$156 Find Cheap Flights from Chicago Midway Airport to Los Cabos

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 1/18. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Los Cabos

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Los Cabos, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Los Cabos, as well as popular online travel agencies
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Flight Deals

Book Cheap Midway to Los Cabos Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Los Cabos that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Los Cabos

Mon, Dec 1 - Sat, Dec 6
Delta Logo
6:00 am - 12:10 pmMDW-SJD
7h 10m1 stop
Delta Logo
2:40 pm - 11:47 pmSJD-MDW
8h 07m1 stop
$416Delta
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Wed, Nov 19 - Wed, Dec 3
Southwest Logo
5:25 am - 12:10 pmMDW-SJD
7h 45m1 stop
Southwest Logo
2:05 pm - 10:10 pmSJD-MDW
7h 05m1 stop
$418Southwest
Find Deal
Mon, Dec 1 - Sat, Dec 6
Delta Logo
6:00 am - 12:10 pmMDW-SJD
7h 10m1 stop
Delta Logo
4:50 pm - 8:54 amSJD-MDW
15h 04m2 stops
$421Delta
Find Deal
Tue, Nov 18 - Mon, Nov 24
Delta Logo
6:00 am - 12:10 pmMDW-SJD
7h 10m1 stop
Delta Logo
9:32 am - 11:40 pmSJD-MDW
13h 08m2 stops
$423Delta
Find Deal
Sun, Jan 18 - Sun, Jan 25
Southwest Logo
6:15 am - 1:10 pmMDW-SJD
7h 55m1 stop
Southwest Logo
2:05 pm - 12:25 amSJD-MDW
9h 20m1 stop
$427Southwest
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Sun, Jan 18 - Sun, Jan 25
Delta Logo
6:45 am - 2:09 pmMDW-SJD
8h 24m1 stop
Delta Logo
9:35 am - 10:26 pmSJD-MDW
11h 51m2 stops
$428Delta
Find Deal
Sat, Jan 10 - Sat, Jan 31
Aeromexico Logo
11:21 am - 8:40 amMDW-SJD
22h 19m2 stops
Aeromexico Logo
9:35 am - 10:26 pmSJD-MDW
11h 51m2 stops
$471Aeromexico
Find Deal
Mon, Mar 16 - Sun, Mar 22
Volaris Logo
6:49 pm - 10:36 amMDW-SJD
17h 47m2 stops
Volaris Logo
3:02 pm - 5:34 pmSJD-MDW
24h 32m2 stops
$476Volaris
Find Deal
Mon, Mar 16 - Sun, Mar 22
Volaris Logo
6:49 pm - 10:36 amMDW-SJD
17h 47m2 stops
Volaris Logo
11:54 am - 5:34 pmSJD-MDW
27h 40m3 stops
$489Volaris
Find Deal
Tue, Mar 17 - Tue, Mar 24
Aeromexico Logo
6:00 am - 11:35 amMDW-SJD
7h 35m1 stop
Aeromexico Logo
12:40 pm - 9:46 pmSJD-MDW
7h 06m1 stop
$536Aeromexico
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to Los Cabos flights

Get data-powered insights and trends into flights from Midway to Los Cabos to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Los Cabos flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Los Cabos from Chicago Midway Airport found in the last 72 hours was to San José del Cabo, at $2,039 round-trip. The most popular route is from Chicago Midway Airport (MDW) to San José del Cabo (SJD), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $2,039.

Can I save money by flying with a layover from Chicago Midway Airport to Los Cabos?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $366, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Los Cabos?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Los Cabos, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Los Cabos is October, when tickets cost $471 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $1,994 and $995 respectively.

Good to know

Low seasonJune
Cheapest flight$157
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 12% lower on average.
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 from Chicago Midway Airport to Los Cabos 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 from Chicago Midway Airport to Los Cabos with an airline and back 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 from Chicago Midway Airport to Los Cabos up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Los Cabos?

    The cheapest time of day to fly to Los Cabos is generally in the morning, when round-trip flights cost $938 on average. The most expensive time of day to fly to Los Cabos is generally in the morning, which is peak travel time and where the average cost of a ticket is $938.

  • How many flights are there between Chicago Midway Airport and Los Cabos per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Los Cabos, with an average flight time of 4h 50m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 1 flights.

Reviews of the top airline flying from Midway to Los Cabos

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Los Cabos. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
SouthwestOverall score based on 4241 reviews
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Everything you need to know for your flight to Los Cabos

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