LGA - MDW

$53 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 7/5. 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
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Flights 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, Sep 2 - Tue, Sep 9
Southwest Logo
9:35 pm - 10:55 pmLGA-MDW
2h 20mnonstop
Southwest Logo
5:55 pm - 9:10 pmMDW-LGA
2h 15mnonstop
$140Southwest
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Wed, Aug 13 - Fri, Aug 15
Southwest Logo
9:35 pm - 10:55 pmLGA-MDW
2h 20mnonstop
Southwest Logo
8:15 pm - 11:25 pmMDW-LGA
2h 10mnonstop
$143Southwest
Find Deal
Sat, Aug 23 - Mon, Aug 25
Southwest Logo
10:55 am - 12:20 pmLGA-MDW
2h 25mnonstop
Southwest Logo
6:05 pm - 9:20 pmMDW-LGA
2h 15mnonstop
$156Southwest
Find Deal
Wed, Sep 10 - Wed, Sep 17
Southwest Logo
6:00 am - 7:20 amLGA-MDW
2h 20mnonstop
Southwest Logo
7:05 pm - 10:15 pmMDW-LGA
2h 10mnonstop
$157Southwest
Find Deal
Mon, Aug 11 - Fri, Aug 15
Southwest Logo
9:10 am - 10:35 amLGA-MDW
2h 25mnonstop
Southwest Logo
8:15 pm - 11:25 pmMDW-LGA
2h 10mnonstop
$159Southwest
Find Deal
Mon, Aug 11 - Thu, Aug 14
Southwest Logo
6:00 am - 7:20 amLGA-MDW
2h 20mnonstop
Southwest Logo
8:15 pm - 11:25 pmMDW-LGA
2h 10mnonstop
$160Southwest
Find Deal
Tue, Sep 16 - Tue, Sep 23
Southwest Logo
7:55 am - 2:25 pmLGA-MDW
7h 30m1 stop
Southwest Logo
7:05 pm - 10:15 pmMDW-LGA
2h 10mnonstop
$166Southwest
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Tue, Aug 5 - Sat, Aug 23
Southwest Logo
9:00 am - 10:25 amLGA-MDW
2h 25mnonstop
Southwest Logo
5:40 pm - 8:50 pmMDW-LGA
2h 10mnonstop
$167Southwest
Find Deal
Thu, Jul 10 - Wed, Jul 16
Frontier Logo
10:55 pm - 11:41 amLGA-MDW
13h 46m1 stop
Frontier Logo
11:39 am - 11:32 pmMDW-LGA
10h 53m1 stop
$190Frontier
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Thu, Jul 10 - Mon, Jul 14
Frontier Logo
10:55 pm - 11:41 amLGA-MDW
13h 46m1 stop
Frontier Logo
12:35 pm - 10:09 pmMDW-LGA
8h 34m1 stop
$200Frontier
Find Deal
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 September, where tickets cost $206 (return) on average. On the other hand, the most expensive months are June and August, where the average cost of round-trip tickets is $394 and $317 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 11 weeks before departure.

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Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$53
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 11% 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 $53 for a one-way ticket and $140 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 $124 or less one-way and $271 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 4279 reviews
7.1Food
8.6Crew
8.2Boarding
8.0Comfort
7.6Entertainment
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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.

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)

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