$141 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 2/14. 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

Sat, Feb 14 - Sat, Feb 21
Frontier Logo
6:00 am - 1:20 pm
MDW
-
SJD
8h 20m1 stop
Frontier Logo
3:59 pm - 2:26 pm
SJD
-
MDW
21h 27m2 stops
$385Frontier
Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
6:25 am - 9:14 pm
MDW
-
SJD
15h 49m2 stops
Multiple Airlines Logo
3:01 pm - 11:45 am
SJD
-
MDW
19h 44m1 stop
$470Multiple Airlines
Wed, Jan 7 - Wed, Jan 14
Southwest Logo
5:05 am - 1:40 pm
MDW
-
SJD
9h 35m1 stop
Southwest Logo
2:20 pm - 10:50 pm
SJD
-
MDW
7h 30m1 stop
$480Southwest
Wed, Jan 7 - Wed, Jan 14
Southwest Logo
6:15 am - 1:10 pm
MDW
-
SJD
7h 55m1 stop
Southwest Logo
2:20 pm - 5:05 am
SJD
-
MDW
13h 45m2 stops
$485Southwest
Sun, Mar 1 - Fri, Mar 6
Southwest Logo
6:15 am - 1:55 pm
MDW
-
SJD
8h 40m1 stop
Southwest Logo
1:35 pm - 6:30 pm
SJD
-
MDW
3h 55mnonstop
$490Southwest
Wed, Jan 7 - Wed, Jan 14
Southwest Logo
8:55 pm - 1:40 pm
MDW
-
SJD
17h 45m2 stops
Southwest Logo
12:35 pm - 10:40 pm
SJD
-
MDW
9h 05m2 stops
$495Southwest
Mon, Jan 26 - Fri, Jan 30
Delta Logo
6:00 am - 5:36 pm
MDW
-
SJD
12h 36m2 stops
Delta Logo
6:05 am - 10:22 pm
SJD
-
MDW
15h 17m2 stops
$500Delta
Sat, Mar 14 - Fri, Mar 20
Delta Logo
1:09 pm - 10:40 am
MDW
-
SJD
23h 31m2 stops
Delta Logo
2:30 pm - 8:46 am
SJD
-
MDW
16h 16m2 stops
$505Delta
Tue, Feb 17 - Tue, Feb 24
Delta Logo
6:00 am - 2:09 pm
MDW
-
SJD
9h 09m1 stop
Delta Logo
1:45 pm - 10:44 pm
SJD
-
MDW
7h 59m1 stop
$511Delta
Tue, May 12 - Tue, May 19
Delta Logo
6:00 am - 11:08 am
MDW
-
SJD
7h 08m1 stop
Delta Logo
6:04 am - 9:45 pm
SJD
-
MDW
13h 41m2 stops
$522Delta
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 $467 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 $467.

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 $398, 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 February, when the average cost of round-trip tickets is $1,293 and $948 respectively.

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Good to know

Low seasonJune
Cheapest flight$150
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 3% 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 $795 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 $795.

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.
7.9
SouthwestOverall score based on 4250 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything you need to know for your flight to Los Cabos

Information on your arrival and departure airports

Chicago Midway Airport (MDW)