LGA - MDW

$69 Find Cheap Flights from New York LaGuardia Airport to Chicago Midway Airport

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 5/28. 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

KAYAK searches 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
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Flights Deals

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.

Recent round-trip flight deals from LaGuardia to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from LaGuardia to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
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 13 - Wed, May 14
Southwest Logo
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
Southwest Logo
1:05 pm - 4:10 pmMDW-LGA
2h 05mnonstop
$157Southwest
Find Deal
Wed, May 14 - Wed, May 21
Southwest Logo
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
Southwest Logo
7:50 pm - 11:00 pmMDW-LGA
2h 10mnonstop
$158Southwest
Find Deal
Wed, May 28 - Thu, May 29
Southwest Logo
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
Southwest Logo
5:40 pm - 11:10 pmMDW-LGA
4h 30m1 stop
$163Southwest
Find Deal
Wed, May 14 - Wed, May 21
Southwest Logo
3:40 pm - 9:10 pmLGA-MDW
6h 30m1 stop
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$167Southwest
Find Deal
Tue, May 13 - Wed, May 14
Southwest Logo
6:30 am - 7:50 amLGA-MDW
2h 20mnonstop
Southwest Logo
6:10 am - 9:10 amMDW-LGA
2h 00mnonstop
$173Southwest
Find Deal
Thu, May 29 - Mon, Jun 2
Southwest Logo
6:05 am - 7:25 amLGA-MDW
2h 20mnonstop
Southwest Logo
8:00 pm - 11:10 pmMDW-LGA
2h 10mnonstop
$177Southwest
Find Deal
Tue, Jul 1 - Thu, Jul 3
Southwest Logo
6:30 am - 7:50 amLGA-MDW
2h 20mnonstop
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$178Southwest
Find Deal
Thu, May 29 - Wed, Jun 4
Frontier Logo
6:30 am - 11:26 amLGA-MDW
5h 56m1 stop
Frontier Logo
10:48 am - 11:03 pmMDW-LGA
11h 15m1 stop
$198Frontier
Find Deal
Wed, May 14 - Sat, May 17
Frontier Logo
6:30 am - 11:26 amLGA-MDW
5h 56m1 stop
Frontier Logo
1:19 pm - 8:59 pmMDW-LGA
6h 40m1 stop
$205Frontier
Find Deal
Wed, May 14 - Thu, May 15
Useful Info

KAYAK's insights & trends for LaGuardia to Midway flights

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 round-trip 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, Wednesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago Midway Airport back to New York LaGuardia Airport, the best deals are generally found on Wednesday, with Sunday 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 round-trip 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 July, where tickets cost $151 (return) on average. On the other hand, the most expensive months are June and August, where the average cost of round-trip tickets is $406 and $312 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from New York LaGuardia Airport to Chicago Midway Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonJuly
High seasonSeptember
Cheapest flight$69
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly and prices are also 20% 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.

Flights from LaGuardia to Midway: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from LaGuardia to Midway 
SheenaFlew with SouthwestJun 2024
Get to the airport early. NY airports are always busy, even when you have TSA pre check
AyeshaFlew with SouthwestDec 2023
Great airports at both location. Always like flying southwest. Best airline.

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 $69 for a one-way ticket and $137 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, JetBlue, and Alaska Airlines 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 MAX 8 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.

KAYAK’s top tips for finding a cheap flight from New York LaGuardia Airport to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $126 or less one-way and $242 or less round-trip.

Prefer to fly direct from New York LaGuardia Airport to Chicago Midway Airport?

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

Direct 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

Direct 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 airlines 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
SouthwestOverall score based on 4294 reviews
7.1Food
7.6Entertainment
8.6Crew
8.0Comfort
8.2Boarding
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Seats were comfortable but dont recline at all. Checkin online was easy but didnt provide a gate until last minute. Flight attendants were very unkind, not friendly and didnt go over safety procedures in case of a crash. No free snacks or beverages, not even water.

Spirit airlines was extremely uncomfortable. The seats were hard.. the constant up selling (from lack of food or even water to $15 for wi fi ) was annoying. Not a recommended airlines

Our experience was not a good one. Our flight got cancelled and was not given any accommodations due to the inconvenience. We lost time on our vacation due to this inconvenience

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

I was traveling with my son and it was our first time with spirit so I didn’t realize our seats weren’t assigned. They scrambled and gave us seats next to each other. Also My son got sick on the plane and they really took care of him. Super family friendly crew and experience!

Great. I didn't eat or drink anything, nor did I have an option to be entertained, so i answered "okay"... but those categoriesreally don't apply. Everything else was great.

Everything you need to know for your flight from LaGuardia to Midway

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