MDW - NYC

$41 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 5/7. 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.
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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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Cheap Flight Deals 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.

Recent round-trip flight deals from Midway to New York

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to New York.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
4:28 pm - 11:03 pmMDW-LGA
5h 35m1 stop
6:30 am - 11:26 amLGA-MDW
5h 56m1 stop
$98Frontier
Find Deal
Wed, Apr 23 - Wed, May 7
8:30 am - 10:00 pmMDW-LGA
12h 30m1 stop
10:00 pm - 11:31 amLGA-MDW
14h 31m1 stop
$100Frontier
Find Deal
Tue, Mar 4 - Wed, Mar 5
4:40 pm - 12:43 amMDW-JFK
7h 03m1 stop
9:00 am - 7:45 pmJFK-MDW
11h 45m1 stop
$100Frontier
Find Deal
Tue, Apr 1 - Tue, Apr 8
7:50 pm - 11:00 pmMDW-LGA
2h 10mnonstop
9:45 pm - 11:00 pmLGA-MDW
2h 15mnonstop
$147Southwest
Find Deal
Thu, May 1 - Fri, May 2
5:50 pm - 9:00 pmMDW-LGA
2h 10mnonstop
9:45 pm - 11:00 pmLGA-MDW
2h 15mnonstop
$148Southwest
Find Deal
Tue, Apr 8 - Wed, Apr 16
5:59 pm - 10:59 pmMDW-EWR
4h 00m1 stop
5:55 am - 8:40 amEWR-MDW
3h 45m1 stop
$167Delta
Find Deal
Tue, Apr 15 - Thu, Apr 17
12:51 pm - 8:30 pmMDW-EWR
6h 39m1 stop
9:35 am - 12:35 pmEWR-MDW
4h 00m1 stop
$172Delta
Find Deal
Tue, Apr 1 - Wed, Apr 30
7:26 pm - 9:04 pmMDW-EWR
24h 38m2 stops
9:55 am - 2:03 pmEWR-MDW
5h 08m1 stop
Sun, Jun 1 - Fri, Jun 6
2:53 pm - 10:05 amMDW-EWR
18h 12m1 stop
12:55 pm - 8:22 amEWR-MDW
20h 27m1 stop
$290Allegiant Air
Find Deal
Fri, Jun 6 - Sun, Jun 8
2:22 pm - 9:05 amMDW-EWR
17h 43m2 stops
3:48 pm - 12:32 pmEWR-MDW
21h 44m2 stops
Thu, Mar 6 - Sat, Mar 8

Flights from Midway to New York - Travel Insights & Trends

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to New York.
Our data shows that the cheapest route for a return flight from Chicago Midway Airport to New York cost $147 and was between Chicago Midway Airport (MDW) and New York LaGuardia Airport (LGA). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $147.

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

The average price of all round-trip flights from Chicago Midway Airport to New York clicked on KAYAK for each day over the last 12 months.
When flying from Chicago Midway Airport to New York, you should consider leaving on a Saturday and avoid Thursdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

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 January, where tickets cost $213 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $408 and $351 respectively.

Good to know

Low season

May

High season

January

Cheapest flight

$41
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 24% lower on average.
Flight from Chicago Midway Airport to New York John F Kennedy 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 $41 for a one-way ticket and $98 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, Delta, and JetBlue 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.

  • 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 Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to New York are Southwest and Delta. With an average price for the route of $270 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $421 and an overall rating of 8.0.

  • 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.

See more FAQs

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 $88 or less one-way and $185 or less round-trip.

Prefer to fly direct from Chicago Midway Airport 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
See more direct flights

Top 4 airlines serving 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.
8.1
SouthwestOverall score based on 4411 reviews
7.1Food
8.1Comfort
8.7Crew
7.6Entertainment
8.2Boarding
Airline reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

Everything was ok!! Just bags came up a little be late.

Tasty snacks. On-time departure and early arrival. Luggage arrived quickly at the carrousel. The only negative was a man behind us that was heavily inebriated. He was served 3 double drinks during the flight. There was no telling how much he had before the flight. He was so out of it that he spilled a drink and broke the heavy liquor glass on the floor. I don't believe he should have been served so much alcohol on a two-hour flight.

It was terrible, I sat next to a person with a cat, I'm allergic to animal dander, my discomfort was extreme

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Flight heavily delayed. No food available despite purchasing an upgrade. No in cabin service.

It was not in Delta's control, but when we landed, we ended up parking at the wrong gate, and so everyone was already ready to deplane and had their carryon bags, ready to leave. But we had to sit down and move to the proper gate. This process took over 30 minutes. Again, not Delta's fault - more so on the staff at JFK

My Flight was cancelled and there was no other options available for me to Travel on that date and my options for the next day was all connecting flights that would have me in the airports all day before reaching my destination

First, the flight was schedule to leave at 12:08. Delayed to 12:38. It is 12:58 and I am sitting at the gate. The staff are not communicating with us (just tell me it’s gonna be five hours if that’s the case, quit hufflepuffing around like you’re trying to board us when the plane isn’t even here and you don’t know where your crew are. I’m still waiting for any communication about the further delay. This is a rebooked flight from a cancelled flight yesterday, when the airline failed to fulfill its fiduciary responsibility to hotel and cover transport for overnight cancelations. Asking about the food on the flight? What food?!? Delta doesn’t serve meals unless you pay for them and you really want me to give delta a high rating for passing out processed snacks (fun size!)? Can we be for real. Delta is cementing itself in history as one of the cheap, stingy, outdated, glory days are over airlines, and it shows. I took this flight knowing delta was going to provide below level service but this is beyond burgers!! I can’t believe a multi billion or dollar company looked straight in my eyes yesterday and I told me this wasn’t their fault and there for the extra cost in hotel and hundreds of dollars in Ubers are MY RESPONSIBILITY. The only thing I am at fault for is believing delta is reputable company worthy of my dollars. I’m not even sure I want to be compensated unless it is cash because I would rather die never traveling again than to put money in their pockets.

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Fast check-in. Went through security quickly enough. Got their early. And the crew took care of my seating at the gate. The cost for 1 checked bag is ridiculous! $79!? Cmon!! The seating on the plane was very cramped, like sardines. I did not want to pay extra just to pick a seat. Might have to next time.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

The flight was delayed over an hour and we had to sit on the plane. Crew does not apologize due to the delay. Spirit will NEVER do anything to give a customer a better experience. A child next to me was kicking me the whole time. I don't ever enjoy flying with Spirit.

Easy! As long as you don’t mind no frills, our flight was enjoyable and on time

Fantastic. Had handicapped traveler and they helped us through security, helped with boarding, helped put wheelchair together, and were all very patient. A pleasant change from previous spirit flights I’ve taken. Highly recommend.

particularly nothing to like plane just turned to be a hmm flying bus, yet in buses from another country at least drink and snack are free ... and seat could be just a bit more ..adjustable? ok ok i know i am asking for too much but ..dreaming is not forbidden yet

The flight was delayed, and we waited for more than an hour on the plane.

Could at least have little recline in economy seats and windows to the last row, they were super uncomfortable and lots of chit chat and disturbance from the operation of crew members and other passengers

Was told by one of the helpers at spirit in Detroit that I had to pay for my bag that could fit on the over head bin after I asked her repeatedly well what about the over head bin can’t my bag fit in there she said no I had to check it. Then sent me the long way to the tsa when my gate was the other way. I didn’t have that problem in Chicago.

The check in process was a mess for no reason. I spent an hour waiting in line trying to get them to print my boarding pass and as a result I missed my flight.

The airline used deceptive tactics to charge us more for our trip. Search Frontier Class Action Lawsuit to find out more or read the hundreds of reviews that have nearly identical stories.. don't fly this airline.. you've been warned.

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

Very easy with the app to board and staff skills

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

Flight was changed (according to Frontier, by Kayak) without my notification. And all flights were delayed by at least an hour and a half. Uncomfortable plane. Bad service. Will never fly Frontier again.

My experience with the phoenix airport was terrible, the personnel lay the ticket counter charged me for a carry on that fit in the carry on size box, and the two women I spoke with were terribly rude and not willing to help.,,, there was one lady “candy” on the flight crew that was amazing and is the only reason I stayed on the flight at all, because the other stewards helping people to get seated on the plane were terrible

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

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