MDW - SJD

$183 Find Cheap Flights from Chicago Midway Airport to San José del Cabo - 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 San José del Cabo departing on 8/13. 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

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$531
Volaris
Fri 10/9Tue 10/13
MDW - SJD • 2 stops
Cheapest one-way
$183
Volaris
Thu 8/13
MDW - SJD • 1 stop
Top airlines
Cheapest • from $531 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $854 (round-trip)
Shortest trip • 7h 09m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 42% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San José del Cabo!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to San José del Cabo (MDW-SJD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to San José del Cabo 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 San José del Cabo

Fri, Oct 9 - Tue, Oct 13
Volaris Logo
8:23 pm - 3:59 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
21h 36m2 stops Guadalajara Miguel Hidal Mexico City Toluca Intl
Volaris Logo
7:37 pm - 7:04 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
21h 27m2 stops Tijuana Rodriguez Guadalajara Miguel Hidal
$531Volaris
Fri, Oct 9 - Tue, Oct 13
Volaris Logo
8:23 pm - 3:59 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
21h 36m2 stops Guadalajara Miguel Hidal Mexico City Toluca Intl
Volaris Logo
7:37 pm - 7:04 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
21h 27m2 stops Tijuana Rodriguez Guadalajara Miguel Hidal
$537Volaris
Fri, Oct 30 - Fri, Nov 6
Multiple Airlines Logo
8:23 pm - 12:34 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
18h 11m1 stop Guadalajara Miguel Hidal
Multiple Airlines Logo
7:27 am - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
8h 20m1 stop Guadalajara Miguel Hidal
$544Multiple Airlines
Fri, Sep 4 - Mon, Sep 7
Multiple Airlines Logo
8:23 pm - 12:26 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
18h 03m1 stop Guadalajara Miguel Hidal
Multiple Airlines Logo
8:05 am - 6:05 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
32h 00m2 stops Mexico City Felipe Ángeles Intl San Luis Potosi
$547Multiple Airlines
Thu, Oct 1 - Mon, Nov 2
Multiple Airlines Logo
7:30 pm - 2:15 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
20h 45m2 stops San Luis Potosi Guadalajara Miguel Hidal
Multiple Airlines Logo
7:27 am - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
8h 20m1 stop Guadalajara Miguel Hidal
$552Multiple Airlines
Fri, Nov 6 - Mon, Nov 9
Multiple Airlines Logo
6:17 pm - 4:31 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
23h 14m1 stop Guadalajara Miguel Hidal
Multiple Airlines Logo
7:27 am - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
8h 20m1 stop Guadalajara Miguel Hidal
$557Multiple Airlines
Fri, Oct 9 - Tue, Oct 13
Volaris Logo
8:23 pm - 11:29 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
17h 06m1 stop Guadalajara Miguel Hidal
Volaris Logo
7:37 pm - 7:04 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
21h 27m2 stops Tijuana Rodriguez Guadalajara Miguel Hidal
$565Volaris
Sun, Sep 6 - Sun, Sep 13
Volaris Logo
8:23 pm - 11:29 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
17h 06m1 stop Guadalajara Miguel Hidal
Volaris Logo
7:47 pm - 7:04 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
21h 17m2 stops Mexico City Benito Juarez Guadalajara Miguel Hidal
$566Volaris
Sun, Oct 4 - Thu, Oct 8
Southwest Logo
7:00 am - 1:15 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
8h 15m1 stop Houston Hobby
Southwest Logo
1:05 pm - 12:35 amSJD  San José del Cabo Los Cabos-MDW Chicago Midway
9h 30m1 stop San Diego
$607Southwest
Sun, Aug 30 - Wed, Sep 2
Southwest Logo
7:20 am - 1:10 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
7h 50m1 stop Houston Hobby
Southwest Logo
11:40 am - 11:10 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
9h 30m1 stop Houston Hobby
$607Southwest
Booking Insights

KAYAK's insights & trends for Midway to San José del Cabo flights

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

What is the cheapest month to fly from Chicago Midway Airport to San José del Cabo?

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 San José del Cabo, 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 San José del Cabo is October, where tickets cost $471 (return) on average. On the other hand, the most expensive months are August and December, where the average cost of round-trip tickets is $1,485 and $1,460 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to San José del Cabo?

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $324 on average.

Good to know

Low season

October

Cheapest flight

$183
Best time to beat the crowds with an average 40% 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

When to book flights from Midway to San José del Cabo

Are your dates flexible? Find out the best times to travel from Midway to San José del Cabo based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to San José del Cabo flights

  • What is the cheapest flight from Chicago Midway Airport to San José del Cabo?

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to San José del Cabo was $183 for a one-way ticket and $531 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and San José del Cabo?

    A passport is required to fly from Chicago Midway Airport to San José del Cabo.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to San José del Cabo?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to San José del Cabo flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to San José del Cabo?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to San José del Cabo flight route.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to San José del Cabo?

    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 San José del Cabo.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San José del Cabo 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 San José del Cabo?

    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 San José del Cabo with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SJD can sometimes prove cheaper using this method.

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

    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 San José del Cabo from Chicago Midway Airport 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 San José del Cabo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San José del Cabo. 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 San José del Cabo? 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 4216 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
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
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 from Midway to San José del Cabo

Information on your arrival and departure airports