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Cheap flights from San José del Cabo to Chicago from $205

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.
Multiple Airlines Logo
8:11 am - 10:55 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
13h 44m1 stop Monterrey Gen Mariano Escobedo
Multiple Airlines 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
$342Multiple Airlines
Thu, Nov 5 - Tue, Nov 10
Multiple Airlines Logo
8:49 am - 10:55 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
13h 06m2 stops Culiacán Fedl De Bachigualato Monterrey Gen Mariano Escobedo
Multiple Airlines 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
$342Multiple Airlines
Sun, Nov 1 - Tue, Nov 10
Multiple Airlines Logo
8:49 am - 10:55 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
13h 06m2 stops Culiacán Fedl De Bachigualato Monterrey Gen Mariano Escobedo
Multiple Airlines 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
$342Multiple Airlines
Wed, Nov 4 - Tue, Nov 10
Multiple Airlines Logo
12:42 pm - 10:55 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
9h 13m1 stop Monterrey Gen Mariano Escobedo
Multiple Airlines 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
$342Multiple Airlines
Fri, Nov 6 - Tue, Nov 10
Multiple Airlines Logo
12:42 pm - 10:55 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
9h 13m1 stop Monterrey Gen Mariano Escobedo
Multiple Airlines 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
$344Multiple Airlines
Fri, Nov 6 - Sat, Nov 7
Multiple Airlines Logo
8:11 am - 10:55 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
13h 44m1 stop Monterrey Gen Mariano Escobedo
Multiple Airlines 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
$344Multiple Airlines
Thu, Nov 5 - Sat, Nov 7
Multiple Airlines Logo
8:49 am - 10:55 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
13h 06m2 stops Culiacán Fedl De Bachigualato Monterrey Gen Mariano Escobedo
Multiple Airlines 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
$344Multiple Airlines
Wed, Nov 4 - Sat, Nov 7
Multiple Airlines Logo
8:49 am - 10:55 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
13h 06m2 stops Culiacán Fedl De Bachigualato Monterrey Gen Mariano Escobedo
Multiple Airlines 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
$344Multiple Airlines
Sun, Nov 1 - Sat, Nov 7
United Airlines Logo
11:55 am - 6:08 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
4h 13mnonstop
United Airlines Logo
9:03 am - 1:03 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
5h 00mnonstop
$490United Airlines
Thu, Oct 29 - Mon, Nov 2
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
5:30 am - 2:32 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
10h 02m1 stop Houston George Bush Intcntl
$490United Airlines
Wed, Nov 4 - Mon, Nov 9

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

Our best Volaris deals on San José del Cabo to Chicago O'Hare Intl Airport flight tickets
Volaris
Oct 31
SJD3:38 pmSan José del Cabo Los Cabos
12h 05m
1 stop
ORD5:43 amChicago O'Hare Intl
Nov 10
ORD6:29 amChicago O'Hare Intl
9h 31m
1 stop
SJD3:00 pmSan José del Cabo Los Cabos
$345
Volaris
Oct 31
SJD3:38 pmSan José del Cabo Los Cabos
12h 05m
1 stop
ORD5:43 amChicago O'Hare Intl
Nov 7
ORD6:29 amChicago O'Hare Intl
9h 31m
1 stop
SJD3:00 pmSan José del Cabo Los Cabos
$347
Volaris
Sep 29
SJD7:47 pmSan José del Cabo Los Cabos
8h 05m
1 stop
ORD5:52 amChicago O'Hare Intl
Oct 6
ORD7:35 amChicago O'Hare Intl
13h 29m
1 stop
SJD7:04 pmSan José del Cabo Los Cabos
$351

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
Nov 1
SJD8:49 amSan José del Cabo Los Cabos
13h 06m
2 stops
ORD10:55 pmChicago O'Hare Intl
Nov 12
ORD12:35 amChicago O'Hare Intl
7h 56m
1 stop
SJD7:31 amSan José del Cabo Los Cabos
$379
Viva
Nov 1
SJD9:31 pmSan José del Cabo Los Cabos
24h 19m
1 stop
ORD10:50 pmChicago O'Hare Intl
Nov 12
ORD12:35 amChicago O'Hare Intl
7h 56m
1 stop
SJD7:31 amSan José del Cabo Los Cabos
$390
Viva
Jan 23
SJD8:53 amSan José del Cabo Los Cabos
26h 17m
2 stops
ORD12:10 pmChicago O'Hare Intl
Jan 28
ORD1:05 amChicago O'Hare Intl
13h 48m
1 stop
SJD1:53 pmSan José del Cabo Los Cabos
$409

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.

Fly from

Fly to

Route

Depart

Return

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

Thu 11/5

8:11 am-10:55 pm

1 stop13h 44m

Chicago O'Hare Intl

Tue 11/10

6:29 am-3:00 pm

1 stop9h 31m

$342

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Sun 11/1

8:49 am-10:55 pm

2 stops13h 06m

Chicago O'Hare Intl

Tue 11/10

6:29 am-3:00 pm

1 stop9h 31m

$342

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Wed 11/4

8:49 am-10:55 pm

2 stops13h 06m

Chicago O'Hare Intl

Tue 11/10

6:29 am-3:00 pm

1 stop9h 31m

$342

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Fri 11/6

12:42 pm-10:55 pm

1 stop9h 13m

Chicago O'Hare Intl

Tue 11/10

6:29 am-3:00 pm

1 stop9h 31m

$342

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Fri 11/6

12:42 pm-10:55 pm

1 stop9h 13m

Chicago O'Hare Intl

Sat 11/7

6:29 am-3:00 pm

1 stop9h 31m

$344

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Thu 11/5

8:11 am-10:55 pm

1 stop13h 44m

Chicago O'Hare Intl

Sat 11/7

6:29 am-3:00 pm

1 stop9h 31m

$344

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Wed 11/4

8:49 am-10:55 pm

2 stops13h 06m

Chicago O'Hare Intl

Sat 11/7

6:29 am-3:00 pm

1 stop9h 31m

$344

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Sun 11/1

8:49 am-10:55 pm

2 stops13h 06m

Chicago O'Hare Intl

Sat 11/7

6:29 am-3:00 pm

1 stop9h 31m

$344
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 10/29

11:55 am-6:08 pm

Nonstop4h 13m

Chicago O'Hare Intl

Mon 11/2

9:03 am-1:03 pm

Nonstop5h 00m

$490

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Wed 11/4

12:55 pm-6:11 pm

Nonstop4h 16m

Chicago O'Hare Intl

Mon 11/9

5:30 am-2:32 pm

1 stop10h 02m

$490

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 October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San José del Cabo averaging around $437.

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 $448. 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 $616.

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.

Can stopping save me money on San José del Cabo to Chicago O'Hare Intl Airport flights?

You could potentially save up to 2% on your flight if you consider stops on a San José del Cabo to Chicago O'Hare Intl Airport flight.

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

As of September 2026, prices for San José del Cabo to Chicago O'Hare Intl Airport flights are approximately 11% 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

$205

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 $205. 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 $342.
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
7.4
10,214 reviews
Search United Airlines flights

Traveling to a place near Chicago?

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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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