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Cheap flights from Singapore to Chicago Midway Airport from S$ 803

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 28-7. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
5 Apr — 12 Apr1
1 adult

Cheap flight deals from Singapore to Midway

Keep the following information in mind while searching for Singapore to Midway flight deals. Data was last updated 31 March 2025.

Round-trip from

S$ 1,992

One-way from

S$ 803

Popular in

August

Cheapest in

February

Average price

S$ 1,387
Delta
  • Delta
  • 10-6-18-7
  • 4 total stops
  • 55h 39m total
  • Singapore to Chicago
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28-7
  • 28-7
  • 2 total stops
  • 43h 15m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (S$ 197 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (S$ 47 potential savings vs. average return price).
Search Deals
Average for round-trip flights in March 2025
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Find flight deals from Singapore to Midway

Cheapest flights from Singapore to Midway
Explore the most affordable flight options available from Singapore to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 31 March 2025.

Mon 7-422:30SIN - MDW
2 stops27h 05mDelta
Sun 20-409:20MDW - SIN
2 stops30h 40mDelta
Deal found 30-3S$ 1,656
Wed 7-500:40SIN - MDW
2 stops27h 50mKLM
Tue 13-518:25MDW - SIN
2 stops32h 05mKLM
Deal found 31-3S$ 2,669
Mon 9-600:40SIN - MDW
2 stops27h 59mMultiple Airlines
Fri 18-717:59MDW - SIN
2 stops25h 26mMultiple Airlines
Deal found 29-3S$ 2,764
Wed 23-701:10SIN - MDW
2 stops24h 20mKorean Air
Sun 3-809:30MDW - SIN
2 stops25h 10mKorean Air
Deal found 30-3S$ 3,300

Cheapflights Fare Finder

Customise your flight search to find flights from Singapore to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 200,618 searches. Data last updated 31 March 2025.
Use the filters below to find and compare flights from Singapore to Chicago Midway Airport that are best for you.

Fly from

Singapore

Fly to

Midway

Route

Depart

Return

Price

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 10-6

22:30-12:29

2 stops26h 59m

Chicago Midway

Fri 18-7

06:00-23:40

2 stops28h 40m

S$ 1,992

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 7-5

00:40-15:30

2 stops27h 50m

Chicago Midway

Tue 13-5

18:25-15:30

2 stops32h 05m

S$ 2,669

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 9-6

00:40-15:39

2 stops27h 59m

Chicago Midway

Fri 18-7

17:59-08:25

2 stops25h 26m

S$ 2,764

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 23-7

01:10-12:30

2 stops24h 20m

Chicago Midway

Sun 3-8

09:30-23:40

2 stops25h 10m

S$ 3,300

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 28-7

02:30-08:45

2 stops43h 15m

S$ 803

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 17-6

01:10-21:38

2 stops33h 28m

S$ 1,387

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 19-8

00:40-14:56

2 stops27h 16m

S$ 2,400

Flights are sorted by cheapest return flights first.

Deals found on 30-3

Best time to book a flight from Singapore to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Singapore 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.

Cheapflights Insights

Everything you need to know about your flight from Singapore to Chicago Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 31 March 2025.
Korean Air
8.4
Very Good
1,051 reviews
Check prices

Overall

8.4

Entertainment

8.2

Boarding

8.5

Comfort

8.3

Crew

8.7

Food

8.1

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
1,051 reviews
Korean Air
8.4
Very Good
1,051 reviews
Check prices

Overall

8.4

Entertainment

8.2

Boarding

8.5

Comfort

8.3

Crew

8.7

Food

8.1

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
7,899 reviews
Korean Air
8.4
Very Good
1,051 reviews
Check prices

Overall

8.4

Entertainment

8.2

Boarding

8.5

Comfort

8.3

Crew

8.7

Food

8.1

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
1,321 reviews
Korean Air
8.4
Very Good
1,051 reviews
Check prices

Overall

8.4

Entertainment

8.2

Boarding

8.5

Comfort

8.3

Crew

8.7

Food

8.1

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.

Related info for your journey

Find useful and relevant information for your journey from Singapore to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Singapore to Midway that include hotel bookings?

    Yes. In addition to deals on Singapore to Midway flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Singapore to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Singapore to Midway.

  • Can I find deals for business class flights from Singapore to Midway?

    Yes. Cheapflights offers flight deals from Singapore to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Singapore to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Singapore to O'Hare Intl flights
Singapore to Midway flights

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