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LGA - MDW

Find cheap flights from New York LaGuardia Airport to Chicago Midway Airport from $43

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from LaGuardia to Midway departing on 5/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 5/23
Thu 5/30

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,632,927 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from LaGuardia to Midway (LGA-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from LaGuardia to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:00 pm - 9:22 amLGA-MDW
12h 22m1 stop
4:56 pm - 11:10 pmMDW-LGA
5h 14m1 stop
$86Frontier
Find Deal
Tue, May 14 - Wed, May 15
10:00 pm - 8:51 amLGA-MDW
11h 51m1 stop
4:56 pm - 11:10 pmMDW-LGA
5h 14m1 stop
$98Frontier
Find Deal
Mon, May 6 - Wed, May 15
10:00 pm - 9:22 amLGA-MDW
12h 22m1 stop
4:56 pm - 11:10 pmMDW-LGA
5h 14m1 stop
$103Frontier
Find Deal
Tue, May 14 - Wed, May 15
10:00 pm - 8:51 amLGA-MDW
11h 51m1 stop
4:56 pm - 11:10 pmMDW-LGA
5h 14m1 stop
$107Frontier
Find Deal
Mon, May 6 - Wed, May 8
6:00 am - 9:53 pmLGA-MDW
16h 53m1 stop
12:09 pm - 11:19 pmMDW-LGA
10h 10m1 stop
$112Frontier
Find Deal
Wed, May 22 - Wed, May 29
6:00 am - 9:53 pmLGA-MDW
16h 53m1 stop
6:00 am - 3:30 pmMDW-LGA
8h 30m1 stop
$113Frontier
Find Deal
Wed, May 22 - Sat, Aug 10
6:00 am - 9:53 pmLGA-MDW
16h 53m1 stop
12:09 pm - 11:19 pmMDW-LGA
10h 10m1 stop
$114Frontier
Find Deal
Wed, May 22 - Wed, May 29
6:00 am - 9:53 pmLGA-MDW
16h 53m1 stop
12:09 pm - 11:19 pmMDW-LGA
10h 10m1 stop
$115Frontier
Find Deal
Wed, May 22 - Wed, May 29
1:00 pm - 4:55 pmLGA-MDW
4h 55m1 stop
10:20 am - 1:25 pmMDW-LGA
2h 05mnonstop
$158Southwest
Find Deal
Mon, May 27 - Tue, May 28
7:00 am - 1:55 pmLGA-MDW
7h 55m2 stops
8:15 am - 11:25 amMDW-LGA
2h 10mnonstop
$163Southwest
Find Deal
Sat, Jun 1 - Sun, Jun 2

Flights from LaGuardia to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from LaGuardia to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from New York LaGuardia Airport to Chicago Midway Airport?

The average price of all flights from New York LaGuardia Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
For New York LaGuardia Airport to Chicago Midway Airport, Monday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago Midway Airport back to New York LaGuardia Airport, the best deals are generally found on Saturday, with Friday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from New York LaGuardia Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from New York LaGuardia Airport to Chicago Midway Airport is April, where tickets cost $205 on average. On the other hand, the most expensive months are May and July, where the average cost of tickets is $488 and $438 respectively.

How far in advance should I book a flight from New York LaGuardia Airport to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from New York LaGuardia Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from New York LaGuardia Airport to Chicago Midway Airport, you should book around 5 days before departure. For the absolute cheapest price, our data suggests you should book 88 days before departure.

Which airlines provide the cheapest flights from New York LaGuardia Airport to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Chicago Midway Airport from New York LaGuardia Airport were found on Frontier ($43) and Southwest ($137), and the lowest round-trip tickets were found on Frontier ($86) and Southwest ($158).

How many flights are there between New York LaGuardia Airport and Chicago Midway Airport per day?

Each day, there are between 3 and 8 nonstop flights that take off from New York LaGuardia Airport and land in Chicago Midway Airport, with an average flight time of 2h 27m. The most common departure time is 11:00 am and most flights take off in the morning. Each week, there are 45 flights. The most frequent day of departure is Tuesday, when 18% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between New York LaGuardia Airport and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from New York LaGuardia Airport to Chicago Midway Airport take?

Direct flights take on average 2h 20m to travel the 722 miles between New York LaGuardia Airport and Chicago Midway Airport.

What’s the earliest departure time from New York LaGuardia Airport to Chicago Midway Airport?

Early birds can take the earliest flight from New York LaGuardia Airport at 6:30 am and will be landing in Chicago Midway Airport at 7:55 am.

What’s the latest departure time from New York LaGuardia Airport to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from New York LaGuardia Airport to Chicago Midway Airport jets off at 9:55 pm and lands at 11:15 pm.

Good to know

Low season

September

High season

August

Cheapest flight

$43
Best time to beat the crowds with an average 58% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from New York LaGuardia Airport to Chicago Midway Airport

When to book flights from LaGuardia to Midway

Are your dates flexible? Find out the best times to travel from LaGuardia to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking New York LaGuardia Airport to Chicago Midway Airport flights

  • What is the cheapest flight from New York LaGuardia Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from New York LaGuardia Airport to Chicago Midway Airport was $43 for a one-way ticket and $86 for a round-trip.

  • Do I need a passport to fly between New York LaGuardia Airport and Chicago Midway Airport?

    No, a passport isn't needed to fly from New York LaGuardia Airport to Chicago Midway Airport. However, local authorities might ask for an official ID.

  • Which airlines offer Wi-Fi service onboard planes from New York LaGuardia Airport to Chicago Midway Airport?

    American Airlines, Delta, and JetBlue offer inflight Wi-Fi service on the New York LaGuardia Airport to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from New York LaGuardia Airport to Chicago Midway Airport?

    The Boeing 737-800 is the aircraft model that flies most regularly on the New York LaGuardia Airport to Chicago Midway Airport flight route.

  • On which days can I fly direct from New York LaGuardia Airport to Chicago Midway Airport?

    There are nonstop flights from New York LaGuardia Airport to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from New York LaGuardia Airport to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New York LaGuardia Airport to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York LaGuardia Airport to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from New York LaGuardia Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from New York LaGuardia Airport to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to New York LaGuardia Airport with another airline. Booking your flights between New York LaGuardia Airport and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York LaGuardia Airport to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from New York LaGuardia Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from New York LaGuardia Airport to Chicago Midway Airport?

Find which airlines fly direct from LaGuardia to Midway, which days they fly and book direct flights.

Nonstop departures

New York LaGuardia to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Chicago Midway to New York LaGuardia

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top airline flying from LaGuardia to Midway

 
See real verified KAYAK customer reviews for airlines flying from New York to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from LaGuardia to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 11028 reviews
8.2boarding
8.6crew
7.9comfort
7.5food
8.0entertainment
Airline reviews

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

10.0 ExcellentShayla, Apr 2024ATL - ORD
Read more about Delta reviews

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The helpful attitude of the staff, and being a wheelchair passenger everyone was helpful and understanding. The trip was made comfortable by the upgraded seat which was given without my request, that was a great surprise. Thank you Delta.

Everything went well with the flight. But one of the flight attendants had on inappropriate pants. She had on an old worn out pair of sweat pants. The back seam was unrivaled and should not have been worn for work. If I had not seen her in the airport with the standard type of luggage, I certainly would not have thought she was working for Delta. Not a good look at all for representation.

Great!! I haven’t had a bad experience with them.

The plane was one hour late cause they were doing some reparations with us on the plane no mention I was in the first seat and the door was open the entire time with 8 degrees! The plane was totally dirty no mention old ! The staff was nice but no put together, the attention to details and passenger experience is missing and i always travel first !!! Is better the lounge than the plane! KLM/air France every details is taken care maybe you need a creative creator or experience client need asap was terrible and not memorable for the price that I payed very dissatisfied

Boarding super slow with people allowed to linger in aisles

We flew early evening on New Year's Eve. Our plane was less than half full... Great for the passenger experience -- not so much for the airline lol. Comfortable, spacious, smooth flight -- and early arrival!

First time travel in economy and the worst experience I ever had ! Shame on paying 600 dollars to be in a tuna can ! Service was terrible no even water no even class no even matters your flight attendants were lazy and sloppy very bad experience! After all these years traveling in first and once I try this cause I need to go to a destination for an emergency wow shame on you !

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

Book cheap flights from New York to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from New York to Chicago found on KAYAK in the last 72 hours.
5/8Wed
1 stopFrontier
6h 43mLGA-MDW
$43
5/8Wed
1 stopFrontier
6h 43mLGA-MDW
$44
5/8Wed
1 stopFrontier
6h 43mLGA-MDW
$49
5/8Wed
1 stopFrontier
6h 43mLGA-MDW
$50
5/8Wed
1 stopFrontier
6h 43mLGA-MDW
$51
5/7Tue
1 stop
11h 23mLGA-MDW
$67
5/8Wed
1 stop
6h 44mLGA-MDW
$70
6/19Wed
nonstopSouthwest
2h 20mLGA-MDW
$137
7/3Wed
1 stopDelta
7h 44mLGA-MDW
$227
7/8Mon
1 stopDelta
7h 44mLGA-MDW
$256

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Last minute flights from LaGuardia to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from New York to Chicago that are departing in the next 10 days.
4/25Thu
multi-stopFrontier
17h 03mLGA-MDW
5/29Wed
multi-stopFrontier
10h 10mMDW-LGA
$185
4/27Sat
multi-stopFrontier
8h 50mLGA-MDW
5/4Sat
multi-stopFrontier
11h 40mMDW-LGA
$189
4/27Sat
multi-stopFrontier
8h 50mLGA-MDW
5/2Thu
multi-stopFrontier
10h 43mMDW-LGA
$194
4/26Fri
nonstopSouthwest
2h 25mLGA-MDW
4/27Sat
multi-stopSouthwest
10h 00mMDW-LGA
$425
4/26Fri
nonstopSouthwest
2h 25mLGA-MDW
4/27Sat
nonstopSouthwest
2h 05mMDW-LGA
$433
4/24Wed
nonstopSouthwest
2h 30mLGA-MDW
4/26Fri
nonstopSouthwest
2h 05mMDW-LGA
$434
4/28Sun
multi-stopDelta
5h 15mLGA-MDW
4/28Sun
multi-stopDelta
4h 56mMDW-LGA
$1,162
4/26Fri
multi-stopDelta
7h 45mLGA-MDW
4/29Mon
multi-stopDelta
9h 13mMDW-LGA
$1,208
4/24Wed
multi-stopDelta
3h 50mLGA-MDW
4/24Wed
multi-stopDelta
3h 34mMDW-LGA
$1,266
4/25Thu
multi-stopDelta
3h 50mLGA-MDW
4/25Thu
multi-stopDelta
4h 56mMDW-LGA
$1,286

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New York LaGuardia Airport - Chicago Midway Airport Flights

Departure:

New York LaGuardia Airport (LGA)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - New York LaGuardia Airport

Cabin classes:

$398