US$143️ Cheap Flights from Chicago to San Jose del Cabo (2024)

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Chicago to San Jose del Cabo - Flights Starting at US$143

Book one-way or return flights from Chicago to San Jose del Cabo from as little as US$143. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

We've found these cheap flights for you. You may book a one-way or round trip as per your needs.

We monitor flight fares to help you seize the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Cheapest airlines flights from Chicago to San Jose del Cabo

View airlines operating flights from Chicago to San Jose del Cabo. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Aeromexico

From US$143

Frontier Airlines

From US$152

American Airlines

From US$163

Delta Air Lines

From US$183

Alaska Airlines

From US$188

United Airlines

From US$195

Viva Aerobus

From US$219

Spirit Airlines

From US$228

Volaris

From US$232

Sun Country Airlines

From US$256

ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to San Jose del Cabo

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to San Jose del Cabo.

Cheapest
MDW
06:00
7h 7m
1 transfer
SJD
11:07
Midway International Airport - Los Cabos International Airport
Tue, Aug 20Aeromexico
US$143
ORD
01:55
16h 6m
1 transfer
SJD
16:01
O'Hare International Airport - Los Cabos International Airport
Tue, Aug 20Aeromexico
US$148
RFD
13:35
24h 23m
2 transfer
SJD
11:58
Chicago Rockford International Airport - Los Cabos International Airport
Mon, Jun 10Allegiant Air
US$438
RFD
13:35
24h 23m
2 transfer
SJD
11:58
Chicago Rockford International Airport - Los Cabos International Airport
Mon, Jun 10Allegiant Air
US$438
Find More Flights

Frequently Asked Questions

When are flight tickets from Chicago (CHI) to San Jose del Cabo (SJD) the cheapest?
Airlines adjust prices for flights from Chicago to San Jose del Cabo based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from Chicago (CHI) to San Jose del Cabo (SJD) cost?
According to Trip.com's data, the lowest price is around $594.
How long does it take to fly from Chicago (CHI) to San Jose del Cabo (SJD) and what is the distance?
It takes around 4 hours 35 minutes to fly from Chicago (CHI) to San Jose del Cabo (SJD).
What are the most popular airlines that fly from Chicago (CHI) to San Jose del Cabo (SJD)?
Airlines with flights from Chicago (CHI) to San Jose del Cabo (SJD): American Airlines, Emirates and United Airlines.

How to find a cheap flight from Chicago to San Jose del Cabo

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to San Jose del Cabo. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Chicago to San Jose del Cabo Flight Information

Cheapest nonstop flight price	$143
Cheapest round-trip ticket price	$405
Off-season for travel	February
Peak season for travel	November
Flight distance	2,918.98km
Average flight time	4 hours 35 minutes
Popular airline	American Airlines