stops28h 35m

S$ 1,652

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 4-3

06:00-05:00

2 stops33h 00m

Singapore Changi

Sat 28-3

01:35-22:29

2 stops33h 54m

S$ 1,682

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 26-1

10:35-13:05

2 stops36h 30m

Singapore Changi

Mon 9-2

14:25-12:40

2 stops36h 15m

S$ 1,706

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 23-1

07:45-13:05

2 stops39h 20m

Singapore Changi

Sat 31-1

14:25-12:15

2 stops35h 50m

S$ 1,721

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 25-1

15:40-13:05

3 stops31h 25m

Singapore Changi

Wed 4-2

14:25-14:55

3 stops38h 30m

S$ 1,838

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 9-2

15:40-13:05

3 stops31h 25m

Singapore Changi

Sun 8-3

14:25-10:10

2 stops33h 45m

S$ 1,852

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 22-5

16:35-12:35

3 stops31h 00m

Singapore Changi

Sat 6-6

13:45-05:40

2 stops28h 55m

S$ 1,966

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 23-1

18:14-00:10

2 stops39h 56m

Singapore Changi

Sat 31-1

22:30-11:59

2 stops27h 29m

S$ 2,032

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 26-1

06:00-00:10

2 stops28h 10m

S$ 586

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 18-1

18:30-09:15

2 stops48h 45m

S$ 605

Flights are sorted by cheapest return flights first.

Deals found on 12-12

Showing 1-10 of 18 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 12 December 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 12 December 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, Orlando Airport, Miami. 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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