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 11/12. 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

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 23% 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
$119
Overall average: $257
Frontier
Tue 10/28Sat 11/1
LGA - MDW • 1 stop
Cheapest non-stop
$137
Typical prices: $209-$411
Southwest
Fri 10/31Mon 11/3
LGA - MDW • Non-stop
Top airlines
Frontier
Cheapest • from $119 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 29% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 28% 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

Tue, Oct 28 - Sat, Nov 1
Frontier Logo
6:29 am - 11:38 amLGA-MDW
6h 09m1 stop
Frontier Logo
1:37 pm - 11:27 pmMDW-LGA
8h 50m1 stop
$119Frontier
Find Deal
Thu, Nov 6 - Mon, Nov 10
Frontier Logo
12:30 pm - 6:39 pmLGA-MDW
7h 09m1 stop
Frontier Logo
6:15 am - 7:30 pmMDW-LGA
12h 15m1 stop
$120Frontier
Find Deal
Sat, Nov 1 - Tue, Nov 4
Frontier Logo
11:02 am - 10:12 amLGA-MDW
24h 10m1 stop
Frontier Logo
1:56 pm - 11:27 pmMDW-LGA
8h 31m1 stop
$125Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
10:10 am - 6:04 pmLGA-MDW
8h 54m1 stop
Frontier Logo
8:42 pm - 9:15 amMDW-LGA
11h 33m1 stop
$126Frontier
Find Deal
Fri, Oct 31 - Tue, Nov 4
Frontier Logo
12:30 pm - 9:45 pmLGA-MDW
10h 15m1 stop
Frontier Logo
1:56 pm - 11:27 pmMDW-LGA
8h 31m1 stop
$129Frontier
Find Deal
Thu, Nov 13 - Sun, Nov 16
Frontier Logo
12:30 pm - 10:03 pmLGA-MDW
10h 33m1 stop
Frontier Logo
10:12 am - 3:59 pmMDW-LGA
28h 47m1 stop
$130Frontier
Find Deal
Thu, Nov 13 - Sun, Nov 16
Frontier Logo
12:30 pm - 10:03 pmLGA-MDW
10h 33m1 stop
Frontier Logo
10:12 am - 3:59 pmMDW-LGA
28h 47m1 stop
$131Frontier
Find Deal
Fri, Oct 31 - Tue, Nov 4
Southwest Logo
6:30 pm - 8:00 pmLGA-MDW
2h 30mnonstop
Southwest Logo
5:55 pm - 9:00 pmMDW-LGA
2h 05mnonstop
$137Southwest
Find Deal
Fri, Oct 24 - Mon, Oct 27
Southwest Logo
9:35 pm - 11:05 pmLGA-MDW
2h 30mnonstop
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$138Southwest
Find Deal
Thu, Dec 4 - Sun, Dec 7
Southwest Logo
9:10 am - 10:40 amLGA-MDW
2h 30mnonstop
Southwest Logo
6:10 am - 9:15 amMDW-LGA
2h 05mnonstop
$139Southwest
Find Deal
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.

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 September, where tickets cost $196 (return) on average. On the other hand, the most expensive months are June and August, where the average cost of round-trip tickets is $385 and $328 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, which saves you about 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$69
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 13% 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 $69 for a one-way ticket and $119 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, Alaska Airlines, and Hawaiian 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 $149 or less one-way and $270 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 4235 reviews
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

4.0 OkayAnnette, Oct 2025LGA - MCI
Read more Southwest reviews

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

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)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.