MDW - NYC

$50 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 2/12. 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
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Search 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
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

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

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

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Cheap Flight Deals from Chicago Midway Airport 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 Chicago Midway Airport 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
8:30 am - 10:00 pmMDW-LGA
12h 30m1 stop
10:00 pm - 11:28 amLGA-MDW
14h 28m1 stop
$100Frontier
Find Deal
Tue, Feb 18 - Sat, Feb 22
7:45 am - 5:00 pmMDW-LGA
8h 15m1 stop
10:59 am - 4:16 pmLGA-MDW
6h 17m1 stop
$102Frontier
Find Deal
Mon, Jan 27 - Tue, Feb 4
12:43 pm - 10:00 pmMDW-LGA
8h 17m1 stop
10:00 pm - 11:28 amLGA-MDW
14h 28m1 stop
$103Frontier
Find Deal
Sun, Feb 16 - Sat, Feb 22
9:34 am - 5:05 pmMDW-EWR
6h 31m1 stop
1:00 pm - 6:14 pmEWR-MDW
6h 14m1 stop
$145Delta
Find Deal
Sat, Jan 25 - Tue, Jan 28
6:00 am - 9:10 amMDW-LGA
2h 10mnonstop
6:00 am - 7:35 amLGA-MDW
2h 35mnonstop
$147Southwest
Find Deal
Thu, Jan 23 - Sun, Jan 26
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
9:35 pm - 11:05 pmLGA-MDW
2h 30mnonstop
$148Southwest
Find Deal
Fri, Jan 10 - Mon, Jan 13
5:05 pm - 11:09 pmMDW-EWR
5h 04m1 stop
6:05 am - 10:36 amEWR-MDW
5h 31m1 stop
$158Delta
Find Deal
Sat, Jan 18 - Sat, Jan 25
4:08 pm - 8:04 amMDW-EWR
14h 56m2 stops
10:00 pm - 5:53 pmEWR-MDW
20h 53m1 stop
Thu, Jan 16 - Thu, Jan 23
7:21 pm - 5:33 pmMDW-EWR
21h 12m1 stop
10:00 pm - 5:53 pmEWR-MDW
20h 53m1 stop
Thu, Jan 16 - Thu, Jan 23
7:00 pm - 10:05 amMDW-EWR
14h 05m1 stop
9:55 am - 6:10 pmEWR-MDW
9h 15m1 stop
$416Allegiant Air
Find Deal
Fri, May 30 - Mon, Jun 2

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 $148 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 $148.

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 Mondays 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 September, where tickets cost $157 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $257 and $226 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.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $152 on average.

Good to know

Low season

May

High season

December

Cheapest flight

$50
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Chicago Midway Airport to New York LaGuardia 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 $50 for a one-way ticket and $100 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.

  • 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 $280 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 $359 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 $120 or less one-way and $209 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 4821 reviews
7.7Entertainment
8.2Boarding
8.7Crew
8.1Comfort
7.2Food
Airline reviews

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.

10.0 ExcellentWilliam Drew, Dec 2024SJC - HNL
Read more Southwest reviews

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.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Much better than the.last. flight on SW on Thanksgiving day

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

It went well. Plane wasn't full. Will be great when assigned seating is in place

Everything was great except the food. The pretzels are really crappy.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

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.

Flight was delayed. Had to get rebooked. Diamond medallion but stuck in a crappy seat. Rebooked flight then got delayed again. Then when we finally boarded, we waited another hour for a new crew. Then landed in JFK and sat for another 40 minutes waiting for a crew to come to the gate to be able to deplane. Hot mess all around, which unfortunately is becoming the norm for Delta

My seat was changed at the last minute and I was moved to the last row, right next to the bathroom despite selecting my seat well in advance. I was also made to check my carry on due to space but when I got on the plane there was significant empty overhead space. Picking up my carry on from the luggage carousel added time to my trip which had already been extended due to delay.

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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.

Cancelled after 3 hour delay with no aside from a rebooking three days later.

Delayed each time on a round trip with no significant weather interference. Updates to flight times came after the fact. 30 min behind in boarding and board and phone still show an on time departure. Some mysterious extra 300 miles that came so surprising they had to fuel while we were already on board?

A lady asked to stop the flight after the tunnel pulled away and we began to depart a flight that was already hours late. The attendance respectfully stopped the the plane and had the tunnel return. After the tunnel returned the passenger claimed to have changed her mind . The tunnel was then put in reverse and the passenger remained on the plane .. They should have sent the sick passenger off the plane like initially replaced. They existed a couple off the plane prior to that situation.. So.. all and all.. it was a long and flight.. .

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

I ended up paying $70+ dollars to for a carryon because the website is confusing and misleading. I now realize I did not need to pay that. I request a refund. I will pay extra to other airlines and not fly Frontier again.

With frontier you get what you pay for. The flight was two hours late. It’s a tight fit for the number of people they bring but you get to where you’re going cheap. Sometimes that’s more important than a nifty drink and cool TV..

Charges unexpected. For seat that didnt recline. Please reverse extra seat and carryon charge. Bad business that is a bait and switch.

Although we received an email from Kayak AND the airline, turns out we were not on Frontier’s manifest for the flight. We had to purchase tickets at the gate. Not sure where this transaction fell apart, but it did. We are now disputing the charges for the SLC to PDX flight originally booked through Kayak.

We had an awful experience getting our bags checked in. Frontier’s check in on the app manipulated us into buying the business package because that was the only option available for a checked bag which included two checked bags per person which we did not need. Upon arriving to the airport, we stood in line for what seemed like forever at the baggage check in and there was no one available at the counter. We were first in line and we were afraid we were going to miss our flight due to the baggage attendant being late. After realizing there were a lot of other people waiting at the baggage check in and no one available. I reached out to Frontier and could not get any customer service so I had to call the airport to page the baggage attendant to send someone to the counter to check in our bags before we were able to go through security , I finally spoke to the attendant at the counter and explained to her that we had to pay for two checked bags person a total of six bags when we only had a total of three bags between three people she said to reach out to Frontier and they would issue a refund for the three bags that we paid for and did not need. I reached out to Frontier which I was not able to reach anybody by phone so I had to go through their automated chat feature, which sent me around in circles until I finally reached a representative to assist me. I explained to them what happened and they explained that they were not able to assist me. I continued to push the issue with them as this was very frustrating and they finally put in a customer service ticket where we were issued a flight credit and we were so disappointed because after this experience, we NEVER want to fly Frontier again, and we do not want a credit that we will not use. Frontier charged us almost $500 for us to check three bags which is absolutely absurd! The customer service agents were not able to offer anything else other than a flight credit and I do not feel like my frustrations were truly heard , we will never use Frontier Airlines again ! Truly Theft by Manipulation! They should be ashamed!

I couldn’t check in because the app didn’t work. It took 3 Frontier employees at the counter to get me checked in. Flight left 3 hours after departure time

One crew member was rude about our bags. Be nice about it. We don’t fly a lot. And the fact that you have to pay for a carry on is ridiculous

Book cheap flights from Chicago to New York

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to New York found on KAYAK in the last 72 hours.
2/12Wed
1 stopFrontier
5h 48mMDW-LGA
$50
1/23Thu
1 stopFrontier
8h 35mMDW-LGA
$54
1/10Fri
nonstopSouthwest
2h 05mMDW-LGA
$74
2/18Tue
nonstopSouthwest
2h 05mMDW-LGA
$79
1/10Fri
1 stopDelta
3h 41mMDW-EWR
$83
5/17Sat
1 stopDelta
5h 26mMDW-EWR
$88
1/5Sun
1 stopAllegiant Air
15h 43mMDW-SWF
$137
1/7Tue
2 stops
14h 11mMDW-EWR
$153
1/7Tue
2 stops
12h 39mMDW-LGA
$162
6/13Fri
1 stopAllegiant Air
13h 29mMDW-EWR
$172

Search by stops

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Last minute flights from Midway to New York

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to New York that are departing in the next 10 days.
12/25Wed
nonstopSouthwest
2h 05mMDW-LGA
1/1Wed
nonstopSouthwest
2h 30mLGA-MDW
$297
12/25Wed
nonstopSouthwest
2h 05mMDW-LGA
1/1Wed
nonstopSouthwest
2h 30mLGA-MDW
$313
12/23Mon
nonstopSouthwest
2h 05mMDW-LGA
12/30Mon
multi-stopSouthwest
5h 20mLGA-MDW
$322
12/23Mon
nonstopSouthwest
2h 05mMDW-LGA
12/30Mon
nonstopSouthwest
2h 25mLGA-MDW
$323
12/25Wed
multi-stopDelta
5h 51mMDW-EWR
1/1Wed
multi-stopDelta
6h 08mEWR-MDW
$328
12/23Mon
multi-stopDelta
5h 37mMDW-EWR
1/7Tue
multi-stopDelta
6h 04mEWR-MDW
$348
12/25Wed
multi-stopDelta
5h 59mMDW-JFK
1/4Sat
multi-stopDelta
5h 39mJFK-MDW
$355
12/25Wed
multi-stopFrontier
22h 33mMDW-LGA
1/7Tue
multi-stopFrontier
6h 15mLGA-MDW
$448
12/21Sat
multi-stopFrontier
15h 55mMDW-JFK
12/24Tue
multi-stopFrontier
13h 33mJFK-MDW
$483
12/25Wed
multi-stopFrontier
8h 50mMDW-LGA
12/31Tue
multi-stopFrontier
8h 04mLGA-MDW
$498

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

Information on your arrival and departure airports

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