What airlines fly to San Juan Luis Munoz Marin Intl Airport?

Southwest, Frontier and Delta are the top three most popular airlines that fly to San Juan Luis Munoz Marin Intl Airport from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 55% of people opting to fly with this airline when traveling to San Juan Luis Munoz Marin Intl Airport. Keep in mind that there are 5 different airlines that fly to San Juan Luis Munoz Marin Intl Airport on a routine basis, so you have a few additional options to choose from.

How often are flights from Chicago to San Juan delayed?

Historically, on average around 20% of flights between Chicago and San Juan have experienced a delay on any given week. The average delay length over the past 12 months has been 94 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. Tuesday has historically seen more delays on average compared to the rest of the week.

What is the cheapest airline that flies from Chicago Midway to San Juan Luis Munoz Marin Intl?

Delta, Southwest, and Frontier are the most popular carriers operating from Chicago Midway to San Juan Luis Munoz Marin Intl

Which airline has the best punctuality record on Chicago to San Juan flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 20% of their flights experiencing any sort of delay.

What is the most punctual flight time for Chicago to San Juan flights?

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

How many operators does momondo search for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

As of November 2025, there are 5 operators available to choose from for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport.

What documentation or ID do you need to fly to San Juan Luis Munoz Marin Intl Airport?

The travel and health documents you'll need for your trip to San Juan Luis Munoz Marin Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San Juan Luis Munoz Marin Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$58 Cheap Flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport in 2025/26

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Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:37 pm - 9:55 amMDW-SJU

13h 18m1 stop

4:02 pm - 10:12 pmSJU-MDW

8h 10m1 stop

$216Frontier

Find Deal

Sun, Dec 7 - Sat, Dec 20

7:23 pm - 12:45 amMDW-SJU

27h 22m2 stops

10:42 am - 9:53 pmSJU-MDW

13h 11m1 stop

$220Multiple Airlines

Find Deal

Thu, Dec 4 - Thu, Dec 11

7:44 am - 4:13 pmMDW-SJU

30h 29m1 stop

1:59 am - 11:08 amSJU-MDW

35h 09m2 stops

$221Frontier

Find Deal

Sun, Dec 7 - Sat, Dec 13

8:42 pm - 12:32 pmMDW-SJU

37h 50m2 stops

7:06 pm - 1:59 pmSJU-MDW

20h 53m1 stop

$224Multiple Airlines

Find Deal

Fri, Dec 12 - Sat, Dec 20

10:53 am - 11:44 pmMDW-SJU

10h 51m1 stop

3:55 pm - 10:26 pmSJU-MDW

8h 31m1 stop

$225Delta

Find Deal

Tue, Jan 20 - Tue, Jan 27

6:00 am - 3:06 pmMDW-SJU

7h 06m1 stop

4:11 pm - 11:25 pmSJU-MDW

9h 14m1 stop

$226Frontier

Find Deal

Sat, Jan 31 - Sat, Feb 7

3:10 pm - 2:50 amMDW-SJU

9h 40m1 stop

4:21 pm - 10:12 pmSJU-MDW

7h 51m1 stop

$227Frontier

Find Deal

Thu, Dec 11 - Thu, Dec 18

3:10 pm - 2:50 amMDW-SJU

9h 40m1 stop

3:54 am - 9:19 amSJU-MDW

7h 25m1 stop

$231Frontier

Find Deal

Thu, Dec 11 - Fri, Dec 19

3:52 pm - 9:55 amMDW-SJU

16h 03m1 stop

7:10 am - 1:01 pmSJU-MDW

31h 51m1 stop

$235Frontier

Find Deal

Fri, Dec 5 - Mon, Dec 8

8:56 pm - 9:55 amMDW-SJU

10h 59m1 stop

11:05 am - 7:50 pmSJU-MDW

10h 45m1 stop

$236Frontier

Find Deal

Fri, Jan 23 - Mon, Jan 26

Frontier flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

Our best Frontier deals on Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flight tickets

Frontier

Dec 7

MDW6:37 pmChicago Midway

13h 18m

1 stop

SJU9:55 amSan Juan Luis Munoz Marin Intl

Dec 20

SJU4:02 pmSan Juan Luis Munoz Marin Intl

8h 10m

1 stop

MDW10:12 pmChicago Midway

$216

Find similar

Frontier

Dec 7

MDW7:44 amChicago Midway

30h 29m

1 stop

SJU4:13 pmSan Juan Luis Munoz Marin Intl

Dec 13

SJU1:59 amSan Juan Luis Munoz Marin Intl

35h 09m

2 stops

MDW11:08 amChicago Midway

$221

Find similar

Frontier

Jan 31

MDW6:00 amChicago Midway

7h 06m

1 stop

SJU3:06 pmSan Juan Luis Munoz Marin Intl

Feb 7

SJU4:11 pmSan Juan Luis Munoz Marin Intl

9h 14m

1 stop

MDW11:25 pmChicago Midway

$226

Find similar

Southwest flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

Our best Southwest deals on Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flight tickets

Southwest

Jan 20

MDW9:50 amChicago Midway

11h 20m

1 stop

SJU11:10 pmSan Juan Luis Munoz Marin Intl

Jan 27

SJU6:00 amSan Juan Luis Munoz Marin Intl

9h 20m

2 stops

MDW1:20 pmChicago Midway

$245

Find similar

Southwest

Jan 31

MDW1:00 pmChicago Midway

9h 10m

1 stop

SJU12:10 amSan Juan Luis Munoz Marin Intl

Feb 3

SJU6:10 amSan Juan Luis Munoz Marin Intl

9h 45m

2 stops

MDW1:55 pmChicago Midway

$246

Find similar

Southwest

Feb 1

MDW1:35 pmChicago Midway

8h 30m

2 stops

SJU12:05 amSan Juan Luis Munoz Marin Intl

Feb 5

SJU8:00 amSan Juan Luis Munoz Marin Intl

8h 50m

1 stop

MDW2:50 pmChicago Midway

$252

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 12/7

6:37 pm-9:55 am

1 stop13h 18m

San Juan Luis Munoz Marin Intl

Sat 12/20

4:02 pm-10:12 pm

1 stop8h 10m

$216

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 12/4

7:23 pm-12:45 am

2 stops27h 22m

San Juan Luis Munoz Marin Intl

Thu 12/11

10:42 am-9:53 pm

1 stop13h 11m

$220

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 12/7

7:44 am-4:13 pm

1 stop30h 29m

San Juan Luis Munoz Marin Intl

Sat 12/13

1:59 am-11:08 am

2 stops35h 09m

$221

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 12/12

8:42 pm-12:32 pm

2 stops37h 50m

San Juan Luis Munoz Marin Intl

Sat 12/20

7:06 pm-1:59 pm

1 stop20h 53m

$224

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

10:53 am-11:44 pm

1 stop10h 51m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:55 pm-10:26 pm

1 stop8h 31m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/31

6:00 am-3:06 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Sat 2/7

4:11 pm-11:25 pm

1 stop9h 14m

$226

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 12/11

3:10 pm-2:50 am

1 stop9h 40m

San Juan Luis Munoz Marin Intl

Thu 12/18

4:21 pm-10:12 pm

1 stop7h 51m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 12/11

3:10 pm-2:50 am

1 stop9h 40m

San Juan Luis Munoz Marin Intl

Fri 12/19

3:54 am-9:19 am

1 stop7h 25m

$231

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 12/5

3:52 pm-9:55 am

1 stop16h 03m

San Juan Luis Munoz Marin Intl

Mon 12/8

7:10 am-1:01 pm

1 stop31h 51m

$235

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/23

8:56 pm-9:55 am

1 stop10h 59m

San Juan Luis Munoz Marin Intl

Mon 1/26

11:05 am-7:50 pm

1 stop10h 45m

$236

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How to get the cheapest flight ticket from Chicago Midway Airport to San Juan Luis Munoz Marin Intl 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

What is the typical price of a round-trip flight between Chicago Midway Airport and San Juan Luis Munoz Marin Intl Airport?

What is the cheapest month to fly to San Juan Luis Munoz Marin Intl Airport?

If you aren’t able to travel to San Juan Luis Munoz Marin Intl Airport during the month of May, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $354.

What is the cheapest day to depart on your flight to San Juan Luis Munoz Marin Intl Airport?

On average, the least expensive day to fly to San Juan Luis Munoz Marin Intl Airport from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $393. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Thursday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $444.

What is the cheapest time of day to depart on your flight to San Juan Luis Munoz Marin Intl Airport?

The cheapest time of day to fly to San Juan Luis Munoz Marin Intl Airport is in the evening when flights can be purchased for as low as $314. Flights in the morning are often more expensive with an average ticket price of $450.

What is the cheapest Chicago Midway to San Juan Luis Munoz Marin Intl flight route?

Fly from Chicago Midway to San Juan Luis Munoz Marin Intl for the best Chicago Midway - San Juan Luis Munoz Marin Intl flight prices

How far in advance should I book a flight to San Juan Luis Munoz Marin Intl Airport?

You are more likely to see cheaper flights to San Juan Luis Munoz Marin Intl Airport from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan Luis Munoz Marin Intl Airport for around $425 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan Luis Munoz Marin Intl Airport from Chicago Midway Airport for as low as $362 on momondo.

What cabin class options are available on Chicago Midway to San Juan Luis Munoz Marin Intl flights?

There is only 1 cabin class available to choose from on Chicago Midway to San Juan Luis Munoz Marin Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flight prices changed over time?

As of November 2025, prices for Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flights are approximately 75% more expensive when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport (MDW to SJU) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

Fastest flight time	4h 35m
Direct flights	Mon and Sun

The fastest flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport takes 4h 35m

Direct flights go from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport on Monday and Sunday. There are no airlines offering direct flights.

Search flight deals

How far is Chicago Midway to San Juan Luis Munoz Marin Intl by plane?
Chicago Midway and San Juan Luis Munoz Marin Intl are 2057.4 mi apart from one another. In terms of flight time, this usually takes a little over 6h 58m.
When did momondo last update prices for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?
Prices for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?
As of November 2025, there are 5 operators available to choose from for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport.
How old do you have to be to fly from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport.
What documentation or ID do you need to fly to San Juan Luis Munoz Marin Intl Airport?
The travel and health documents you'll need for your trip to San Juan Luis Munoz Marin Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San Juan Luis Munoz Marin Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport is Boeing 737 MAX 8 (21.28% of total bookings). The next most popular plane models are Airbus A321-100/200 (14.89%), Airbus A321 (sharklets) (14.89%), and Boeing 737-900 (14.89%).
What is the most popular airline from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport is Southwest (53% of total bookings). The next most popular airlines are Frontier (31%), Delta (8%), and Spirit Airlines (4%).

Best airlines flying from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $144	Free Cancellation	Rating 5.8 3,113 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $149	Free Cancellation	Rating 6.3 8,137 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $299	Free Cancellation	Rating 7.4 9,015 reviews	Search United Airlines flights
Delta	PriceFrom $325	Free Cancellation	Rating 7.9 8,008 reviews	Search Delta flights
Southwest	PriceFrom $380	Free Cancellation	Rating 8.0 4,235 reviews	Search Southwest flights

Carolina

Fajardo

Dorado

Luquillo

Caguas

Humacao

Rio Grande

Bayamón

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Juan?

Finding the right flight to San Juan from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San Juan quick and easy, saving you time and money.

Can I find flights from Chicago to San Juan with flexible booking policies on momondo?

All flight searches from Chicago to San Juan on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San Juan?

Once all potential Chicago to San Juan flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Chicago to San Juan flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your San Juan Luis Munoz Marin Intl Airport trip

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Chicago Midway Airport flight routes

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Flights from Chicago Midway to Tampa

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San Juan Luis Munoz Marin Intl Airport flight routes

Flights from New York John F Kennedy Intl to San Juan Luis Munoz Marin Intl

Flights from Newark to San Juan Luis Munoz Marin Intl

Flights from Orlando to San Juan Luis Munoz Marin Intl

Flights from Philadelphia to San Juan Luis Munoz Marin Intl

Flights from Boston Logan Intl to San Juan Luis Munoz Marin Intl

Cheap flights from Chicago Midway Airport to San Juan from $113

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Big names and deals

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Frontier flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

Our best Frontier deals on Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flight tickets

Southwest flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

Our best Southwest deals on Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport that are best for you.

See travel insights to San Juan from

How to get the cheapest flight ticket from Chicago Midway Airport to San Juan Luis Munoz Marin Intl 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

What is the typical price of a round-trip flight between Chicago Midway Airport and San Juan Luis Munoz Marin Intl Airport?

What is the cheapest month to fly to San Juan Luis Munoz Marin Intl Airport?

If you aren’t able to travel to San Juan Luis Munoz Marin Intl Airport during the month of May, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $354.

What is the cheapest day to depart on your flight to San Juan Luis Munoz Marin Intl Airport?

What is the cheapest time of day to depart on your flight to San Juan Luis Munoz Marin Intl Airport?

The cheapest time of day to fly to San Juan Luis Munoz Marin Intl Airport is in the evening when flights can be purchased for as low as $314. Flights in the morning are often more expensive with an average ticket price of $450.

What is the cheapest Chicago Midway to San Juan Luis Munoz Marin Intl flight route?

Fly from Chicago Midway to San Juan Luis Munoz Marin Intl for the best Chicago Midway - San Juan Luis Munoz Marin Intl flight prices

How far in advance should I book a flight to San Juan Luis Munoz Marin Intl Airport?

What cabin class options are available on Chicago Midway to San Juan Luis Munoz Marin Intl flights?

There is only 1 cabin class available to choose from on Chicago Midway to San Juan Luis Munoz Marin Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flight prices changed over time?

As of November 2025, prices for Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flights are approximately 75% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago Midway to San Juan Luis Munoz Marin Intl?

Delta, Southwest, and Frontier are the most popular carriers operating from Chicago Midway to San Juan Luis Munoz Marin Intl

What airlines fly to San Juan Luis Munoz Marin Intl Airport?

How often are flights from Chicago to San Juan delayed?

Historically, on average around 20% of flights between Chicago and San Juan have experienced a delay on any given week. The average delay length over the past 12 months has been 94 minutes.

What is the most punctual flight time for Chicago to San Juan flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning 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. Tuesday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to San Juan flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 20% of their flights experiencing any sort of delay.

When to book flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

Cheap Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport (MDW to SJU) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

Fastest flight time

Direct flights

How far is Chicago Midway to San Juan Luis Munoz Marin Intl by plane?

When did momondo last update prices for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

How many operators does momondo search for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

How old do you have to be to fly from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

What documentation or ID do you need to fly to San Juan Luis Munoz Marin Intl Airport?

What is the most popular plane model from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

What is the most popular airline from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

Best airlines flying from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport with momondo

Traveling to a place near San Juan?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Juan?

Can I find flights from Chicago to San Juan with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to San Juan?

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

An easier way to manage your San Juan Luis Munoz Marin Intl 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 San Juan

Chicago Midway Airport flight routes

According to popular flight searches on momondo this year