S$811 Cheap Flights from Chicago to Singapore

View S$811 flight on Wed, 15 Oct, 2025Opens in a new window

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

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Cheap Flights from Chicago to Singapore (MDW-SIN)

Prices were available within the past 7 days and start at S$811 for one-way flights and S$2,383 for return, for the period specified. Prices and availability are subject to change. Additional terms apply.
Air France
Fri, 20 Jun - Thu, 10 Jul
MDW
Chicago
SIN
Singapore
S$2,383
Return
Found 5 days ago
Select Air France flight, departing Fri, 20 Jun from Chicago to Singapore, returning Thu, 10 Jul, priced at S$2,383 Found 5 days ago
KLM
Fri, 20 Jun - Thu, 10 Jul
MDW
Chicago
SIN
Singapore
S$2,391
Return
Found 5 days ago
Select KLM flight, departing Fri, 20 Jun from Chicago to Singapore, returning Thu, 10 Jul, priced at S$2,391 Found 5 days ago
KLM
Fri, 20 Jun - Thu, 10 Jul
MDW
Chicago
SIN
Singapore
S$2,399
Return
Found 5 days ago
Select KLM flight, departing Fri, 20 Jun from Chicago to Singapore, returning Thu, 10 Jul, priced at S$2,399 Found 5 days ago
Air France
Fri, 20 Jun - Thu, 10 Jul
MDW
Chicago
SIN
Singapore
S$2,447
Return
Found 5 days ago
Select Air France flight, departing Fri, 20 Jun from Chicago to Singapore, returning Thu, 10 Jul, priced at S$2,447 Found 5 days ago
KLM
Fri, 20 Jun - Thu, 10 Jul
MDW
Chicago
SIN
Singapore
S$2,455
Return
Found 5 days ago
Select KLM flight, departing Fri, 20 Jun from Chicago to Singapore, returning Thu, 10 Jul, priced at S$2,455 Found 5 days ago
KLM
Fri, 20 Jun - Thu, 10 Jul
MDW
Chicago
SIN
Singapore
S$2,463
Return
Found 5 days ago
Select KLM flight, departing Fri, 20 Jun from Chicago to Singapore, returning Thu, 10 Jul, priced at S$2,463 Found 5 days ago
Air France
Fri, 20 Jun - Thu, 10 Jul
MDW
Chicago
SIN
Singapore
S$2,511
Return
Found 5 days ago
Select Air France flight, departing Fri, 20 Jun from Chicago to Singapore, returning Thu, 10 Jul, priced at S$2,511 Found 5 days ago
KLM
Fri, 20 Jun - Thu, 10 Jul
MDW
Chicago
SIN
Singapore
S$2,519
Return
Found 5 days ago
Select KLM flight, departing Fri, 20 Jun from Chicago to Singapore, returning Thu, 10 Jul, priced at S$2,519 Found 5 days ago
Delta
Fri, 20 Jun - Thu, 10 Jul
MDW
Chicago
SIN
Singapore
S$2,744
Return
Found 5 days ago
Select Delta flight, departing Fri, 20 Jun from Chicago to Singapore, returning Thu, 10 Jul, priced at S$2,744 Found 5 days ago
Korean Air
Sun, 27 Jul - Sun, 3 Aug
MDW
Chicago
SIN
Singapore
S$6,914
Return
Found 10 hours ago
Select Korean Air flight, departing Sun, 27 Jul from Chicago to Singapore, returning Sun, 3 Aug, priced at S$6,914 Found 10 hours ago
Chicago to Singapore route information
Origin airport
Midway Intl.
Destination airport
Changi
Airlines serving
KLM, Korean Air
Return price
S$2,383
Distance
14986 km

Perfect flights from Chicago to Singapore

Your Journey from Chicago to Singapore

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Singapore 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 Korean Air, Delta, KLM, Air France. Our selection of flights from Midway Intl. to Changi 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 Chicago to Singapore Flights

Experience the joy of finding cheap flights from Midway Intl. to Changi that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$811 and roundtrip prices from S$2,383*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Singapore 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 Singapore

Picture yourself stepping off the plane in Singapore 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 Chicago to Singapore 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 Chicago to Singapore.
 

Beyond the Flight – Exploring Singapore

With Expedia, your adventure extends beyond the flight. Explore Singapore 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 Chicago to Singapore 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 Chicago to Singapore 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 Chicago Airport to SIN?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from Chicago Airport to Changi Airport was S$2,383. Great fares don’t last long, so make sure you book yours ASAP. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MDW to Singapore Airport?
This differs between air carriers, as each has its own terms and conditions. Head to the Customer Service Portal, where there are easy instructions on how to cancel your flight online.
How do I find cheap flights from Midway Airport to Changi Airport 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 MDW to Singapore Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from MDW to Changi Airport?
The distance is around 15,100 kilometres, so fill your carry-on luggage with all the things you need to make your journey comfortable. Wondering what to take on board your Chicago to Singapore flight? A sleep mask, earplugs and a travel pillow are among the essentials.
Which airlines fly direct from MDW to Singapore Airport?
Flying nonstop between Midway Airport and Singapore Airport isn’t possible right now. However, you’ll still be able to find a flight to Singapore with at least one stop.
Are Midway Intl. Airport (MDW) to Singapore Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Midway Intl. Airport (MDW) to Changi Airport (SIN) last minute could save you some serious cash. However, it might cost you a whole lot more! If you’d prefer not to take any chances, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains up to 12 months in advance. If your preferred air carrier hasn’t released tickets yet, check back often as deals are updated on Expedia all the time.

Explore a world of travel with Expedia

Chicago Airports

Chicago

O'Hare Intl. to Singapore
S$1,054.83
*Available to Expedia members.