$38 Cheap Flights from Newark Liberty Intl. Airport (EWR) to Chicago (MDW)

View $38 flight on Sun, Jan 18, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $38 for one-way flights and $71 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Nov 11 - Thu, Nov 13
EWR
New York
MDW
Chicago
$71 Roundtrip, found 3 hours ago
$71
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, Nov 11 from New York to Chicago, returning Thu, Nov 13, priced at $71 found 3 hours ago
Frontier Airlines
Tue, Nov 11 - Thu, Nov 13
EWR
New York
MDW
Chicago
$74 Roundtrip, just found
$74
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Nov 11 from New York to Chicago, returning Thu, Nov 13, priced at $74 just found
Frontier Airlines
Thu, Jan 15 - Sun, Jan 18
EWR
New York
MDW
Chicago
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jan 15 from New York to Chicago, returning Sun, Jan 18, priced at $80 found 1 day ago
Frontier Airlines
Thu, Nov 6 - Tue, Nov 11
EWR
New York
MDW
Chicago
$81 Roundtrip, just found
$81
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Nov 6 from New York to Chicago, returning Tue, Nov 11, priced at $81 just found
Frontier Airlines
Thu, Nov 6 - Thu, Nov 13
EWR
New York
MDW
Chicago
$84 Roundtrip, found 2 hours ago
$84
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Nov 6 from New York to Chicago, returning Thu, Nov 13, priced at $84 found 2 hours ago
Frontier Airlines
Thu, Nov 13 - Sat, Nov 15
EWR
New York
MDW
Chicago
$87 Roundtrip, found 6 hours ago
$87
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from New York to Chicago, returning Sat, Nov 15, priced at $87 found 6 hours ago
Frontier Airlines
Sun, Nov 23 - Tue, Nov 25
EWR
New York
MDW
Chicago
$88 Roundtrip, found 1 hour ago
$88
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Nov 23 from New York to Chicago, returning Tue, Nov 25, priced at $88 found 1 hour ago
Frontier Airlines
Tue, Nov 11 - Tue, Nov 25
EWR
New York
MDW
Chicago
$89 Roundtrip, found 20 hours ago
$89
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Tue, Nov 11 from New York to Chicago, returning Tue, Nov 25, priced at $89 found 20 hours ago
Frontier Airlines
Thu, Nov 13 - Thu, Nov 20
EWR
New York
MDW
Chicago
$90 Roundtrip, just found
$90
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Nov 13 from New York to Chicago, returning Thu, Nov 20, priced at $90 just found
Frontier Airlines
Thu, Jan 15 - Sun, Jan 18
EWR
New York
MDW
Chicago
$91 Roundtrip, found 4 hours ago
$91
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Jan 15 from New York to Chicago, returning Sun, Jan 18, priced at $91 found 4 hours ago

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

October is typically the cheapest month to fly

From $101 - $541 per traveler.

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 center is 23 minutes. Flights from $114
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $114

Frequently asked questions

How much does a flight from Liberty Intl. Airport (EWR) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $38 or cheap return flight from $71 from Liberty Intl. Airport (EWR) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Liberty Intl. Airport (EWR) to Midway Intl. Airport (MDW)?
The cheapest month to fly from EWR to MDW is November, when there's less demand. Off-peak months are generally when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Liberty Intl. Airport (EWR) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare different airlines and find the most affordable carrier that'll fly you from EWR to MDW. Then, sort your results by "Price (lowest to highest)" to snag a good deal.
How many flights per day from Liberty Intl. Airport (EWR) to Midway Intl. Airport (MDW)?
There are no daily direct flights available from Liberty Intl. Airport (EWR) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be on your way in no time.
What day of the week has the most flights from EWR to MDW?
Friday is generally the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on a range of factors, such as the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Liberty Intl. Airport (EWR) to Midway Intl. Airport (MDW)?
Choose a flight from Liberty Intl. Airport (EWR) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays. Departures later than this are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Liberty Intl. Airport (EWR)?
Explore your flight options from Liberty Intl. Airport (EWR) to O'Hare Intl. Airport (ORD). This is the only airport in Chicago you can land at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Liberty Intl. Airport (EWR) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from EWR to MDW are typically more expensive. For the lowest prices, start looking for flights early. That being said, if you can play around with your travel dates, you may land a cheap fare right before your journey.
Is it cheaper to book an EWR to MDW flight and hotel package?
You'll generally save money by securing an EWR to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. Once you've selected your preferred flights and accommodations, you can add extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Liberty Intl. Airport (EWR) to Midway Intl. Airport (MDW)?
It's generally possible to cancel or reschedule your EWR to MDW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Origin airport
Newark Liberty Intl. Airport
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$71
Distance
707 mi
Average flight time
2 hours 25 mins

Book with confidence

Newark Liberty Intl. Airport to Chicago Flights

The cheapest times to fly from Newark Liberty Intl. Airport to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Newark Liberty Intl. Airport to Chicago are during the month of November. You can find some of the cheapest flights from Newark Liberty Intl. Airport to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Newark Liberty Intl. Airport to Chicago

Sunday is one of the best days to book for cheap flights from Newark Liberty Intl. Airport to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Newark Liberty Intl. Airport to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Newark Liberty Intl. Airport to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $38 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Newark Liberty Intl. Airport to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Newark Liberty Intl. Airport to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Newark Liberty Intl. Airport to Chicago Flights

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*Available to One Key members.