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Find cheap flights from Chicago Midway Airport to Los Cabos from $173

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 6/5. 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
Sat 6/29
Sat 7/6

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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

$173
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly with an average 14% 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 10457 reviews
8.6Crew
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

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!

Business class was economy with a table in the middle seat. That is worse than economy. No food and no entertainment. Very poor representation.

Book cheap flights from Chicago to Los Cabos

Recent round-trip flight deals

8/25Sun
1 stopAeromexico
7h 00mMDW-SJD
8/28Wed
1 stopAeromexico
7h 41mSJD-MDW
$406
8/13Tue
1 stopDelta
7h 00mMDW-SJD
8/20Tue
1 stopDelta
7h 41mSJD-MDW
$416
8/13Tue
1 stopDelta
7h 00mMDW-SJD
8/16Fri
1 stopDelta
21h 39mSJD-MDW
$424
8/4Sun
1 stopDelta
7h 00mMDW-SJD
8/14Wed
1 stopDelta
7h 41mSJD-MDW
$431
8/12Mon
1 stopDelta
7h 00mMDW-SJD
8/16Fri
1 stopDelta
21h 39mSJD-MDW
$439
8/3Sat
1 stopAeromexico
21h 13mMDW-SJD
8/6Tue
1 stopAeromexico
7h 41mSJD-MDW
$454
7/7Sun
2 stopsSouthwest
11h 55mMDW-SJD
7/14Sun
2 stopsSouthwest
19h 10mSJD-MDW
$498
7/7Sun
1 stopSouthwest
8h 35mMDW-SJD
7/14Sun
1 stopSouthwest
12h 50mSJD-MDW
$526
8/30Fri
1 stopVolaris
7h 53mMDW-SJD
9/2Mon
1 stopVolaris
16h 16mSJD-MDW
$590
11/7Thu
1 stopVolaris
11h 17mMDW-SJD
11/11Mon
1 stopVolaris
16h 16mSJD-MDW
$593

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Recent one-way flight deals

6/5Wed
2 stops
26h 50mMDW-SJD
$173
6/27Thu
2 stops
25h 10mMDW-SJD
$224
6/13Thu
2 stops
34h 50mMDW-SJD
$232
6/28Fri
1 stopVolaris
12h 17mMDW-SJD
$271
6/20Thu
1 stopVolaris
12h 17mMDW-SJD
$274
6/11Tue
1 stopVolaris
12h 17mMDW-SJD
$336
6/4Tue
2 stopsDelta
14h 58mMDW-SJD
$441
6/20Thu
2 stopsDelta
11h 08mMDW-SJD
$445
6/20Thu
2 stopsDelta
11h 08mMDW-SJD
$516
6/28Fri
2 stopsDelta
12h 20mMDW-SJD
$566

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Last minute flights from Midway to Los Cabos

Last minute flight, train and bus deals

6/2Sun
multi-stop
12h 05mMDW-SJD
6/9Sun
multi-stop
24h 27mSJD-MDW
$499
6/2Sun
multi-stop
12h 05mMDW-SJD
6/9Sun
multi-stop
21h 16mSJD-MDW
$529
6/2Sun
multi-stopVolaris
18h 27mMDW-SJD
6/9Sun
multi-stopVolaris
14h 30mSJD-MDW
$665
6/2Sun
multi-stopVolaris
20h 23mMDW-SJD
6/9Sun
multi-stopVolaris
14h 30mSJD-MDW
$775
6/4Tue
multi-stopDelta
14h 58mMDW-SJD
6/9Sun
multi-stopDelta
11h 57mSJD-MDW
$912
5/31Fri
multi-stopDelta
15h 06mMDW-SJD
6/3Mon
multi-stopDelta
13h 12mSJD-MDW
$971
6/4Tue
multi-stopAeromexico
28h 55mMDW-SJD
6/9Sun
multi-stopAeromexico
22h 26mSJD-MDW
$1,036
6/4Tue
multi-stopVolaris
12h 17mMDW-SJD
6/9Sun
multi-stopVolaris
11h 40mSJD-MDW
$1,160
5/31Fri
multi-stopDelta
11h 09mMDW-SJD
6/3Mon
multi-stopDelta
7h 38mSJD-MDW
$1,166
5/31Fri
multi-stopAeromexico
7h 18mMDW-SJD
6/3Mon
multi-stopAeromexico
7h 38mSJD-MDW
$1,316

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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:

$639
$728
$477
$37