MDW - NYC

$94 Find Cheap Flights from Chicago Midway Airport to New York - Compare and Save

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 8/4. 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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Everything you should know

Cheapest round-trip
$185
Typical prices: $300-$426
Southwest
Wed 8/5Sat 9/19
MDW - LGA • 2 stops
Cheapest non-stop
$186
Typical prices: $365-$457
Southwest
Thu 8/20Sun 8/23
MDW - LGA • Non-stop
Top airlines
Cheapest • from $185 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 2h 06m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest • 28% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 77% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $181 (round-trip)
Shortest trip • 4h 48m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 71% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to New York

Wed, Aug 5 - Sat, Sep 19
Southwest Logo
8:50 am - 5:05 pm
MDW
-
LGA
7h 15m
2 stops
Southwest Logo
7:00 am - 1:20 pm
LGA
-
MDW
7h 20m
2 stops
$185Southwest
Thu, Aug 20 - Sat, Aug 22
Southwest Logo
7:15 am - 1:55 pm
MDW
-
LGA
5h 40m
1 stop
Southwest Logo
8:20 am - 2:05 pm
LGA
-
MDW
6h 45m
1 stop
$186Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
7:45 am - 5:05 pm
MDW
-
LGA
8h 20m
1 stop
Southwest Logo
6:00 am - 7:15 am
LGA
-
MDW
2h 15mnonstop
$187Southwest
Fri, Jul 31 - Wed, Aug 5
Southwest Logo
7:45 pm - 11:00 pm
MDW
-
LGA
2h 15mnonstop
Southwest Logo
7:10 am - 1:55 pm
LGA
-
MDW
7h 45m
1 stop
$188Southwest
Thu, Sep 17 - Sun, Sep 20
Delta Logo
1:19 pm - 7:30 pm
MDW
-
EWR
5h 11m
1 stop
Delta Logo
6:00 am - 9:07 am
EWR
-
MDW
4h 07m
1 stop
$202Delta
Sat, Aug 15 - Tue, Sep 15
Delta Logo
6:42 pm - 11:25 pm
MDW
-
EWR
3h 43m
1 stop
Delta Logo
1:00 pm - 6:33 pm
EWR
-
MDW
6h 33m
1 stop
$227Delta
Mon, Aug 17 - Wed, Aug 19
Frontier Logo
11:06 am - 9:28 pm
MDW
-
EWR
9h 22m
1 stop
Frontier Logo
5:55 am - 10:47 pm
EWR
-
MDW
17h 52m
1 stop
$235Frontier
Mon, Aug 24 - Mon, Aug 31
Frontier Logo
6:05 am - 1:03 am
MDW
-
EWR
17h 58m
1 stop
Frontier Logo
5:55 am - 10:55 am
EWR
-
MDW
6h 00m
1 stop
$237Frontier
Thu, Oct 29 - Sun, Nov 1
Multiple Airlines Logo
10:08 am - 10:29 am
MDW
-
SWF
23h 21m
1 stop
Multiple Airlines Logo
11:58 am - 10:58 am
SWF
-
MDW
24h 00m
2 stops
$313Multiple Airlines
Sun, Dec 6 - Sun, Dec 13
Multiple Airlines Logo
6:10 pm - 8:52 am
MDW
-
SWF
13h 42m
1 stop
Multiple Airlines Logo
9:36 am - 7:02 pm
SWF
-
MDW
10h 26m
1 stop
$427Multiple Airlines
Booking Insights

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

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.

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

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

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

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

The absolute cheapest return flight from Chicago Midway Airport to New York costs $187 on the route between Chicago Midway Airport (MDW) and New York LaGuardia Airport (LGA). However, over the past month, flights between Chicago Midway Airport (MDW) and Newark Airport (EWR) were, on average, 28% cheaper than other Chicago Midway Airport-New York routes. The most popular route is between Chicago Midway Airport (MDW) and New York LaGuardia Airport (LGA).

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 $29 (return) on average. On the other hand, the most expensive months are July and June, where the average cost of round-trip tickets is $177 and $169 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 $231 on average.

Good to know

Low seasonFebruary
Cheapest flight$94
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 35% 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 5 days, the lowest price for a flight from Chicago Midway Airport to New York was $94 for a one-way ticket and $185 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.

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

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

  • 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 Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to New York are Southwest and Frontier. With an average price for the route of $320 and an overall rating of 7.9, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $163 and an overall rating of 5.6.

  • 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.

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 $163 or less one-way and $234 or less round-trip.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway 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

Reviews of the top airlines flying 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.
7.9
SouthwestOverall score based on 4250 reviews
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

It good. Just not that plane didn’t have power outlets to charge devices etc.

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Plane and crew on board were fine. Everything else was terrible.

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

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Would be great if Frontier can Assign Seats together under one PNR

They cancelled the flight and did nothing. I should be compensated for my uber rides to and from airport. Not a good service by frontier or kayak.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

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

Information on your arrival and departure airports