S$819 Cheap Flights from Singapore to Chicago

View S$819 flight on Tue, 16 Sep, 2025Opens in a new window

Popular airlines from Singapore Changi Airport (SIN) to Chicago Midway Airport (MDW)

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Cheap Flights from Singapore to Chicago (SIN-MDW)

Prices were available within the past 7 days and start at S$819 for one-way flights and S$1,823 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 1 Apr - Mon, 20 Apr
SIN
Singapore
MDW
Chicago
S$1,823 Return, found 6 days ago
S$1,823
Return
found 6 days ago
Select Delta flight, departing Wed, 1 Apr from Singapore to Chicago, returning Mon, 20 Apr, priced at S$1,823 found 6 days ago
Delta
Thu, 21 Aug - Sat, 30 Aug
SIN
Singapore
MDW
Chicago
S$1,850 Return, found 21 hours ago
S$1,850
Return
found 21 hours ago
Select Delta flight, departing Thu, 21 Aug from Singapore to Chicago, returning Sat, 30 Aug, priced at S$1,850 found 21 hours ago
Delta
Mon, 22 Sep - Fri, 26 Sep
SIN
Singapore
MDW
Chicago
S$1,883 Return, found 18 hours ago
S$1,883
Return
found 18 hours ago
Select Delta flight, departing Mon, 22 Sep from Singapore to Chicago, returning Fri, 26 Sep, priced at S$1,883 found 18 hours ago
Delta
Wed, 1 Apr - Mon, 20 Apr
SIN
Singapore
MDW
Chicago
S$1,923 Return, found 6 days ago
S$1,923
Return
found 6 days ago
Select Delta flight, departing Wed, 1 Apr from Singapore to Chicago, returning Mon, 20 Apr, priced at S$1,923 found 6 days ago
Delta
Wed, 1 Apr - Mon, 20 Apr
SIN
Singapore
MDW
Chicago
S$1,963 Return, found 6 days ago
S$1,963
Return
found 6 days ago
Select Delta flight, departing Wed, 1 Apr from Singapore to Chicago, returning Mon, 20 Apr, priced at S$1,963 found 6 days ago
Delta
Thu, 21 Aug - Sat, 30 Aug
SIN
Singapore
MDW
Chicago
S$1,990 Return, found 21 hours ago
S$1,990
Return
found 21 hours ago
Select Delta flight, departing Thu, 21 Aug from Singapore to Chicago, returning Sat, 30 Aug, priced at S$1,990 found 21 hours ago
Delta
Wed, 1 Apr - Mon, 20 Apr
SIN
Singapore
MDW
Chicago
S$2,023 Return, found 6 days ago
S$2,023
Return
found 6 days ago
Select Delta flight, departing Wed, 1 Apr from Singapore to Chicago, returning Mon, 20 Apr, priced at S$2,023 found 6 days ago
Korean Air
Thu, 21 Aug - Sat, 30 Aug
SIN
Singapore
MDW
Chicago
S$2,063 Return, found 21 hours ago
S$2,063
Return
found 21 hours ago
Select Korean Air flight, departing Thu, 21 Aug from Singapore to Chicago, returning Sat, 30 Aug, priced at S$2,063 found 21 hours ago
KLM
Wed, 1 Apr - Mon, 20 Apr
SIN
Singapore
MDW
Chicago
S$2,738 Return, found 6 days ago
S$2,738
Return
found 6 days ago
Select KLM flight, departing Wed, 1 Apr from Singapore to Chicago, returning Mon, 20 Apr, priced at S$2,738 found 6 days ago
Air France
Thu, 21 Aug - Sat, 30 Aug
SIN
Singapore
MDW
Chicago
S$4,437 Return, found 21 hours ago
S$4,437
Return
found 21 hours ago
Select Air France flight, departing Thu, 21 Aug from Singapore to Chicago, returning Sat, 30 Aug, priced at S$4,437 found 21 hours ago
Singapore to Chicago route information
Origin airport
Changi
Destination airport
Midway Intl.
Airlines serving
Air France, Delta, KLM, Korean Air
Return price
S$1,823
Distance
14986 km

Perfect flights from Singapore to Chicago

Your Journey from Singapore to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Singapore to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, Korean Air, Asiana Airlines, Air France, KLM. Our selection of flights from Changi to Midway Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Singapore to Chicago Flights

Experience the joy of finding cheap flights from Changi to Midway Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$819 and roundtrip prices from S$1,823*.
 

Pre-Flight Essentials

Ensure a smooth journey from Singapore to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Singapore to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Singapore to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Singapore to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Singapore to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from SIN to Midway Airport?
Round-trip journeys between SIN and MDW start from S$1,823. This is based on fares offered within the last 7 days on Expedia for flights departing within the next year --- make your booking ASAP so you don't miss out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Changi Airport (SIN) to MDW?
When it comes to cancellation fees, each airline has a different set of terms and conditions. If you decide to cancel your getaway, visit our Customer Service Portal.
How do I find cheap flights from SIN to MDW that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Changi Airport to Chicago Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Changi Airport (SIN) to Midway Airport?
The distance is around 15,100 kilometres. Travel pillow? Check. Noise-cancelling headphones? Check. You'd be wise to pack all the travel comforts for this long-haul Singapore to Chicago flight.
Which airlines fly direct from Singapore Airport to Midway Intl. Airport (MDW)?
Currently, no airlines offer flights directly from Changi Airport (SIN) to Midway Airport. You'll have to book a flight with one or more stops. To get the best connections and price, lock in your airfare well in advance.
Are Singapore Airport to MDW flight tickets cheaper when they're purchased at the last minute?
Flight prices change all the time, so not always. While last-minute flight deals between SIN and Chicago Airport are possible, it's also a good idea to keep an eye on prices well before you fly. In fact, some airlines publish their prices up to a year prior to the departure date. Expedia is continuously updating the best airfare bargains around, so keep checking and be ready to grab your seat when prices drop.

Explore a world of travel with Expedia

Chicago Airports

Chicago

Singapore to O'Hare Intl.
S$875.60
*Available to Expedia members.