S$1,268 Cheap Flights from Singapore to Chicago

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Cheap Flights from Singapore to Chicago (SIN-MDW)

Prices were available within the past 7 days and start at S$1,268 for one-way flights and S$2,406 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Singapore Airlines
Sun, 1 Sep - Fri, 6 Sep
SIN
Singapore
MDW
Chicago
S$2,406 Return, found 2 days ago
S$2,406
Return
found 2 days ago
Select Singapore Airlines flight, departing Sun, 1 Sep from Singapore to Chicago, returning Fri, 6 Sep, priced at S$2,406 found 2 days ago
Delta
Sat, 11 May - Sat, 22 Jun
SIN
Singapore
MDW
Chicago
S$2,476 Return, found 4 days ago
S$2,476
Return
found 4 days ago
Select Delta flight, departing Sat, 11 May from Singapore to Chicago, returning Sat, 22 Jun, priced at S$2,476 found 4 days ago
Singapore Airlines
Sun, 1 Sep - Fri, 6 Sep
SIN
Singapore
MDW
Chicago
S$2,478 Return, found 2 days ago
S$2,478
Return
found 2 days ago
Select Singapore Airlines flight, departing Sun, 1 Sep from Singapore to Chicago, returning Fri, 6 Sep, priced at S$2,478 found 2 days ago
Korean Air
Mon, 17 Jun - Sun, 30 Jun
SIN
Singapore
MDW
Chicago
S$2,508 Return, found 4 days ago
S$2,508
Return
found 4 days ago
Select Korean Air flight, departing Mon, 17 Jun from Singapore to Chicago, returning Sun, 30 Jun, priced at S$2,508 found 4 days ago
Delta
Wed, 1 May - Sun, 5 May
SIN
Singapore
MDW
Chicago
S$2,512 Return, found 3 days ago
S$2,512
Return
found 3 days ago
Select Delta flight, departing Wed, 1 May from Singapore to Chicago, returning Sun, 5 May, priced at S$2,512 found 3 days ago
Delta
Wed, 1 May - Wed, 8 May
SIN
Singapore
MDW
Chicago
S$2,512 Return, found 6 days ago
S$2,512
Return
found 6 days ago
Select Delta flight, departing Wed, 1 May from Singapore to Chicago, returning Wed, 8 May, priced at S$2,512 found 6 days ago
Delta
Wed, 1 May - Sun, 5 May
SIN
Singapore
MDW
Chicago
S$2,513 Return, found 3 days ago
S$2,513
Return
found 3 days ago
Select Delta flight, departing Wed, 1 May from Singapore to Chicago, returning Sun, 5 May, priced at S$2,513 found 3 days ago
Singapore Airlines
Sun, 1 Sep - Fri, 6 Sep
SIN
Singapore
MDW
Chicago
S$2,556 Return, found 2 days ago
S$2,556
Return
found 2 days ago
Select Singapore Airlines flight, departing Sun, 1 Sep from Singapore to Chicago, returning Fri, 6 Sep, priced at S$2,556 found 2 days ago
Singapore Airlines
Sun, 1 Sep - Fri, 6 Sep
SIN
Singapore
MDW
Chicago
S$2,557 Return, found 2 days ago
S$2,557
Return
found 2 days ago
Select Singapore Airlines flight, departing Sun, 1 Sep from Singapore to Chicago, returning Fri, 6 Sep, priced at S$2,557 found 2 days ago
Delta
Wed, 1 May - Sun, 5 May
SIN
Singapore
MDW
Chicago
S$2,586 Return, found 3 days ago
S$2,586
Return
found 3 days ago
Select Delta flight, departing Wed, 1 May from Singapore to Chicago, returning Sun, 5 May, priced at S$2,586 found 3 days ago
Singapore to Chicago route information
Origin airport
Changi
Destination airport
Midway Intl.
Airlines serving
Delta
Return price
S$2,405
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, Asiana Airlines, Singapore Airlines, Korean Air. 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$1,268 and roundtrip prices from S$2,406*.
 

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$2,406. 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.
Chicago Airports

Chicago

Singapore to O'Hare Intl.
S$1,410.70
*Available to Expedia members.