MDW - LGA

$69 Find Cheap Flights from Chicago Midway Airport to New York LaGuardia 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 Midway to LaGuardia departing on 5/13. 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 New York LaGuardia Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New York, 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 Chicago to New York, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$143
Typical prices: $409-$254
Frontier
Sat 5/2Mon 5/4
MDW - LGA • 1 stop
Cheapest non-stop
$156
Typical prices: $431-$211
Southwest
Sat 5/2Sat 5/2
MDW - LGA • Non-stop
Top airlines
Cheapest • from $143 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 03m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 79% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 49% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 31% price drop
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 LaGuardia!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to LaGuardia (MDW-LGA)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to LaGuardia 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 Midway to LaGuardia

Sat, May 2 - Mon, May 4
Frontier Logo
6:00 am - 11:14 pm
MDW
-
LGA
16h 14m
1 stop
Frontier Logo
10:00 pm - 10:02 pm
LGA
-
MDW
25h 02m
1 stop
$143Frontier
Sat, May 2 - Sat, May 2
Southwest Logo
5:30 am - 8:30 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
3:35 pm - 5:15 pm
LGA
-
MDW
2h 40mnonstop
$156Southwest
Tue, Apr 28 - Fri, May 1
Frontier Logo
2:15 pm - 11:14 pm
MDW
-
LGA
7h 59m
1 stop
Frontier Logo
10:00 pm - 6:37 pm
LGA
-
MDW
21h 37m
1 stop
$159Frontier
Tue, Apr 28 - Sat, May 2
Frontier Logo
2:15 pm - 11:14 pm
MDW
-
LGA
7h 59m
1 stop
Frontier Logo
8:25 pm - 7:41 am
LGA
-
MDW
12h 16m
1 stop
$160Frontier
Thu, Apr 30 - Sat, May 2
Frontier Logo
6:00 am - 5:45 pm
MDW
-
LGA
10h 45m
1 stop
Frontier Logo
8:25 pm - 7:41 am
LGA
-
MDW
12h 16m
1 stop
$162Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
2:15 pm - 11:14 pm
MDW
-
LGA
7h 59m
1 stop
Frontier Logo
10:00 pm - 11:09 am
LGA
-
MDW
14h 09m
1 stop
$163Frontier
Tue, Apr 28 - Tue, May 5
Frontier Logo
2:15 pm - 8:59 pm
MDW
-
LGA
5h 44m
1 stop
Frontier Logo
10:00 pm - 11:09 am
LGA
-
MDW
14h 09m
1 stop
$164Frontier
Wed, May 13 - Tue, Aug 18
Frontier Logo
12:04 pm - 8:56 pm
MDW
-
LGA
7h 52m
1 stop
Frontier Logo
6:25 am - 11:12 am
LGA
-
MDW
5h 47m
1 stop
$165Frontier
Thu, Apr 30 - Mon, May 4
Frontier Logo
6:00 am - 5:45 pm
MDW
-
LGA
10h 45m
1 stop
Frontier Logo
10:00 pm - 10:02 pm
LGA
-
MDW
25h 02m
1 stop
$167Frontier
Sat, Apr 25 - Sat, May 2
Southwest Logo
5:30 am - 8:30 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
9:55 am - 11:20 am
LGA
-
MDW
2h 25mnonstop
$168Southwest
Booking Insights

KAYAK's insights & trends for Midway to LaGuardia flights

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

How much is a round-trip flight from Chicago Midway Airport to New York LaGuardia 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 Chicago Midway Airport to New York LaGuardia Airport departing in May.

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

The average price of all round-trip flights from Chicago Midway Airport to New York LaGuardia Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to New York LaGuardia Airport on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago Midway Airport to New York LaGuardia Airport. For your return ticket, we recommend flying on a Tuesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to New York LaGuardia 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 Chicago Midway Airport to New York LaGuardia Airport is October, where tickets cost $229 (return) on average. On the other hand, the most expensive months are April and August, where the average cost of round-trip tickets is $409 and $408 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to New York LaGuardia 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 $238 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to New York LaGuardia 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 Chicago Midway Airport to New York LaGuardia Airport, you should book around 3 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonDecember
Cheapest flight$69
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago Midway Airport to New York LaGuardia Airport

When to book flights from Midway to LaGuardia

Are your dates flexible? Find out the best times to travel from Midway to LaGuardia 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 Chicago Midway Airport to New York LaGuardia Airport flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to New York LaGuardia Airport was $69 for a one-way ticket and $143 for a round-trip.

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

    No

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

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

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to New York LaGuardia Airport flight route.

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

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

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to New York LaGuardia Airport from Chicago Midway 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 Chicago Midway Airport to New York LaGuardia 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 New York LaGuardia Airport with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and LGA 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 Chicago Midway Airport to New York LaGuardia 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 New York LaGuardia Airport from Chicago Midway 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 Chicago Midway Airport to New York LaGuardia Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $181 or less one-way and $233 or less round-trip.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to New York LaGuardia.
Find which airlines fly direct from Chicago Midway Airport to New York LaGuardia Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

Reviews of the top airline flying from Midway to LaGuardia

 
See real verified KAYAK customer reviews for airlines flying from Chicago to New York. 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 Midway to LaGuardia? 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 4331 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
Airline reviews

The new boarding process was easy and straightforward. Very pleasant.

10.0 ExcellentAnonymous, Apr 2026
LAS - OKC
Read more Southwest reviews

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

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

Information on your arrival and departure airports