A modern building with large glass windows, a brick facade, and a brick pathway.

S$776 Cheap Flights from Chicago to Southampton

View S$776 flight on Mon, 5 Oct, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Southampton (SOU)

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 40% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Southampton (MDW-SOU)

Prices were available within the past 7 days and start at S$776 for one-way flights and S$1,399 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, 5 Oct - Mon, 12 Oct
MDW
Chicago
SOU
Southampton
S$1,399 Return, found 2 hours ago
S$1,399
Return
found 2 hours ago
Select Delta flight, departing Mon, 5 Oct from Chicago to Southampton, returning Mon, 12 Oct, priced at S$1,399 found 2 hours ago
Virgin Atlantic
Wed, 30 Sept - Wed, 7 Oct
MDW
Chicago
SOU
Southampton
S$1,405 Return, found 5 days ago
S$1,405
Return
found 5 days ago
Select Virgin Atlantic flight, departing Wed, 30 Sept from Chicago to Southampton, returning Wed, 7 Oct, priced at S$1,405 found 5 days ago
KLM
Mon, 5 Oct - Mon, 12 Oct
MDW
Chicago
SOU
Southampton
S$1,434 Return, found 2 hours ago
S$1,434
Return
found 2 hours ago
Select KLM flight, departing Mon, 5 Oct from Chicago to Southampton, returning Mon, 12 Oct, priced at S$1,434 found 2 hours ago
KLM
Wed, 30 Sept - Wed, 7 Oct
MDW
Chicago
SOU
Southampton
S$1,441 Return, found 5 days ago
S$1,441
Return
found 5 days ago
Select KLM flight, departing Wed, 30 Sept from Chicago to Southampton, returning Wed, 7 Oct, priced at S$1,441 found 5 days ago
Delta
Wed, 30 Sept - Wed, 7 Oct
MDW
Chicago
SOU
Southampton
S$1,469 Return, found 5 days ago
S$1,469
Return
found 5 days ago
Select Delta flight, departing Wed, 30 Sept from Chicago to Southampton, returning Wed, 7 Oct, priced at S$1,469 found 5 days ago
Delta
Mon, 5 Oct - Mon, 12 Oct
MDW
Chicago
SOU
Southampton
S$1,473 Return, found 2 hours ago
S$1,473
Return
found 2 hours ago
Select Delta flight, departing Mon, 5 Oct from Chicago to Southampton, returning Mon, 12 Oct, priced at S$1,473 found 2 hours ago
KLM
Wed, 30 Sept - Wed, 7 Oct
MDW
Chicago
SOU
Southampton
S$1,488 Return, found 5 days ago
S$1,488
Return
found 5 days ago
Select KLM flight, departing Wed, 30 Sept from Chicago to Southampton, returning Wed, 7 Oct, priced at S$1,488 found 5 days ago
Delta
Mon, 5 Oct - Mon, 12 Oct
MDW
Chicago
SOU
Southampton
S$1,498 Return, found 2 hours ago
S$1,498
Return
found 2 hours ago
Select Delta flight, departing Mon, 5 Oct from Chicago to Southampton, returning Mon, 12 Oct, priced at S$1,498 found 2 hours ago
Delta
Wed, 30 Sept - Wed, 7 Oct
MDW
Chicago
SOU
Southampton
S$1,505 Return, found 5 days ago
S$1,505
Return
found 5 days ago
Select Delta flight, departing Wed, 30 Sept from Chicago to Southampton, returning Wed, 7 Oct, priced at S$1,505 found 5 days ago
Delta
Mon, 5 Oct - Mon, 12 Oct
MDW
Chicago
SOU
Southampton
S$1,508 Return, found 2 hours ago
S$1,508
Return
found 2 hours ago
Select Delta flight, departing Mon, 5 Oct from Chicago to Southampton, returning Mon, 12 Oct, priced at S$1,508 found 2 hours ago
KLM
Mon, 5 Oct - Mon, 12 Oct
MDW
Chicago
SOU
Southampton
S$1,572 Return, found 2 hours ago
S$1,572
Return
found 2 hours ago
Select KLM flight, departing Mon, 5 Oct from Chicago to Southampton, returning Mon, 12 Oct, priced at S$1,572 found 2 hours ago
Delta
Mon, 5 Oct - Mon, 12 Oct
MDW
Chicago
SOU
Southampton
S$1,582 Return, found 2 hours ago
S$1,582
Return
found 2 hours ago
Select Delta flight, departing Mon, 5 Oct from Chicago to Southampton, returning Mon, 12 Oct, priced at S$1,582 found 2 hours ago
Delta
Mon, 5 Oct - Mon, 12 Oct
MDW
Chicago
SOU
Southampton
S$1,620 Return, found 2 hours ago
S$1,620
Return
found 2 hours ago
Select Delta flight, departing Mon, 5 Oct from Chicago to Southampton, returning Mon, 12 Oct, priced at S$1,620 found 2 hours ago

Travel information

Origin airport
Midway Intl.
Destination airport
Southampton
Airlines serving
Delta, KLM
Roundtrip price
S$1,398
Distance
6281 km

Book with confidence

Perfect flights from Chicago to Southampton

Your Journey from Chicago to Southampton

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Southampton 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, KLM, Virgin Atlantic. Our selection of flights from Midway Intl. to Southampton 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 Southampton Flights

Experience the joy of finding cheap flights from Midway Intl. to Southampton that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$776 and roundtrip prices from S$1,399*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Southampton 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 Southampton

Picture yourself stepping off the plane in Southampton 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 Southampton 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 Southampton.
 

Beyond the Flight – Exploring Southampton

With Expedia, your adventure extends beyond the flight. Explore Southampton 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 Southampton 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 Southampton with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Chicago to Southampton

Explore a world of travel with Expedia

*Available to Expedia members.