S$818 Cheap Flights from Singapore to Chicago

View S$818 flight on Fri, 22 May, 2026Opens 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$818 for one-way flights and S$1,921 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Asiana Airlines
Sat, 15 Nov - Sat, 22 Nov
SIN
Singapore
MDW
Chicago
S$1,921 Return, found 6 days ago
S$1,921
Return
found 6 days ago
Select Asiana Airlines flight, departing Sat, 15 Nov from Singapore to Chicago, returning Sat, 22 Nov, priced at S$1,921 found 6 days ago
Asiana Airlines
Sat, 15 Nov - Sat, 22 Nov
SIN
Singapore
MDW
Chicago
S$1,951 Return, found 6 days ago
S$1,951
Return
found 6 days ago
Select Asiana Airlines flight, departing Sat, 15 Nov from Singapore to Chicago, returning Sat, 22 Nov, priced at S$1,951 found 6 days ago
Asiana Airlines
Sat, 15 Nov - Sat, 22 Nov
SIN
Singapore
MDW
Chicago
S$2,063 Return, found 6 days ago
S$2,063
Return
found 6 days ago
Select Asiana Airlines flight, departing Sat, 15 Nov from Singapore to Chicago, returning Sat, 22 Nov, priced at S$2,063 found 6 days ago
Asiana Airlines
Sat, 15 Nov - Sat, 22 Nov
SIN
Singapore
MDW
Chicago
S$2,093 Return, found 6 days ago
S$2,093
Return
found 6 days ago
Select Asiana Airlines flight, departing Sat, 15 Nov from Singapore to Chicago, returning Sat, 22 Nov, priced at S$2,093 found 6 days ago
Asiana Airlines
Mon, 22 Dec - Fri, 27 Mar
SIN
Singapore
MDW
Chicago
S$2,096 Return, found 3 days ago
S$2,096
Return
found 3 days ago
Select Asiana Airlines flight, departing Mon, 22 Dec from Singapore to Chicago, returning Fri, 27 Mar, priced at S$2,096 found 3 days ago
Delta
Wed, 29 Jul - Wed, 26 Aug
SIN
Singapore
MDW
Chicago
S$2,125 Return, found 4 days ago
S$2,125
Return
found 4 days ago
Select Delta flight, departing Wed, 29 Jul from Singapore to Chicago, returning Wed, 26 Aug, priced at S$2,125 found 4 days ago
Delta
Wed, 10 Dec - Wed, 7 Jan
SIN
Singapore
MDW
Chicago
S$2,262 Return, found 10 hours ago
S$2,262
Return
found 10 hours ago
Select Delta flight, departing Wed, 10 Dec from Singapore to Chicago, returning Wed, 7 Jan, priced at S$2,262 found 10 hours ago
Korean Air
Sat, 15 Nov - Sat, 22 Nov
SIN
Singapore
MDW
Chicago
S$2,438 Return, found 6 days ago
S$2,438
Return
found 6 days ago
Select Korean Air flight, departing Sat, 15 Nov from Singapore to Chicago, returning Sat, 22 Nov, priced at S$2,438 found 6 days ago
KLM
Wed, 10 Dec - Wed, 7 Jan
SIN
Singapore
MDW
Chicago
S$2,771 Return, found 10 hours ago
S$2,771
Return
found 10 hours ago
Select KLM flight, departing Wed, 10 Dec from Singapore to Chicago, returning Wed, 7 Jan, priced at S$2,771 found 10 hours ago
Air France
Sat, 15 Nov - Sat, 22 Nov
SIN
Singapore
MDW
Chicago
S$2,864 Return, found 6 days ago
S$2,864
Return
found 6 days ago
Select Air France flight, departing Sat, 15 Nov from Singapore to Chicago, returning Sat, 22 Nov, priced at S$2,864 found 6 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from S$1,089
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from S$1,089

Frequently asked questions

How much is a flight from SIN to Midway Airport?
Round-trip journeys between SIN and MDW start from S$1,921. 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.

Travel information

Travel information

Origin airport
Changi
Destination airport
Midway Intl.
Return price
S$1,920
Distance
14986 km

Book with confidence

Book with confidence

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, Asiana Airlines, Korean Air, 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$818 and roundtrip prices from S$1,921*.
 

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.
Perfect flights from Singapore to Chicago

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Chicago Airports

Chicago

Singapore to O'Hare Intl.
S$1,088.10
*Available to Expedia members.