Flights from Chicago to San Jose del Cabo from $218

Compare All CHI to SJD Flights

Prices are per person for one-way travel. Click “Book” to complete your reservation on the partner site.

1 of 1 flight

Airline	Schedule	Stops	Duration	Price
Y4 Y4 · 703	01:40 CHI 19:40 SJD	0 stop(s)	18h 0m	$218 Best	Book →

Airport Information

Key details about departure and arrival airports for this route

SJD

Los Cabos International Airport

City: San José del Cabo
Country: MX
Type: Large Airport
Elevation: 374 ft

SJD Airport Guide →

Tips for Chicago to San Jose del Cabo Flights

Save money and travel smarter with these route-specific tips

📅 When to Book

Book CHI–SJD flights 6–8 weeks in advance for the best prices. Last-minute fares are typically 40–60% more expensive on this route.

💰 Price Trends

The average fare is $218, but prices as low as $218 are available.

✈ Direct vs Connecting

No direct flights currently listed. Consider flexible dates or nearby airports for better connections.

📍 Flexible Dates

Flying midweek (Tuesday–Thursday) on CHI–SJD is typically 15–30% cheaper. Use our price comparison to spot the best day to fly.

Top Hotels in San Jose del Cabo

Book accommodation at your destination — top-rated stays near SJD airport

Grand Velas Boutique Hotel Los Cabos

San Jose Del Cabo, 5★

10.0 $1,262/night

Zadun, a Ritz-Carlton Reserve

San Jose Del Cabo, 5★

10.0 $974/night

Chileno Bay Resort & Residences, Auberge Resorts Collection

San Jose Del Cabo, 5★

10.0 Check Price

Cabo Surf Hotel

San Jose Del Cabo, 5★

10.0 $500/night

Casa Natalia Boutique Hotel Adults Only

San Jose Del Cabo, 4★

10.0 $166/night

Garza Blanca Resort & SPA Los Cabos

San Jose Del Cabo, 5★

9.8 Check Price

Frequently Asked Questions

Everything you need to know about flying CHI to SJD

What is the cheapest flight from Chicago to San Jose del Cabo?

The cheapest flight from Chicago (CHI) to San Jose del Cabo (SJD) currently starts at $218 with Y4. Prices are updated regularly and may vary by date and availability.

How many airlines fly from CHI to SJD?

We found 1 airline(s) operating on the CHI–SJD route, including Y4.

Are there direct flights from Chicago to San Jose del Cabo?

No direct flights are currently listed on this route. All available options involve at least one stop. Consider flexible dates or nearby airports for better connection options.

What is the average flight price on this route?

The average flight price from Chicago to San Jose del Cabo is approximately $218. Prices range from $218 to $218 depending on airline, time, and class.

How long is the flight from CHI to SJD?

The average flight duration from Chicago to San Jose del Cabo is approximately 18 hours 0 minutes. Direct flights are typically shorter than connecting options.

What is the baggage allowance on CHI–SJD flights?

Baggage allowance varies by airline and fare class. Most economy fares on this route include 1 carry-on (7–8 kg) and 1 checked bag (20–23 kg). Always confirm baggage rules on the airline's site at booking — low-cost carriers may charge for checked bags.