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Cheap flights from San José del Cabo to Chicago from $163

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 2/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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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
4:08 pm - 4:36 am
SJD
-
ORD
11h 28m1 stop
Volaris Logo
7:23 am - 3:25 pm
ORD
-
SJD
10h 02m1 stop
$322Volaris
Thu, Mar 5 - Sun, Mar 8
Viva Logo
5:05 pm - 11:25 pm
SJD
-
ORD
29h 20m1 stop
Viva Logo
12:55 am - 4:25 pm
ORD
-
SJD
16h 30m1 stop
$350Viva
Wed, Feb 25 - Tue, Mar 3
Volaris Logo
11:07 am - 11:47 pm
SJD
-
ORD
10h 40m1 stop
Volaris Logo
7:40 am - 7:04 pm
ORD
-
SJD
13h 24m1 stop
$369Volaris
Fri, Apr 17 - Tue, Apr 21
Viva Logo
5:05 pm - 11:25 pm
SJD
-
ORD
29h 20m1 stop
Viva Logo
12:55 am - 4:30 pm
ORD
-
SJD
16h 35m1 stop
$370Viva
Thu, Feb 12 - Tue, Feb 17
Volaris Logo
4:34 pm - 11:19 am
SJD
-
ORD
17h 45m2 stops
Volaris Logo
7:23 am - 3:25 pm
ORD
-
SJD
10h 02m1 stop
$372Volaris
Thu, Mar 5 - Sun, Mar 8
Volaris Logo
4:08 pm - 4:36 am
SJD
-
ORD
11h 28m1 stop
Volaris Logo
6:23 am - 3:20 pm
ORD
-
SJD
9h 57m1 stop
$379Volaris
Mon, Jan 19 - Mon, Jan 26
Viva Logo
6:30 pm - 11:50 pm
SJD
-
ORD
28h 20m2 stops
Viva Logo
12:55 am - 4:30 pm
ORD
-
SJD
16h 35m1 stop
$391Viva
Thu, Feb 12 - Tue, Feb 17
Alaska Airlines Logo
12:21 pm - 2:58 pm
SJD
-
ORD
25h 37m1 stop
Alaska Airlines Logo
3:07 pm - 12:41 pm
ORD
-
SJD
22h 34m1 stop
$398Alaska Airlines
Fri, Feb 13 - Tue, Feb 17
Alaska Airlines Logo
12:21 pm - 11:59 pm
SJD
-
ORD
10h 38m1 stop
Alaska Airlines Logo
8:20 am - 12:41 pm
ORD
-
SJD
29h 21m1 stop
$408Alaska Airlines
Fri, Feb 13 - Tue, Feb 17
Alaska Airlines Logo
3:16 pm - 4:33 pm
SJD
-
ORD
24h 17m2 stops
Alaska Airlines Logo
3:07 pm - 12:41 pm
ORD
-
SJD
22h 34m1 stop
$419Alaska Airlines
Fri, Feb 13 - Tue, Feb 17

Delta flights from San José del Cabo to Chicago O'Hare Intl Airport

Our best Delta deals on San José del Cabo to Chicago O'Hare Intl Airport flight tickets
Delta
Feb 12
SJD4:56 pmSan José del Cabo Los Cabos
14h 42m
2 stops
ORD8:38 amChicago O'Hare Intl
Feb 18
ORD5:25 amChicago O'Hare Intl
13h 12m
2 stops
SJD5:37 pmSan José del Cabo Los Cabos
$451
Find similar
Delta
Jan 12
SJD4:32 pmSan José del Cabo Los Cabos
15h 11m
2 stops
ORD8:43 amChicago O'Hare Intl
Jan 17
ORD5:59 pmChicago O'Hare Intl
15h 41m
2 stops
SJD8:40 amSan José del Cabo Los Cabos
$497
Find similar
Delta
Jan 12
SJD4:32 pmSan José del Cabo Los Cabos
15h 11m
2 stops
ORD8:43 amChicago O'Hare Intl
Jan 17
ORD5:59 pmChicago O'Hare Intl
15h 41m
2 stops
SJD8:40 amSan José del Cabo Los Cabos
$498
Find similar

American Airlines flights from San José del Cabo to Chicago O'Hare Intl Airport

Our best American Airlines deals on San José del Cabo to Chicago O'Hare Intl Airport flight tickets
American Airlines
Feb 12
SJD12:30 pmSan José del Cabo Los Cabos
4h 17m
ORD5:47 pmChicago O'Hare Intl
Feb 18
ORD5:00 amChicago O'Hare Intl
11h 33m
1 stop
SJD3:33 pmSan José del Cabo Los Cabos
$501
Find similar
American Airlines
Feb 25
SJD12:56 pmSan José del Cabo Los Cabos
4h 18m
ORD6:14 pmChicago O'Hare Intl
Mar 4
ORD8:05 amChicago O'Hare Intl
4h 49m
SJD11:54 amSan José del Cabo Los Cabos
$508
Find similar
American Airlines
Jan 12
SJD12:32 pmSan José del Cabo Los Cabos
4h 15m
ORD5:47 pmChicago O'Hare Intl
Jan 17
ORD9:00 pmChicago O'Hare Intl
15h 50m
1 stop
SJD11:50 amSan José del Cabo Los Cabos
$522
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San José del Cabo to Chicago O'Hare Intl Airport 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 December 8, 2025.
Use the filters below to find and compare flights from San José del Cabo to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 3/5

4:08 pm-4:36 am

1 stop11h 28m

Chicago O'Hare Intl

Sun 3/8

7:23 am-3:25 pm

1 stop10h 02m

$322

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 2/25

5:05 pm-11:25 pm

1 stop29h 20m

Chicago O'Hare Intl

Tue 3/3

12:55 am-4:25 pm

1 stop16h 30m

$350

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 4/17

11:07 am-11:47 pm

1 stop10h 40m

Chicago O'Hare Intl

Tue 4/21

7:40 am-7:04 pm

1 stop13h 24m

$369

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 2/12

5:05 pm-11:25 pm

1 stop29h 20m

Chicago O'Hare Intl

Tue 2/17

12:55 am-4:30 pm

1 stop16h 35m

$370

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 3/5

4:34 pm-11:19 am

2 stops17h 45m

Chicago O'Hare Intl

Sun 3/8

7:23 am-3:25 pm

1 stop10h 02m

$372

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Mon 1/19

4:08 pm-4:36 am

1 stop11h 28m

Chicago O'Hare Intl

Mon 1/26

6:23 am-3:20 pm

1 stop9h 57m

$379

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 2/12

6:30 pm-11:50 pm

2 stops28h 20m

Chicago O'Hare Intl

Tue 2/17

12:55 am-4:30 pm

1 stop16h 35m

$391

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 2/13

12:21 pm-2:58 pm

1 stop25h 37m

Chicago O'Hare Intl

Tue 2/17

3:07 pm-12:41 pm

1 stop22h 34m

$398

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 2/13

12:21 pm-11:59 pm

1 stop10h 38m

Chicago O'Hare Intl

Tue 2/17

8:20 am-12:41 pm

1 stop29h 21m

$408

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 2/13

3:16 pm-4:33 pm

2 stops24h 17m

Chicago O'Hare Intl

Tue 2/17

3:07 pm-12:41 pm

1 stop22h 34m

$419

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 O'Hare Intl Airport

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 cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport 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. On the other hand, Tuesday is the most expensive day to depart from San José del Cabo because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $679.

What is the cheapest San José del Cabo Los Cabos to Chicago O'Hare Intl 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 O'Hare Intl flight prices

What cabin class options are available on San José del Cabo Los Cabos to Chicago O'Hare Intl flights?

There are 3 cabin classes available to choose from on San José del Cabo Los Cabos to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between San José del Cabo to Chicago O'Hare Intl Airport.

How have San José del Cabo to Chicago O'Hare Intl Airport flight prices changed over time?

As of December 2025, prices for San José del Cabo to Chicago O'Hare Intl Airport flights are approximately 16% cheaper when compared to flights at the same time last year.

When to book flights from San José del Cabo to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San José del Cabo to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport (SJD to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San José del Cabo to Chicago O'Hare Intl Airport

Best Price Found

$258

Fastest flight time

4h 09m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from San José del Cabo in the past 72 hours is $258. The best round-trip flight deal from San José del Cabo to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $428.
The fastest flight from San José del Cabo to Chicago O'Hare Intl Airport takes 4h 09m
Direct flights go from San José del Cabo to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is San José del Cabo Los Cabos to Chicago O'Hare Intl by plane?

    A flight from San José del Cabo Los Cabos to Chicago O'Hare Intl will travel around 1810.6 mi. In terms of flight time, this usually takes a little over 4h 09m.

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

    Prices for flights from San José del Cabo Los Cabos Airport to Chicago O'Hare Intl Airport are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from San José del Cabo to Chicago O'Hare Intl Airport?

  • What is the most popular airline from San José del Cabo to Chicago O'Hare Intl Airport?

Best airlines flying from San José del Cabo to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from San José del Cabo to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $361Free CancellationRating
7.4
9,076 reviews
Search United Airlines flights

  • United Airlines Flights From San José del Cabo to Chicago O'Hare Intl Airport

    The lowest priced United Airlines flight from San José del Cabo to Chicago O'Hare Intl Airport from the last 72 hours was $361. Generally, United Airlines has 7 flights on this route every week with an average price of $447. United Airlines is rated 7.4/10 by our users.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
Benton Harbor

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San José del Cabo to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo enables you to select and highlight flights to Chicago from San José del Cabo with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San José del Cabo to Chicago.

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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