Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago Midway Airport to San José del Cabo
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Aeromexico flights from Chicago Midway Airport to San José del Cabo
Our best Aeromexico deals on Chicago Midway Airport to San José del Cabo flight tickets
Delta flights from Chicago Midway Airport to San José del Cabo
Our best Delta deals on Chicago Midway Airport to San José del Cabo flight tickets
See travel insights to San José del Cabo from
How to get the cheapest flight ticket from Chicago Midway Airport to San José del Cabo
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to San José del Cabo?
The cheapest month to fly to San José del Cabo from Chicago Midway Airport is in August. Flight prices, which tend to average around $548, are often lower during this time because this is during the off-season. If you’re not able to fly to San José del Cabo in August, then January is your next best option. Flight prices from Chicago Midway Airport to San José del Cabo during January average around $563.
What is the cheapest day to depart on your flight to San José del Cabo?
According to our data, Tuesday is the cheapest day to fly to San José del Cabo from Chicago Midway Airport. The lowest ticket price found for a Tuesday departure recently was $588. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $714.
What is the cheapest time of day to depart on your flight to San José del Cabo?
Flying to San José del Cabo from Chicago Midway Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $313 when looking at flights departing in the afternoon. Flights to San José del Cabo are more costly in the morning, with an average ticket price of $654. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago Midway to San José del Cabo Los Cabos flight route?
Fly from Chicago Midway to San José del Cabo Los Cabos for the best Chicago Midway - San José del Cabo Los Cabos flight prices
When to book flights from Chicago Midway Airport to San José del Cabo
Cheap Chicago Midway Airport to San José del Cabo (MDW to SJD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José del Cabo
Best Price Found | $148 |
|---|---|
Fastest flight time | 5h 50m |
Direct flights | Sun |
Airports in San José del Cabo | 1 airport |
How far is Chicago Midway to San José del Cabo Los Cabos by plane?
Chicago Midway and San José del Cabo Los Cabos are 1808.5 mi apart from one another. Typically, this will take 5h 50m by plane in normal conditions.
When did momondo last update prices for flights from Chicago Midway Airport to San José del Cabo Los Cabos Airport?
Prices for flights from Chicago Midway Airport to San José del Cabo Los Cabos Airport are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to San José del Cabo Los Cabos Airport?
As of July 2025, there is 1 operator available to choose from for flights from Chicago Midway Airport to San José del Cabo Los Cabos Airport.
How old do you have to be to fly from Chicago Midway Airport to San José del Cabo Los Cabos Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José del Cabo Los Cabos Airport.
What documentation or ID do you need to fly to San José del Cabo Los Cabos Airport?
The travel and health documents you'll need for your trip to San José del Cabo Los Cabos Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José del Cabo Los Cabos Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to San José del Cabo?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to San José del Cabo is Boeing 737-800 (26.67% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (13.33%), Boeing 737-900 (13.33%), and Airbus A319 (6.67%).
What is the most popular airline from Chicago Midway Airport to San José del Cabo?
Based on momondo bookings for flights between Chicago Midway Airport and San José del Cabo, the leading airline is Southwest, making up 100% of the total bookings.
Best airlines flying from Chicago Midway Airport to San José del Cabo
Compare and see reviews for airlines that fly from Chicago Midway Airport to San José del Cabo with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $543 | Free Cancellation | Rating 8.0 4,273 reviews |
Traveling to a place near San José del Cabo?
Book flights to San José del Cabo if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to San José del Cabo?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to San José del Cabo from Chicago.
Can I find flights from Chicago to San José del Cabo with flexible booking policies on momondo?
All flight searches from Chicago to San José del Cabo on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to San José del Cabo?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to San José del Cabo.
I’m not ready to book a flight from Chicago to San José del Cabo right now. Can momondo alert me if prices change?
If you are simply researching potential flights to San José del Cabo, momondo offers a useful price alert feature which will track prices for flights to San José del Cabo from Chicago and alert you when they change.