Cheap Flight Tickets from Chicago (CHI) to San Jose del Cabo (SJD)

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Latest Flight Deals from Chicago to San Jose del Cabo

Book one-way or return flights from Chicago to San Jose del Cabo from as little as TRY 4,916. Choose from the popular airlines below and book your flight today!

One way
Return

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

Searching for the best last minute flight from Chicago to San Jose del Cabo? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to San Jose del Cabo. Stay updated on price trends and snag the best deals for your upcoming trip.

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

Airlines Flying 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.

Frontier Airlines

From TRY 4,912

Aeromexico

From TRY 5,614

Delta Air Lines

From TRY 5,945

American Airlines

From TRY 6,218

United Airlines

From TRY 6,643

Viva Aerobus

From TRY 7,099

Spirit Airlines

From TRY 7,394

Volaris

From TRY 7,435

Sun Country Airlines

From TRY 8,311

Alaska Airlines

From TRY 8,338

ANA airlines

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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
11:32
25h 20m
1 transfer
SJD
10:52
Midway International Airport - Los Cabos International Airport
Wed, Aug 7Frontier Airlines
TRY 4,916
ORD
07:24
16h 27m
1 transfer
SJD
21:51
O'Hare International Airport - Los Cabos International Airport
Tue, Jun 18Aeromexico
TRY 5,619
RFD
13:35
24h 23m
2 transfer
SJD
11:58
Chicago Rockford International Airport - Los Cabos International Airport
Mon, Jun 10Allegiant Air
TRY 14,211
RFD
13:35
24h 23m
2 transfer
SJD
11:58
Chicago Rockford International Airport - Los Cabos International Airport
Mon, Jun 10Allegiant Air
TRY 14,211
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How do I find the cheapest flights?

When are flight 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 date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Chicago (CHI) to San Jose del Cabo (SJD) cost?
According to Trip.com's data, the lowest price is around TRY 18,822.
How long is the flights from Chicago (CHI) to San Jose del Cabo (SJD)?
It takes about 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.
What's the most popular airline for direct flights from Chicago (CHI) to San Jose del Cabo (SJD)?
American Airlines operates 1 direct flights from Chicago (CHI) to San Jose del Cabo (SJD).
How many airports in San Jose del Cabo (SJD)?
There are 1 airport(s) in San Jose del Cabo (SJD): Los Cabos International Airport.

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

Flight Information from Chicago to San Jose del Cabo

Cheapest direct flight price	TRY 4,916
Cheapest return ticket price	TRY 13,212
Off-season for travel	February
Peak season for travel	August
Flight distance	2,918.98km
Average flight time	4 hours 35 minutes
Popular airline	Aeromexico