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Cheap flights from New York to Chicago Midway Airport from $53

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New York to Chicago Midway Airport departing on 11/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from New York to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from New York to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from New York to Chicago.

Cheap last minute flights

Planning a quick getaway from New York to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from New York to Chicago

Find recent round-trip train or bus tickets from New York to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
10:59 am - 9:29 pmLGA-MDW
11h 30m1 stop
3:12 pm - 10:00 pmMDW-LGA
5h 48m1 stop
$105Frontier
Find Deal
Thu, Jan 30 - Tue, Feb 4
3:00 pm - 1:54 pmJFK-MDW
23h 54m1 stop
11:33 am - 1:59 pmMDW-JFK
25h 26m1 stop
$106Frontier
Find Deal
Thu, Dec 5 - Mon, Dec 9
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$148Southwest
Find Deal
Fri, Dec 6 - Mon, Dec 9
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$164Southwest
Find Deal
Mon, Jan 6 - Wed, Jan 8
9:37 am - 1:08 pmEWR-MDW
4h 31m1 stop
6:28 pm - 11:09 pmMDW-EWR
3h 41m1 stop
$166Delta
Find Deal
Thu, Jan 9 - Sun, Jan 12
12:20 pm - 5:02 pmEWR-MDW
5h 42m1 stop
6:49 pm - 12:59 amMDW-EWR
5h 10m1 stop
$176Delta
Find Deal
Tue, Nov 19 - Wed, Nov 20
10:00 pm - 1:57 pmEWR-MDW
16h 57m1 stop
4:21 pm - 8:10 amMDW-EWR
14h 49m1 stop
Mon, Feb 3 - Sun, Feb 9
5:45 am - 1:33 amLGA-MDW
20h 48m2 stops
2:02 pm - 11:39 amMDW-LGA
44h 37m2 stops
Sun, Nov 10 - Sat, Nov 16
6:50 am - 11:10 amEWR-MDW
5h 20m1 stop
12:05 pm - 6:00 pmMDW-EWR
4h 55m1 stop
$423Porter Airlines
Find Deal
Wed, Dec 4 - Wed, Dec 11
6:50 am - 11:10 amEWR-MDW
5h 20m1 stop
12:05 pm - 7:50 pmMDW-EWR
6h 45m1 stop
$424Porter Airlines
Find Deal
Wed, Dec 4 - Wed, Dec 11
12:29 pm - 12:13 pmLGA-MDW
24h 44m1 stop
$53Frontier
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Wed, Nov 13
11:00 am - 9:22 pmJFK-MDW
11h 22m1 stop
$54Frontier
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Sat, Nov 23
5:29 pm - 7:55 amLGA-MDW
15h 26m1 stop
$54Frontier
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Wed, Nov 13
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
$74Southwest
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Sat, Dec 7
1:00 pm - 6:14 pmEWR-MDW
6h 14m1 stop
$83Delta
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Thu, Jan 9
8:00 am - 2:34 pmEWR-MDW
7h 34m1 stop
$87Delta
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Wed, Nov 20
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
$90Southwest
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Tue, Dec 31
9:15 am - 11:24 pmEWR-MDW
15h 09m1 stop
Mon, Jan 13
8:55 am - 10:45 pmLGA-MDW
38h 50m2 stops
Wed, Dec 4
6:08 pm - 12:49 pmEWR-MDW
19h 41m3 stops
$269Spirit Airlines
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Sun, Nov 17
10:59 pm - 11:56 amLGA-MDW
13h 57m1 stop
11:59 am - 8:59 pmMDW-LGA
8h 00m1 stop
$125Frontier
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Sat, Nov 9 - Wed, Nov 13
10:59 pm - 11:56 amLGA-MDW
13h 57m1 stop
11:18 am - 10:08 pmMDW-LGA
9h 50m1 stop
$135Frontier
Find Deal
Sat, Nov 9 - Tue, Nov 12
5:45 am - 1:33 amLGA-MDW
20h 48m2 stops
2:02 pm - 8:00 amMDW-LGA
16h 58m1 stop
Sun, Nov 10 - Sat, Nov 16
5:45 am - 1:33 amLGA-MDW
20h 48m2 stops
2:02 pm - 11:39 amMDW-LGA
44h 37m2 stops
Sun, Nov 10 - Sat, Nov 16
9:45 pm - 9:00 amLGA-MDW
12h 15m1 stop
7:25 am - 1:25 pmMDW-LGA
5h 00m1 stop
$272Southwest
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Sun, Nov 10 - Sun, Nov 17
9:45 pm - 9:00 amLGA-MDW
12h 15m1 stop
7:00 am - 9:00 pmMDW-LGA
13h 00m2 stops
$277Southwest
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Sun, Nov 10 - Sun, Nov 17
1:00 pm - 5:03 pmEWR-MDW
5h 03m1 stop
6:49 pm - 12:59 amMDW-EWR
5h 10m1 stop
$343Delta
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Fri, Nov 8 - Tue, Nov 12
12:59 pm - 5:03 pmJFK-MDW
5h 04m1 stop
5:42 pm - 11:25 pmMDW-JFK
4h 43m1 stop
$373Delta
Find Deal
Sat, Nov 9 - Tue, Nov 12
10:55 am - 7:39 pmEWR-MDW
9h 44m1 stop
11:15 am - 11:05 amMDW-EWR
22h 50m2 stops
$594Allegiant Air
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Fri, Nov 8 - Sun, Nov 10
10:55 am - 7:39 pmEWR-MDW
9h 44m1 stop
11:15 am - 11:05 amMDW-EWR
22h 50m2 stops
$596Allegiant Air
Find Deal
Fri, Nov 8 - Sun, Nov 10
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$148Southwest
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Sat, Dec 7 - Wed, Dec 11
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$164Southwest
Find Deal
Mon, Jan 6 - Wed, Jan 8
4:30 pm - 6:10 pmLGA-MDW
2h 40mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$168Southwest
Find Deal
Fri, Nov 22 - Mon, Nov 25
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$180Southwest
Find Deal
Tue, Nov 12 - Tue, Nov 19
9:20 am - 10:55 amLGA-MDW
2h 35mnonstop
2:25 pm - 5:25 pmMDW-LGA
2h 00mnonstop
$183Southwest
Find Deal
Mon, Nov 25 - Mon, Nov 25
9:20 am - 10:55 amLGA-MDW
2h 35mnonstop
8:50 am - 11:55 amMDW-LGA
2h 05mnonstop
$188Southwest
Find Deal
Thu, Nov 21 - Thu, Nov 28
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
6:00 am - 9:05 amMDW-LGA
2h 05mnonstop
$193Southwest
Find Deal
Fri, Dec 6 - Sun, Dec 8
11:15 am - 12:45 pmLGA-MDW
2h 30mnonstop
6:00 am - 9:05 amMDW-LGA
2h 05mnonstop
$200Southwest
Find Deal
Thu, Nov 14 - Tue, Nov 19
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$204Southwest
Find Deal
Wed, Nov 13 - Wed, Nov 13
9:50 pm - 11:15 pmLGA-MDW
2h 25mnonstop
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$207Southwest
Find Deal
Sun, Nov 24 - Wed, Nov 27

Frontier flights from New York to Chicago Midway Airport

Our best Frontier deals on New York to Chicago Midway Airport flight tickets
Frontier
Jan 30
LGA10:59 amNew York LaGuardia
11h 30m
1 stop
MDW9:29 pmChicago Midway
Feb 4
MDW3:12 pmChicago Midway
5h 48m
1 stop
LGA10:00 pmNew York LaGuardia
Frontier
Dec 5
JFK3:00 pmNew York John F Kennedy Intl
23h 54m
1 stop
MDW1:54 pmChicago Midway
Dec 9
MDW11:33 amChicago Midway
25h 26m
1 stop
JFK1:59 pmNew York John F Kennedy Intl
Frontier
Nov 16
JFK3:00 pmNew York John F Kennedy Intl
9h 56m
1 stop
MDW11:56 pmChicago Midway
Nov 18
MDW8:20 pmChicago Midway
15h 02m
1 stop
JFK12:22 pmNew York John F Kennedy Intl

Porter Airlines flights from New York to Chicago Midway Airport

Our best Porter Airlines deals on New York to Chicago Midway Airport flight tickets
Porter Airlines
Dec 4
EWR6:50 amNewark
5h 20m
1 stop
MDW11:10 amChicago Midway
Dec 11
MDW12:05 pmChicago Midway
4h 55m
1 stop
EWR6:00 pmNewark
Porter Airlines
Dec 4
EWR6:50 amNewark
5h 20m
1 stop
MDW11:10 amChicago Midway
Dec 11
MDW12:05 pmChicago Midway
6h 45m
1 stop
EWR7:50 pmNewark
Porter Airlines
Nov 14
EWR7:40 amNewark
10h 00m
2 stops
MDW4:40 pmChicago Midway
Nov 18
MDW5:35 pmChicago Midway
13h 40m
1 stop
EWR8:15 amNewark

How to get the cheapest flight ticket from New York to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

January. The cheapest time of year to fly to Chicago Midway Airport from New York is January. Most expensive is May

What is the cheapest day to depart New York for Chicago Midway Airport?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday

When is the cheapest time to fly from New York to Chicago Midway Airport?

In the evening. New York to Chicago Midway Airport flights are approximately 28% more expensive in the morning than in the evening

What is the cheapest airline that flies to Chicago Midway Airport from New York?

Spirit Airlines. Spirit Airlines, Southwest, and Delta are the most popular carriers operating from New York to Chicago Midway Airport

How far in advance should you book New York to Chicago Midway Airport flights?

48 days before. The cheapest time to buy a flight from New York to Chicago Midway Airport is approximately 48 days to departure

How many flights depart from New York to Chicago Midway Airport on average per day?

As of November 2024, 5 flights take off from New York and land in Chicago Midway Airport each day. The most common flight departure time for this route is 9:00AM, with 43% of daily flights taking off at noon.

How many flights depart from New York to Chicago Midway Airport on average per week?

The number of flights available between New York and Chicago Midway Airport is 41 per week as of November 2024. The most frequent departure day is Sunday, with 17% of weekly flights leaving on this day.

Can stopping save me money on New York to Chicago Midway Airport flights?

You could potentially save up to 28% on your flight if you consider stops on a New York to Chicago Midway Airport flight.

How have New York to Chicago Midway Airport flight prices changed over time?

As of November 2024, prices for New York to Chicago Midway Airport flights are approximately 6% cheaper when compared to flights at the same time last year.

When to book flights from New York to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from New York to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap New York to Chicago Midway Airport (NYC to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New York to Chicago Midway Airport

Best Price Found

$53

Fastest flight time

2h 25m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from New York in the past 72 hours is $53. The best round-trip flight deal from New York to Chicago Midway Airport found on momondo in the last 72 hours is $105.
The fastest flight from New York to Chicago Midway Airport takes 2h 25m
Direct flights go from New York to Chicago Midway Airport every day.

  • How far is New York to Chicago Midway by plane?

    Chicago Midway is 716.7 mi away from New York. Flights usually cover this in 2h 25m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from New York to Chicago Midway Airport?

    Prices for flights from New York to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from New York to Chicago Midway Airport?

  • How old do you have to be to fly from New York to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New York to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from New York to Chicago Midway Airport?

  • What is the most popular airline from New York to Chicago Midway Airport?


Best airlines flying from New York to Chicago Midway Airport

Compare and see reviews for airlines that fly from New York to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $105Free CancellationRating
6.3
8,178 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $146Free CancellationRating
8.1
5,082 reviews
Search Southwest flights
DeltaPriceFrom $167Free CancellationRating
8.0
8,830 reviews
Search Delta flights
  • Southwest Flights From New York to Chicago Midway Airport

    Across 21 Southwest flights from New York to Chicago Midway Airport this week, the average price was $240, with the best Southwest deals starting from $146 round-trip. 5,082 users have rated Southwest on momondo, with an average score of 8.1/10.


Why use momondo?

Why should I use momondo to find a flight deal from New York to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from New York.

Can I find flights from New York to Chicago with flexible booking policies on momondo?

All flight searches from New York to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from New York to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from New York.

I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from New York and alert you when they change.


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