Cheap Flights from Chicago to San Jose Cabo

Compare Chicago Midway to San Jose Cabo flight deals

Find the cheapest month or even day of the year to fly to San Jose Cabo

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Flight deals from Chicago Midway to San Jose Cabo

Looking for a cheap last-minute deal or the best return flight from Chicago Midway to San Jose Cabo? Find the lowest prices on one-way and return tickets right here.

San Jose Cabo.$667 per passenger.Departing Tue, 21 May, returning Wed, 29 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 21 May, arriving in San Jose Cabo.Inbound indirect flight with Delta, departs from San Jose Cabo on Wed, 29 May, arriving in Chicago Midway.Price includes taxes and charges.From $667, select.

San Jose Cabo.$906 per passenger.Departing Sat, 22 Jun, returning Thu, 27 Jun.Return flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago Midway on Sat, 22 Jun, arriving in San Jose Cabo.Inbound indirect flight with Volaris, departs from San Jose Cabo on Thu, 27 Jun, arriving in Chicago Midway.Price includes taxes and charges.From $906, select.

San Jose Cabo.$939 per passenger.Departing Sat, 25 May, returning Sat, 1 Jun.Return flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago Midway on Sat, 25 May, arriving in San Jose Cabo.Inbound indirect flight with Volaris, departs from San Jose Cabo on Sat, 1 Jun, arriving in Chicago Midway.Price includes taxes and charges.From $939, select.

San Jose Cabo.$1,014 per passenger.Departing Thu, 25 Jul, returning Sun, 28 Jul.Return flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago Midway on Thu, 25 Jul, arriving in San Jose Cabo.Inbound indirect flight with Volaris, departs from San Jose Cabo on Sun, 28 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $1,014, select.

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Find the cheapest month to fly from Chicago Midway to San Jose Cabo

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to San Jose Cabo flights are currently cheapest in May.

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Direct flights from Chicago Midway to San Jose Cabo

Southwest Airlines

Chicago Midway to San Jose Cabo: Alternative routes

Compare routes from Chicago Midway to San Jose Cabo below. You may find an airport to fly into that's cheaper, faster, or easier than San Jose Cabo.

Chicago to San Jose Cabo: Flight information

The things to know before you go.

Cheapest flight found	$667
Cheapest month to fly	May
Average flight time	5 hrs, 10 mins
Most popular airline	Southwest Airlines
Average flights per week	1

Finding cheap flights from Chicago Midway to San Jose Cabo: Frequently asked questions

: The best price we found for a return flight from Chicago Midway to San Jose Cabo is $667. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
: 5 hours and 10 minutes is the average flight time from Chicago Midway to San Jose Cabo.
: Southwest Airlines flies direct from Chicago Midway to San Jose Cabo.
: As of April 2024, there is one flight per week flying from Chicago Midway to San Jose Cabo.
: The cheapest month to fly from Chicago Midway to San Jose Cabo is usually May.
: After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to San Jose Cabo Airport on Tuesday, 21 May 2024.
: Yes – the average flight time is 5 hours and 10 minutes.
: We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to San Jose Cabo but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
: We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to San Jose Cabo is around 40 days in advance, so don’t leave your flight to the last minute.
: Currently, Delta offers the cheapest flight tickets to San Jose Cabo.

How to find cheap flights to San Jose Cabo (SJD) from Chicago (MDW) in 2024

Looking for cheap tickets from Chicago Midway to San Jose Cabo? Return tickets start from $667 and one-way flights to San Jose Cabo from Chicago Midway start from $306

Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Chicago Midway to San Jose Cabo. And with us there are no hidden fees - what you see is what you pay.
Compare flight deals to San Jose Cabo from Chicago from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to San Jose Cabo start from $306 one-way.
Flex your dates to find the best MDW-SJD ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to San Jose Cabo from Chicago Midway.
Set up a Price Alert. You can easily track the fare of your cheap Chicago Midway-San Jose Cabo flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
Fly without stops. Only interested in direct flights between Chicago Midway and San Jose Cabo? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results. Airlines that fly direct include: Southwest Airlines
Flexible on when you travel? The cheapest month to fly from Chicago Midway to San Jose Cabo is May.
Find the cheapest Business class flights from Chicago Midway and San Jose Cabo. We scour the internet for the best Business, Premium Economy and First Class flight fares to San Jose Cabo, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
Include nearby airports in your search. Widen your search for Chicago Midway to San Jose Cabo flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.
Search for cheap flights regardless of where you are. To get the best flight booking experience when out and about, download the app and search for plane tickets between Chicago Midway and San Jose Cabo whenever you want.

Combine your flight to San Jose Cabo from Chicago Midway with hotels and car hire

Once you've secured your cheap flight ticket from Chicago Midway to San Jose Cabo, discover the best prices and exclusive rates for hotels in San Jose Cabo or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.

Plan the rest of your trip from Chicago to San Jose Cabo

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.