Flights from Chicago (MDW) to Los Cabos (SJD) from USD115

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San Jose del Cabo

Fly with Volaris from Chicago to San Jose del Cabo

When city skyscrapers give way to sun-kissed beaches and desert landscapes, you know you’re in for a change of pace. If your soul is craving warm nights, ocean breezes, and Baja flavors, Volaris’ flights from Chicago to San Jose del Cabo offer the perfect escape. Thanks to frequent Chicago to Los Cabos flights, heading to Los Cabos Mexico for a relaxing getaway is easier—and often more affordable—than you'd think.

Cabo San Lucas with the magical colors of the sunset.

Before you take off, here’s everything you need to prep for a smooth flight:

  • Check-in: Arrive at Chicago O’Hare (ORD) 3 hours early for international flights. Use Volaris online check-in to save time.
  • Documents: U.S. citizens need a valid passport. Mexican nationals should carry a passport and FMM form.
  • Luggage: Volaris includes a personal item and carry-on. Check fare details to add checked bags ahead of time.
  • Weather in San José del Cabo: Expect warm, dry conditions year-round. Pack light layers, swimwear, and sun protection.
  • Things to do in Chicago: Before your flight, visit the Riverwalk, take in skyline views from the Skydeck, or explore Millennium Park.
Volaris airbus “Alfredo” landing.

Los Cabos International Airport (SJD) is located about 13 kilometers from downtown San José del Cabo. The airport is clean and efficient, with currency exchange, free Wi-Fi, car rentals, and taxi stands available.

Transportation options include shared shuttles, private transfers, and taxis. Ride apps are also available outside the airport gates.

Once you're settled, grab fresh seafood at La Lupita or sip a cold agua fresca in Plaza Mijares—an ideal intro to San José del Cabo downtown.

Panoramic view of Cabo San Lucas from the rooftop of a restaurant.

Artistic, peaceful, and full of surprises—San José del Cabo is a place to slow down and take it all in:

Plaza Mijares
The town’s central plaza is surrounded by historic buildings, restaurants, and public art.

Art District
Open-air galleries and artisan boutiques make this neighborhood vibrant. Thursdays are best for the Art Walk.

Estero San José
A protected estuary with walking trails, ideal for birdwatching and nature photography.

Palmilla Beach
A calm, swimmable beach perfect for families or paddleboarding.

Organic Market
Held on weekends, it’s a great place to try local food and crafts.

Colorful painting in the front of a colonial building, in Cabo San Lucas centric zone.

Here’s how to fill your days with new experiences:

Day 1: Culture & Color

  • Walk the Art District and meet local creators.
  • Visit Mission San José del Cabo Church.
  • Enjoy a sunset cocktail at a beachfront lounge.

Day 2: Outdoor Fun

  • Paddleboard at Palmilla Beach.
  • Hike nearby canyons or ride horses along the coast.
  • Explore boutique shops and cafés in the old town.

Day 3: Hidden Highlights

  • Take a day trip to Miraflores or Santiago for hot springs and nature.
  • Try Baja-style fish tacos at a roadside stand.
  • Experience nightlife with live music in a rooftop bar.
A commercial street with souvenir shops in Cabo San Jose.
  • Book early to lock in cheap flights from Chicago to Los Cabos.
  • Walk around the Art District during the day and visit again in the evening—the vibe totally changes.
  • Pack reef-safe sunscreen to help protect marine life.
  • Don’t skip the estuary trail—it’s a quiet escape right in town.
  • For currency exchange, it’s better to wait until you're in town than doing it at the airport.

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