Find Cheap Flights from Chicago Midway to San José del Cabo Los Cabos (MDW - SJD)

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FAQs for Booking Chicago Midway to San José del Cabo Los Cabos Flights

How long does a flight from Chicago Midway to San José del Cabo Los Cabos take?
An average nonstop flight takes 7h 30m, covering a distance of 1805 miles.
Which airlines provide the cheapest flights from Chicago Midway to San José del Cabo Los Cabos?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($291), Aeromexico ($339) and Multiple Airlines ($372).
Do I need a passport to fly between Chicago Midway and San José del Cabo Los Cabos?
Yes.

Book cheap flights from Chicago Midway to San José del Cabo Los Cabos (round-trip)

Airports
Origin
Chicago
$291
only
$291
Destination
San José del Cabo
$291
only
$291
Tue, Jan 16
MDW
SJD
7h 35m
Mon, Jan 22
SJD
MDW
9h 33m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14128 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PNS
Mediocre 2.0

Wouldn't know wasn't able to make it to the flight

The fact that for the second time in 2 months Delta issues kept me from making my flight

SLC
FAT
Good 6.6

Staff was friendly

Plane was tiny

MSN
LGA
Mediocre 3.3

3.5 hours late.

ATL
SLC
Good 7.0

We purchased food. Bread was stale, and fell apart in your hands.

JNB
ATL
Okay 4.0

Older plane and seemingly frustrated crew. They had very little patience.

Wed, Dec 13
MDW
SJD
25h 33m
Mon, Dec 25
SJD
MDW
8h 38m
Trip: 13 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4656 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
SFO
MEX
Good 7.3

I like that there are USB charging ports under the tv for every seat.

PDX
MEX
Good 7.6

Flight on time. Lots of legroom. (Exit row.)

Chaotic boarding.

SJO
MEX
Excellent 8.6

Great seats with individual screens for free movies

No vegetarian option Long back up at Mexico City customs

MIA
MEX
Good 6.0

Every time I would fly out in Aeromexico we never payed for luggage I don’t know why they changed their policy to charge for every bag.

ACA
MEX
Good 6.0

Smooth flight

People make you feel dumb when you have a question or they need to repeat something they mentioned before. Is very hard to understand sometimes trough the speaker.

Thu, Mar 15
MDW
SJD
12h 32m
Wed, Mar 21
SJD
MDW
9h 08m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 16
MDW
SJD
7h 35m
Mon, Jan 22
SJD
MDW
9h 33m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14128 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
MKE
ATL
Mediocre 3.3

Everyone did try to be helpful but it seems that no one at Delta really knew anything that was going on today

The fact that I missed yet another connection because of a Delta issue. The difference is that this time there was not another connection for me to go to and I was told I would be provided a hotel in Atlanta which was not the case. I had to transfer to a flight 2 hrs away from my home only to still be on the floor of Atl airport because they are unable to appropriately de-ice planes.

SJC
LAS
Good 7.3

Quick friendly service from crew and captain.

First class seat was broken was reclined and super uncomfortable the whole flight the plane was super outdated and old.

JNB
ATL
Okay 4.0

Older plane and seemingly frustrated crew. They had very little patience.

MSN
LGA
Mediocre 3.3

3.5 hours late.

SLC
PHX
Mediocre 2.0

My flight got delayed for twelve hours with no compensation for a hotel.

Tue, Mar 6
MDW
SJD
7h 30m
Tue, Mar 13
SJD
MDW
26h 12m
Trip: 7 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4656 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
JFK
Excellent 9.6

Flight attendant Antonio was great! Friendly, funny and kind.

ACA
MEX
Good 6.0

Smooth flight

People make you feel dumb when you have a question or they need to repeat something they mentioned before. Is very hard to understand sometimes trough the speaker.

SFO
MEX
Good 7.3

I like that there are USB charging ports under the tv for every seat.

MEX
IAD
Good 6.0

Same

Same

SJO
MEX
Excellent 8.6

Great seats with individual screens for free movies

No vegetarian option Long back up at Mexico City customs

Fri, Feb 2
MDW
SJD
8h 51m
Mon, Feb 5
SJD
MDW
9h 33m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14128 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
SJC
LAS
Good 7.3

Quick friendly service from crew and captain.

First class seat was broken was reclined and super uncomfortable the whole flight the plane was super outdated and old.

ATL
PNS
Mediocre 2.0

Wouldn't know wasn't able to make it to the flight

The fact that for the second time in 2 months Delta issues kept me from making my flight

MKE
ATL
Mediocre 3.3

Everyone did try to be helpful but it seems that no one at Delta really knew anything that was going on today

The fact that I missed yet another connection because of a Delta issue. The difference is that this time there was not another connection for me to go to and I was told I would be provided a hotel in Atlanta which was not the case. I had to transfer to a flight 2 hrs away from my home only to still be on the floor of Atl airport because they are unable to appropriately de-ice planes.

SLC
PHX
Mediocre 2.0

My flight got delayed for twelve hours with no compensation for a hotel.

JFK
LHR
Excellent 8.0

Space looked a bit cramped in business class but I was pleasantly surprised at the length of the flat bed and the additional foot well space once I'd reclined the seat.

Need to fix the flickering lights in the JFK club lounge, the opposite of relaxing!

Fri, May 18
MDW
SJD
11h 59m
Sat, May 26
SJD
MDW
22h 18m
Trip: 9 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4656 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MIA
MEX
Good 6.0

Every time I would fly out in Aeromexico we never payed for luggage I don’t know why they changed their policy to charge for every bag.

SFO
MEX
Good 7.3

I like that there are USB charging ports under the tv for every seat.

MEX
MZT
Mediocre 2.0

Aeromexico truly is the worst airline on the planet. I travel all the time and I am the type of person who never complains. Six months ago when I came to Mexico and my daughter’s fiancé died of a heart attack they gave me the worst service of my life. And now again today they’re completely 100% at fault for me missing my flight. I was seven hours at the airport waiting for the flight and they didn’t post it on the boards. They never put a gate up. Other people also missed the flight. They offered no compensation, they wouldn’t pay for a hotel or a shuttle, absolutely reprehensible. Do not do business with this company

SFO
GDL
Mediocre 2.0

Our flight got changed and we received no notification. Instead of 1 stop we ended up with two. Two flights were delayed therefore we missed the third one. Just a terrible experience. The staff was very rude, had no people skills, and didn’t know how to explain the situation.

PDX
MEX
Good 7.6

Flight on time. Lots of legroom. (Exit row.)

Chaotic boarding.

Tue, Feb 6
MDW
SJD
7h 35m
Mon, Feb 12
SJD
MDW
14h 47m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14128 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
MKE
ATL
Mediocre 3.3

Everyone did try to be helpful but it seems that no one at Delta really knew anything that was going on today

The fact that I missed yet another connection because of a Delta issue. The difference is that this time there was not another connection for me to go to and I was told I would be provided a hotel in Atlanta which was not the case. I had to transfer to a flight 2 hrs away from my home only to still be on the floor of Atl airport because they are unable to appropriately de-ice planes.

MSN
LGA
Mediocre 3.3

3.5 hours late.

SJC
LAS
Good 7.3

Quick friendly service from crew and captain.

First class seat was broken was reclined and super uncomfortable the whole flight the plane was super outdated and old.

MSP
CMH
Good 7.3

The initial boarding process was quick, smooth flight

I've never had a flight wait over 30 minutes past departure got other people to make a connection and get on to this flight. Seems beyond normal and wrong to those that were there in time and on the flight to support an on time departure

LAX
HNL
Okay 5.0

The gate agents were gruff, but helpful. Stewards were super friendly.

Even though I had picked out two seats together, they had us separated. Very thankfully they put us back together after the fact - that was wonderful & appreciated. But entertainment system also didn’t work, and as always, seats are disgustingly uncomfortable. Also odd that they made us check bags with so many empty overhead bins.

Thu, Apr 19
MDW
SJD
15h 01m
Mon, Apr 23
SJD
MDW
22h 10m
Trip: 5 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4656 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
PDX
MEX
Good 7.6

Flight on time. Lots of legroom. (Exit row.)

Chaotic boarding.

SJO
MEX
Excellent 8.6

Great seats with individual screens for free movies

No vegetarian option Long back up at Mexico City customs

ACA
MEX
Good 6.0

Smooth flight

People make you feel dumb when you have a question or they need to repeat something they mentioned before. Is very hard to understand sometimes trough the speaker.

MEX
MZT
Mediocre 2.0

Aeromexico truly is the worst airline on the planet. I travel all the time and I am the type of person who never complains. Six months ago when I came to Mexico and my daughter’s fiancé died of a heart attack they gave me the worst service of my life. And now again today they’re completely 100% at fault for me missing my flight. I was seven hours at the airport waiting for the flight and they didn’t post it on the boards. They never put a gate up. Other people also missed the flight. They offered no compensation, they wouldn’t pay for a hotel or a shuttle, absolutely reprehensible. Do not do business with this company

MEX
UIO
Good 7.6

We got an upgrade to 1st class. However because it’s an older plane, 1st class was just recliner seats. This was an overnight flight, so anything helped. It would have been nicer to have seats lay further back in 1st class. We did not have food since we slept the whole way.

Mon, Feb 12
MDW
SJD
7h 35m
Fri, Feb 16
SJD
MDW
8h 33m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14128 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
MKE
ATL
Mediocre 3.3

Everyone did try to be helpful but it seems that no one at Delta really knew anything that was going on today

The fact that I missed yet another connection because of a Delta issue. The difference is that this time there was not another connection for me to go to and I was told I would be provided a hotel in Atlanta which was not the case. I had to transfer to a flight 2 hrs away from my home only to still be on the floor of Atl airport because they are unable to appropriately de-ice planes.

SLC
BOI
Good 7.6

SLC ground gate crew was awesome.

SLC
PHX
Mediocre 2.0

My flight got delayed for twelve hours with no compensation for a hotel.

JFK
LHR
Excellent 8.0

Space looked a bit cramped in business class but I was pleasantly surprised at the length of the flat bed and the additional foot well space once I'd reclined the seat.

Need to fix the flickering lights in the JFK club lounge, the opposite of relaxing!

MSN
LGA
Mediocre 3.3

3.5 hours late.

Wed, Mar 7
MDW
SJD
15h 07m
Wed, Mar 14
SJD
MDW
14h 18m
Trip: 7 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4656 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MIA
MEX
Good 6.0

Every time I would fly out in Aeromexico we never payed for luggage I don’t know why they changed their policy to charge for every bag.

PDX
MEX
Good 7.6

Flight on time. Lots of legroom. (Exit row.)

Chaotic boarding.

MEX
MZT
Mediocre 2.0

Aeromexico truly is the worst airline on the planet. I travel all the time and I am the type of person who never complains. Six months ago when I came to Mexico and my daughter’s fiancé died of a heart attack they gave me the worst service of my life. And now again today they’re completely 100% at fault for me missing my flight. I was seven hours at the airport waiting for the flight and they didn’t post it on the boards. They never put a gate up. Other people also missed the flight. They offered no compensation, they wouldn’t pay for a hotel or a shuttle, absolutely reprehensible. Do not do business with this company

SJO
MEX
Excellent 8.6

Great seats with individual screens for free movies

No vegetarian option Long back up at Mexico City customs

MEX
IAD
Good 6.0

Same

Same

Fri, Jan 5
MDW
SJD
7h 35m
Mon, Jan 8
SJD
MDW
14h 43m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14128 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
MKE
ATL
Mediocre 3.3

Everyone did try to be helpful but it seems that no one at Delta really knew anything that was going on today

The fact that I missed yet another connection because of a Delta issue. The difference is that this time there was not another connection for me to go to and I was told I would be provided a hotel in Atlanta which was not the case. I had to transfer to a flight 2 hrs away from my home only to still be on the floor of Atl airport because they are unable to appropriately de-ice planes.

SLC
BOI
Good 7.6

SLC ground gate crew was awesome.

JNB
ATL
Okay 4.0

Older plane and seemingly frustrated crew. They had very little patience.

LAX
HNL
Okay 5.0

The gate agents were gruff, but helpful. Stewards were super friendly.

Even though I had picked out two seats together, they had us separated. Very thankfully they put us back together after the fact - that was wonderful & appreciated. But entertainment system also didn’t work, and as always, seats are disgustingly uncomfortable. Also odd that they made us check bags with so many empty overhead bins.

SLC
FAT
Good 6.6

Staff was friendly

Plane was tiny

Tue, Dec 12
MDW
SJD
7h 33m
Mon, Dec 18
SJD
MDW
13h 31m
Trip: 7 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4656 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
SFO
MEX
Good 7.3

I like that there are USB charging ports under the tv for every seat.

MEX
YVR
Good 6.6

The crew was very nice.

The screen at my seat did not work. Nobody told me why or mentioned it to me. While I was sleeping a flight attendant took away my tray of food before I was finishing eating.

PDX
MEX
Good 7.6

Flight on time. Lots of legroom. (Exit row.)

Chaotic boarding.

MEX
UIO
Good 7.6

We got an upgrade to 1st class. However because it’s an older plane, 1st class was just recliner seats. This was an overnight flight, so anything helped. It would have been nicer to have seats lay further back in 1st class. We did not have food since we slept the whole way.

MEX
IAD
Good 6.0

Same

Same

Fri, May 25
MDW
SJD
11h 59m
Mon, May 28
SJD
MDW
29h 52m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4656 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
UIO
Good 7.6

We got an upgrade to 1st class. However because it’s an older plane, 1st class was just recliner seats. This was an overnight flight, so anything helped. It would have been nicer to have seats lay further back in 1st class. We did not have food since we slept the whole way.

YVR
MEX
Okay 4.0

The flight was delayed over 2 and a half hours, missed our connecting flight in Mexico City. The in flight entertainment stopped working half way through the flight, didn’t work again. Bad customer service, didn’t even apologize

ACA
MEX
Good 6.0

Smooth flight

People make you feel dumb when you have a question or they need to repeat something they mentioned before. Is very hard to understand sometimes trough the speaker.

SJO
MEX
Excellent 8.6

Great seats with individual screens for free movies

No vegetarian option Long back up at Mexico City customs

SFO
GDL
Mediocre 2.0

Our flight got changed and we received no notification. Instead of 1 stop we ended up with two. Two flights were delayed therefore we missed the third one. Just a terrible experience. The staff was very rude, had no people skills, and didn’t know how to explain the situation.

Fri, Jun 8
MDW
SJD
12h 09m
Sun, Jun 10
SJD
MDW
26h 35m
Trip: 3 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4656 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MIA
MEX
Good 6.0

Every time I would fly out in Aeromexico we never payed for luggage I don’t know why they changed their policy to charge for every bag.

MEX
MZT
Mediocre 2.0

Aeromexico truly is the worst airline on the planet. I travel all the time and I am the type of person who never complains. Six months ago when I came to Mexico and my daughter’s fiancé died of a heart attack they gave me the worst service of my life. And now again today they’re completely 100% at fault for me missing my flight. I was seven hours at the airport waiting for the flight and they didn’t post it on the boards. They never put a gate up. Other people also missed the flight. They offered no compensation, they wouldn’t pay for a hotel or a shuttle, absolutely reprehensible. Do not do business with this company

MEX
JFK
Excellent 9.6

Flight attendant Antonio was great! Friendly, funny and kind.

SJO
MEX
Excellent 8.6

Great seats with individual screens for free movies

No vegetarian option Long back up at Mexico City customs

MEX
UIO
Good 7.6

We got an upgrade to 1st class. However because it’s an older plane, 1st class was just recliner seats. This was an overnight flight, so anything helped. It would have been nicer to have seats lay further back in 1st class. We did not have food since we slept the whole way.

Sun, Jun 17
MDW
SJD
24h 37m
Sun, Jun 24
SJD
MDW
22h 13m
Trip: 8 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4656 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
IAD
Good 6.0

Same

Same

SFO
GDL
Mediocre 2.0

Our flight got changed and we received no notification. Instead of 1 stop we ended up with two. Two flights were delayed therefore we missed the third one. Just a terrible experience. The staff was very rude, had no people skills, and didn’t know how to explain the situation.

MEX
MZT
Mediocre 2.0

Aeromexico truly is the worst airline on the planet. I travel all the time and I am the type of person who never complains. Six months ago when I came to Mexico and my daughter’s fiancé died of a heart attack they gave me the worst service of my life. And now again today they’re completely 100% at fault for me missing my flight. I was seven hours at the airport waiting for the flight and they didn’t post it on the boards. They never put a gate up. Other people also missed the flight. They offered no compensation, they wouldn’t pay for a hotel or a shuttle, absolutely reprehensible. Do not do business with this company

MEX
UIO
Good 7.6

We got an upgrade to 1st class. However because it’s an older plane, 1st class was just recliner seats. This was an overnight flight, so anything helped. It would have been nicer to have seats lay further back in 1st class. We did not have food since we slept the whole way.

YVR
MEX
Okay 4.0

The flight was delayed over 2 and a half hours, missed our connecting flight in Mexico City. The in flight entertainment stopped working half way through the flight, didn’t work again. Bad customer service, didn’t even apologize

Fri, Mar 2
MDW
SJD
11h 17m
Fri, Mar 9
SJD
MDW
8h 23m
Trip: 8 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4656 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
UIO
Good 7.6

We got an upgrade to 1st class. However because it’s an older plane, 1st class was just recliner seats. This was an overnight flight, so anything helped. It would have been nicer to have seats lay further back in 1st class. We did not have food since we slept the whole way.

MEX
YVR
Good 6.6

The crew was very nice.

The screen at my seat did not work. Nobody told me why or mentioned it to me. While I was sleeping a flight attendant took away my tray of food before I was finishing eating.

SFO
MEX
Good 7.3

I like that there are USB charging ports under the tv for every seat.

MIA
MEX
Good 6.0

Every time I would fly out in Aeromexico we never payed for luggage I don’t know why they changed their policy to charge for every bag.

SJO
MEX
Excellent 8.6

Great seats with individual screens for free movies

No vegetarian option Long back up at Mexico City customs

Sun, Dec 24
MDW
SJD
7h 30m
Sun, Dec 31
SJD
MDW
7h 18m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14128 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
MKE
ATL
Mediocre 3.3

Everyone did try to be helpful but it seems that no one at Delta really knew anything that was going on today

The fact that I missed yet another connection because of a Delta issue. The difference is that this time there was not another connection for me to go to and I was told I would be provided a hotel in Atlanta which was not the case. I had to transfer to a flight 2 hrs away from my home only to still be on the floor of Atl airport because they are unable to appropriately de-ice planes.

ATL
SLC
Good 7.0

We purchased food. Bread was stale, and fell apart in your hands.

SLC
BOI
Good 7.6

SLC ground gate crew was awesome.

SJC
LAS
Good 7.3

Quick friendly service from crew and captain.

First class seat was broken was reclined and super uncomfortable the whole flight the plane was super outdated and old.

JFK
LHR
Excellent 8.0

Space looked a bit cramped in business class but I was pleasantly surprised at the length of the flat bed and the additional foot well space once I'd reclined the seat.

Need to fix the flickering lights in the JFK club lounge, the opposite of relaxing!

Mon, Jan 1
MDW
SJD
7h 30m
Fri, Jan 5
SJD
MDW
23h 44m
$1221
Trip: 5 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 4656 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
SFO
GDL
Mediocre 2.0

Our flight got changed and we received no notification. Instead of 1 stop we ended up with two. Two flights were delayed therefore we missed the third one. Just a terrible experience. The staff was very rude, had no people skills, and didn’t know how to explain the situation.

YVR
MEX
Okay 4.0

The flight was delayed over 2 and a half hours, missed our connecting flight in Mexico City. The in flight entertainment stopped working half way through the flight, didn’t work again. Bad customer service, didn’t even apologize

MEX
IAD
Good 6.0

Same

Same

MEX
UIO
Good 7.6

We got an upgrade to 1st class. However because it’s an older plane, 1st class was just recliner seats. This was an overnight flight, so anything helped. It would have been nicer to have seats lay further back in 1st class. We did not have food since we slept the whole way.

SJO
MEX
Excellent 8.6

Great seats with individual screens for free movies

No vegetarian option Long back up at Mexico City customs

*
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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.