MDW - NYC

$59 Find Cheap Flights from Chicago Midway Airport to New York

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to New York departing on 3/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to New York

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New York, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New York, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$97
Frontier
Thu 3/19Tue 3/24
MDW - EWR • Non-stop
Cheapest one-way
$59
Typical prices: $166-$180
Frontier
Sun 3/8
MDW - EWR • Non-stop
Top airlines
Frontier
Cheapest • from $97 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 02m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
MDW
-
EWR
Cheapest • 51% average savings
MDW
-
LGA
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Southwest
Most punctual • 81% on-time
Night flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Atlanta (ATL)
Cheapest • Avg $180 (round-trip)
Detroit (DTW)
Shortest trip • 3h 32m (one-way)
Insights
Insights
Insights
Insights
When to travel
October
Cheapest • 27% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to New York!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to New York (MDW-NYC)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to New York that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to New York

Thu, Mar 19 - Tue, Mar 24
Frontier Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
Frontier Logo
11:30 am - 1:02 pm
EWR
-
MDW
2h 32mnonstop
$97Frontier
Sun, Mar 8 - Tue, Mar 10
Frontier Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
Frontier Logo
11:30 am - 1:02 pm
EWR
-
MDW
2h 32mnonstop
$98Frontier
Sun, Mar 8 - Tue, Mar 10
Frontier Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
Frontier Logo
11:30 am - 1:02 pm
EWR
-
MDW
2h 32mnonstop
$99Frontier
Thu, Apr 16 - Wed, Apr 22
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$102Frontier
Wed, Apr 22 - Fri, Apr 24
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$104Frontier
Wed, Apr 8 - Tue, Apr 14
Southwest Logo
7:25 pm - 10:30 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
6:00 am - 7:25 am
LGA
-
MDW
2h 25mnonstop
$147Southwest
Thu, Mar 26 - Mon, Apr 27
Southwest Logo
8:20 pm - 11:20 pm
MDW
-
LGA
2h 00mnonstop
Southwest Logo
9:45 pm - 11:10 pm
LGA
-
MDW
2h 25mnonstop
$152Southwest
Wed, Mar 18 - Tue, Mar 24
Southwest Logo
5:10 am - 8:10 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
6:50 am - 8:20 am
LGA
-
MDW
2h 30mnonstop
$157Southwest
Sat, May 9 - Sat, May 9
Southwest Logo
5:30 am - 8:30 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
6:05 pm - 7:30 pm
LGA
-
MDW
2h 25mnonstop
$158Southwest
Sat, Mar 14 - Mon, Mar 16
Multiple Airlines Logo
2:56 pm - 11:08 am
MDW
-
SWF
19h 12m
1 stop
Multiple Airlines Logo
7:51 pm - 12:14 pm
SWF
-
MDW
17h 23m
1 stop
$533Multiple Airlines
Booking Insights

KAYAK's insights & trends for Midway to New York flights

Get data-powered insights and trends into flights from Midway to New York to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to New York flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago Midway Airport to New York costs $55 on the route between Chicago Midway Airport (MDW) and Newark Airport (EWR). Over the past month, this route was, on average, 51% cheaper than other Chicago Midway Airport-New York routes. The most popular route is between Chicago Midway Airport (MDW) and New York LaGuardia Airport (LGA).

What is the cheapest month to fly from Chicago Midway Airport to New York?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to New York, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to New York is October, where tickets cost $167 (return) on average. On the other hand, the most expensive months are February and May, where the average cost of round-trip tickets is $284 and $277 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to New York?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $202, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$59
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago Midway Airport to Newark Liberty Airport

When to book flights from Midway to New York

Are your dates flexible? Find out the best times to travel from Midway to New York based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to New York flights

  • What is the cheapest flight from Chicago Midway Airport to New York?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to New York was $59 for a one-way ticket and $97 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and New York?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Chicago Midway Airport to New York?

    On your way to New York, you’ll fly out from Chicago Midway. You’ll be landing in one of New York’s 3 airports: Newark, New York John F Kennedy Intl, or New York LaGuardia.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to New York?

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Chicago Midway Airport to New York flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to New York?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to New York flight route.

  • Which airline alliances offer flights from Chicago Midway Airport to New York?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and New York.

  • On which days can I fly direct from Chicago Midway Airport to New York?

    There are nonstop flights from Chicago Midway Airport to New York on a daily basis.

  • Which is the best airline for flights from Chicago to New York, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to New York are Southwest and United Airlines. With an average price for the route of $257 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $321 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to New York?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to New York.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to New York?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to New York from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to New York?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to New York with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to New York?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to New York from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to New York

  • Looking for a cheap flight? 25% of our users found flights on this route for $75 or less one-way and $147 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to New York?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to New York.
Find which airlines fly direct from Chicago Midway Airport to New York, which days they fly and book direct flights.

Direct departures

Chicago Midway to New York

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

New York to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying from Midway to New York

 
See real verified KAYAK customer reviews for airlines flying from Chicago to New York. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to New York? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4300 reviews
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

10.0 ExcellentTy&Steph, Feb 2026
CLT - STL
Read more Southwest reviews

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

Everything you need to know for your flight from Midway to New York

Information on your arrival and departure airports