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Cheap flights from New York to Chicago Midway Airport from $49

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.
11:00 am - 7:06 pmJFK-MDW
9h 06m1 stop
12:43 pm - 6:30 amMDW-JFK
16h 47m1 stop
$104Frontier
Find Deal
Wed, Jan 29 - Thu, Jan 30
11:02 am - 12:11 pmJFK-MDW
26h 09m1 stop
11:33 am - 1:59 pmMDW-JFK
25h 26m1 stop
$109Frontier
Find Deal
Thu, Jan 9 - Mon, Jan 13
8:55 am - 4:14 pmLGA-MDW
8h 19m1 stop
7:30 am - 5:00 pmMDW-LGA
8h 30m1 stop
Tue, Jan 7 - Thu, Jan 9
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$148Southwest
Find Deal
Sat, Dec 7 - Mon, Dec 9
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$163Southwest
Find Deal
Tue, Dec 31 - Wed, Jan 8
9:37 am - 1:08 pmEWR-MDW
4h 31m1 stop
10:57 am - 5:06 pmMDW-EWR
5h 09m1 stop
$166Delta
Find Deal
Wed, Jan 8 - Wed, Jan 22
9:37 am - 1:08 pmEWR-MDW
4h 31m1 stop
6:28 pm - 11:09 pmMDW-EWR
3h 41m1 stop
$176Delta
Find Deal
Thu, Jan 9 - Sun, Jan 12
8:55 am - 5:18 pmLGA-MDW
9h 23m1 stop
11:33 am - 5:00 pmMDW-LGA
28h 27m1 stop
Thu, Dec 5 - Mon, Dec 9
11:15 am - 4:40 pmEWR-MDW
6h 25m1 stop
11:25 am - 6:00 pmMDW-EWR
5h 35m1 stop
$500Porter Airlines
Find Deal
Tue, Dec 17 - Thu, Dec 19
6:50 am - 11:10 amEWR-MDW
5h 20m1 stop
12:05 pm - 7:50 pmMDW-EWR
6h 45m1 stop
$507Porter Airlines
Find Deal
Wed, Dec 11 - Mon, Dec 16
11:00 am - 4:14 pmJFK-MDW
6h 14m1 stop
$49Frontier
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Tue, Jan 14
10:59 am - 4:14 pmLGA-MDW
6h 15m1 stop
$49Frontier
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Tue, Jan 14
9:35 pm - 11:05 pmLGA-MDW
2h 30mnonstop
$74Southwest
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Fri, Jan 31
9:37 am - 1:08 pmEWR-MDW
4h 31m1 stop
$83Delta
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Thu, Jan 9
12:43 pm - 5:47 pmEWR-MDW
6h 04m1 stop
$84Delta
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Tue, Jan 7
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
$89Southwest
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Tue, Dec 24
3:05 pm - 11:29 pmEWR-MDW
9h 24m1 stop
Sat, Jan 18
5:35 pm - 4:14 pmEWR-MDW
23h 39m1 stop
Mon, Jan 6
11:01 am - 3:03 pmSWF-MDW
29h 02m1 stop
$201Allegiant Air
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Mon, Dec 23
10:51 am - 10:18 amSWF-MDW
24h 27m1 stop
$242Allegiant Air
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Wed, Apr 16
10:59 pm - 11:56 amLGA-MDW
13h 57m1 stop
9:48 pm - 5:00 pmMDW-LGA
18h 12m1 stop
$200Frontier
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Sat, Nov 23 - Wed, Nov 27
10:59 pm - 11:56 amLGA-MDW
13h 57m1 stop
9:00 am - 10:09 pmMDW-LGA
12h 09m1 stop
$230Frontier
Find Deal
Sat, Nov 23 - Tue, Nov 26
10:59 pm - 11:56 amLGA-MDW
13h 57m1 stop
9:00 am - 10:09 pmMDW-LGA
12h 09m1 stop
$240Frontier
Find Deal
Sat, Nov 23 - Mon, Nov 25
9:50 pm - 11:15 pmLGA-MDW
2h 25mnonstop
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$314Southwest
Find Deal
Fri, Nov 22 - Tue, Nov 26
6:15 am - 12:20 pmLGA-MDW
7h 05m1 stop
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$323Southwest
Find Deal
Fri, Nov 22 - Tue, Nov 26
1:22 pm - 6:02 pmEWR-MDW
5h 40m1 stop
11:59 am - 6:00 pmMDW-EWR
5h 01m1 stop
$332Delta
Find Deal
Mon, Nov 25 - Thu, Nov 28
9:12 am - 11:15 pmEWR-MDW
15h 03m2 stops
6:05 am - 9:00 pmMDW-EWR
13h 55m1 stop
Thu, Nov 21 - Thu, Nov 28
12:35 pm - 11:15 pmEWR-MDW
11h 40m1 stop
6:05 am - 9:00 pmMDW-EWR
13h 55m1 stop
Thu, Nov 21 - Thu, Nov 28
9:33 am - 12:49 pmEWR-MDW
4h 16m1 stop
9:30 am - 6:00 pmMDW-EWR
7h 30m1 stop
$353Delta
Find Deal
Sat, Nov 23 - Wed, Nov 27
10:55 am - 8:04 pmEWR-MDW
10h 09m1 stop
9:09 pm - 10:05 amMDW-EWR
11h 56m1 stop
$569Allegiant Air
Find Deal
Thu, Nov 21 - Fri, Nov 22
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$148Southwest
Find Deal
Sat, Dec 7 - Mon, Dec 9
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$163Southwest
Find Deal
Tue, Dec 31 - Wed, Jan 8
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
6:00 am - 9:05 amMDW-LGA
2h 05mnonstop
$164Southwest
Find Deal
Fri, Dec 6 - Thu, Dec 19
6:55 pm - 8:25 pmLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$168Southwest
Find Deal
Tue, Dec 3 - Wed, Dec 11
9:50 pm - 11:15 pmLGA-MDW
2h 25mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$169Southwest
Find Deal
Fri, Dec 13 - Fri, Jan 3
6:30 pm - 8:10 pmLGA-MDW
2h 40mnonstop
2:20 pm - 5:20 pmMDW-LGA
2h 00mnonstop
$183Southwest
Find Deal
Sat, Feb 15 - Tue, Feb 18
4:25 pm - 6:00 pmLGA-MDW
2h 35mnonstop
12:45 pm - 3:50 pmMDW-LGA
2h 05mnonstop
$188Southwest
Find Deal
Sat, Jan 11 - Sat, Jan 18
9:35 pm - 11:05 pmLGA-MDW
2h 30mnonstop
6:00 am - 9:10 amMDW-LGA
2h 10mnonstop
$190Southwest
Find Deal
Thu, Jan 9 - Sun, Jan 12
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
6:00 am - 9:05 amMDW-LGA
2h 05mnonstop
$192Southwest
Find Deal
Fri, Dec 6 - Sun, Dec 8
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
6:00 am - 9:05 amMDW-LGA
2h 05mnonstop
$193Southwest
Find Deal
Tue, Dec 10 - Thu, Dec 12

Frontier flights from New York to Chicago Midway Airport

Our best Frontier deals on New York to Chicago Midway Airport flight tickets
Frontier
Jan 29
JFK11:00 amNew York John F Kennedy Intl
9h 06m
1 stop
MDW7:06 pmChicago Midway
Jan 30
MDW12:43 pmChicago Midway
16h 47m
1 stop
JFK6:30 amNew York John F Kennedy Intl
Frontier
Jan 9
JFK11:02 amNew York John F Kennedy Intl
26h 09m
1 stop
MDW12:11 pmChicago Midway
Jan 13
MDW11:33 amChicago Midway
25h 26m
1 stop
JFK1:59 pmNew York John F Kennedy Intl
Frontier
Dec 5
JFK11:19 amNew York John F Kennedy Intl
25h 22m
1 stop
MDW11:41 amChicago Midway
Dec 9
MDW5:01 amChicago Midway
28h 15m
1 stop
JFK10:16 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 8
EWR9:37 amNewark
4h 31m
1 stop
MDW1:08 pmChicago Midway
Jan 22
MDW10:57 amChicago Midway
5h 09m
1 stop
EWR5:06 pmNewark
Delta
Jan 9
EWR9:37 amNewark
4h 31m
1 stop
MDW1:08 pmChicago Midway
Jan 12
MDW6:28 pmChicago Midway
3h 41m
1 stop
EWR11:09 pmNewark
Delta
Dec 10
EWR7:05 amNewark
5h 53m
1 stop
MDW11:58 amChicago Midway
Dec 17
MDW10:38 amChicago Midway
4h 53m
1 stop
EWR4:31 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 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 34% more expensive at noon than in the evening

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

You could potentially save up to 33% 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 5% 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

$49

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 $49. The best round-trip flight deal from New York to Chicago Midway Airport found on momondo in the last 72 hours is $104.
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
8,174 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $147Free CancellationRating
8.1
5,014 reviews
Search Southwest flights
DeltaPriceFrom $167Free CancellationRating
8.0
8,756 reviews
Search Delta flights
  • Southwest Flights From New York to Chicago Midway Airport

    Across 42 Southwest flights from New York to Chicago Midway Airport this week, the average price was $258, with the best Southwest deals starting from $147 round-trip. 5,014 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.


An easier way to manage your Chicago Midway Airport trip

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