Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 5/26. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

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.
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
5:50 pm - 9:00 pmMDW-LGA
2h 10mnonstop
$143Southwest
Find Deal
Sun, Apr 20 - Tue, Apr 22
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
5:50 pm - 9:00 pmMDW-LGA
2h 10mnonstop
$149Southwest
Find Deal
Tue, Apr 29 - Tue, May 6
6:05 am - 1:15 pmEWR-MDW
8h 10m1 stop
4:15 pm - 1:07 amMDW-EWR
7h 52m1 stop
$179Delta
Find Deal
Sat, May 10 - Tue, May 13
1:13 pm - 5:59 pmEWR-MDW
5h 46m1 stop
4:59 pm - 11:03 pmMDW-EWR
5h 04m1 stop
$188Delta
Find Deal
Sat, Apr 26 - Tue, Apr 29
6:00 am - 11:26 amJFK-MDW
6h 26m1 stop
2:12 pm - 12:20 amMDW-JFK
9h 08m1 stop
$196Frontier
Find Deal
Wed, May 14 - Wed, May 21
10:00 pm - 9:16 amEWR-MDW
12h 16m1 stop
8:30 am - 9:01 pmMDW-EWR
11h 31m1 stop
$198Frontier
Find Deal
Mon, Apr 28 - Sun, May 11
11:55 am - 3:37 pmEWR-MDW
28h 42m1 stop
8:36 pm - 11:05 amMDW-EWR
13h 29m1 stop
$229Allegiant Air
Find Deal
Tue, Jun 10 - Fri, Jun 13
9:55 am - 9:41 amEWR-MDW
24h 46m1 stop
10:31 am - 9:05 amMDW-EWR
21h 34m1 stop
$232Allegiant Air
Find Deal
Thu, Jul 10 - Mon, Jul 14
9:55 am - 8:42 amEWR-MDW
23h 47m1 stop
11:43 am - 9:22 pmMDW-EWR
32h 39m2 stops
Thu, Aug 21 - Sun, Aug 24
12:27 pm - 1:29 pmEWR-MDW
26h 02m2 stops
10:59 am - 10:57 pmMDW-EWR
34h 58m2 stops
Sat, Apr 19 - Mon, Apr 21

Southwest flights from New York to Chicago Midway Airport

Our best Southwest deals on New York to Chicago Midway Airport flight tickets
Southwest
Apr 20
LGA6:10 amNew York LaGuardia
2h 20m
MDW7:30 amChicago Midway
Apr 22
MDW5:50 pmChicago Midway
2h 10m
LGA9:00 pmNew York LaGuardia
Southwest
Apr 29
LGA6:10 amNew York LaGuardia
2h 20m
MDW7:30 amChicago Midway
May 6
MDW5:50 pmChicago Midway
2h 10m
LGA9:00 pmNew York LaGuardia
Southwest
May 13
LGA6:25 pmNew York LaGuardia
5h 45m
1 stop
MDW11:10 pmChicago Midway
May 28
MDW8:20 pmChicago Midway
2h 05m
LGA11:25 pmNew York LaGuardia

Delta flights from New York to Chicago Midway Airport

Our best Delta deals on New York to Chicago Midway Airport flight tickets
Delta
May 10
EWR6:05 amNewark
8h 10m
1 stop
MDW1:15 pmChicago Midway
May 13
MDW4:15 pmChicago Midway
7h 52m
1 stop
EWR1:07 amNewark
Delta
Apr 26
EWR1:13 pmNewark
5h 46m
1 stop
MDW5:59 pmChicago Midway
Apr 29
MDW4:59 pmChicago Midway
5h 04m
1 stop
EWR11:03 pmNewark
Delta
May 20
EWR5:59 amNewark
3h 41m
1 stop
MDW8:40 amChicago Midway
May 25
MDW6:25 pmChicago Midway
3h 45m
1 stop
EWR11:10 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 $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 $273. 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 $414.

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 $362. 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 March 2025, prices for New York to Chicago Midway Airport flights are approximately 53% 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

$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 $143.
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 $88Free CancellationRating
6.3
7,883 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $148Free CancellationRating
8.0
4,275 reviews
Search Southwest flights
DeltaPriceFrom $203Free CancellationRating
8.0
7,899 reviews
Search Delta flights
  • Southwest Flights From New York to Chicago Midway Airport

    Across 36 Southwest flights from New York to Chicago Midway Airport this week, the average price was $249, with the best Southwest deals starting from $148 round-trip. 4,275 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Crown Point
Munster
Monticello
Chesterton
Porter
Griffith
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.


An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Sat 4/5
Sat 4/12

Find better results for your trip to Chicago