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Find cheap flights from Chicago Midway Airport to Los Cabos from $212

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Los Cabos departing on 5/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Wed 6/5
Wed 6/12

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Best Los Cabos Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Good to know

Low season

June

High season

March

Cheapest flight

$212
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago Midway Airport to San José del Cabo

FAQs - booking Los Cabos flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Los Cabos?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Los Cabos.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Los Cabos?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Los Cabos from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Los Cabos?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Los Cabos with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Los Cabos?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Los Cabos from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airlines flying from Midway to Los Cabos

 
Need help choosing which airline to fly with from Midway to Los Cabos? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10818 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

I had a great travel experience as there weren't any delays and I was able to get to Mexico City on time for conference.

The plane was so outdated, that it made it uncomfortable. The temperature was hot during the whole flight

Happy attentive flight crew. All in all good flight the night flight works well. Getting into Mexico City early so you don't get caught up it all the immigration and custom ques, additionally, this helps when exiting the airport and crossing the city to your final destination. All works very well and would do it again

Some entertainment and food/snack service would have been nice

All the pessengers should be wait in a line útil the creo and piloto are arrived.

Planes seat could be bigger very uncomfortable for tall humans.

Atraso de dos horas y media con vuelos sobre vendidos

Great airplane The confort was within the high standards. My only little problem was That all the movies ( only 3) was on Spanish, even though I was selecting the audio on English it didn't happen. After that I highly recommend aeromexico

1 hour waiting for suitcases to come out traveling in business class and food in business class is a sandwich? Avoid Aeromexico .

Aeromexico es siempre una buena opción, relación precio calidad adecuada!

No space reserved for anyone who didn’t have underseat in front of them. Made it inconvenient to get the backs secured. No inflight entertainment in the 190. Bring your own! Food was excellent and we were surprised to get a full breakfast.

Book cheap flights from Chicago to Los Cabos

Recent round-trip flight deals

6/11Tue
2 stops
10h 45mMDW-SJD
6/14Fri
1 stop
13h 40mSJD-MDW
$406
6/4Tue
1 stop
12h 05mMDW-SJD
6/11Tue
1 stop
14h 52mSJD-MDW
$416
6/6Thu
1 stopVolaris
22h 09mMDW-SJD
6/13Thu
1 stopVolaris
13h 40mSJD-MDW
$419
6/11Tue
1 stop
12h 05mMDW-SJD
6/14Fri
1 stop
13h 40mSJD-MDW
$420
6/11Tue
2 stops
10h 45mMDW-SJD
6/18Tue
1 stop
14h 52mSJD-MDW
$425
9/13Fri
2 stopsDelta
13h 40mMDW-SJD
9/20Fri
2 stopsDelta
13h 43mSJD-MDW
$446
9/26Thu
2 stopsDelta
13h 40mMDW-SJD
10/1Tue
2 stopsDelta
13h 43mSJD-MDW
$456
6/6Thu
2 stopsVolaris
18h 27mMDW-SJD
6/13Thu
1 stopVolaris
13h 40mSJD-MDW
$461
9/26Thu
1 stopAeromexico
21h 22mMDW-SJD
10/1Tue
1 stopAeromexico
7h 32mSJD-MDW
$514
7/13Sat
1 stopAeromexico
21h 22mMDW-SJD
7/16Tue
1 stopAeromexico
7h 29mSJD-MDW
$532

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Recent one-way flight deals

5/23Thu
2 stops
25h 05mMDW-SJD
$212
7/15Mon
1 stopVolaris
12h 17mMDW-SJD
$228
5/23Thu
3 stops
14h 00mMDW-SJD
$270
5/23Thu
1 stop
12h 05mMDW-SJD
$369
6/20Thu
2 stopsDelta
11h 08mMDW-SJD
$370
7/15Mon
2 stopsDelta
13h 42mMDW-SJD
$435
5/25Sat
1 stopDelta
8h 49mMDW-SJD
$442
5/25Sat
1 stopDelta
8h 49mMDW-SJD
$537
6/20Thu
1 stopDelta
6h 55mMDW-SJD
$790

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Last minute flights from Midway to Los Cabos

Last minute flight, train and bus deals

5/11Sat
multi-stop
12h 05mMDW-SJD
5/15Wed
multi-stop
15h 32mSJD-MDW
$486
5/8Wed
multi-stopDelta
15h 06mMDW-SJD
5/14Tue
multi-stopDelta
14h 00mSJD-MDW
$631
5/8Wed
multi-stopDelta
11h 09mMDW-SJD
5/14Tue
multi-stopDelta
7h 38mSJD-MDW
$646
5/10Fri
multi-stopAeromexico
7h 18mMDW-SJD
5/15Wed
multi-stopAeromexico
7h 38mSJD-MDW
$785
5/10Fri
multi-stopDelta
12h 31mMDW-SJD
5/15Wed
multi-stopDelta
7h 38mSJD-MDW
$811
5/8Wed
multi-stopDelta
11h 31mMDW-SJD
5/11Sat
multi-stopDelta
7h 38mSJD-MDW
$836
5/11Sat
multi-stopAeromexico
25h 01mMDW-SJD
5/18Sat
multi-stopAeromexico
7h 38mSJD-MDW
$866
5/11Sat
multi-stopAeromexico
21h 33mMDW-SJD
5/18Sat
multi-stopAeromexico
7h 38mSJD-MDW
$867
5/10Fri
multi-stopDelta
15h 06mMDW-SJD
5/15Wed
multi-stopDelta
13h 03mSJD-MDW
$871
5/8Wed
multi-stopDelta
15h 06mMDW-SJD
5/11Sat
multi-stopDelta
13h 08mSJD-MDW
$886

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Chicago Midway Airport - Los Cabos Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Los Cabos - Chicago Midway Airport

Cabin classes:

$527
$546
$292
$27