Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 321,000 hotels worldwide and 400 airlines worldwide.

Secure incredible value with Expedia's Price Guarantee.

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap MDW to SJD Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago

$215.51

Cheap MDW to SJD Flights

Question : In the next four weeks, what day should you book your trip?
Answer : Dec 15th has seen bookings (as of Nov 20th) as cheap as $325. That comes in 48% below the average price for this route. Saving now means you'll have more money in your hand for the trip.

Question : Is there an alternative to Chicago Midway International Airport (MDW) for getting you to San Jose Cabo?
Answer : O'Hare International Airport is just 16 miles away, and, on average, flights are 21% cheaper for the upcoming months. Save a few bucks and put it toward your next trip.

Question : How many days should you spend in San Jose Cabo?
Answer : Passengers from MDW to SJD stay five days on average.

Question : How much should a trip from Chicago (MDW) to San Jose Cabo (SJD) cost?
Answer : Flight prices are fluctuating a lot more for this route than most routes from the United States, as they're ranging anywhere from $270 to $1,755. Remember, you can save by booking further in advance.

Question : Which airline is offering the cheapest flight from MDW to SJD?
Answer : Delta Air Lines is offering the best deal at $270. Better snatch it up quickly because prices range all the way up to $1,755 over the next three months.

Question : If your plans are flexible, have you considered changing your departure day?
Answer : Friday is your cheapest day to fly in the month of December. Being flexible with your travel days garners even more savings during booking.

Chicago to Los Cabos Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to Los Cabos will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Los Cabos.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with MDW to SJD flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to SJD with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.