LGA - MDW

$94 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 6/13. 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
1 adult, Economy, 0 bags

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

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

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

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

Everything you should know

Cheapest round-trip
$177
Typical prices: $400-$283
Southwest
Wed 6/17Wed 6/24
LGA - MDW • Non-stop
Cheapest non-stop
$177
Typical prices: $411-$325
Southwest
Sat 6/20Wed 6/24
LGA - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $177 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 28m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Southwest
Most punctual • 78% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 43% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 36% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from LaGuardia to Midway

Wed, Jun 17 - Wed, Jun 24
Southwest Logo
6:00 am - 7:20 am
LGA
-
MDW
2h 20mnonstop
Southwest Logo
5:15 am - 8:15 am
MDW
-
LGA
2h 00mnonstop
$177Southwest
Fri, Jul 3 - Tue, Jul 7
Southwest Logo
9:30 pm - 10:55 pm
LGA
-
MDW
2h 25mnonstop
Southwest Logo
5:15 am - 8:15 am
MDW
-
LGA
2h 00mnonstop
$182Southwest
Sat, Aug 15 - Wed, Aug 19
Southwest Logo
7:35 am - 8:55 am
LGA
-
MDW
2h 20mnonstop
Southwest Logo
5:20 pm - 11:00 pm
MDW
-
LGA
4h 40m
1 stop
$186Southwest
Wed, Jun 24 - Tue, Jun 30
Southwest Logo
6:00 am - 7:20 am
LGA
-
MDW
2h 20mnonstop
Southwest Logo
5:50 pm - 8:55 pm
MDW
-
LGA
2h 05mnonstop
$187Southwest
Thu, Aug 20 - Thu, Aug 27
Southwest Logo
3:00 pm - 7:45 pm
LGA
-
MDW
5h 45m
1 stop
Southwest Logo
5:00 am - 8:00 am
MDW
-
LGA
2h 00mnonstop
$188Southwest
Tue, Jun 30 - Fri, Jul 3
Southwest Logo
6:00 am - 7:20 am
LGA
-
MDW
2h 20mnonstop
Southwest Logo
12:55 pm - 4:00 pm
MDW
-
LGA
2h 05mnonstop
$192Southwest
Sat, Jul 4 - Tue, Jul 7
Southwest Logo
12:50 pm - 8:40 pm
LGA
-
MDW
8h 50m
1 stop
Southwest Logo
7:45 pm - 11:00 pm
MDW
-
LGA
2h 15mnonstop
$193Southwest
Fri, Aug 14 - Mon, Aug 17
Southwest Logo
8:55 pm - 10:15 pm
LGA
-
MDW
2h 20mnonstop
Southwest Logo
7:50 pm - 10:55 pm
MDW
-
LGA
2h 05mnonstop
$195Southwest
Thu, Jul 9 - Mon, Jul 13
Southwest Logo
6:00 am - 7:20 am
LGA
-
MDW
2h 20mnonstop
Southwest Logo
7:45 pm - 11:00 pm
MDW
-
LGA
2h 15mnonstop
$197Southwest
Sat, Jun 13 - Sat, Jun 20
Southwest Logo
6:05 am - 2:45 pm
LGA
-
MDW
9h 40m
1 stop
Southwest Logo
5:25 pm - 8:30 pm
MDW
-
LGA
2h 05mnonstop
$198Southwest
Booking Insights

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.

How much is a round-trip flight from New York LaGuardia Airport to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from New York LaGuardia Airport to Chicago Midway Airport departing in June.

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, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway Airport back to New York LaGuardia Airport, the best deals are generally found on Saturday, 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 January, where tickets cost $185 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $410 and $356 respectively.

Can I save money by flying with a layover from New York LaGuardia Airport to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $335 on average.

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 3 weeks before departure, which saves you about 43% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$94
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly with an average 12% increase in price.
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 $91 for a one-way ticket and $177 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, JetBlue, Delta, 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 737-800 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.

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 $173 or less one-way and $284 or less round-trip.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from New York LaGuardia to Chicago Midway.
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

Reviews of the 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
SouthwestOverall score based on 4264 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

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

Information on your arrival and departure airports

New York LaGuardia Airport (LGA)
Midway (MDW)