What is the cheapest airline that flies from New York LaGuardia to Chicago Midway?

Southwest is the most popular carrier operating from New York LaGuardia to Chicago Midway

What is the most punctual flight time for New York to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

How often are flights from New York to Chicago delayed?

Historically, on average around 20% of flights between New York and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 141 minutes.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on New York to Chicago flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

How old do you have to be to fly from New York LaGuardia Airport to Chicago Midway Airport?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from New York LaGuardia Airport to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$62 Cheap Flights from New York LaGuardia Airport to Chicago Midway Airport in 2025/26

Q: How many flights depart from New York LaGuardia Airport to Chicago Midway Airport on average per day?

The number of flights available between New York LaGuardia Airport and Chicago Midway Airport is 4 per day as of December 2025. The most frequent departure time is 2:00PM, with 45% of daily flights leaving in the afternoon.

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4:59 pm - 10:19 pm

LGA

MDW

6h 20m1 stop

9:38 am - 3:59 pm

MDW

LGA

5h 21m1 stop

$128Frontier

Fri, Jan 30 - Sat, Jan 31

4:59 pm - 10:19 pm

LGA

MDW

6h 20m1 stop

1:20 pm - 9:29 pm

MDW

LGA

7h 09m1 stop

$129Frontier

Fri, Jan 30 - Wed, Feb 4

6:20 am - 11:45 am

LGA

MDW

6h 25m1 stop

1:00 pm - 11:29 am

MDW

LGA

21h 29m1 stop

$134Frontier

Sun, Jan 25 - Sun, Feb 8

6:00 am - 7:40 am

LGA

MDW

2h 40mnonstop

5:55 pm - 9:00 pm

MDW

LGA

2h 05mnonstop

$139Southwest

Fri, Jan 9 - Mon, Jan 12

6:25 am - 12:05 pm

LGA

MDW

6h 40m1 stop

6:20 am - 3:59 pm

MDW

LGA

8h 39m1 stop

$145Frontier

Tue, Jan 20 - Thu, Jan 22

12:30 pm - 10:19 pm

LGA

MDW

10h 49m1 stop

6:10 am - 4:29 pm

MDW

LGA

9h 19m1 stop

$146Frontier

Tue, Jan 13 - Thu, Jan 15

6:00 am - 7:40 am

LGA

MDW

2h 40mnonstop

5:55 pm - 9:00 pm

MDW

LGA

2h 05mnonstop

$148Southwest

Wed, Jan 7 - Wed, Jan 14

6:00 am - 7:40 am

LGA

MDW

2h 40mnonstop

6:05 am - 9:10 am

MDW

LGA

2h 05mnonstop

$149Southwest

Thu, Jan 8 - Thu, Jan 15

4:30 pm - 2:06 pm

LGA

MDW

22h 36m1 stop

6:23 am - 4:29 pm

MDW

LGA

9h 06m1 stop

$152Frontier

Thu, Jan 8 - Tue, Jan 13

9:00 am - 10:40 am

LGA

MDW

2h 40mnonstop

7:15 pm - 10:20 pm

MDW

LGA

2h 05mnonstop

$153Southwest

Thu, Jan 15 - Sun, Jan 18

Frontier flights from New York LaGuardia Airport to Chicago Midway Airport

Our best Frontier deals on New York LaGuardia Airport to Chicago Midway Airport flight tickets

Frontier

Jan 30

LGA4:59 pmNew York LaGuardia

6h 20m

1 stop

MDW10:19 pmChicago Midway

Jan 31

MDW9:38 amChicago Midway

5h 21m

1 stop

LGA3:59 pmNew York LaGuardia

$128

Find similar

Frontier

Jan 30

LGA4:59 pmNew York LaGuardia

6h 20m

1 stop

MDW10:19 pmChicago Midway

Feb 4

MDW1:20 pmChicago Midway

7h 09m

1 stop

LGA9:29 pmNew York LaGuardia

$129

Find similar

Frontier

Jan 25

LGA6:20 amNew York LaGuardia

6h 25m

1 stop

MDW11:45 amChicago Midway

Feb 8

MDW1:00 pmChicago Midway

21h 29m

1 stop

LGA11:29 amNew York LaGuardia

$134

Find similar

Southwest flights from New York LaGuardia Airport to Chicago Midway Airport

Our best Southwest deals on New York LaGuardia Airport to Chicago Midway Airport flight tickets

Southwest

Jan 9

LGA6:00 amNew York LaGuardia

2h 40m

MDW7:40 amChicago Midway

Jan 12

MDW5:55 pmChicago Midway

2h 05m

LGA9:00 pmNew York LaGuardia

$139

Find similar

Southwest

Jan 7

LGA6:00 amNew York LaGuardia

2h 40m

MDW7:40 amChicago Midway

Jan 14

MDW5:55 pmChicago Midway

2h 05m

LGA9:00 pmNew York LaGuardia

$148

Find similar

Southwest

Jan 8

LGA6:00 amNew York LaGuardia

2h 40m

MDW7:40 amChicago Midway

Jan 15

MDW6:05 amChicago Midway

2h 05m

LGA9:10 amNew York LaGuardia

$149

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from New York LaGuardia Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/30

4:59 pm-10:19 pm

1 stop6h 20m

Chicago Midway

Sat 1/31

9:38 am-3:59 pm

1 stop5h 21m

$128

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/30

4:59 pm-10:19 pm

1 stop6h 20m

Chicago Midway

Wed 2/4

1:20 pm-9:29 pm

1 stop7h 09m

$129

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sun 1/25

6:20 am-11:45 am

1 stop6h 25m

Chicago Midway

Sun 2/8

1:00 pm-11:29 am

1 stop21h 29m

$134

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/9

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 1/12

5:55 pm-9:00 pm

Nonstop2h 05m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 1/20

6:25 am-12:05 pm

1 stop6h 40m

Chicago Midway

Thu 1/22

6:20 am-3:59 pm

1 stop8h 39m

$145

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 1/13

12:30 pm-10:19 pm

1 stop10h 49m

Chicago Midway

Thu 1/15

6:10 am-4:29 pm

1 stop9h 19m

$146

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 1/7

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Wed 1/14

5:55 pm-9:00 pm

Nonstop2h 05m

$148

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/8

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Thu 1/15

6:05 am-9:10 am

Nonstop2h 05m

$149

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/8

4:30 pm-2:06 pm

1 stop22h 36m

Chicago Midway

Tue 1/13

6:23 am-4:29 pm

1 stop9h 06m

$152

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/15

9:00 am-10:40 am

Nonstop2h 40m

Chicago Midway

Sun 1/18

7:15 pm-10:20 pm

Nonstop2h 05m

$153

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How to get the cheapest flight ticket from New York LaGuardia Airport to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from New York LaGuardia Airport, with most prices found around $196. If you are unable to visit Chicago Midway Airport during the month of September, then departing from New York LaGuardia Airport during the month February is also very affordable. Most momondo users find prices during this month for around $208.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from New York LaGuardia Airport. The lowest ticket price found for a Tuesday departure recently was $267. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from New York LaGuardia Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $416.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from New York LaGuardia Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $228 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $357. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest New York LaGuardia to Chicago Midway flight route?

Fly from New York LaGuardia to Chicago Midway for the best New York LaGuardia - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from New York LaGuardia Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $274 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from New York LaGuardia Airport for as low as $168 on momondo.

What cabin class options are available on New York LaGuardia to Chicago Midway flights?

There is only 1 cabin class available to choose from on New York LaGuardia to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have New York LaGuardia Airport to Chicago Midway Airport flight prices changed over time?

When to book flights from New York LaGuardia Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from New York LaGuardia Airport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap New York LaGuardia Airport to Chicago Midway Airport (LGA to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New York LaGuardia Airport to Chicago Midway Airport

Best Price Found	$171
Fastest flight time	2h 20m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from New York LaGuardia Airport in the past 72 hours is $171. The best round-trip flight deal from New York LaGuardia Airport to Chicago Midway Airport found on momondo in the last 72 hours is $292.

The fastest flight from New York LaGuardia Airport to Chicago Midway Airport takes 2h 20m

Direct flights go from New York LaGuardia Airport to Chicago Midway Airport every day.

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How far is New York LaGuardia to Chicago Midway by plane?
New York LaGuardia and Chicago Midway are 722.4 mi apart from one another. Typically, this will take 2h 20m by plane in normal conditions.
When did momondo last update prices for flights from New York LaGuardia Airport to Chicago Midway Airport?
Prices for flights from New York LaGuardia Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from New York LaGuardia Airport to Chicago Midway Airport?
The number of operators available for flights from New York LaGuardia Airport to Chicago Midway Airport is 1 as of December 2025.
How old do you have to be to fly from New York LaGuardia Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from New York LaGuardia Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from New York LaGuardia Airport to Chicago Midway Airport?
Based on momondo bookings for flights between New York LaGuardia Airport and Chicago Midway Airport, the leading plane model is Boeing 737-800, making up 13.01% of the total bookings. Other popular models include Boeing 737 MAX 8 with 12.46%, Airbus A321neo with 8.82%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 8.53%.
What is the most popular airline from New York LaGuardia Airport to Chicago Midway Airport?
Based on momondo bookings for flights between New York LaGuardia Airport and Chicago Midway Airport, the leading airline is Southwest, making up 100% of the total bookings.

Best airlines flying from New York LaGuardia Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from New York LaGuardia Airport to Chicago Midway Airport with momondo

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $151	Free Cancellation	Rating 7.9 4,252 reviews		Search Southwest flights

Southwest Flights From New York LaGuardia Airport to Chicago Midway Airport
Southwest flight deals from New York LaGuardia Airport to Chicago Midway Airport start from $151 round-trip. Over the 30 Southwest flights for this route in a normal week, average airfare is usually $273 round-trip - but some users have found much cheaper deals with momondo.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

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Why should I use momondo to find a flight deal from New York to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from New York to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from New York to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from New York with this policy.

How can momondo help me find flights from New York to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from New York. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for New York to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Cheap flights from New York LaGuardia Airport to Chicago from $62

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Frontier flights from New York LaGuardia Airport to Chicago Midway Airport

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Southwest flights from New York LaGuardia Airport to Chicago Midway Airport

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How to get the cheapest flight ticket from New York LaGuardia Airport to Chicago Midway Airport

What is the cheapest month to fly to Chicago Midway Airport?

What is the cheapest day to depart on your flight to Chicago Midway Airport?

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

What is the cheapest New York LaGuardia to Chicago Midway flight route?

Fly from New York LaGuardia to Chicago Midway for the best New York LaGuardia - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

What cabin class options are available on New York LaGuardia to Chicago Midway flights?

There is only 1 cabin class available to choose from on New York LaGuardia to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have New York LaGuardia Airport to Chicago Midway Airport flight prices changed over time?

What is the cheapest airline that flies from New York LaGuardia to Chicago Midway?

Southwest is the most popular carrier operating from New York LaGuardia to Chicago Midway

How often are flights from New York to Chicago delayed?

Historically, on average around 20% of flights between New York and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 141 minutes.

What is the most punctual flight time for New York to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on New York to Chicago flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

How many flights depart from New York LaGuardia Airport to Chicago Midway Airport on average per day?

The number of flights available between New York LaGuardia Airport and Chicago Midway Airport is 4 per day as of December 2025. The most frequent departure time is 2:00PM, with 45% of daily flights leaving in the afternoon.

How many flights depart from New York LaGuardia Airport to Chicago Midway Airport on average per week?

30 flights are operational weekly from New York LaGuardia Airport to Chicago Midway Airport as of December 2025. The most popular departure day for this route is Mon, with 23% of flights per week taking off on this day.

When to book flights from New York LaGuardia Airport to Chicago Midway Airport

Cheap New York LaGuardia Airport to Chicago Midway Airport (LGA to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New York LaGuardia Airport to Chicago Midway Airport

Best Price Found

Fastest flight time

Direct flights

How far is New York LaGuardia to Chicago Midway by plane?

When did momondo last update prices for flights from New York LaGuardia Airport to Chicago Midway Airport?

How many operators does momondo search for flights from New York LaGuardia Airport to Chicago Midway Airport?

How old do you have to be to fly from New York LaGuardia Airport to Chicago Midway Airport?

What documentation or ID do you need to fly to Chicago Midway Airport?

What is the most popular plane model from New York LaGuardia Airport to Chicago Midway Airport?

What is the most popular airline from New York LaGuardia Airport to Chicago Midway Airport?

Best airlines flying from New York LaGuardia Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from New York LaGuardia Airport to Chicago Midway Airport with momondo

Southwest Flights From New York LaGuardia Airport to Chicago Midway Airport

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from New York to Chicago?

Can I find flights from New York to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from New York to Chicago?

I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Chicago

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