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

Search hundreds of travel sites at once for deals on flights to Chicago Midway

Wed 1/24
Wed 1/31
Any month
Compare vs. KAYAK |

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $445 or less.

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

How long does a flight from San Jose Juan Santamaria Intl to Chicago Midway take?
An average nonstop flight takes 8h 53m, covering a distance of 2207 miles.
Which airlines provide the cheapest flights from San Jose Juan Santamaria Intl to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Aeromexico ($396) and Delta ($462)
Do I need a passport to fly between San Jose Juan Santamaria Intl and Chicago Midway?
Yes.
What’s the cheapest day of the week to fly San Jose Juan Santamaria Intl to Chicago Midway?
For San Jose Juan Santamaria Intl to Chicago Midway, Tuesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago Midway back to San Jose Juan Santamaria Intl, the best deals are generally found on Tuesday, with Friday being the most expensive.

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

Airports
Origin
San Jose
$396
only
$396
Destination
Chicago
$396
only
$396
Tue, Mar 6
SJO
MDW
16h 40m
Tue, Mar 20
MDW
SJO
25h 40m
Trip: 14 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5229 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
GDL
SFO
Okay 4.3

swift flight so that we could get off of the plane quicker.

getting in and out of the seat was awful. especially when the seat in front is reclined. the armrest on the aisle seat should be able to move up as the others in the row did. the metal underneath the armrest is pretty sharp and jagged, scraped my palm as i was trying to get the seatbelt to buckle.

LAX
MEX
Excellent 8.6

Good service. Nice to have a meal and drinks for still a relatively short flight. Seats were more spacious than I was expecting.

Flights were delayed.

MEX
ORD
Okay 4.3

Check in at Mexico on our way to Chicago, they were rude and trying to intimidate , the flight itself what normal experience

MEX
PDX
Excellent 10.0

Best entertainment

MEX
YVR
Good 6.3

Overall planes were ontime Staff pleasant. Tv entertainment was certainly adequate

Food was terrible Both trips a bun with mystery meat and cheese And a pudding on the side My last overnight trip my seat didn’t recline making sleeping almost impossible

Thu, May 17
SJO
MDW
8h 53m
Thu, May 24
MDW
SJO
13h 10m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
SMF
Good 6.3

For a 3 hour flight no onboard entertainment. Such a let down

MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

TYS
ATL
Excellent 8.4

Everything went well...on time, quick boarding and free gate check of bag.

ATL
TYS
Excellent 9.5

Flight less than 2/3 full, lots of room for comfort. On time, no need to gate check carry on.

nothing, it was great.

ATL
MEX
Excellent 10.0

In some Delta flights that I had in the past the plane was just ok, not bad, not good. But this plane ATL-MEX was great, very nice and conformable plane, it looks and feels excellent!

Tue, Feb 6
SJO
MDW
15h 20m
Tue, Feb 13
MDW
SJO
12h 23m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5229 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
ORD
Okay 4.3

Check in at Mexico on our way to Chicago, they were rude and trying to intimidate , the flight itself what normal experience

MEX
CUN
Excellent 8.0

Surprise first class!

MEX
PDX
Excellent 10.0

Best entertainment

MEX
YVR
Good 6.3

Overall planes were ontime Staff pleasant. Tv entertainment was certainly adequate

Food was terrible Both trips a bun with mystery meat and cheese And a pudding on the side My last overnight trip my seat didn’t recline making sleeping almost impossible

DTW
MEX
Okay 5.3

Plane waited on another family to connect to this flight, in turn causing our flight to arrivw in Mexico City an hour later. Baggage was slow staff in airport were aware of us trying to connect. They radiod that we were on our way to gate yet still closed gate doors before we arrived at the gate

Tue, Jul 31
SJO
MDW
12h 32m
Tue, Aug 7
MDW
SJO
10h 00m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
SLC
Mediocre 2.0

Nothing!

Everything

ATL
SJD
Excellent 8.0

On time departure, actually got to Cabo early.

The seat in front of mine had a broken reclining lock mechanism and the passenger kept trying to switch from recline to sitting up and it wouldn't latch in the upright position, so he kept jerking the seatback up and down for the entire 4 hour flight. Also the rows were so tight, and seatbacks were so close together, that the reclining seat in front of me was 6 inches from my face.

SJD
ATL
Good 7.6

Our Delta plane was brand spanking new. Everything worked and the inflight entertainment system was fantastic with many movies to choose from, free headphones, games, tv shows, etc. The crew was polite and the seating at least as comfortable as expected for a 4 hour flight.

The restrooms in the rear of the plane were remarkably small, even by airline standards. I'm a somewhat larger person and I fit, but I know a lot of people who would literally not be able to fit on the toilet without touching both of the sidewalls or risk getting stuck in there. The boarding process at San Jose Del Cabo was the most ridiculous setup I've ever experienced. There were numerous flights boarding out of the same gates and at least 3 or 4 lines for different destinations forming on a ramp just outside the gates. There were guys with signs trying to herd people into the correct lines and then loading the people onto buses which took you out to the planes. The planes were loading from both the front and rear doors and people were getting tangled up inside because of the haphazard loading process. Very easy for a person to end up on an incorrect plane!!

JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

MSP
SMF
Good 6.3

For a 3 hour flight no onboard entertainment. Such a let down

Thu, Apr 12
SJO
MDW
8h 53m
Thu, Apr 19
MDW
SJO
8h 05m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORD
ATL
Excellent 10.0

My flight was great. Boarding was easy and the seats were comfortable.

DEN
SLC
Mediocre 2.0

Nothing!

Everything

JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

JFK
SLC
Good 6.3

Too many turbulences !!!

SJD
ATL
Good 7.6

Our Delta plane was brand spanking new. Everything worked and the inflight entertainment system was fantastic with many movies to choose from, free headphones, games, tv shows, etc. The crew was polite and the seating at least as comfortable as expected for a 4 hour flight.

The restrooms in the rear of the plane were remarkably small, even by airline standards. I'm a somewhat larger person and I fit, but I know a lot of people who would literally not be able to fit on the toilet without touching both of the sidewalls or risk getting stuck in there. The boarding process at San Jose Del Cabo was the most ridiculous setup I've ever experienced. There were numerous flights boarding out of the same gates and at least 3 or 4 lines for different destinations forming on a ramp just outside the gates. There were guys with signs trying to herd people into the correct lines and then loading the people onto buses which took you out to the planes. The planes were loading from both the front and rear doors and people were getting tangled up inside because of the haphazard loading process. Very easy for a person to end up on an incorrect plane!!

Mon, Apr 23
SJO
MDW
9h 17m
Fri, Apr 27
MDW
SJO
6h 46m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
SLC
Mediocre 2.0

Nothing!

Everything

DTW
PVR
Excellent 8.6

Easy flight from check-in to boarding to deplaning.

Nothing really! No entertainment and nothing but almonds eaten.

ATL
MEX
Excellent 10.0

In some Delta flights that I had in the past the plane was just ok, not bad, not good. But this plane ATL-MEX was great, very nice and conformable plane, it looks and feels excellent!

ORD
ATL
Excellent 10.0

My flight was great. Boarding was easy and the seats were comfortable.

JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

Fri, Jan 26
SJO
MDW
15h 20m
Wed, Feb 7
MDW
SJO
12h 45m
Trip: 13 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5229 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
CUN
Excellent 8.0

Surprise first class!

MEX
PDX
Excellent 10.0

Best entertainment

DTW
MEX
Okay 5.3

Plane waited on another family to connect to this flight, in turn causing our flight to arrivw in Mexico City an hour later. Baggage was slow staff in airport were aware of us trying to connect. They radiod that we were on our way to gate yet still closed gate doors before we arrived at the gate

PDX
MEX
Excellent 8.0

Seemed fine!

LAX
MEX
Excellent 8.6

Good service. Nice to have a meal and drinks for still a relatively short flight. Seats were more spacious than I was expecting.

Flights were delayed.

Fri, Jun 15
SJO
MDW
14h 50m
Thu, Jun 21
MDW
SJO
8h 00m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

ATL
TYS
Excellent 9.5

Flight less than 2/3 full, lots of room for comfort. On time, no need to gate check carry on.

nothing, it was great.

DTW
PVR
Excellent 8.6

Easy flight from check-in to boarding to deplaning.

Nothing really! No entertainment and nothing but almonds eaten.

ATL
SJD
Excellent 8.0

On time departure, actually got to Cabo early.

The seat in front of mine had a broken reclining lock mechanism and the passenger kept trying to switch from recline to sitting up and it wouldn't latch in the upright position, so he kept jerking the seatback up and down for the entire 4 hour flight. Also the rows were so tight, and seatbacks were so close together, that the reclining seat in front of me was 6 inches from my face.

Wed, Mar 28
SJO
MDW
9h 19m
Sun, Apr 1
MDW
SJO
9h 04m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

ORD
ATL
Excellent 10.0

My flight was great. Boarding was easy and the seats were comfortable.

ATL
SJD
Excellent 8.0

On time departure, actually got to Cabo early.

The seat in front of mine had a broken reclining lock mechanism and the passenger kept trying to switch from recline to sitting up and it wouldn't latch in the upright position, so he kept jerking the seatback up and down for the entire 4 hour flight. Also the rows were so tight, and seatbacks were so close together, that the reclining seat in front of me was 6 inches from my face.

MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

JFK
SLC
Good 6.3

Too many turbulences !!!

Fri, Jun 29
SJO
MDW
15h 47m
Sat, Jul 7
MDW
SJO
12h 45m
$1050
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5229 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
GDL
MEX
Excellent 10.0

Aeromexico treats everyone like there in first class

PDX
MEX
Excellent 8.0

Seemed fine!

LAX
MEX
Excellent 8.6

Good service. Nice to have a meal and drinks for still a relatively short flight. Seats were more spacious than I was expecting.

Flights were delayed.

MEX
PDX
Excellent 10.0

Best entertainment

DTW
MEX
Okay 5.3

Plane waited on another family to connect to this flight, in turn causing our flight to arrivw in Mexico City an hour later. Baggage was slow staff in airport were aware of us trying to connect. They radiod that we were on our way to gate yet still closed gate doors before we arrived at the gate

San Jose Juan Santamaria Intl to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from San Jose Juan Santamaria Intl
Flight Price $396
Distance 2207 miles
Airlines Aeromexico, Delta
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

^
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.