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Cheap flights from San José del Cabo to Chicago from $208

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San José del Cabo to Chicago departing on 12/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from San José del Cabo to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
Volaris Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
$349Volaris
Thu, Sep 17 - Sat, Sep 26
Volaris Logo
12:02 pm - 11:47 pm
SJD
-
ORD
9h 45m
1 stop
Volaris Logo
2:53 am - 11:29 am
ORD
-
SJD
10h 36m
1 stop
$365Volaris
Tue, Jul 7 - Mon, Jul 13
Volaris Logo
12:02 pm - 11:47 pm
SJD
-
ORD
9h 45m
1 stop
Volaris Logo
2:53 am - 11:29 am
ORD
-
SJD
10h 36m
1 stop
$367Volaris
Wed, Jul 8 - Fri, Jul 10
Volaris Logo
3:36 pm - 12:55 am
SJD
-
ORD
7h 19m
1 stop
Volaris Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
$371Volaris
Fri, Jul 17 - Sat, Jul 18
Volaris Logo
3:36 pm - 12:55 am
SJD
-
ORD
7h 19m
1 stop
Volaris Logo
2:53 am - 8:16 am
ORD
-
SJD
7h 23m
1 stop
$378Volaris
Thu, Jul 16 - Fri, Jul 17
Delta Logo
12:12 pm - 10:36 pm
SJD
-
MDW
8h 24m
1 stop
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
$424Delta
Wed, Aug 5 - Sun, Aug 9
Southwest Logo
10:40 am - 10:00 pm
SJD
-
MDW
9h 20m
1 stop
Southwest Logo
6:10 am - 12:15 pm
MDW
-
SJD
8h 05m
1 stop
$584Southwest
Thu, Sep 17 - Sun, Sep 27
Delta Logo
12:15 pm - 10:25 pm
SJD
-
MDW
8h 10m
1 stop
Delta Logo
6:05 am - 5:25 pm
MDW
-
SJD
13h 20m
2 stops
$589Delta
Thu, Sep 17 - Sun, Sep 27
Southwest Logo
11:15 am - 9:15 pm
SJD
-
MDW
8h 00m
1 stop
Southwest Logo
7:05 am - 12:25 pm
MDW
-
SJD
7h 20m
1 stop
$660Southwest
Fri, Jul 17 - Sun, Jul 19
Multiple Airlines Logo
7:50 pm - 6:37 pm
SJD
-
MDW
20h 47m
3 stops
Multiple Airlines Logo
8:23 pm - 2:51 pm
MDW
-
SJD
20h 28m
1 stop
$687Multiple Airlines
Mon, Jul 13 - Mon, Jul 20

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Volaris flights from San José del Cabo to Chicago

Our best Volaris deals on San José del Cabo to Chicago flight tickets
Volaris
Sep 17
SJD7:47 pmSan José del Cabo Los Cabos
8h 05m
1 stop
ORD5:52 amChicago O'Hare Intl
Sep 26
ORD1:40 amChicago O'Hare Intl
10h 29m
1 stop
SJD10:09 amSan José del Cabo Los Cabos
$349
Volaris
Jun 17
SJD7:47 pmSan José del Cabo Los Cabos
8h 05m
1 stop
ORD5:52 amChicago O'Hare Intl
Jun 23
ORD7:35 amChicago O'Hare Intl
13h 29m
1 stop
SJD7:04 pmSan José del Cabo Los Cabos
$362
Volaris
Jul 7
SJD12:02 pmSan José del Cabo Los Cabos
9h 45m
1 stop
ORD11:47 pmChicago O'Hare Intl
Jul 13
ORD2:53 amChicago O'Hare Intl
10h 36m
1 stop
SJD11:29 amSan José del Cabo Los Cabos
$365

Delta flights from San José del Cabo to Chicago

Our best Delta deals on San José del Cabo to Chicago flight tickets
Delta
Aug 5
SJD12:12 pmSan José del Cabo Los Cabos
8h 24m
1 stop
MDW10:36 pmChicago Midway
Aug 9
MDW6:05 amChicago Midway
7h 02m
1 stop
SJD11:07 amSan José del Cabo Los Cabos
$424
Delta
Aug 12
SJD6:10 amSan José del Cabo Los Cabos
15h 47m
2 stops
ORD11:57 pmChicago O'Hare Intl
Aug 16
ORD5:30 amChicago O'Hare Intl
15h 18m
2 stops
SJD6:48 pmSan José del Cabo Los Cabos
$589
Delta
Aug 12
SJD2:24 pmSan José del Cabo Los Cabos
15h 32m
2 stops
ORD7:56 amChicago O'Hare Intl
Aug 16
ORD7:04 amChicago O'Hare Intl
13h 44m
1 stop
SJD6:48 pmSan José del Cabo Los Cabos
$592

momondo Fare Finder

 
Customize your flight search to find flights from San José del Cabo to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated June 10, 2026.
Use the filters below to find and compare flights from San José del Cabo to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 9/17

7:47 pm-5:52 am

1 stop8h 05m

Chicago O'Hare Intl

Sat 9/26

1:40 am-10:09 am

1 stop10h 29m

$349

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Tue 7/7

12:02 pm-11:47 pm

1 stop9h 45m

Chicago O'Hare Intl

Mon 7/13

2:53 am-11:29 am

1 stop10h 36m

$365

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 7/8

12:02 pm-11:47 pm

1 stop9h 45m

Chicago O'Hare Intl

Fri 7/10

2:53 am-11:29 am

1 stop10h 36m

$367

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 7/17

3:36 pm-12:55 am

1 stop7h 19m

Chicago O'Hare Intl

Sat 7/18

1:40 am-10:09 am

1 stop10h 29m

$371
Quickest round-trip

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 7/16

3:36 pm-12:55 am

1 stop7h 19m

Chicago O'Hare Intl

Fri 7/17

2:53 am-8:16 am

1 stop7h 23m

$378

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 8/5

12:12 pm-10:36 pm

1 stop8h 24m

Chicago Midway

Sun 8/9

6:05 am-11:07 am

1 stop7h 02m

$424

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 9/17

10:40 am-10:00 pm

1 stop9h 20m

Chicago Midway

Sun 9/27

6:10 am-12:15 pm

1 stop8h 05m

$584

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 9/17

12:15 pm-10:25 pm

1 stop8h 10m

Chicago Midway

Sun 9/27

6:05 am-5:25 pm

2 stops13h 20m

$589

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 7/17

11:15 am-9:15 pm

1 stop8h 00m

Chicago Midway

Sun 7/19

7:05 am-12:25 pm

1 stop7h 20m

$660

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mon 7/13

7:50 pm-6:37 pm

3 stops20h 47m

Chicago Midway

Mon 7/20

8:23 pm-2:51 pm

1 stop20h 28m

$687

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from San José del Cabo to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between San José del Cabo and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from San José del Cabo, with most prices found around $262. If you’re not able to fly to Chicago in September, then December is your next best option. Flight prices from San José del Cabo to Chicago during December average around $315.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $445. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from San José del Cabo to Chicago for around $962.

What is the cheapest San José del Cabo Los Cabos to Chicago flight route?

Fly from San José del Cabo Los Cabos to Chicago O'Hare Intl for the best San José del Cabo Los Cabos - Chicago flight prices

What cabin class options are available on San José del Cabo to Chicago flights?

There are 3 cabin classes available to choose from on San José del Cabo to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on San José del Cabo to Chicago flights?

You could potentially save up to 13% on your flight if you consider stops on a San José del Cabo to Chicago flight.

How have San José del Cabo to Chicago flight prices changed over time?

As of June 2026, prices for San José del Cabo to Chicago flights are approximately 18% more expensive when compared to flights at the same time last year.

When to book flights from San José del Cabo to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from San José del Cabo to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San José del Cabo to Chicago (SJD to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San José del Cabo to Chicago

Fastest flight time

7h 03m

Direct flights

Every day

Airports in Chicago

3 airports
The fastest flight from San José del Cabo to Chicago takes 7h 03m
Direct flights go from San José del Cabo to Chicago every day.
There are 3 airports in Chicago. From San José del Cabo there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from San José del Cabo to Chicago

  • How far is San José del Cabo Los Cabos to Chicago by plane?

    A flight from San José del Cabo Los Cabos to Chicago will travel around 1817.1 mi. 7h 03m is a normal flight duration for this route.

  • When did momondo last update prices for flights from San José del Cabo Los Cabos Airport to Chicago?

    Prices for flights from San José del Cabo Los Cabos Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from San José del Cabo Los Cabos Airport to Chicago?

  • How old do you have to be to fly from San José del Cabo Los Cabos Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San José del Cabo Los Cabos Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from San José del Cabo to Chicago?

  • What is the most popular airline from San José del Cabo to Chicago?

Best airlines flying from San José del Cabo to Chicago

Compare and see reviews for airlines that fly from San José del Cabo to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $329Free CancellationRating
7.4
9,804 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Portage
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from San José del Cabo to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from San José del Cabo to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from San José del Cabo to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from San José del Cabo on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from San José del Cabo to Chicago?

Once you have performed a search for San José del Cabo to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from San José del Cabo to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for San José del Cabo to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport