$219 Find Cheap Flights from Chicago Midway Airport to Los Cabos - Compare and Save

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 11/1. 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

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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, Sep 28 - Wed, Sep 30
Aeromexico Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
Aeromexico Logo
12:12 pm - 10:44 pm
SJD
-
MDW
8h 32m
1 stop
$488Aeromexico
Mon, Sep 28 - Wed, Sep 30
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
Delta Logo
6:11 am - 10:44 pm
SJD
-
MDW
14h 33m
2 stops
$498Delta
Tue, Sep 22 - Fri, Sep 25
Delta Logo
1:00 pm - 10:30 pm
MDW
-
SJD
11h 30m
2 stops
Delta Logo
9:17 am - 10:44 pm
SJD
-
MDW
11h 27m
2 stops
$498Delta
Tue, Sep 22 - Fri, Sep 25
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
Delta Logo
9:17 am - 10:44 pm
SJD
-
MDW
11h 27m
2 stops
$498Delta
Sun, Sep 13 - Sun, Sep 20
Multiple Airlines Logo
8:23 pm - 3:59 pm
MDW
-
SJD
21h 36m
2 stops
Multiple Airlines Logo
4:10 pm - 7:04 pm
SJD
-
MDW
24h 54m
2 stops
$521Multiple Airlines
Mon, Nov 2 - Mon, Nov 9
Multiple Airlines Logo
6:17 pm - 4:10 pm
MDW
-
SJD
22h 53m
1 stop
Multiple Airlines Logo
7:27 am - 4:47 pm
SJD
-
MDW
8h 20m
1 stop
$526Multiple Airlines
Mon, Nov 2 - Fri, Nov 6
Multiple Airlines Logo
6:17 pm - 4:10 pm
MDW
-
SJD
22h 53m
1 stop
Multiple Airlines Logo
7:27 am - 4:47 pm
SJD
-
MDW
8h 20m
1 stop
$529Multiple Airlines
Fri, Sep 25 - Tue, Sep 29
Multiple Airlines Logo
8:23 pm - 12:26 pm
MDW
-
SJD
18h 03m
1 stop
Multiple Airlines Logo
1:12 pm - 7:04 pm
SJD
-
MDW
27h 52m
1 stop
$534Multiple Airlines
Wed, Jan 20 - Wed, Jan 27
Southwest Logo
5:20 am - 11:40 am
MDW
-
SJD
7h 20m
1 stop
Southwest Logo
12:35 pm - 11:00 pm
SJD
-
MDW
9h 25m
2 stops
$538Southwest
Wed, Jan 20 - Wed, Jan 27
Southwest Logo
7:55 am - 1:55 pm
MDW
-
SJD
7h 00m
1 stop
Southwest Logo
12:00 pm - 9:00 pm
SJD
-
MDW
8h 00m
1 stop
$538Southwest
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 5 days was to San José del Cabo, at $759 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 5 days was $759.

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

The average price for all round-trip flights from Chicago Midway Airport to Los Cabos depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Los Cabos is generally in the morning, when round-trip flights cost $712 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 $712.

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 $411, 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 $1,460 and $1,112 respectively.

Find deals

Good to know

Low season

January

Cheapest flight

$219
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 6% 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.

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 4229 reviews
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
MDW - ATL
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

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

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Everything you need to know for your flight to Los Cabos

Information on your arrival and departure airports

Chicago Midway Airport (MDW)