$178 Find Cheap Flights from Chicago Midway Airport to Los Cabos

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 Los Cabos departing on 7/21. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Los Cabos

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Los Cabos, 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 Los Cabos, as well as popular online travel agencies
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Flights Deals

Best Los Cabos Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
San José del Cabo
San José del Cabo2 stops$400
San José del Cabo
San José del Cabo2 stops$400

Cheap Flights from Midway to Los Cabos

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Los Cabos 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 Los Cabos

Sun, Aug 24 - Fri, Aug 29
Delta Logo
6:04 am - 6:31 pmMDW-SJD
14h 27m2 stops
Delta Logo
6:02 am - 9:49 pmSJD-MDW
13h 47m2 stops
$400Delta
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Tue, Aug 26 - Thu, Sep 4
Delta Logo
6:00 am - 11:23 amMDW-SJD
7h 23m1 stop
Delta Logo
6:00 am - 9:26 pmSJD-MDW
13h 26m2 stops
$405Delta
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Sun, Sep 7 - Fri, Sep 12
Southwest Logo
5:30 am - 1:10 pmMDW-SJD
9h 40m2 stops
Southwest Logo
1:45 pm - 11:40 pmSJD-MDW
7h 55m1 stop
$439Southwest
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Sat, Aug 23 - Thu, Aug 28
Southwest Logo
5:20 am - 11:20 amMDW-SJD
8h 00m1 stop
Southwest Logo
1:45 pm - 11:40 pmSJD-MDW
7h 55m1 stop
$440Southwest
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Sun, Oct 26 - Wed, Nov 19
Aeromexico Logo
6:00 am - 11:30 amMDW-SJD
7h 30m1 stop
Aeromexico Logo
6:00 am - 9:44 pmSJD-MDW
14h 44m2 stops
$449Aeromexico
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Sat, Oct 25 - Fri, Nov 14
Aeromexico Logo
6:00 am - 12:25 pmMDW-SJD
8h 25m1 stop
Aeromexico Logo
6:00 am - 9:44 pmSJD-MDW
14h 44m2 stops
$489Aeromexico
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Fri, Aug 22 - Thu, Aug 28
Logo
8:39 pm - 11:11 amMDW-SJD
16h 32m1 stop
Logo
7:25 am - 7:16 pmSJD-MDW
9h 51m1 stop
$573
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Sat, Jun 28 - Sun, Jul 6
Logo
8:39 pm - 7:40 amMDW-SJD
13h 01m1 stop
Logo
8:10 am - 7:16 pmSJD-MDW
9h 06m1 stop
$692
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Wed, Jul 30 - Wed, Aug 6
Volaris Logo
8:39 pm - 7:54 pmMDW-SJD
25h 15m2 stops
Volaris Logo
11:07 am - 7:16 pmSJD-MDW
30h 09m3 stops
$792Volaris
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Sat, Sep 27 - Wed, Oct 1
Volaris Logo
10:41 pm - 8:04 pmMDW-SJD
23h 23m3 stops
Volaris Logo
11:07 am - 7:16 pmSJD-MDW
30h 09m3 stops
$1,001Volaris
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KAYAK's insights & trends for Midway to Los Cabos flights

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

What is the cheapest Chicago Midway Airport to Los Cabos flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Los Cabos.

The cheapest ticket to Los Cabos from Chicago Midway Airport found in the last 72 hours was to San José del Cabo, at $680 round-trip. The most popular route is from Chicago Midway Airport (MDW) to San José del Cabo (SJD), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $680.

Can I save money by flying with a layover from Chicago Midway Airport to Los Cabos?

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 $342, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Los Cabos?

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 Los Cabos, 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 Los Cabos is August, when tickets cost $548 (return) on average. On the other hand, the most expensive months are November and September, when the average cost of round-trip tickets is $1,078 and $859 respectively.

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Good to know

Low seasonJune
High seasonJuly
Cheapest flight$178
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Chicago Midway Airport to San José del Cabo

FAQs - booking Los Cabos flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Los Cabos?

    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 Los Cabos.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Los Cabos 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 Los Cabos?

    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 from Chicago Midway Airport to Los Cabos with an airline and back with another airline.

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

    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 from Chicago Midway Airport to Los Cabos up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Los Cabos?

    The cheapest time of day to fly to Los Cabos is generally in the morning, when round-trip flights cost $938 on average. The most expensive time of day to fly to Los Cabos is generally in the morning, which is peak travel time and where the average cost of a ticket is $938.

Top airline flying from Midway to Los Cabos

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Los Cabos. 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 Los Cabos? 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 4278 reviews
8.2Boarding
8.0Comfort
7.6Entertainment
8.6Crew
7.1Food
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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.

Everything you need to know for your flight to Los Cabos

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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