MDW - NYC

$134 Find Cheap Flights from Chicago Midway Airport to New York - Compare and Save

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Everything you should know

Cheapest round-trip
$259
Typical prices: $167-$361
Frontier
Mon 11/26Sat 12/1
MDW - LGA • 1 stop
Cheapest non-stop
$259
Typical prices: $166-$354
Southwest
Fri 12/14Sun 12/16
MDW - LGA • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 05m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 48% average savings
Most popular
Insights
Insights
Avoid delays
Most punctual • 77% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 50% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 25% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $297 (round-trip)
Shortest trip • 7h 42m (one-way)
Insights
Insights
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Flight Deals

Cheap Flights from Midway to New York (MDW-NYC)

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

Recent round-trip flight deals from Midway to New York

Sat, Dec 5 - Tue, Dec 8
Southwest Logo
11:50 am - 2:50 pmMDW  Chicago Midway-LGA New York LaGuardia
2h 00mnonstop
Southwest Logo
8:30 am - 10:05 amLGA  New York LaGuardia-MDW Chicago Midway
2h 35mnonstop
$260Southwest
Fri, Dec 4 - Tue, Dec 8
Southwest Logo
7:05 pm - 10:10 pmMDW  Chicago Midway-LGA New York LaGuardia
2h 05mnonstop
Southwest Logo
6:40 am - 8:05 amLGA  New York LaGuardia-MDW Chicago Midway
2h 25mnonstop
$260Southwest
Tue, Nov 10 - Fri, Nov 20
Frontier Logo
6:08 am - 4:01 pmMDW  Chicago Midway-LGA New York LaGuardia
8h 53m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:30 am - 11:55 amLGA  New York LaGuardia-MDW Chicago Midway
6h 25m1 stop Atlanta Hartsfield-Jackson
$260Frontier
Tue, Nov 17 - Tue, Nov 17
Frontier Logo
6:08 am - 4:01 pmMDW  Chicago Midway-LGA New York LaGuardia
8h 53m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
5:30 pm - 11:47 pmLGA  New York LaGuardia-MDW Chicago Midway
7h 17m1 stop Atlanta Hartsfield-Jackson
$260Frontier
Fri, Nov 13 - Tue, Nov 17
Southwest Logo
7:15 pm - 10:20 pmMDW  Chicago Midway-LGA New York LaGuardia
2h 05mnonstop
Southwest Logo
6:35 pm - 8:15 pmLGA  New York LaGuardia-MDW Chicago Midway
2h 40mnonstop
$260Southwest
Sat, Nov 14 - Tue, Dec 1
Frontier Logo
12:20 pm - 8:59 pmMDW  Chicago Midway-LGA New York LaGuardia
7h 39m1 stop Dallas/Fort Worth
Frontier Logo
8:36 pm - 9:26 amLGA  New York LaGuardia-MDW Chicago Midway
13h 50m1 stop Dallas/Fort Worth
$260Frontier
Wed, Nov 18 - Sat, Nov 21
Delta Logo
6:00 am - 12:30 pmMDW  Chicago Midway-EWR Newark
5h 30m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:37 am - 12:51 pmEWR  Newark-MDW Chicago Midway
4h 14m1 stop Detroit Metropolitan Wayne County
$272Delta
Fri, Nov 13 - Mon, Nov 16
Delta Logo
11:27 am - 5:29 pmMDW  Chicago Midway-EWR Newark
5h 02m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:55 pm - 6:04 pmEWR  Newark-MDW Chicago Midway
6h 09m1 stop Detroit Metropolitan Wayne County
$277Delta
Fri, Dec 4 - Mon, Dec 7
Multiple Airlines Logo
5:02 pm - 12:29 amMDW  Chicago Midway-EWR Newark
6h 27m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
9:55 am - 11:33 amEWR  Newark-MDW Chicago Midway
50h 38m2 stops Cincinnati Cinci./N. Kentucky Atlanta Hartsfield-Jackson
$292Multiple Airlines
Wed, Nov 11 - Fri, Nov 13
Multiple Airlines Logo
6:42 pm - 10:36 amMDW  Chicago Midway-EWR Newark
14h 54m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
9:55 am - 2:26 pmEWR  Newark-MDW Chicago Midway
5h 31m1 stop Knoxville McGhee Tyson
$301Multiple Airlines
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to New York flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Chicago Midway Airport to New York typically range from $167 to $361. The lowest price found in the past 5 days was $259, on Frontier.

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

Chicago Midway Airport (MDW) to Newark Airport (EWR) is the cheapest Chicago Midway Airport to New York route, averaging $154 round-trip. Other Chicago Midway Airport to New York routes average $371, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Chicago Midway Airport to New York. It’s 10% cheaper than the average day, while Monday is the most expensive, with prices 23% higher.

What’s the cheapest month to fly from Chicago Midway Airport to New York?

•November is the cheapest month to fly from Chicago Midway Airport to New York at $191 round-trip.
•September ($328) and July ($325) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 71% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago Midway Airport to New York the cheapest?

Flights from Chicago Midway Airport to New York are cheapest 7 weeks before departure. Booking in this window typically costs about 50% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for Chicago Midway Airport to New York flights

Low season

September

Cheapest flight

$134
Beat the crowds with an average 32% drop in travelers.
The most popular month to fly with an average 42% increase in travelers.
One-way 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

Your Chicago Midway Airport to New York flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago Midway Airport to New York?

    These are the earliest and latest flight times available from Chicago Midway Airport to New York:

    • Earliest: departs at 5:00 am and lands at 7:05 am
    • Latest: departs at 8:05 pm and lands at 10:10 pm.

    The flight takes about 2h 05m.

  • What cabin classes can I book on flights from Chicago Midway Airport to New York?

    Two cabin classes are available on flights from Chicago Midway Airport to New York:

    • Economy Class
    • First Class

  • How long is a flight from Chicago Midway Airport to New York?

    A nonstop flight from Chicago Midway Airport to New York takes 2h 05m, covering 717 miles.

  • Do I need a passport to fly from Chicago Midway Airport to New York?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago Midway Airport to New York flight?

    Round-trip flights from Chicago Midway Airport to New York range from $167 to $361, with an average of $254 over the past 12 months. Anything below $167 counts as a good deal.

  • How expensive are last-minute Chicago Midway Airport to New York flights?

    Last-minute fares on this route (booked within two weeks of departure) run 62% above the $254 route average. Book 7 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago Midway Airport to New York?

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $252 round-trip, compared to $297 via a layover through Detroit Metropolitan Wayne County (DTW).

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to New York?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$91 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Chicago Midway Airport to New York spread across the day?

    Morning is the busiest departure period on Chicago Midway Airport to New York flights, with 51% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 16%, and night flights for 0%.

  • Have flight prices from Chicago Midway Airport to New York changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $259 to $1,813. That means the highest observed fare was about 7x higher than the lowest one.

  • Which airlines offer Wi-Fi on Chicago Midway Airport to New York flights?

    JetBlue is the only airline on the Chicago Midway Airport to New York route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Chicago Midway Airport to New York looking right now?

    One-way fares from Chicago Midway Airport to New York are currently lower than usual. Average one-way flight prices are about $144, which is 23% below the typical average for this route.

  • What car rental options are available in New York?

    Since New York is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near New York John F Kennedy Intl Airport (JFK) — daily rates from around $21:

    • Ace
    • Budget
    • Hertz
    • Dollar
    • Avis

    Near New York LaGuardia Airport (LGA) — daily rates from around $16:

    • Ace
    • Budget
    • Hertz
    • Avis
    • Dollar

    Near Newark Airport (EWR) — daily rates from around $28:

    • Ace
    • Budget
    • Alamo
    • Hertz
    • Dollar

  • Which airports can I use when flying from Chicago Midway Airport to New York?

    Flights from Chicago Midway Airport to New York usually depart from Chicago Midway (MDW) and may arrive at several airports in New York area, including Newark (EWR), New York John F Kennedy Intl (JFK) and New York LaGuardia (LGA).

  • What time of day has the fewest delays on flights from Chicago Midway Airport to New York?

    Night flights have the fewest delays on this route, while evening departures tend to have the most.

  • At what point is a flight considered delayed from Chicago Midway Airport to New York?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago Midway Airport to New York route, 23% of flights were delayed in the past 3 months, with delays averaging 1h 51m.

  • Which airports do connecting flights from Chicago Midway Airport to New York pass through?

    One-stop flights from Chicago Midway Airport to New York most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 74% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 24% of one-stop connections
    • Nashville Intl (BNA) - 3% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to New York?

    Yes. Flexible dates can save you up to 27% on flights from Chicago Midway Airport to New York. Tuesday is the cheapest departure day at $231 round-trip on average, while Monday is the most expensive at $313, a difference of $82.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago Midway Airport to New York?

    Only Southwest operates flights between Chicago Midway Airport and New York.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to New York?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 45m, compared with 7h 42m via Nashville Intl (BNA) and 9h 10m via Atlanta Hartsfield-Jackson (ATL).

  • What is the time difference between Chicago Midway Airport and New York?

    New York is 1 hour ahead of Chicago Midway Airport (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in New York?

    Some of the most popular sights in New York are Times Square, New York City Center and Madison Square Garden. These are among the most viewed places in New York on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Chicago Midway Airport to New York flights?

    Among airlines operating Chicago Midway Airport to New York flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago Midway Airport to New York flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago Midway Airport to New York flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure and avoid flying on Monday. On this route, Tuesday flights average $231, about $82 less than Monday fares (26% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 7 weeks before you fly. On this route, that window historically saves about 50% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to New York trip for November. Fares historically average $191 round-trip in that month - typically $137 less than the most expensive month, which is September (based on the last 12 months).
  • For the best chance of arriving on time, fly with Southwest. Over the past three months, 77% of Southwest flights from Chicago Midway Airport to New York arrived on time, slightly above the route average of 77%. When flights on this route arrive late, they're delayed by an average of 1h 51m, so choosing an airline with strong on-time performance can make a difference if you're on a tight schedule.
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Newark Airport.

    • DoubleTree by Hilton Newark Airport
    • Holiday Inn Newark International Airport By IHG
    • Hampton Inn by Hilton Newark Airport

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

More options for your flight from Midway to New York

Complete your trip to New York with a hotel stay or car rental