NYC - MDW

$54 Find Cheap Flights from New York to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New York to Midway departing on 1/13. 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 Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago.
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Everything you should know

Cheapest round-trip
$110
Typical prices: $186-$239
Frontier
Thu 1/15Sun 1/18
EWR - MDW • 1 stop
Cheapest non-stop
$125
Frontier
Thu 3/19Sun 3/22
EWR - MDW • Non-stop
Top airlines
Frontier
Cheapest • from $110 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
EWR-MDW
Cheapest • 43% average savings
LGA-MDW
Most popular
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 37% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New York to Midway 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 New York to Midway

Thu, Jan 15 - Sun, Jan 18
Frontier Logo
11:30 am - 10:19 pm
EWR
-
MDW
11h 49m1 stop
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
$110Frontier
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
11:30 am - 10:19 pm
EWR
-
MDW
11h 49m1 stop
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
$111Frontier
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
11:30 am - 10:19 pm
EWR
-
MDW
11h 49m1 stop
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
$112Frontier
Wed, Jan 14 - Thu, Jan 15
Frontier Logo
11:30 am - 10:19 pm
EWR
-
MDW
11h 49m1 stop
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
$122Frontier
Thu, Jan 15 - Sat, Jan 17
Frontier Logo
10:30 pm - 12:02 am
EWR
-
MDW
2h 32mnonstop
Frontier Logo
8:22 am - 1:13 am
MDW
-
EWR
15h 51m1 stop
$123Frontier
Wed, Mar 4 - Sun, Mar 8
Frontier Logo
10:30 pm - 2:26 pm
EWR
-
MDW
16h 56m1 stop
Frontier Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
$124Frontier
Thu, Mar 19 - Sun, Mar 22
Frontier Logo
11:30 am - 1:02 pm
EWR
-
MDW
2h 32mnonstop
Frontier Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
$125Frontier
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
5:25 am - 7:09 pm
EWR
-
MDW
14h 44m2 stops
Multiple Airlines Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
$130Multiple Airlines
Sun, Jan 25 - Sun, Feb 1
Southwest Logo
9:00 am - 10:40 am
LGA
-
MDW
2h 40mnonstop
Southwest Logo
6:05 pm - 9:10 pm
MDW
-
LGA
2h 05mnonstop
$139Southwest
Wed, Jan 21 - Wed, Jan 28
Southwest Logo
9:45 pm - 11:15 pm
LGA
-
MDW
2h 30mnonstop
Southwest Logo
5:55 pm - 9:00 pm
MDW
-
LGA
2h 05mnonstop
$148Southwest
Booking Insights

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

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

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

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

The cheapest return flight from New York to Chicago Midway Airport costs $59 on the route between Newark Airport (EWR) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 43% cheaper than other New York-Chicago Midway Airport routes. The most popular route is between New York LaGuardia Airport (LGA) and Chicago Midway Airport (MDW).

What’s the cheapest day of the week to fly from New York to Chicago Midway Airport?

The average price of all round-trip flights from New York to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from New York to Chicago Midway Airport, look for departures on Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Saturday is the cheapest day to fly and Thursday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from New York to Chicago Midway Airport, 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 New York to Chicago Midway Airport is January, where tickets cost $188 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $378 and $375 respectively.

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

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 $295, prices are generally cheapest when you fly direct.

Good to know

Low seasonJanuary
Cheapest flight$54
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Newark Liberty Airport to Chicago Midway Airport

When to book flights from New York to Midway

Are your dates flexible? Find out the best times to travel from New York to Midway 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 New York to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from New York to Chicago Midway Airport was $54 for a one-way ticket and $110 for a round-trip.

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

    No

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

    New York is served by 3 major airports and there is only 1 main airport in Chicago Midway Airport. You will leave New York from one of these airports: Newark, New York John F Kennedy Intl, or New York LaGuardia. You will be arriving at Chicago Midway.

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

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

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

    The Boeing 737-800 is the aircraft model that flies most regularly on the New York to Chicago Midway Airport flight route.

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

    Star Alliance, and SkyTeam are the airline alliances operating flights between New York and Chicago Midway Airport, with Star Alliance being the most commonly used for this route.

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

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

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

    The two airlines most popular with KAYAK users for flights from New York to Chicago are Southwest and Delta. With an average price for the route of $306 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $336 and an overall rating of 7.9.

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

    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 New York to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from New York 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 New York to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to New York with another airline.

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

    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 Chicago Midway Airport from New York 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 New York to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $133 or less one-way and $179 or less round-trip.

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

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

Direct departures

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

Direct returns

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

Reviews of the top 5 airlines serving from New York to Midway

 
See real verified KAYAK customer reviews for airlines flying from New York to Chicago. 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 New York to Midway? 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 4258 reviews
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
Airline reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

10.0 ExcellentAnonymous, Dec 2025
DAL - CHS
Read more Southwest reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

I truly love flying with Delta. They have always treated me with the upmost respect

The flight was great. The gate location was way to far away!!!

Cramped seating for me. Luckily it wasn’t a long flight

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

I believe that a four-hour trip should have a meal. Delta had none.

Was charged for my luggage despite having been on one ticket from an international flight. Too tired to argue after 15 hours on flight. Was charged for rechecking it at JFK airport. Not sure why those off Kenya Airways were required to do that.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

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

Other airlines flying to New York

Flight deals from the most popular airlines with KAYAK users flying the route