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.

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).

What is the cheapest time of day to fly from SIN to MDW?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Singapore to Chicago Midway Airport as you normally would.

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.

S$ 727+ Cheap Flights from Singapore to Chicago Midway Airport

Cheap flight deals from Singapore to Midway

Enter your travel dates to find the best prices.

Cheapest

Best

Last-minute

One-way

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 27 October 2026.

Sun 8-1114:25 -

2 stops34h 55m

Wed 11-1115:45 -

2 stops31h 20m

Deal found 25-10S$ 1,522

Thu 5-1102:00 -

2 stops33h 15m

Mon 9-1116:45 -

2 stops30h 20m

Deal found 22-10S$ 1,528

Mon 9-1114:25 -

2 stops29h 40m

Thu 12-1116:45 -

2 stops30h 20m

Deal found 26-10S$ 1,607

Wed 18-1114:25 -

2 stops29h 30m

Mon 23-1116:45 -

2 stops30h 20m

Deal found 25-10S$ 1,610

Mon 9-1122:30 -

2 stops33h 34m

Tue 24-1117:13 -

2 stops41h 02m

Deal found 26-10S$ 1,623

Tue 22-1214:25 -

2 stops29h 40m

Sun 3-118:05 -

2 stops29h 00m

Deal found 26-10S$ 1,688

Find flight deals from Singapore to Midway

Round-trip from	S$ 1,377
One-way from	S$ 727
Popular in	August
Cheapest in	October
Average price	S$ 1,198

Delta
11-2-26-2
4 total stops
67h 30m total
Singapore to Chicago

Search Deals

Delta
23-11-31-12
2 total stops
35h 14m total
Singapore to Chicago

Search Deals

Highest demand for flights based on searches. 15% potential increase in price (S$ 353 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 7% potential price decrease (S$ 144 potential savings vs. average return price).

Search Deals

Average for round-trip flights in October 2026

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from Singapore to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Mon 23-11

01:40-22:54

2 stops35h 14m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 727

Fastest return journey

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Thu 18-3

01:40-16:25

2 stops27h 45m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 800

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Mon 9-11

14:25-06:05

2 stops29h 40m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 902

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 17-11

02:00-22:25

2 stops34h 25m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 914

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Fri 11-12

10:30-15:04

2 stops42h 34m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 928

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sat 12-12

22:30-16:50

2 stops56h 20m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 1,174

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sun 29-11

18:10-11:33

3 stops55h 23m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 1,175

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 12-1

13:15-05:55

2 stops30h 40m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 1,322

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Thu 1-4

13:45-11:25

2 stops34h 40m

Chicago Midway

Sat 10-4

18:20-12:35

2 stops29h 15m

S$ 1,532

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Thu 5-11

02:00-01:10

3 stops37h 10m

Chicago Midway

Mon 9-11

16:45-13:05

2 stops30h 20m

S$ 1,547

Flights are sorted by cheapest return flights first.

Deals found on 25-10

Showing 1-10 of 16 resultsSorted by cheapest first

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.

SIN-MDW

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.

Related info for your journey

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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes

Complete your trip

Direct flights to United States

Flights by cabin class

Other flight options

Popular flights

Alternative routes for Singapore to Midway

Singapore to O'Hare Intl flights

Fly with Cheapflights

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book With Flexibility

Our users can plan ahead with confidence and find flights with no change fees.

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

Cheap flights from Singapore to Chicago Midway Airport from S$ 727

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 23-11. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Singapore to Midway

Cheapest flights from Singapore to MidwayExplore 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 27 October 2026.

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 27 October 2026.

Best flights from Singapore to MidwayDiscover carefully curated flight deals from Singapore to Midway that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 27 October 2026.

Discover carefully curated flight deals from Singapore to Midway that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 27 October 2026.

Last-minute flights from Singapore to MidwayDiscover last-minute flight deals from Singapore to Midway. Data last updated 27 October 2026 and is based on user searches.

Discover last-minute flight deals from Singapore to Midway. Data last updated 27 October 2026 and is based on user searches.

One-way flights from Singapore to MidwaySearch for one-way flight options from Singapore to Midway. Find affordable one-way fares based on user searches. Data last updated 27 October 2026.

Search for one-way flight options from Singapore to Midway. Find affordable one-way fares based on user searches. Data last updated 27 October 2026.

Find flight deals from Singapore to Midway

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Singapore to Chicago Midway Airport that are best for you.

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.

Related info for your journey

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

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

How can I find direct flights from Singapore to Midway?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Singapore to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.

Direct flights to United States

Book a non-stop flight to one of these other cities located in United States.

Search flights from Singapore to Midway by cabin class

Find flights from Singapore to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Singapore and Midway flights

Browse other Singapore and Midway flight options. Last updated on 27 October 2026.

Popular flight searches

Check out other popular destinations found by fellow travellers in 2026

Fly with Cheapflights

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

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

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

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

100% Free

Book With Flexibility

Travel Smart

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 27 October 2026.

Best flights from Singapore to Midway
Discover carefully curated flight deals from Singapore to Midway that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 27 October 2026.

Last-minute flights from Singapore to Midway
Discover last-minute flight deals from Singapore to Midway. Data last updated 27 October 2026 and is based on user searches.

One-way flights from Singapore to Midway
Search for one-way flight options from Singapore to Midway. Find affordable one-way fares based on user searches. Data last updated 27 October 2026.