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Cheap flights from New York to Chicago Midway Airport from $50

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 1/14. 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 - 4:16 pmLGA-MDW
6h 17m1 stop
8:12 am - 3:00 pmMDW-LGA
5h 48m1 stop
$101Frontier
Find Deal
Di, Feb 4 - Mi, Feb 12
11:02 am - 3:16 pmJFK-MDW
29h 14m1 stop
11:33 am - 1:59 pmMDW-JFK
25h 26m1 stop
$103Frontier
Find Deal
Sa, Jan 11 - Mo, Jan 13
5:00 pm - 9:55 amLGA-MDW
17h 55m1 stop
11:33 am - 3:56 pmMDW-LGA
27h 23m1 stop
$103Frontier
Find Deal
Sa, Jan 11 - Mo, Jan 13
11:00 am - 7:06 pmJFK-MDW
9h 06m1 stop
12:43 pm - 6:30 amMDW-JFK
16h 47m1 stop
$104Frontier
Find Deal
Mi, Jan 22 - Mo, Jan 27
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
6:00 am - 9:10 amMDW-LGA
2h 10mnonstop
$148Southwest
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Do, Jan 9 - Mo, Jan 13
6:15 am - 7:50 amLGA-MDW
2h 35mnonstop
8:15 pm - 11:20 pmMDW-LGA
2h 05mnonstop
$153Southwest
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Sa, Feb 22 - Do, Feb 27
9:37 am - 1:08 pmEWR-MDW
4h 31m1 stop
9:34 am - 5:05 pmMDW-EWR
6h 31m1 stop
$158Delta
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Di, Jan 21 - Sa, Jan 25
6:05 am - 10:36 amEWR-MDW
5h 31m1 stop
9:34 am - 5:05 pmMDW-EWR
6h 31m1 stop
$162Delta
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Sa, Jan 11 - Sa, Jan 18
10:00 pm - 11:29 pmEWR-MDW
26h 29m1 stop
7:25 am - 9:01 amMDW-EWR
24h 36m1 stop
Fr, Jan 24 - So, Jan 26
10:00 pm - 11:29 pmEWR-MDW
26h 29m1 stop
7:25 am - 8:04 amMDW-EWR
47h 39m3 stops
Fr, Jan 24 - So, Jan 26
11:00 am - 4:14 pmJFK-MDW
6h 14m1 stop
$50Frontier
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Di, Jan 14
10:59 am - 4:14 pmLGA-MDW
6h 15m1 stop
$50Frontier
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Di, Jan 14
11:00 am - 6:26 pmJFK-MDW
8h 26m1 stop
$54Frontier
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Do, Jan 23
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
$74Southwest
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Fr, Jan 10
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
$79Southwest
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Mi, Feb 19
8:55 am - 4:14 pmLGA-MDW
8h 19m1 stop
Di, Jan 7
11:29 am - 4:21 pmEWR-MDW
5h 52m1 stop
$83Delta
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Di, Jan 14
9:40 am - 12:30 pmEWR-MDW
3h 50m1 stop
$88Delta
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Sa, Mai 31
5:21 pm - 5:46 pmSWF-MDW
25h 25m1 stop
$142Allegiant Air
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Mo, Mrz 17
5:45 am - 11:35 pmLGA-MDW
18h 50m2 stops
Fr, Jan 3
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
6:00 am - 9:10 amMDW-LGA
2h 10mnonstop
$346Southwest
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Di, Dez 24 - Do, Jan 9
6:00 am - 10:20 amLGA-MDW
5h 20m1 stop
8:30 am - 11:35 amMDW-LGA
2h 05mnonstop
$412Southwest
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Mo, Dez 23 - Di, Jan 7
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
2:00 pm - 9:00 pmMDW-LGA
6h 00m1 stop
$414Southwest
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Di, Dez 24 - Do, Jan 9
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
8:35 am - 5:20 pmMDW-LGA
7h 45m2 stops
$449Southwest
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Di, Dez 24 - Do, Jan 9
12:29 pm - 11:14 pmLGA-MDW
11h 45m1 stop
7:00 am - 9:02 pmMDW-LGA
13h 02m1 stop
$533Frontier
Find Deal
Fr, Dez 20 - So, Jan 12
6:00 am - 8:50 amEWR-MDW
3h 50m1 stop
5:07 pm - 12:29 amMDW-EWR
6h 22m1 stop
$556Delta
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Mo, Dez 23 - Di, Jan 14
6:00 am - 8:50 amEWR-MDW
3h 50m1 stop
10:57 am - 5:06 pmMDW-EWR
5h 09m1 stop
$593Delta
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Mo, Dez 23 - Mi, Jan 15
12:29 pm - 11:14 pmLGA-MDW
11h 45m1 stop
8:00 am - 10:00 pmMDW-LGA
13h 00m1 stop
$613Frontier
Find Deal
Fr, Dez 20 - Do, Jan 2
12:10 pm - 4:17 pmEWR-MDW
5h 07m1 stop
6:00 am - 12:15 pmMDW-EWR
5h 15m1 stop
$626Delta
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Fr, Dez 20 - Mi, Jan 8
10:03 am - 10:33 pmJFK-MDW
13h 30m1 stop
4:08 pm - 9:03 amMDW-JFK
15h 55m1 stop
$633Frontier
Find Deal
Sa, Dez 21 - Di, Dez 31
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
6:00 am - 9:10 amMDW-LGA
2h 10mnonstop
$148Southwest
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Do, Jan 9 - Mo, Jan 13
6:15 am - 7:50 amLGA-MDW
2h 35mnonstop
8:15 pm - 11:20 pmMDW-LGA
2h 05mnonstop
$153Southwest
Find Deal
Sa, Feb 22 - Do, Feb 27
6:15 am - 7:50 amLGA-MDW
2h 35mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$158Southwest
Find Deal
Sa, Feb 15 - Di, Feb 18
9:05 am - 10:45 amLGA-MDW
2h 40mnonstop
6:00 am - 9:10 amMDW-LGA
2h 10mnonstop
$163Southwest
Find Deal
Di, Jan 7 - Mi, Jan 8
9:05 am - 10:45 amLGA-MDW
2h 40mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$168Southwest
Find Deal
Sa, Jan 11 - Mo, Jan 13
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
5:50 am - 9:00 amMDW-LGA
2h 10mnonstop
$169Southwest
Find Deal
Do, Jan 30 - So, Feb 16
9:30 pm - 11:00 pmLGA-MDW
2h 30mnonstop
5:50 am - 9:00 amMDW-LGA
2h 10mnonstop
$174Southwest
Find Deal
Di, Feb 18 - So, Feb 23
3:30 pm - 5:10 pmLGA-MDW
2h 40mnonstop
6:00 pm - 9:05 pmMDW-LGA
2h 05mnonstop
$183Southwest
Find Deal
Di, Jan 7 - Di, Jan 21
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$185Southwest
Find Deal
Mo, Jan 6 - Mi, Jan 8
9:05 am - 10:45 amLGA-MDW
2h 40mnonstop
8:05 am - 11:15 amMDW-LGA
2h 10mnonstop
$188Southwest
Find Deal
Sa, Jan 18 - Sa, Jan 25

Frontier flights from New York to Chicago Midway Airport

Our best Frontier deals on New York to Chicago Midway Airport flight tickets
Frontier
Feb 4
LGA10:59 amNew York LaGuardia
6h 17m
1 stop
MDW4:16 pmChicago Midway
Feb 12
MDW8:12 amChicago Midway
5h 48m
1 stop
LGA3:00 pmNew York LaGuardia
Frontier
Jan 11
JFK11:02 amNew York John F Kennedy Intl
29h 14m
1 stop
MDW3:16 pmChicago Midway
Jan 13
MDW11:33 amChicago Midway
25h 26m
1 stop
JFK1:59 pmNew York John F Kennedy Intl
Frontier
Jan 22
JFK11:00 amNew York John F Kennedy Intl
9h 06m
1 stop
MDW7:06 pmChicago Midway
Jan 27
MDW12:43 pmChicago Midway
16h 47m
1 stop
JFK6:30 amNew York John F Kennedy Intl

Delta flights from New York to Chicago Midway Airport

Our best Delta deals on New York to Chicago Midway Airport flight tickets
Delta
Jan 21
EWR9:37 amNewark
4h 31m
1 stop
MDW1:08 pmChicago Midway
Jan 25
MDW9:34 amChicago Midway
6h 31m
1 stop
EWR5:05 pmNewark
Delta
Jan 11
EWR6:05 amNewark
5h 31m
1 stop
MDW10:36 amChicago Midway
Jan 18
MDW9:34 amChicago Midway
6h 31m
1 stop
EWR5:05 pmNewark
Delta
Jan 8
EWR12:43 pmNewark
6h 04m
1 stop
MDW5:47 pmChicago Midway
Jan 10
MDW6:28 pmChicago Midway
3h 41m
1 stop
EWR11:09 pmNewark

See travel insights to Chicago from

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 typical price of a round-trip flight between New York and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from New York, with most prices found around $188. If you are unable to visit Chicago Midway Airport during the month of January, then departing from New York during the month June is also very affordable. Most momondo users find prices during this month for around $208.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from New York. The lowest ticket price found for a Tuesday departure recently was $228. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from New York because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $454.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from New York in the evening is the least expensive time of day to depart. momondo users have found prices as low as $228 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $294. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Fly from New York LaGuardia to Chicago Midway for the best New York - Chicago Midway flight prices

What cabin class options are available on New York to Chicago Midway flights?

There are 1 cabin classes available to choose from on New York to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

You could potentially save up to 32% 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 December 2024, prices for New York to Chicago Midway Airport flights are approximately 18% more expensive 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

$50

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from New York in the past 72 hours is $50. The best round-trip flight deal from New York to Chicago Midway Airport found on momondo in the last 72 hours is $101.
The fastest flight from New York to Chicago Midway Airport takes 2h 20m
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 $115Free CancellationRating
6.3
8,120 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $147Free CancellationRating
8.1
4,836 reviews
Search Southwest flights
DeltaPriceFrom $167Free CancellationRating
8.0
8,600 reviews
Search Delta flights
  • Southwest Flights From New York to Chicago Midway Airport

    Across 10 Southwest flights from New York to Chicago Midway Airport this week, the average price was $256, with the best Southwest deals starting from $147 round-trip. 4,836 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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