Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from San José del Cabo to Chicago from $58

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 1/24. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
11:07 am - 11:47 pm
SJD
-
ORD
10h 40m1 stop
Volaris Logo
7:40 am - 7:04 pm
ORD
-
SJD
13h 24m1 stop
$329Volaris
Mon, Apr 13 - Sun, Apr 26
Viva Logo
8:30 am - 11:50 pm
SJD
-
ORD
14h 20m1 stop
Viva Logo
12:55 am - 4:30 pm
ORD
-
SJD
16h 35m1 stop
$347Viva
Fri, Feb 13 - Thu, Feb 19
Multiple Airlines Logo
2:15 pm - 11:50 pm
SJD
-
ORD
32h 35m2 stops
Multiple Airlines Logo
11:59 pm - 4:30 pm
ORD
-
SJD
17h 31m1 stop
$349Multiple Airlines
Thu, Feb 19 - Tue, Feb 24
Volaris Logo
12:11 pm - 10:29 pm
SJD
-
ORD
9h 18m1 stop
Volaris Logo
11:59 pm - 11:30 am
ORD
-
SJD
12h 31m1 stop
$361Volaris
Thu, Feb 19 - Tue, Feb 24
United Airlines Logo
12:50 pm - 6:01 pm
SJD
-
ORD
4h 11mnonstop
United Airlines Logo
9:03 am - 1:03 pm
ORD
-
SJD
5h 00mnonstop
$372United Airlines
Fri, Feb 13 - Mon, Feb 16
United Airlines Logo
12:50 pm - 6:01 pm
SJD
-
ORD
4h 11mnonstop
United Airlines Logo
8:40 am - 2:42 pm
ORD
-
SJD
7h 02m1 stop
$373United Airlines
Fri, Feb 13 - Mon, Feb 16
Aeromexico Logo
6:05 am - 11:56 pm
SJD
-
ORD
16h 51m2 stops
Aeromexico Logo
2:54 pm - 10:27 pm
ORD
-
SJD
8h 33m1 stop
$377Aeromexico
Fri, Feb 13 - Mon, Feb 16
Aeromexico Logo
6:05 am - 10:31 pm
SJD
-
MDW
15h 26m2 stops
Aeromexico Logo
12:45 pm - 9:31 am
MDW
-
SJD
21h 46m2 stops
$378Aeromexico
Fri, Feb 13 - Mon, Feb 16
Delta Logo
4:56 pm - 8:40 am
SJD
-
ORD
14h 44m2 stops
Delta Logo
5:25 am - 5:37 pm
ORD
-
SJD
13h 12m2 stops
$378Delta
Thu, Feb 19 - Tue, Feb 24
Delta Logo
4:32 pm - 8:52 am
SJD
-
MDW
15h 20m2 stops
Delta Logo
5:31 pm - 8:40 am
MDW
-
SJD
16h 09m2 stops
$509Delta
Mon, Jan 12 - Sat, Jan 17

United Airlines flights from San José del Cabo to Chicago

Our best United Airlines deals on San José del Cabo to Chicago flight tickets
United Airlines
Feb 13
SJD12:50 pmSan José del Cabo Los Cabos
4h 11m
ORD6:01 pmChicago O'Hare Intl
Feb 16
ORD9:03 amChicago O'Hare Intl
5h 00m
SJD1:03 pmSan José del Cabo Los Cabos
$372
Find similar
United Airlines
Feb 13
SJD12:50 pmSan José del Cabo Los Cabos
4h 11m
ORD6:01 pmChicago O'Hare Intl
Feb 16
ORD8:40 amChicago O'Hare Intl
7h 02m
1 stop
SJD2:42 pmSan José del Cabo Los Cabos
$373
Find similar
United Airlines
Feb 13
SJD12:50 pmSan José del Cabo Los Cabos
4h 11m
ORD6:01 pmChicago O'Hare Intl
Feb 20
ORD5:50 pmChicago O'Hare Intl
18h 10m
1 stop
SJD11:00 amSan José del Cabo Los Cabos
$419
Find similar

Aeromexico flights from San José del Cabo to Chicago

Our best Aeromexico deals on San José del Cabo to Chicago flight tickets
Aeromexico
Feb 13
SJD6:05 amSan José del Cabo Los Cabos
16h 51m
2 stops
ORD11:56 pmChicago O'Hare Intl
Feb 16
ORD2:54 pmChicago O'Hare Intl
8h 33m
1 stop
SJD10:27 pmSan José del Cabo Los Cabos
$377
Find similar
Aeromexico
Feb 13
SJD6:05 amSan José del Cabo Los Cabos
15h 26m
2 stops
MDW10:31 pmChicago Midway
Feb 16
MDW12:45 pmChicago Midway
21h 46m
2 stops
SJD9:31 amSan José del Cabo Los Cabos
$378
Find similar
Aeromexico
Feb 13
SJD1:45 pmSan José del Cabo Los Cabos
7h 46m
1 stop
MDW10:31 pmChicago Midway
Feb 16
MDW6:00 amChicago Midway
9h 09m
1 stop
SJD2:09 pmSan José del Cabo Los Cabos
$379
Find similar

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 December 31, 2025.
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

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Mon 4/13

11:07 am-11:47 pm

1 stop10h 40m

Chicago O'Hare Intl

Sun 4/26

7:40 am-7:04 pm

1 stop13h 24m

$329

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 2/13

8:30 am-11:50 pm

1 stop14h 20m

Chicago O'Hare Intl

Thu 2/19

12:55 am-4:30 pm

1 stop16h 35m

$347

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 2/19

2:15 pm-11:50 pm

2 stops32h 35m

Chicago O'Hare Intl

Tue 2/24

11:59 pm-4:30 pm

1 stop17h 31m

$349

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 2/19

12:11 pm-10:29 pm

1 stop9h 18m

Chicago O'Hare Intl

Tue 2/24

11:59 pm-11:30 am

1 stop12h 31m

$361

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 2/13

12:50 pm-6:01 pm

Nonstop4h 11m

Chicago O'Hare Intl

Mon 2/16

9:03 am-1:03 pm

Nonstop5h 00m

$372

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 2/13

12:50 pm-6:01 pm

Nonstop4h 11m

Chicago O'Hare Intl

Mon 2/16

8:40 am-2:42 pm

1 stop7h 02m

$373

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 2/13

6:05 am-11:56 pm

2 stops16h 51m

Chicago O'Hare Intl

Mon 2/16

2:54 pm-10:27 pm

1 stop8h 33m

$377

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/13

6:05 am-10:31 pm

2 stops15h 26m

Chicago Midway

Mon 2/16

12:45 pm-9:31 am

2 stops21h 46m

$378

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 2/19

4:56 pm-8:40 am

2 stops14h 44m

Chicago O'Hare Intl

Tue 2/24

5:25 am-5:37 pm

2 stops13h 12m

$378

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mon 1/12

4:32 pm-8:52 am

2 stops15h 20m

Chicago Midway

Sat 1/17

5:31 pm-8:40 am

2 stops16h 09m

$509

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 Friday, the most expensive travel day of the week, you can expect to see flight prices from San José del Cabo to Chicago for around $781.

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 Los Cabos to Chicago flights?

There are 3 cabin classes available to choose from on San José del Cabo Los Cabos 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 12% 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 December 2025, prices for San José del Cabo to Chicago flights are approximately 29% 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

Best Price Found

$278

Fastest flight time

4h 09m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from San José del Cabo in the past 72 hours is $278. The best round-trip flight deal from San José del Cabo to Chicago found on momondo in the last 72 hours is $485.
The fastest flight from San José del Cabo to Chicago takes 4h 09m
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), Chicago Midway (MDW).
Search flight deals

  • 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. 4h 09m 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 $361Free CancellationRating
7.4
9,129 reviews
Search United Airlines flights

  • United Airlines Flights From San José del Cabo to Chicago

    The lowest priced United Airlines flight from San José del Cabo to Chicago from the last 72 hours was $361. Generally, United Airlines has 16 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 1/30
Fri 2/6
By creating a price alert you accept our terms of use and privacy policy.

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