S$104 Cheap Flights from Newark Liberty Intl. Airport to Chicago

View S$104 flight on Wed, 15 Oct, 2025Opens in a new window

Popular airlines from Newark Liberty Intl. Airport (EWR) to Chicago Midway Airport (MDW)

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

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

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Newark Liberty Intl. Airport to Chicago (EWR-MDW)

Prices were available within the past 7 days and start at S$104 for one-way flights and S$215 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 15 Oct - Wed, 22 Oct
EWR
New York
MDW
Chicago
S$215 Return, found 3 days ago
S$215
Return
found 3 days ago
Select Delta flight, departing Wed, 15 Oct from New York to Chicago, returning Wed, 22 Oct, priced at S$215 found 3 days ago
Delta
Wed, 8 Oct - Wed, 15 Oct
EWR
New York
MDW
Chicago
S$249 Return, found 3 days ago
S$249
Return
found 3 days ago
Select Delta flight, departing Wed, 8 Oct from New York to Chicago, returning Wed, 15 Oct, priced at S$249 found 3 days ago
Delta
Wed, 8 Oct - Wed, 15 Oct
EWR
New York
MDW
Chicago
S$282 Return, found 3 days ago
S$282
Return
found 3 days ago
Select Delta flight, departing Wed, 8 Oct from New York to Chicago, returning Wed, 15 Oct, priced at S$282 found 3 days ago
Delta
Wed, 15 Oct - Wed, 22 Oct
EWR
New York
MDW
Chicago
S$285 Return, found 3 days ago
S$285
Return
found 3 days ago
Select Delta flight, departing Wed, 15 Oct from New York to Chicago, returning Wed, 22 Oct, priced at S$285 found 3 days ago
Delta
Wed, 15 Oct - Wed, 22 Oct
EWR
New York
MDW
Chicago
S$320 Return, found 3 days ago
S$320
Return
found 3 days ago
Select Delta flight, departing Wed, 15 Oct from New York to Chicago, returning Wed, 22 Oct, priced at S$320 found 3 days ago
Delta
Wed, 8 Oct - Wed, 15 Oct
EWR
New York
MDW
Chicago
S$330 Return, found 3 days ago
S$330
Return
found 3 days ago
Select Delta flight, departing Wed, 8 Oct from New York to Chicago, returning Wed, 15 Oct, priced at S$330 found 3 days ago
Delta
Wed, 15 Oct - Wed, 22 Oct
EWR
New York
MDW
Chicago
S$356 Return, found 3 days ago
S$356
Return
found 3 days ago
Select Delta flight, departing Wed, 15 Oct from New York to Chicago, returning Wed, 22 Oct, priced at S$356 found 3 days ago
Delta
Wed, 8 Oct - Wed, 15 Oct
EWR
New York
MDW
Chicago
S$364 Return, found 3 days ago
S$364
Return
found 3 days ago
Select Delta flight, departing Wed, 8 Oct from New York to Chicago, returning Wed, 15 Oct, priced at S$364 found 3 days ago
Delta
Wed, 8 Oct - Wed, 15 Oct
EWR
New York
MDW
Chicago
S$376 Return, found 3 days ago
S$376
Return
found 3 days ago
Select Delta flight, departing Wed, 8 Oct from New York to Chicago, returning Wed, 15 Oct, priced at S$376 found 3 days ago
Delta
Wed, 15 Oct - Wed, 22 Oct
EWR
New York
MDW
Chicago
S$401 Return, found 3 days ago
S$401
Return
found 3 days ago
Select Delta flight, departing Wed, 15 Oct from New York to Chicago, returning Wed, 22 Oct, priced at S$401 found 3 days ago

Find the cheapest month to fly from New York (EWR) to Chicago (MDW)

February is typically the cheapest month to fly

From S$159 - S$498 per traveller.

Graph displaying average flight prices per month

Newark Liberty Intl. Airport to Chicago route information
Origin airport
Newark Liberty Intl. Airport
Destination airport
Midway Intl.
Return price
S$215
Distance
1132 km

Perfect flights from Newark Liberty Intl. Airport to Chicago

Your Journey from Newark Liberty Intl. Airport to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Newark Liberty Intl. Airport 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. Our selection of flights from Newark Liberty Intl. Airport 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 Newark Liberty Intl. Airport to Chicago Flights

Experience the joy of finding cheap flights from Newark Liberty Intl. Airport 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$104 and roundtrip prices from S$215*.
 

Pre-Flight Essentials

Ensure a smooth journey from Newark Liberty Intl. Airport 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 Newark Liberty Intl. Airport 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 Newark Liberty Intl. Airport 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 Newark Liberty Intl. Airport 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 Newark Liberty Intl. Airport 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 Liberty Intl. Airport (EWR) to Midway Airport?
Pack your bags, because round-trip journeys from Newark Airport to Chicago Airport start from S$215. That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can go up quickly, so book now to secure the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Liberty Intl. Airport (EWR) to Chicago Airport?
Most flights can be cancelled online, but whether you are charged a fee differs between airlines. If you do need to cancel your holiday, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from EWR to Chicago 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 EWR to Chicago Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from EWR to MDW?
A flight distance of just 1,150 kilometres separates Newark and Chicago. Once you're up in the skies, you won't get a chance to do much more than flip through the pages of the in-flight magazine.
Which airlines fly direct from Liberty Intl. Airport (EWR) to Midway Intl. Airport (MDW)?
You won't find any airlines flying directly between Liberty Intl. Airport (EWR) and Chicago Airport, so be ready to make at least one stop on your journey. A layover, whether short or long, can be a nice way to break up a trip!
Are Liberty Intl. Airport (EWR) to MDW flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Liberty Intl. Airport (EWR) to MDW last minute could be your ticket to a fantastic deal. However, it could end up costing you a whole lot more! If you'd rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains as far ahead as 12 months in advance. If your preferred carrier hasn't released tickets yet, check back frequently as deals are updated on Expedia all the time.

Explore a world of travel with Expedia

Chicago Airports

Chicago

Newark Liberty Intl. Airport to O'Hare Intl.
S$214.90
Newark Liberty Intl. Airport Airports

New York

*Available to Expedia members.