Find Cheap Flights from Chicago Midway to San Jose Juan Santamaria Intl (MDW - SJO)

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FAQs for Booking Chicago Midway to San Jose Juan Santamaria Intl Flights

How long does a flight from Chicago Midway to San Jose Juan Santamaria Intl take?
An average nonstop flight takes 6h 36m, covering a distance of 2207 miles.
Which airlines provide the cheapest flights from Chicago Midway to San Jose Juan Santamaria Intl?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($416), Southwest ($495) and Aeromexico ($1202).
Do I need a passport to fly between Chicago Midway and San Jose Juan Santamaria Intl?
Yes.
What’s the cheapest day of the week to fly Chicago Midway to San Jose Juan Santamaria Intl?
For Chicago Midway to San Jose Juan Santamaria Intl, Tuesday is the cheapest day to fly on average and Friday is the most expensive. Flying from San Jose Juan Santamaria Intl back to Chicago Midway, the best deals are generally found on Sunday, with Thursday being the most expensive.

Book cheap flights from Chicago Midway to San Jose Juan Santamaria Intl (round-trip)

Airports
Origin
Chicago
$416
only
$416
Destination
San Jose
$416
only
$416
Tue, Jan 30
MDW
SJO
6h 46m
Mon, Feb 5
SJO
MDW
9h 22m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

Sat, Feb 24
MDW
SJO
8h 35m
Sat, Mar 3
SJO
MDW
11h 00m
Trip: 8 days
8.5ExcellentShow reviews
Overall 8.5 Excellent
Based on 5907 reviews
Boarding
8.8
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
SJO
FLL
Excellent 8.6

Confort and kindness of crew

Nothing. So far so good

DTW
BNA
Excellent 10.0

On time and great service very smooth Landing staff very professional

Very helpful at all my questions extremely polite and very knowledgeable

CMH
LAS
Okay 5.6

The passengers. The peanuts. The cookies when available. The free bags.

Four hours is my limit in this aircraft, so I don’t mind changing planes in Las Vegas as long as I make the connection. Overhead compartment is tighter on one side of the plane than the other.

FLL
AUS
Excellent 8.5

Boarding area had plenty of seats and power connections. Clean cheap no-frills friendly flight. Arrived about 10 minutes late but otherwise uneventful. Flight crew was always on the move with drinks or trash bags.Lots of stations for self check in (and none were broken) so the process was quick and efficient. Hertz check-in is fast and efficient.

WiFi broken. No USB power at seat. No fault of Southwest, but the only good thing to say about the Ft Lauderdale airport is that it's better than Miami. Return rental car, down 2 flights, cross to terminal, up one flight to check bag, back down to security, long TSA lines (thank you TSA PreCheck), long hike to gate A3. Most (all?) food stalls closed (at 6:30 pm!).

FLL
BNA
Excellent 10.0

Very full flight

Tue, Feb 6
MDW
SJO
8h 56m
Wed, Feb 14
SJO
MDW
9h 24m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

Wed, Mar 7
MDW
SJO
6h 46m
Mon, Mar 12
SJO
MDW
9h 17m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

PTY
ATL
Excellent 9.6

Crew was kind, entertainment and food were good

Seats are really tight

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

Thu, Apr 19
MDW
SJO
8h 05m
Mon, Apr 23
SJO
MDW
14h 48m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
OMA
ATL
Good 7.6

My comfort zone seat

AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

PTY
ATL
Excellent 9.6

Crew was kind, entertainment and food were good

Seats are really tight

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

Tue, May 15
MDW
SJO
6h 46m
Sat, May 26
SJO
MDW
9h 17m
Trip: 12 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

OMA
ATL
Good 7.6

My comfort zone seat

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

PTY
ATL
Excellent 9.6

Crew was kind, entertainment and food were good

Seats are really tight

Sun, Dec 10
MDW
SJO
11h 55m
Thu, Dec 14
SJO
MDW
8h 00m
Trip: 5 days
8.5ExcellentShow reviews
Overall 8.5 Excellent
Based on 5907 reviews
Boarding
8.8
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
BNA
SAT
Excellent 10.0

All of the Destination that they travel too and adding new destinations

Plane very comfortable wi fi a great Plus seats are extremely comfortable.

BWI
FLL
Mediocre 2.0

Nothing

Unruly passenger was not dealt with by flight attendants

DTW
BNA
Excellent 10.0

On time and great service very smooth Landing staff very professional

Very helpful at all my questions extremely polite and very knowledgeable

AUS
FLL
Excellent 8.5

Sometime Southwest has poor direct fares, other times they are great. This one was exceptional. On-time departure and landing. Gate area in both airports was good, with enough seating for the full flights, and lots of electrical outlets. Gate agent was able to fix my TSA number and reprint my ticket, not all airlines can/will do this.

No charging ports on plane.

FLL
AUS
Excellent 8.5

Boarding area had plenty of seats and power connections. Clean cheap no-frills friendly flight. Arrived about 10 minutes late but otherwise uneventful. Flight crew was always on the move with drinks or trash bags.Lots of stations for self check in (and none were broken) so the process was quick and efficient. Hertz check-in is fast and efficient.

WiFi broken. No USB power at seat. No fault of Southwest, but the only good thing to say about the Ft Lauderdale airport is that it's better than Miami. Return rental car, down 2 flights, cross to terminal, up one flight to check bag, back down to security, long TSA lines (thank you TSA PreCheck), long hike to gate A3. Most (all?) food stalls closed (at 6:30 pm!).

Thu, Mar 29
MDW
SJO
13h 15m
Sat, Apr 7
SJO
MDW
15h 45m
$1202
Trip: 10 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4480 reviews
Overall
7.4
Boarding
7.4
Comfort
7.3
Crew
7.8
Entertainment
7.1
Food
6.9
MCO
MEX
Excellent 9.6

Service was good, airplane was comfortable, and each seat has a TV with a good selection of complimentary entertainment.

$25 checked bag fee on a flight from USA to Mexico.

MEX
LAX
Excellent 10.0

Seats were comfortable, even in economy. Personal entertainment at each seat with a good selection of movies and easy way to navigate to English language. The flight attendants were very nice, and they provided not only drinks but also a full snack tray to each person. Flight was right on time and announcement were in Spanish and English which was important for me as I don't speak Spanish..

MEX
JFK
Mediocre 2.0

The airline

SFO
GDL
Mediocre 3.6

The sits were to close to next line and the sitting was so hard and flat as on a wood bench, almost no cushion.

SMF
GDL
Good 6.0

The bags took forever to come out and we missed our second flight. We didn't know we had to pick up our luggage to be put onto the next flight

Fri, Nov 24
MDW
SJO
6h 50m
Wed, Dec 6
SJO
MDW
7h 45m
Trip: 13 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

Sat, Mar 10
MDW
SJO
12h 10m
Thu, Mar 15
SJO
MDW
24h 29m
$1277
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 23
MDW
SJO
7h 07m
Sun, Jan 28
SJO
MDW
9h 24m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
OMA
ATL
Good 7.6

My comfort zone seat

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

Sat, Apr 21
MDW
SJO
8h 00m
Tue, Apr 24
SJO
MDW
8h 53m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

Sun, Mar 4
MDW
SJO
6h 36m
Sat, Mar 10
SJO
MDW
9h 17m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

OMA
ATL
Good 7.6

My comfort zone seat

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

Mon, Jan 8
MDW
SJO
8h 40m
Thu, Jan 11
SJO
MDW
9h 22m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

OMA
ATL
Good 7.6

My comfort zone seat

PTY
ATL
Excellent 9.6

Crew was kind, entertainment and food were good

Seats are really tight

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

Sat, Feb 3
MDW
SJO
6h 46m
Mon, Feb 12
SJO
MDW
12h 25m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

PTY
ATL
Excellent 9.6

Crew was kind, entertainment and food were good

Seats are really tight

Tue, Dec 12
MDW
SJO
6h 55m
Thu, Dec 28
SJO
MDW
9h 24m
$1052
Trip: 17 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
OMA
ATL
Good 7.6

My comfort zone seat

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

Fri, Mar 23
MDW
SJO
10h 00m
Mon, Apr 2
SJO
MDW
14h 48m
$1067
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

Wed, Dec 13
MDW
SJO
6h 55m
Sat, Jan 6
SJO
MDW
8h 13m
$1549
Trip: 25 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

Fri, Dec 29
MDW
SJO
8h 10m
Sat, Jan 6
SJO
MDW
8h 13m
$1564
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

*
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.