NYC - MDW

$60 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 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 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, 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 New York to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$92
Overall average: $367
Frontier
Tue 4/14Sat 4/18
EWR - MDW • Non-stop
Cheapest one-way
$59
Typical prices: $89-$239
Frontier
Sun 3/8
EWR - MDW • Non-stop
Top airlines
Frontier
Cheapest • from $92 (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 34m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
EWR
-
MDW
Cheapest • 56% average savings
LGA
-
MDW
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Southwest
Most punctual • 80% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 48% price drop
May
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 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

Tue, Apr 14 - Sat, Apr 18
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$92Frontier
Fri, Apr 17 - Mon, Apr 20
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$95Frontier
Tue, Mar 17 - Thu, Mar 19
Frontier Logo
11:30 am - 1:02 pm
EWR
-
MDW
2h 32mnonstop
Frontier Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
$96Frontier
Wed, Apr 15 - Sat, Apr 18
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$97Frontier
Sun, Mar 8 - Thu, Mar 12
Frontier Logo
11:30 am - 1:02 pm
EWR
-
MDW
2h 32mnonstop
Frontier Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
$98Frontier
Sat, Apr 18 - Wed, Apr 22
Southwest Logo
7:35 am - 9:00 am
LGA
-
MDW
2h 25mnonstop
Southwest Logo
9:30 am - 12:35 pm
MDW
-
LGA
2h 05mnonstop
$147Southwest
Wed, Mar 25 - Sun, Apr 5
Southwest Logo
9:00 am - 10:35 am
LGA
-
MDW
2h 35mnonstop
Southwest Logo
8:05 am - 11:15 am
MDW
-
LGA
2h 10mnonstop
$152Southwest
Tue, Mar 24 - Thu, Mar 26
Southwest Logo
6:50 am - 8:20 am
LGA
-
MDW
2h 30mnonstop
Southwest Logo
8:20 pm - 11:20 pm
MDW
-
LGA
2h 00mnonstop
$157Southwest
Wed, Apr 29 - Sun, May 3
Southwest Logo
8:55 pm - 10:30 pm
LGA
-
MDW
2h 35mnonstop
Southwest Logo
5:20 am - 8:20 am
MDW
-
LGA
2h 00mnonstop
$158Southwest
Thu, Jul 30 - Mon, Aug 3
Multiple Airlines Logo
9:38 am - 6:36 pm
SWF
-
MDW
9h 58m
1 stop
Multiple Airlines Logo
7:41 pm - 11:08 am
MDW
-
SWF
14h 27m
1 stop
$469Multiple Airlines
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.

How much is a round-trip flight from New York to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from New York to Chicago Midway Airport departing in April.

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 $48 on the route between Newark Airport (EWR) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 56% 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 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 $149 (return) on average. On the other hand, the most expensive months are June and August, where the average cost of round-trip tickets is $375 and $369 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 $151, prices are generally cheapest when you fly direct.

Good to know

Low seasonJanuary
Cheapest flight$59
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly with an average 1% increase in price.
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 $59 for a one-way ticket and $92 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, Delta, and JetBlue 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 Airbus A321neo 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?

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

  • 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 $308 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 $370 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 $101 or less one-way and $152 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 4300 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
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.

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Smooth boarding, pleasant and professional lady checking us in. Crew service was excellent, again pleasant, but professional. Nice touch-down on landing! Thank you Delta. 💗

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

We departed early and made up time in the air allowing us to arrive 30 minutes early. Capt was incredibly genuine and thanked every passenger for flying with Delta. Completely humble and professional!

Got on the plane and sat there for an hour before departure.

They double booked seats, the gate staff changed my ticket as I was boarding she went over to the computer and changed it without telling me. She messed up an entire three row section for me and others. Other travelers were outraged but the gate staff were so rude, so condescending saying it wasn't their problem to solve. I would rate this a zero if I could. Will not fly Delta again I'll stick with United and American.

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

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

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

Not seat assigned because overbooking. We could go because some people decided to give their seats.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

I waited for 4+ extra hours to even board when i was fighting off a cold. So i was sitting there in the airport with a fever and chills while spirit wasted my time. Then once on the plane we had at least an extra hour of taxiing before and after takeoff. Really poor airline, no amenities to speak of, and a lack of organization that will just ruin your experience.

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

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 New York to Midway

Other airlines flying to New York

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