MDW - NYC

$49 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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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
8:12 am - 3:00 pmMDW-LGA
5h 48m1 stop
10:00 pm - 11:28 amLGA-MDW
14h 28m1 stop
$100Frontier
Find Deal
Wed, Feb 19 - Wed, Feb 19
8:12 am - 3:00 pmMDW-LGA
5h 48m1 stop
10:00 pm - 11:28 amLGA-MDW
14h 28m1 stop
$101Frontier
Find Deal
Wed, Feb 12 - Wed, Feb 12
7:25 am - 5:00 pmMDW-LGA
8h 35m1 stop
10:59 am - 4:16 pmLGA-MDW
6h 17m1 stop
$106Frontier
Find Deal
Thu, Feb 6 - Tue, Feb 11
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
9:35 pm - 11:05 pmLGA-MDW
2h 30mnonstop
$147Southwest
Find Deal
Tue, Feb 11 - Wed, Feb 12
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
9:35 pm - 11:05 pmLGA-MDW
2h 30mnonstop
$157Southwest
Find Deal
Fri, Feb 7 - Tue, Feb 11
5:05 pm - 11:09 pmMDW-EWR
5h 04m1 stop
9:37 am - 1:05 pmEWR-MDW
4h 28m1 stop
$159Delta
Find Deal
Sat, Mar 1 - Tue, Mar 4
6:00 am - 9:10 amMDW-LGA
2h 10mnonstop
11:25 am - 1:00 pmLGA-MDW
2h 35mnonstop
$161Southwest
Find Deal
Wed, Feb 19 - Wed, Feb 19
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
3:30 pm - 5:10 pmLGA-MDW
2h 40mnonstop
$162Southwest
Find Deal
Tue, Feb 11 - Thu, Feb 13
5:05 pm - 12:48 amMDW-EWR
6h 43m1 stop
6:00 am - 10:16 amEWR-MDW
5h 16m1 stop
$163Delta
Find Deal
Tue, Feb 18 - Sat, Feb 22
5:05 pm - 11:09 pmMDW-EWR
5h 04m1 stop
9:37 am - 1:05 pmEWR-MDW
4h 28m1 stop
$167Delta
Find Deal
Sat, Feb 15 - Tue, Feb 18

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 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 February, where tickets cost $188 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $394 and $351 respectively.

Good to know

Low season

May

High season

December

Cheapest flight

$49
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 28% 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 $49 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 $282 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 $371 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 $96 or less one-way and $179 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 4662 reviews
8.1Comfort
7.2Food
8.2Boarding
7.7Entertainment
8.7Crew
Airline reviews

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.

10.0 ExcellentRachel, Jan 2025TPA - MDW
Read more Southwest reviews

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.

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

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.

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.

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.

The seats were extremely hard and uncomfortable, even for a budget airline.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Charging $74 for one checked bag is outrageous. I will never fly Frontier again.

Boarding was very well executed. Got my bag right away.

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