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Cheap flight deals from Chicago to San Jose del Cabo Starting at €116

Whether you’re going for a one-way or round-trip to San Jose del Cabo, we’ve got you covered! Check out these different flight options from Chicago below.

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD08:20
        4h 55m
        Nonstop
        SJD12:15
        Sun, Feb 23|Chicago - San Jose del Cabo|American Airlines
        €192€266
        28% OFF
        28% OFF
        €266€192

        Choose American Airlines flights from Chicago to San Jose del Cabo. The one-way direct flight with American Airlines departs from O'Hare International Airport on Sun, Feb 23, arriving at Los Cabos International Airport. One-way Prices start from €192 including taxes and charges.

      • MDW09:00
        5h
        Nonstop
        SJD12:00
        Wed, Mar 19|Chicago - San Jose del Cabo|Southwest Airlines
        €234€266
        12% OFF
        12% OFF
        €266€234

        Choose Southwest Airlines flights from Chicago to San Jose del Cabo. The one-way direct flight with Southwest Airlines departs from Midway International Airport on Wed, Mar 19, arriving at Los Cabos International Airport. One-way Prices start from €234 including taxes and charges.

      • MDW19:55
        15h 47m
        1 stop
        SJD10:42
        Mon, Feb 24|Chicago - San Jose del Cabo|Volaris
        €116€266
        56% OFF
        56% OFF
        €266€116

        Choose Volaris flights from Chicago to San Jose del Cabo. The one-way connecting flight with Volaris departs from Midway International Airport on Mon, Feb 24, arriving at Los Cabos International Airport. One-way Prices start from €116 including taxes and charges.

      • ORD02:25
        19h 50m
        1 stop
        SJD20:15
        Tue, Mar 11|Chicago - San Jose del Cabo|Viva
        €120
        €120

        Choose Viva flights from Chicago to San Jose del Cabo. The one-way connecting flight with Viva departs from O'Hare International Airport on Tue, Mar 11, arriving at Los Cabos International Airport. One-way Prices start from €120 including taxes and charges.

      • ORD02:25
        19h 50m
        1 stop
        SJD20:15
        Mon, Mar 10|Chicago - San Jose del Cabo|Viva
        €120
        €120

        Choose Viva flights from Chicago to San Jose del Cabo. The one-way connecting flight with Viva departs from O'Hare International Airport on Mon, Mar 10, arriving at Los Cabos International Airport. One-way Prices start from €120 including taxes and charges.

      • ORD01:00
        10h 42m
        1 stop
        SJD10:42
        Thu, Mar 6|Chicago - San Jose del Cabo|Viva
        €126
        €126

        Choose Viva flights from Chicago to San Jose del Cabo. The one-way connecting flight with Viva departs from O'Hare International Airport on Thu, Mar 6, arriving at Los Cabos International Airport. One-way Prices start from €126 including taxes and charges.

      • ORD06:35
        10h 16m
        1 stop
        SJD14:51
        Fri, Mar 28|Chicago - San Jose del Cabo|Viva
        €126
        €126

        Choose Viva flights from Chicago to San Jose del Cabo. The one-way connecting flight with Viva departs from O'Hare International Airport on Fri, Mar 28, arriving at Los Cabos International Airport. One-way Prices start from €126 including taxes and charges.

      • ORD02:00
        11h 16m
        1 stop
        SJD11:16
        Wed, Mar 12|Chicago - San Jose del Cabo|Viva
        €127
        €127

        Choose Viva flights from Chicago to San Jose del Cabo. The one-way connecting flight with Viva departs from O'Hare International Airport on Wed, Mar 12, arriving at Los Cabos International Airport. One-way Prices start from €127 including taxes and charges.

      • ORD02:00
        11h 16m
        1 stop
        SJD11:16
        Wed, Mar 26|Chicago - San Jose del Cabo|Viva
        €127
        €127

        Choose Viva flights from Chicago to San Jose del Cabo. The one-way connecting flight with Viva departs from O'Hare International Airport on Wed, Mar 26, arriving at Los Cabos International Airport. One-way Prices start from €127 including taxes and charges.

      • ORD01:00
        17h 44m
        1 stop
        SJD17:44
        Wed, Mar 5|Chicago - San Jose del Cabo|Viva
        €129
        €129

        Choose Viva flights from Chicago to San Jose del Cabo. The one-way connecting flight with Viva departs from O'Hare International Airport on Wed, Mar 5, arriving at Los Cabos International Airport. One-way Prices start from €129 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        SJD02:00 pm
        Sun, Feb 23|Chicago - San Jose del Cabo|American Airlines
        Find More Flights
        Find More Flights

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

Chicago to San Jose del Cabo flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. VB187

    Viva

    01:40

    ORD

    4.2h

    04:50

    MEX

    SMTWTFS
    Search

  2. VB9496

    Viva

    18:55

    NLU

    2.3h

    20:10

    SJD

    SMTWTFS

  3. Y4701

    Volaris

    01:40

    ORD

    4.2h

    04:50

    MEX

    -M-W-FS
    Search

  4. VB9496

    Viva

    18:55

    NLU

    2.3h

    20:10

    SJD

    SMTWTFS

  5. Y41703

    Volaris

    01:45

    ORD

    4.4h

    05:07

    GDL

    SMTWTFS
    Search

  6. Y41140

    Volaris

    07:14

    GDL

    1.6h

    07:50

    SJD

    S-TWTFS

  7. VB547

    Viva

    01:50

    ORD

    4.6h

    05:25

    GDL

    SMTWTFS
    Search

  8. Y41148

    Volaris

    19:32

    GDL

    1.6h

    20:07

    SJD

    S-T----

  9. VB547

    Viva

    01:50

    ORD

    4.6h

    05:25

    GDL

    SMTWTFS
    Search

  10. VB3156

    Viva

    14:15

    GDL

    1.6h

    14:50

    SJD

    SMTWTFS

  11. VB547

    Viva

    01:50

    ORD

    4.6h

    05:25

    GDL

    SMTWTFS
    Search

  12. Y41144

    Volaris

    10:40

    GDL

    1.6h

    11:16

    SJD

    -M-W-F-

  13. AM689

    Aeromexico

    01:59

    ORD

    4.4h

    05:25

    MEX

    SMTWTFS
    Search

  14. Y4550

    Volaris

    15:35

    TLC

    2.1h

    16:39

    SJD

    -MTW-FS

  15. AA370

    American Airlines

    05:00

    ORD

    2.5h

    07:28

    DFW

    SMTWTFS
    Search

  16. AA389

    American Airlines

    08:40

    DFW

    2.8h

    11:30

    MEX

    SMTWTFS

  17. VB9496

    Viva

    18:55

    NLU

    2.3h

    20:10

    SJD

    SMTWTFS

  18. VB633

    Viva

    12:35

    ORD

    3.5h

    15:05

    MTY

    S-TWTFS
    Search

  19. VB4324

    Viva

    06:55

    MTY

    2.1h

    08:00

    SJD

    SMTWTFS

  20. Y45507

    Volaris

    18:34

    ORD

    3.5h

    21:05

    MTY

    S-T-T-S
    Search

  21. VB4324

    Viva

    06:55

    MTY

    2.1h

    08:00

    SJD

    SMTWTFS
Find more flights and airlines

When is the cheapest time to fly from Chicago to San Jose del Cabo?

These price trend charts carefully monitor and predict how flight prices from Chicago to San Jose del Cabo will change. Keep a close eye on them to understand when the best time to buy your tickets is.

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

Frequently Asked Questions

  • When are flight tickets 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 do flights from Chicago (CHI) to San Jose del Cabo (SJD) cost?

    According to Trip.com's data, the lowest price is around €487.

  • How long does it take to fly from Chicago (CHI) to San Jose del Cabo (SJD)?

    It takes about 4 hours 47 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): Emirates, American Airlines and United Airlines.

  • What's the most popular airline for non-stop flights from Chicago (CHI) to San Jose del Cabo (SJD)?

    American Airlines operates 1 non-stop flights from Chicago (CHI) to San Jose del Cabo (SJD).

  • How many airports are there in San Jose del Cabo (SJD)?

    There are 1 airport(s) near San Jose del Cabo (SJD): Los Cabos International Airport.

How to find a cheap flight from Chicago to San Jose del Cabo

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Chicago to San Jose del Cabo

Cheapest direct flight price€116
Cheapest return ticket price€409
Off-season for travelMarch
Peak season for travelMay
Flight distance2,918.98 km
Average flight time4 hours 47 minutes
Popular airlineAeromexico

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