MDW - SJD

$179 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 8/11. 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 San José del Cabo

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José del Cabo, 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 San José del Cabo, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$534
Typical prices: $718-$668
Volaris
Thu 7/16Sun 7/19
MDW - SJD • 1 stop
Cheapest one-way
$179
Volaris
Tue 8/11
MDW - SJD • 1 stop
Top airlines
Volaris
Cheapest • from $534 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Phoenix (PHX)
Cheapest • Avg $726 (round-trip)
Phoenix (PHX)
Shortest trip • 6h 50m (one-way)
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 100% price drop
April
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

Thu, Jul 16 - Sun, Jul 19
Volaris Logo
8:49 pm - 8:16 am
MDW
-
SJD
13h 27m
1 stop
Volaris Logo
8:50 am - 7:04 pm
SJD
-
MDW
8h 14m
1 stop
$534Volaris
Mon, Aug 10 - Thu, Aug 13
Southwest Logo
5:55 am - 12:50 pm
MDW
-
SJD
8h 55m
1 stop
Southwest Logo
11:40 am - 11:45 pm
SJD
-
MDW
10h 05m
2 stops
$586Southwest
Mon, Aug 10 - Thu, Aug 13
Southwest Logo
5:30 am - 12:50 pm
MDW
-
SJD
9h 20m
2 stops
Southwest Logo
10:40 am - 10:40 pm
SJD
-
MDW
10h 00m
2 stops
$590Southwest
Sun, Aug 9 - Fri, Aug 14
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
Delta Logo
6:10 am - 10:36 pm
SJD
-
MDW
14h 26m
2 stops
$596Delta
Sun, Aug 9 - Wed, Aug 12
Delta Logo
6:42 pm - 11:07 am
MDW
-
SJD
18h 25m
2 stops
Delta Logo
12:12 pm - 10:36 pm
SJD
-
MDW
8h 24m
1 stop
$600Delta
Fri, Jul 10 - Wed, Jul 15
Volaris Logo
8:23 pm - 8:16 am
MDW
-
SJD
13h 53m
1 stop
Volaris Logo
8:50 am - 7:04 pm
SJD
-
MDW
8h 14m
1 stop
$605Volaris
Mon, Nov 23 - Tue, Dec 1
Multiple Airlines Logo
6:07 pm - 12:24 pm
MDW
-
SJD
19h 17m
1 stop
Multiple Airlines Logo
12:50 pm - 4:39 pm
SJD
-
MDW
26h 49m
2 stops
$611Multiple Airlines
Mon, Nov 23 - Tue, Dec 1
Multiple Airlines Logo
6:07 pm - 12:24 pm
MDW
-
SJD
19h 17m
1 stop
Multiple Airlines Logo
11:16 am - 4:39 pm
SJD
-
MDW
28h 23m
1 stop
$612Multiple Airlines
Wed, Jul 29 - Wed, Aug 5
Delta Logo
6:00 am - 11:11 am
MDW
-
SJD
7h 11m
1 stop
Delta Logo
12:12 pm - 10:36 pm
SJD
-
MDW
8h 24m
1 stop
$615Delta
Sun, Aug 2 - Fri, Aug 7
Delta Logo
6:00 am - 11:11 am
MDW
-
SJD
7h 11m
1 stop
Delta Logo
2:24 pm - 8:39 am
SJD
-
MDW
16h 15m
2 stops
$619Delta
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.

How much is a round-trip flight from Chicago Midway Airport to San José del Cabo?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to San José del Cabo departing in July.

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 August, where tickets cost $0 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $2,039 and $1,112 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 $688 on average.

Find deals

Good to know

Low seasonOctober
Cheapest flight$179
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly and prices are also 14% 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 $179 for a one-way ticket and $534 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.
7.9
SouthwestOverall score based on 4237 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

4.0 OkaySteven, Jun 2026
ONT - LAS
Read more Southwest reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

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.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

Everything you need to know for your flight from Midway to San José del Cabo

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
San José del Cabo (SJD)