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Cheap flights from Singapore to Chicago Midway Airport from S$ 898

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 8-10. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
9 Jul — 16 Jul1
1 adult

Cheap flight deals from Singapore to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Singapore (SIN) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 4 July 2025.

Round-trip from

S$ 1,544

One-way from

S$ 898

Popular in

January

Cheapest in

April

Average price

S$ 1,730
Delta
  • Delta
  • 12-8-31-8
  • 4 total stops
  • 64h 54m total
  • Singapore to Chicago
8-10
  • 8-10
  • 3 total stops
  • 40h 41m total
  • Singapore to Chicago
Highest demand for flights based on searches. 5% potential increase in price (S$ 112 potential increase over avg. return price).
Cheapest flight prices on average. 2% potential price decrease (S$ 44 potential savings vs. average return price).
Average for round-trip flights in July 2025

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 4 July 2025.

Tue 12-822:30SIN - MDW
2 stops36h 14mDelta
Sun 31-806:00MDW - SIN
2 stops28h 40mDelta
Deal found 2-7S$ 1,545
Mon 11-801:10SIN - MDW
2 stops24h 18mMultiple Airlines
Sun 31-809:31MDW - SIN
2 stops25h 09mMultiple Airlines
Deal found 2-7S$ 2,546
Mon 4-800:40SIN - MDW
2 stops28h 30mKLM
Tue 12-818:42MDW - SIN
2 stops31h 48mKLM
Deal found 2-7S$ 2,880
Mon 11-801:10SIN - MDW
2 stops24h 18mKorean Air
Sun 31-809:31MDW - SIN
2 stops25h 09mKorean Air
Deal found 3-7S$ 3,401

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 4 July 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 12-8

22:30-21:44

2 stops36h 14m

Chicago Midway

Sun 31-8

06:00-23:40

2 stops28h 40m

S$ 1,545

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 11-8

01:10-12:28

2 stops24h 18m

Chicago Midway

Sun 31-8

09:31-23:40

2 stops25h 09m

S$ 2,546

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 4-8

00:40-16:10

2 stops28h 30m

Chicago Midway

Tue 12-8

18:42-15:30

2 stops31h 48m

S$ 2,880

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 11-8

01:10-12:28

2 stops24h 18m

Chicago Midway

Sun 31-8

09:31-23:40

2 stops25h 09m

S$ 3,401

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 26-8

01:10-12:28

2 stops24h 18m

S$ 1,013

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 30-7

13:45-23:17

3 stops46h 32m

S$ 1,037

Flights are sorted by cheapest return flights first.

Deals found on 3-7

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.

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 4 July 2025.
Check out reviews from past customers who have flown with Korean Air, Delta, andKLM from Singapore to Chicago Midway Airport to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.5

Crew

8.7

Overall

8.4

Entertainment

8.2

Comfort

8.3

Food

8.1

Reviews

1 / 20
10.0
Excellent

Myung Suk,May 2025

ICN - LAX

The flight was less crowded and the economic class seat was at least 5 inches longer than other airlines.

Boarding

8.5

Crew

8.7

Overall

8.4

Entertainment

8.2

Comfort

8.3

Food

8.1

Reviews

1 / 20
10.0
Excellent

Myung Suk,May 2025

ICN - LAX

The flight was less crowded and the economic class seat was at least 5 inches longer than other airlines.
8.0
Very Good

Boarding

8.5

Crew

8.7

Overall

8.4

Entertainment

8.2

Comfort

8.3

Food

8.1

Reviews

1 / 20
10.0
Excellent

Myung Suk,May 2025

ICN - LAX

The flight was less crowded and the economic class seat was at least 5 inches longer than other airlines.

Boarding

8.5

Crew

8.7

Overall

8.4

Entertainment

8.2

Comfort

8.3

Food

8.1

Reviews

1 / 20
10.0
Excellent

Myung Suk,May 2025

ICN - LAX

The flight was less crowded and the economic class seat was at least 5 inches longer than other airlines.

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.
  • What airport do you fly from for flights from Singapore to Chicago Midway?

    Singapore Changi (SIN) is the airport you will fly out of if you book a flight from Singapore to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Changi; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Singapore airport to Chicago Midway. It is only a 16.9 km journey to Changi (SIN) from Singapore’s city centre.

  • 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.

See more FAQs

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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.

Fly with Cheapflights

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How does Cheapflights help users find flights from Singapore to Midway?

Cheapflights makes it easy to find Singapore to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Singapore to Midway?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Singapore.

Can Cheapflights find flights from Singapore to Midway with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Singapore to Midway, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Singapore to Midway become cheaper?

Not ready to book yet? You can track prices for flights from Singapore to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.

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