MDW - SJD

$148 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 5/20. 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

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

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

Everything you should know

Cheapest round-trip
$454
Delta
Wed 5/6Wed 5/13
MDW - SJD • 2 stops
Cheapest non-stop
$699
Southwest
Mon 3/30Mon 4/6
MDW - SJD • Non-stop
Nonstop flights
5 days a week
Mon, Thu, Fri, Sat, Sun
You can fly direct with Southwest. Average duration is 5h 00m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Delta
Cheapest • from $454 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Houston (HOU)
Cheapest • Avg $617 (round-trip)
Phoenix (PHX)
Shortest trip • 6h 50m (one-way)
Insights
Insights
Insights
Insights
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

Wed, May 6 - Wed, May 13
Delta Logo
12:52 pm - 10:18 pm
MDW
-
SJD
11h 26m
2 stops
Delta Logo
6:07 am - 9:09 pm
SJD
-
MDW
13h 02m
2 stops
$454Delta
Wed, Apr 8 - Wed, Apr 15
Delta Logo
6:00 am - 1:14 pm
MDW
-
SJD
9h 14m
1 stop
Delta Logo
12:36 pm - 10:28 pm
SJD
-
MDW
7h 52m
1 stop
$456Delta
Mon, May 11 - Fri, May 15
Southwest Logo
8:35 am - 1:25 pm
MDW
-
SJD
6h 50m
1 stop
Southwest Logo
1:55 pm - 4:35 am
SJD
-
MDW
12h 40m
1 stop
$470Southwest
Wed, Apr 8 - Wed, Apr 15
Delta Logo
6:00 am - 11:30 am
MDW
-
SJD
7h 30m
1 stop
Delta Logo
6:01 am - 10:28 pm
SJD
-
MDW
14h 27m
2 stops
$476Delta
Tue, May 5 - Tue, May 12
Southwest Logo
7:30 am - 1:25 pm
MDW
-
SJD
7h 55m
1 stop
Southwest Logo
2:20 pm - 5:00 am
SJD
-
MDW
12h 40m
1 stop
$486Southwest
Tue, May 5 - Tue, May 12
Delta Logo
6:00 am - 5:48 pm
MDW
-
SJD
13h 48m
2 stops
Delta Logo
6:07 am - 9:09 pm
SJD
-
MDW
13h 02m
2 stops
$495Delta
Thu, Apr 30 - Mon, May 4
Multiple Airlines Logo
2:32 pm - 6:55 pm
MDW
-
SJD
30h 23m
2 stops
Multiple Airlines Logo
2:49 pm - 1:00 pm
SJD
-
MDW
44h 11m
2 stops
$498Multiple Airlines
Sat, May 9 - Wed, May 13
Delta Logo
6:23 am - 12:50 pm
MDW
-
SJD
8h 27m
1 stop
Delta Logo
6:07 am - 9:09 pm
SJD
-
MDW
13h 02m
2 stops
$499Delta
Fri, May 1 - Tue, May 5
Delta Logo
6:00 am - 11:31 am
MDW
-
SJD
7h 31m
1 stop
Delta Logo
6:07 am - 10:28 pm
SJD
-
MDW
14h 21m
2 stops
$509Delta
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
$512Frontier
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.

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 $638, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonOctober
Cheapest flight$148
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 8% 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 $148 for a one-way ticket and $454 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.

  • On which days can I fly direct from Chicago Midway Airport to San José del Cabo?

    There are nonstop flights from Chicago Midway Airport to San José del Cabo on a daily basis.

  • 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 $615 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

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

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 4317 reviews
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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)