MDW - SJD

$150 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 2/21. 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
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Everything you should know

Cheapest round-trip
$478
Overall average: $1,112
Aeromexico
Tue 2/24Sat 2/28
MDW - SJD • 1 stop
Cheapest non-stop
$514
Southwest
Sun 3/8Thu 3/12
MDW - SJD • Non-stop
Top airlines
Aeromexico
Cheapest • from $478 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
October
Cheapest • 35% 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

Tue, Feb 24 - Sat, Feb 28
Aeromexico Logo
6:00 am - 12:40 pm
MDW
-
SJD
7h 40m
1 stop
Aeromexico Logo
1:45 pm - 10:31 pm
SJD
-
MDW
7h 46m
1 stop
$478Aeromexico
Thu, May 7 - Tue, May 12
Aeromexico Logo
10:35 am - 10:25 pm
MDW
-
SJD
13h 50m
2 stops
Aeromexico Logo
6:00 am - 9:45 pm
SJD
-
MDW
13h 45m
2 stops
$480Aeromexico
Thu, Feb 19 - Tue, Feb 24
Delta Logo
6:40 pm - 8:40 am
MDW
-
SJD
15h 00m
2 stops
Delta Logo
1:45 pm - 10:33 pm
SJD
-
MDW
7h 48m
1 stop
$482Delta
Sun, Mar 1 - Fri, Mar 6
Southwest Logo
10:15 pm - 11:05 am
MDW
-
SJD
13h 50m
1 stop
Southwest Logo
1:35 pm - 6:30 pm
SJD
-
MDW
3h 55mnonstop
$483Southwest
Sat, May 23 - Sat, May 30
Delta Logo
6:45 pm - 12:34 pm
MDW
-
SJD
19h 49m
2 stops
Delta Logo
1:35 pm - 8:38 am
SJD
-
MDW
17h 03m
2 stops
$484Delta
Fri, Apr 24 - Fri, Apr 24
Southwest Logo
5:25 am - 10:45 am
MDW
-
SJD
7h 20m
1 stop
Southwest Logo
1:25 pm - 9:55 pm
SJD
-
MDW
6h 30m
1 stop
$490Southwest
Fri, Feb 6 - Sat, Feb 14
Frontier Logo
5:01 pm - 1:36 pm
MDW
-
SJD
21h 35m
1 stop
Frontier Logo
2:38 pm - 7:59 pm
SJD
-
MDW
28h 21m
1 stop
$497Frontier
Fri, Apr 3 - Sat, Apr 11
Frontier Logo
6:00 am - 10:12 am
MDW
-
SJD
30h 12m
1 stop
Frontier Logo
11:27 am - 10:29 pm
SJD
-
MDW
9h 02m
1 stop
$500Frontier
Mon, Feb 23 - Thu, Feb 26
Southwest Logo
5:20 am - 1:55 pm
MDW
-
SJD
9h 35m
2 stops
Southwest Logo
2:35 pm - 12:55 am
SJD
-
MDW
9h 20m
2 stops
$502Southwest
Sat, Feb 28 - Tue, Mar 3
Delta Logo
6:00 am - 2:09 pm
MDW
-
SJD
9h 09m
1 stop
Delta Logo
1:45 pm - 10:33 pm
SJD
-
MDW
7h 48m
1 stop
$503Delta
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 December and February, where the average cost of round-trip tickets is $1,429 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 $584 on average.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$149
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly and prices are also 4% 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 $149 for a one-way ticket and $478 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.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to San José del Cabo

  • Looking for a cheap flight? 25% of our users found flights on this route for $584 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to San José del Cabo?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to San José del Cabo Los Cabos.
Find which airlines fly direct from Chicago Midway Airport to San José del Cabo Los Cabos Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to San José del Cabo Los Cabos

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

San José del Cabo Los Cabos to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

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 4268 reviews
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

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

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

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)