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Cheap flights from San José del Cabo to Chicago from $206

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.
Air Canada Logo
2:45 pm - 9:23 amSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
17h 38m1 stop Toronto Pearson Intl
Air Canada Logo
6:17 pm - 1:50 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
20h 33m1 stop Toronto Pearson Intl
$369Air Canada
Wed, Nov 25 - Wed, Dec 2
Viva Logo
8:11 am - 12:30 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
27h 19m1 stop Monterrey Gen Mariano Escobedo
Viva Logo
2:00 pm - 8:12 amORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
19h 12m1 stop Monterrey Gen Mariano Escobedo
$379Viva
Wed, Feb 10 - Sun, Feb 14
Air Canada Logo
2:45 pm - 3:02 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
23h 17m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:45 am - 1:50 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
30h 05m1 stop Toronto Pearson Intl
$401Air Canada
Wed, Nov 25 - Wed, Dec 2
Volaris Logo
11:16 am - 12:39 amSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
11h 23m1 stop Guadalajara Miguel Hidal
Volaris Logo
7:23 am - 3:35 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
10h 12m1 stop Mexico City Benito Juarez
$405Volaris
Sun, Mar 14 - Wed, Mar 17
Volaris Logo
11:15 am - 11:44 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
11h 29m1 stop Guadalajara Miguel Hidal
Volaris Logo
7:23 am - 3:35 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
10h 12m1 stop Mexico City Benito Juarez
$405Volaris
Fri, Mar 12 - Wed, Mar 17
Volaris Logo
3:38 pm - 4:43 amSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
12h 05m1 stop Mexico City Benito Juarez
Volaris Logo
6:29 am - 3:00 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
9h 31m1 stop Mexico City Benito Juarez
$417Volaris
Fri, Feb 5 - Mon, Feb 8
Multiple Airlines Logo
3:38 pm - 4:43 amSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
12h 05m1 stop Mexico City Benito Juarez
Multiple Airlines Logo
1:10 am - 1:54 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
13h 44m1 stop Mexico City Benito Juarez
$423Multiple Airlines
Fri, Feb 5 - Sun, Feb 7
Volaris Logo
3:38 pm - 4:36 amSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
11h 58m1 stop Mexico City Benito Juarez
Volaris Logo
7:23 am - 3:35 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
10h 12m1 stop Mexico City Benito Juarez
$428Volaris
Sat, Mar 13 - Wed, Mar 17
United Airlines Logo
12:55 pm - 6:11 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
4h 16mnonstop
United Airlines Logo
7:00 am - 1:18 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
7h 18m1 stop Denver Intl
$530United Airlines
Thu, Dec 10 - Tue, Dec 15
United Airlines Logo
12:41 pm - 5:57 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
4h 16mnonstop
United Airlines Logo
9:53 pm - 2:42 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
17h 49m1 stop Denver Intl
$530United Airlines
Wed, Feb 10 - Sun, Feb 14

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

Our best Viva deals on San José del Cabo to Chicago O'Hare Intl Airport flight tickets
Viva
Feb 10
SJD8:11 amSan José del Cabo Los Cabos
27h 19m
1 stop
ORD12:30 pmChicago O'Hare Intl
Feb 14
ORD2:00 pmChicago O'Hare Intl
19h 12m
1 stop
SJD8:12 amSan José del Cabo Los Cabos
$379
Viva
Feb 10
SJD8:11 amSan José del Cabo Los Cabos
27h 19m
1 stop
ORD12:30 pmChicago O'Hare Intl
Feb 14
ORD2:00 pmChicago O'Hare Intl
19h 12m
2 stops
SJD8:12 amSan José del Cabo Los Cabos
$436
Viva
Mar 14
SJD9:36 pmSan José del Cabo Los Cabos
24h 09m
1 stop
ORD11:45 pmChicago O'Hare Intl
Mar 18
ORD2:10 amChicago O'Hare Intl
13h 44m
1 stop
SJD1:54 pmSan José del Cabo Los Cabos
$445

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

Our best United Airlines deals on San José del Cabo to Chicago O'Hare Intl Airport flight tickets
United Airlines
Dec 10
SJD12:55 pmSan José del Cabo Los Cabos
4h 16m
ORD6:11 pmChicago O'Hare Intl
Dec 15
ORD7:00 amChicago O'Hare Intl
7h 18m
1 stop
SJD1:18 pmSan José del Cabo Los Cabos
$530
United Airlines
Dec 10
SJD12:55 pmSan José del Cabo Los Cabos
4h 16m
ORD6:11 pmChicago O'Hare Intl
Dec 15
ORD7:00 amChicago O'Hare Intl
7h 18m
1 stop
SJD1:18 pmSan José del Cabo Los Cabos
$540

momondo Fare Finder

 
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.

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Route

Depart

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Price

Cheapest round-trip

San José del CaboChicago

SJD San José del Cabo Los Cabos - ORD Chicago O'Hare Intl

SJDORD

San José del Cabo Los Cabos

Wed 11/25

2:45 pm-9:23 am

1 stop17h 38m

Chicago O'Hare Intl

Wed 12/2

6:17 pm-1:50 pm

1 stop20h 33m

$369

San José del CaboChicago

SJD San José del Cabo Los Cabos - ORD Chicago O'Hare Intl

SJDORD

San José del Cabo Los Cabos

Wed 2/10

8:11 am-12:30 pm

1 stop27h 19m

Chicago O'Hare Intl

Sun 2/14

2:00 pm-8:12 am

1 stop19h 12m

$379

San José del CaboChicago

SJD San José del Cabo Los Cabos - ORD Chicago O'Hare Intl

SJDORD

San José del Cabo Los Cabos

Wed 11/25

2:45 pm-3:02 pm

2 stops23h 17m

Chicago O'Hare Intl

Wed 12/2

8:45 am-1:50 pm

1 stop30h 05m

$401

San José del CaboChicago

SJD San José del Cabo Los Cabos - ORD Chicago O'Hare Intl

SJDORD

San José del Cabo Los Cabos

Sun 3/14

11:16 am-12:39 am

1 stop11h 23m

Chicago O'Hare Intl

Wed 3/17

7:23 am-3:35 pm

1 stop10h 12m

$405

San José del CaboChicago

SJD San José del Cabo Los Cabos - ORD Chicago O'Hare Intl

SJDORD

San José del Cabo Los Cabos

Fri 3/12

11:15 am-11:44 pm

1 stop11h 29m

Chicago O'Hare Intl

Wed 3/17

7:23 am-3:35 pm

1 stop10h 12m

$405

San José del CaboChicago

SJD San José del Cabo Los Cabos - ORD Chicago O'Hare Intl

SJDORD

San José del Cabo Los Cabos

Fri 2/5

3:38 pm-4:43 am

1 stop12h 05m

Chicago O'Hare Intl

Mon 2/8

6:29 am-3:00 pm

1 stop9h 31m

$417

San José del CaboChicago

SJD San José del Cabo Los Cabos - ORD Chicago O'Hare Intl

SJDORD

San José del Cabo Los Cabos

Fri 2/5

3:38 pm-4:43 am

1 stop12h 05m

Chicago O'Hare Intl

Sun 2/7

1:10 am-1:54 pm

1 stop13h 44m

$423

San José del CaboChicago

SJD San José del Cabo Los Cabos - ORD Chicago O'Hare Intl

SJDORD

San José del Cabo Los Cabos

Sat 3/13

3:38 pm-4:36 am

1 stop11h 58m

Chicago O'Hare Intl

Wed 3/17

7:23 am-3:35 pm

1 stop10h 12m

$428
Quickest round-trip

San José del CaboChicago

SJD San José del Cabo Los Cabos - ORD Chicago O'Hare Intl

SJDORD

San José del Cabo Los Cabos

Thu 12/10

12:55 pm-6:11 pm

Nonstop4h 16m

Chicago O'Hare Intl

Tue 12/15

7:00 am-1:18 pm

1 stop7h 18m

$530

San José del CaboChicago

SJD San José del Cabo Los Cabos - ORD Chicago O'Hare Intl

SJDORD

San José del Cabo Los Cabos

Wed 2/10

12:41 pm-5:57 pm

Nonstop4h 16m

Chicago O'Hare Intl

Sun 2/14

9:53 pm-2:42 pm

1 stop17h 49m

$530

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 month to fly to Chicago O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San José del Cabo averaging around $447.

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 Friday when prices can be found for as low as $578. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday 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 $803.

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 to Chicago O'Hare Intl Airport flights?

There are 2 cabin classes available to choose from on San José del Cabo to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

As of October 2026, prices for San José del Cabo to Chicago O'Hare Intl Airport flights are approximately 22% more expensive 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

$206

Fastest flight time

4h 13m

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 $206. 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 $369.
The fastest flight from San José del Cabo to Chicago O'Hare Intl Airport takes 4h 13m
Direct flights go from San José del Cabo to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from San José del Cabo to Chicago O'Hare Intl Airport

  • 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 13m.

  • 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 $329Free CancellationRating
7.3
10,451 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 $329. Generally, United Airlines has 4 flights on this route every week with an average price of $470. United Airlines is rated 7.3/10 by our users.

Traveling to a place near Chicago?

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

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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