A stunning view of Chicago's skyline and river with prominent skyscrapers and bridges on a cloudy day. — flights from San Jose Del Cabo to Chicago
San José del CaboChicago

Flights from San José del Cabo to Chicago

Nonstop flights from San José del Cabo (SJD) to Chicago (MDW) take about 4h 8m (2,906 km). Volaris flies it. Lowest fare seen: $394 one-way, 1 stop (22 Oct 2026).

All flights to Chicago →

Photo of Chicago: Mik Dominguez on Pexels.

When you land in Chicago

The airport transfer and the few things worth sorting before you fly.

A stunning view of Chicago's skyline and river with prominent skyscrapers and bridges on a cloudy day. — arriving in Chicago

Airport transfer

MDW → Chicago, booked before you fly

A private driver meets you in arrivals at a price agreed when you book. Book with Welcome Pickups.

See transfer prices
Before you flyAirport lounges at Los Cabos →2 lounges at Los Cabos AirportTrains, buses and taxi faresMDW to Chicago: getting into town →Early arrival or late flightLuggage storage in Chicago →11 drop-off points, from $4.90

Things to book in Chicago

All 59 things to do in Chicago →
Skyline view of Chicago's iconic skyscrapers including the John Hancock Center.from €24.10
John Hancock Center 4.5 · 3,029 Tiqets reviews
The historic Tribune Tower in Chicago, featuring its gothic architecture and American flag.from €26.78
Tribune Tower 4.6 · 2,764 Tiqets reviews
View of the historic Wrigley Building in downtown Chicago, showcasing its classic architecture.from €13.38
The Wrigley Building 4.6 · 2,762 Tiqets reviews
Silhouette of visitors walking through a tunnel at Museum Campus, leading outdoors.from €26.78
Museum Campus 4.6 · 2,641 Tiqets reviews

Find hotels in Chicago

Hotels, hostels & more · Trip.com

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Airlines flying San José del Cabo to Chicago

Carriers on SJD–MDW according to our route data and nonstop fares seen as of 22 Oct 2026. Not a complete list.

✈ Volaris

More for this trip

Frequently asked questions — San José del Cabo to Chicago flights

How long is the flight from San José del Cabo to Chicago?
A nonstop flight from San José del Cabo (SJD) to Chicago (MDW) takes about 4h 8m, covering 2,906 km. That is an estimate from the distance — actual time varies with the airline, aircraft and winds, and connecting itineraries take longer.
How far is San José del Cabo from Chicago by air?
The great-circle distance between Los Cabos International Airport and Chicago Midway International Airport is 2,906 km (1,806 miles), a medium-haul route.
Which airlines fly from San José del Cabo to Chicago?
Airlines with flights or nonstop fares on the SJD–MDW route include Volaris. This is not a complete list — schedules change by season, so check the current options before booking.
How much does a flight from San José del Cabo to Chicago cost?
The lowest one-way fare seen recently on SJD–MDW was $394 USD with Volaris (1 stop), departing 22 Oct 2026, found in fare searches as of 22 Oct 2026. Fares change constantly and depend on the date, so check the current price before booking.
Do I need a visa to travel from San José del Cabo to Chicago?
It depends on your passport. Some nationalities can enter Chicago visa-free or get a visa on arrival; others must apply in advance. Use AirConnect's Visa Checker to see the rules for your passport.

Sources: fares from Travelpayouts flight-search data, seen 22 Oct 2026; airlines from each carrier's published network and nonstop fares on sale; distance from OurAirports coordinates; flight time estimated from distance. Fares change daily.

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