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Cheap flights from New York to Chicago Midway Airport from $69

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 5/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from New York to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from New York to Chicago.
Southwest Logo
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$137Southwest
Find Deal
Tue, May 27 - Wed, May 28
Southwest Logo
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$153Southwest
Find Deal
Wed, May 21 - Wed, May 28
Frontier Logo
6:30 am - 11:26 amLGA-MDW
5h 56m1 stop
Frontier Logo
9:34 am - 4:29 pmMDW-LGA
5h 55m1 stop
$176Frontier
Find Deal
Wed, May 7 - Tue, May 13
Frontier Logo
5:59 am - 3:39 pmEWR-MDW
10h 40m1 stop
Frontier Logo
5:36 pm - 12:46 amMDW-EWR
6h 10m1 stop
$178Frontier
Find Deal
Tue, Jun 3 - Tue, Jun 10
Delta Logo
9:46 am - 12:28 pmEWR-MDW
3h 42m1 stop
Delta Logo
4:15 pm - 1:07 amMDW-EWR
7h 52m1 stop
$179Delta
Find Deal
Tue, Jun 3 - Sat, Jun 7
Delta Logo
5:59 am - 8:40 amEWR-MDW
3h 41m1 stop
Delta Logo
9:21 am - 6:01 pmMDW-EWR
7h 40m1 stop
$189Delta
Find Deal
Sat, May 31 - Fri, Jul 4
Allegiant Air Logo
9:55 am - 2:03 pmEWR-MDW
5h 08m1 stop
Allegiant Air Logo
8:36 pm - 9:05 amMDW-EWR
11h 29m1 stop
$246Allegiant Air
Find Deal
Fri, Jun 13 - Mon, Jun 16
Allegiant Air Logo
12:55 pm - 8:22 amEWR-MDW
20h 27m1 stop
Allegiant Air Logo
8:36 pm - 9:05 amMDW-EWR
11h 29m1 stop
$248Allegiant Air
Find Deal
Thu, Jun 12 - Mon, Jun 16
 Logo
5:15 am - 7:14 pmEWR-MDW
14h 59m2 stops
 Logo
8:04 pm - 9:05 amMDW-EWR
12h 01m1 stop
Fri, May 30 - Mon, Jun 2
 Logo
5:15 am - 7:14 pmEWR-MDW
14h 59m2 stops
 Logo
8:04 pm - 9:05 amMDW-EWR
12h 01m1 stop
Fri, May 30 - Mon, Jun 2

Southwest flights from New York to Chicago Midway Airport

Our best Southwest deals on New York to Chicago Midway Airport flight tickets
Southwest
May 27
LGA6:10 amNew York LaGuardia
2h 20m
MDW7:30 amChicago Midway
May 28
MDW8:20 pmChicago Midway
2h 05m
LGA11:25 pmNew York LaGuardia
Southwest
May 21
LGA6:10 amNew York LaGuardia
2h 20m
MDW7:30 amChicago Midway
May 28
MDW8:20 pmChicago Midway
2h 05m
LGA11:25 pmNew York LaGuardia
Southwest
May 28
LGA6:10 amNew York LaGuardia
2h 20m
MDW7:30 amChicago Midway
May 31
MDW6:15 pmChicago Midway
2h 10m
LGA9:25 pmNew York LaGuardia

Frontier flights from New York to Chicago Midway Airport

Our best Frontier deals on New York to Chicago Midway Airport flight tickets
Frontier
May 7
LGA6:30 amNew York LaGuardia
5h 56m
1 stop
MDW11:26 amChicago Midway
May 13
MDW9:34 amChicago Midway
5h 55m
1 stop
LGA4:29 pmNew York LaGuardia
Frontier
Jun 3
EWR5:59 amNewark
10h 40m
1 stop
MDW3:39 pmChicago Midway
Jun 10
MDW5:36 pmChicago Midway
6h 10m
1 stop
EWR12:46 amNewark
Frontier
May 10
LGA10:00 pmNew York LaGuardia
20h 30m
1 stop
MDW5:30 pmChicago Midway
May 13
MDW9:34 amChicago Midway
5h 55m
1 stop
LGA4:29 pmNew York LaGuardia

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 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 $208. If you are unable to visit Chicago Midway Airport during the month of January, then departing from New York during the month October is also very affordable. Most momondo users find prices during this month for around $218.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from New York. The lowest ticket price found for a Wednesday departure recently was $272. 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, Monday 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 $416.

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 $245 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $363. 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.

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

As of April 2025, prices for New York to Chicago Midway Airport flights are approximately 12% 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

$69

Fastest flight time

2h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from New York in the past 72 hours is $69. The best round-trip flight deal from New York to Chicago Midway Airport found on momondo in the last 72 hours is $137.
The fastest flight from New York to Chicago Midway Airport takes 2h 15m
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 15m, 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 $37Free CancellationRating
6.3
7,940 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $148Free CancellationRating
8.0
4,287 reviews
Search Southwest flights
DeltaPriceFrom $203Free CancellationRating
8.0
7,920 reviews
Search Delta flights
  • Southwest Flights From New York to Chicago Midway Airport

    Across 37 Southwest flights from New York to Chicago Midway Airport this week, the average price was $248, with the best Southwest deals starting from $148 round-trip. 4,287 users have rated Southwest on momondo, with an average score of 8.0/10.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
Saint John

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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