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Cheap Flights from San Jose del Cabo to Chicago starting at S$ 255

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip

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

Cheapest time to fly from San Jose del Cabo to Chicago

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

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.
Cheapest Airlines flying from San Jose del Cabo to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Volaris
From S$ 255
Viva Aerobus
From S$ 272
Aeromexico
From S$ 281
Alaska Airlines
From S$ 291
Delta Air Lines
From S$ 297
United Airlines
From S$ 306
American Airlines
From S$ 308
Jetblue Airways
From S$ 390
Southwest Airlines
From S$ 401
Sun Country Airlines
From S$ 574
ANA airlines

Find more flights and airlines

Alternative Routes from San Jose del Cabo to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from San Jose del Cabo to Chicago.

  • Cheapest
    Volaris
    SJD
    12:34
    10h 31m
    1 transfer
    ORD
    01:05
    Los Cabos International Airport - O'Hare International Airport
    Tue, Jun 18Volaris
    S$ 255
  • Volaris
    SJD
    15:31
    16h 16m
    1 transfer
    MDW
    09:47
    Los Cabos International Airport - Midway International Airport
    Thu, May 23Volaris
    S$ 272
  • Volaris
    SJD
    15:31
    16h 16m
    1 transfer
    MDW
    09:47
    Los Cabos International Airport - Midway International Airport
    Thu, May 23Volaris
    S$ 272
    Find More Flights

Frequently Asked Questions

  • When to buy flight tickets from San Jose del Cabo (SJD) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from San Jose del Cabo to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much is a flight from San Jose del Cabo (SJD) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around S$ 671.
  • How long is a flight from San Jose del Cabo (SJD) to Chicago (CHI)?

    It takes about 4 hours 12 minutes to fly from San Jose del Cabo (SJD) to Chicago (CHI).
  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • What are the most popular airlines that fly from San Jose del Cabo (SJD) to Chicago (CHI)?

    Airlines with flights from San Jose del Cabo (SJD) to Chicago (CHI): American Airlines, Emirates, United Airlines and Southwest Airlines.
  • What's the most popular airline for direct flights from San Jose del Cabo (SJD) to Chicago (CHI)?

    United Airlines operates 1 direct flights from San Jose del Cabo (SJD) to Chicago (CHI).
  • How many airports in Chicago?

Find cheapest flight ticket from San Jose del Cabo to Chicago

Cheapest direct flight price

S$ 254

Cheapest return ticket price

S$ 389

Cheapest month

March

Peak season for travel

September