MDW - SJD

$193 Find Cheap Flights from Chicago Midway Airport to San José del Cabo

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 6/9. 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

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
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Cheap Flights from Midway to San José del Cabo

 
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.

Recent round-trip flight deals from Midway to San José del Cabo

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to San José del Cabo.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
6:00 am - 6:03 pmMDW-SJD
14h 03m2 stops
Delta Logo
6:03 am - 9:45 pmSJD-MDW
13h 42m2 stops
$430Delta
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Sat, Jun 14 - Sat, Jun 21
Delta Logo
6:00 am - 11:43 amMDW-SJD
7h 43m1 stop
Delta Logo
1:57 pm - 8:40 amSJD-MDW
16h 43m2 stops
$434Delta
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Mon, Jun 2 - Wed, Jun 4
Delta Logo
6:00 am - 11:22 amMDW-SJD
7h 22m1 stop
Delta Logo
6:01 am - 9:47 pmSJD-MDW
13h 46m2 stops
$458Delta
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Wed, Jul 30 - Wed, Aug 13
Southwest Logo
5:15 am - 9:05 amMDW-SJD
5h 50m1 stop
Southwest Logo
2:20 pm - 12:55 amSJD-MDW
8h 35m2 stops
$462Southwest
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Mon, Jul 21 - Fri, Jul 25
Southwest Logo
7:00 am - 12:20 pmMDW-SJD
7h 20m1 stop
Southwest Logo
12:40 pm - 11:20 pmSJD-MDW
8h 40m1 stop
$486Southwest
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Wed, Jul 30 - Wed, Aug 13
Southwest Logo
5:15 am - 12:20 pmMDW-SJD
9h 05m1 stop
Southwest Logo
2:20 pm - 11:10 pmSJD-MDW
6h 50m1 stop
$488Southwest
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Wed, Jul 16 - Wed, Jul 30
Logo
8:39 pm - 6:55 amMDW-SJD
12h 16m1 stop
Logo
8:29 am - 7:16 pmSJD-MDW
8h 47m1 stop
$602
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Thu, Jul 31 - Mon, Aug 11
Aeromexico Logo
6:00 am - 11:43 amMDW-SJD
7h 43m1 stop
Aeromexico Logo
12:48 pm - 5:43 pmSJD-MDW
26h 55m1 stop
$698Aeromexico
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Sun, May 11 - Wed, May 14
Aeromexico Logo
6:00 am - 11:30 amMDW-SJD
7h 30m1 stop
Aeromexico Logo
12:27 pm - 3:37 pmSJD-MDW
25h 10m1 stop
$719Aeromexico
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Thu, Jul 3 - Tue, Jul 8
WestJet Logo
6:45 pm - 11:53 amMDW-SJD
43h 08m2 stops
WestJet Logo
12:50 pm - 6:07 pmSJD-MDW
27h 17m2 stops
$3,291WestJet
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Tue, Oct 14 - Thu, Oct 23
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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 January, where tickets cost $563 (return) on average. On the other hand, the most expensive months are November and September, where the average cost of round-trip tickets is $1,108 and $859 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.

No, with an average price for the route of $502, prices are generally cheapest when you fly direct.

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Good to know

Low seasonJune
High seasonJuly
Cheapest flight$193
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 1% 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 3 days, the lowest price for a flight from Chicago Midway Airport to San José del Cabo was $193 for a one-way ticket and $430 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?

    American Airlines, Aeromexico, and Delta offer 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.

  • Which airline alliances offer flights from Chicago Midway Airport to San José del Cabo?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and San José del Cabo.

  • 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.

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 4293 reviews
8.0Comfort
7.6Entertainment
7.1Food
8.2Boarding
8.6Crew
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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

Information on your arrival and departure airports

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

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