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Cheap flights from San José del Cabo to Chicago from $197

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 4/23. 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
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
$333Volaris
Wed, Apr 15 - Wed, Apr 22
Volaris Logo
3:36 pm - 12:55 am
SJD
-
ORD
7h 19m
1 stop
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
$358Volaris
Mon, Apr 13 - Mon, Apr 20
Alaska Airlines Logo
3:50 pm - 1:13 pm
SJD
-
ORD
19h 23m
1 stop
Alaska Airlines Logo
8:48 pm - 2:37 pm
ORD
-
SJD
19h 49m
1 stop
$362Alaska Airlines
Thu, Apr 23 - Mon, Apr 27
Alaska Airlines Logo
3:50 pm - 7:03 pm
SJD
-
ORD
25h 13m
1 stop
Alaska Airlines Logo
8:48 pm - 2:37 pm
ORD
-
SJD
19h 49m
1 stop
$363Alaska Airlines
Thu, Apr 23 - Mon, Apr 27
Alaska Airlines Logo
3:50 pm - 11:43 pm
SJD
-
ORD
29h 53m
1 stop
Alaska Airlines Logo
8:50 am - 11:37 am
ORD
-
SJD
28h 47m
1 stop
$364Alaska Airlines
Thu, Apr 23 - Mon, Apr 27
United Airlines Logo
11:52 am - 6:09 pm
SJD
-
ORD
4h 17mnonstop
United Airlines Logo
8:11 pm - 12:05 pm
ORD
-
SJD
17h 54m
1 stop
$373United Airlines
Thu, Apr 23 - Mon, Apr 27
United Airlines Logo
11:52 am - 6:09 pm
SJD
-
ORD
4h 17mnonstop
United Airlines Logo
8:40 am - 11:25 am
ORD
-
SJD
4h 45mnonstop
$374United Airlines
Thu, Apr 23 - Mon, Apr 27
Aeromexico Logo
7:05 pm - 4:26 pm
SJD
-
MDW
19h 21m
2 stops
Aeromexico Logo
6:00 am - 11:31 am
MDW
-
SJD
7h 31m
1 stop
$379Aeromexico
Thu, Apr 23 - Mon, Apr 27
Aeromexico Logo
12:36 pm - 10:28 pm
SJD
-
MDW
7h 52m
1 stop
Aeromexico Logo
6:00 am - 11:31 am
MDW
-
SJD
7h 31m
1 stop
$381Aeromexico
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
5:30 pm - 12:45 am
SJD
-
ORD
53h 15m
2 stops
Multiple Airlines Logo
1:49 pm - 12:25 pm
ORD
-
SJD
24h 36m
1 stop
$381Multiple Airlines
Mon, Apr 13 - Mon, Apr 20

Volaris flights from San José del Cabo to Chicago

Our best Volaris deals on San José del Cabo to Chicago flight tickets
Volaris
Apr 15
SJD7:47 pmSan José del Cabo Los Cabos
8h 05m
1 stop
ORD5:52 amChicago O'Hare Intl
Apr 22
ORD7:35 amChicago O'Hare Intl
13h 29m
1 stop
SJD7:04 pmSan José del Cabo Los Cabos
$333
Volaris
Apr 13
SJD3:36 pmSan José del Cabo Los Cabos
7h 19m
1 stop
ORD12:55 amChicago O'Hare Intl
Apr 20
ORD7:35 amChicago O'Hare Intl
13h 29m
1 stop
SJD7:04 pmSan José del Cabo Los Cabos
$358
Volaris
Apr 12
SJD7:47 pmSan José del Cabo Los Cabos
8h 05m
1 stop
ORD5:52 amChicago O'Hare Intl
Apr 19
ORD7:35 amChicago O'Hare Intl
13h 29m
1 stop
SJD7:04 pmSan José del Cabo Los Cabos
$406

American Airlines flights from San José del Cabo to Chicago

Our best American Airlines deals on San José del Cabo to Chicago flight tickets
American Airlines
Apr 13
SJD12:41 pmSan José del Cabo Los Cabos
6h 52m
1 stop
ORD9:33 pmChicago O'Hare Intl
Apr 20
ORD10:05 amChicago O'Hare Intl
4h 45m
SJD12:50 pmSan José del Cabo Los Cabos
$605
American Airlines
Apr 12
SJD4:25 pmSan José del Cabo Los Cabos
14h 25m
1 stop
ORD8:50 amChicago O'Hare Intl
Apr 19
ORD10:05 amChicago O'Hare Intl
4h 45m
SJD12:50 pmSan José del Cabo Los Cabos
$613
American Airlines
Apr 12
SJD11:32 amSan José del Cabo Los Cabos
4h 25m
ORD5:57 pmChicago O'Hare Intl
Apr 19
ORD10:05 amChicago O'Hare Intl
4h 45m
SJD12:50 pmSan José del Cabo Los Cabos
$1,062

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 March 2, 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

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 4/15

7:47 pm-5:52 am

1 stop8h 05m

Chicago O'Hare Intl

Wed 4/22

7:35 am-7:04 pm

1 stop13h 29m

$333

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Mon 4/13

3:36 pm-12:55 am

1 stop7h 19m

Chicago O'Hare Intl

Mon 4/20

7:35 am-7:04 pm

1 stop13h 29m

$358

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 4/23

3:50 pm-1:13 pm

1 stop19h 23m

Chicago O'Hare Intl

Mon 4/27

8:48 pm-2:37 pm

1 stop19h 49m

$362

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 4/23

3:50 pm-7:03 pm

1 stop25h 13m

Chicago O'Hare Intl

Mon 4/27

8:48 pm-2:37 pm

1 stop19h 49m

$363

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 4/23

3:50 pm-11:43 pm

1 stop29h 53m

Chicago O'Hare Intl

Mon 4/27

8:50 am-11:37 am

1 stop28h 47m

$364

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 4/23

11:52 am-6:09 pm

Nonstop4h 17m

Chicago O'Hare Intl

Mon 4/27

8:11 pm-12:05 pm

1 stop17h 54m

$373

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 4/23

11:52 am-6:09 pm

Nonstop4h 17m

Chicago O'Hare Intl

Mon 4/27

8:40 am-11:25 am

Nonstop4h 45m

$374

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 4/23

7:05 pm-4:26 pm

2 stops19h 21m

Chicago Midway

Mon 4/27

6:00 am-11:31 am

1 stop7h 31m

$379

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 4/23

12:36 pm-10:28 pm

1 stop7h 52m

Chicago Midway

Mon 4/27

6:00 am-11:31 am

1 stop7h 31m

$381

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Mon 4/13

5:30 pm-12:45 am

2 stops53h 15m

Chicago O'Hare Intl

Mon 4/20

1:49 pm-12:25 pm

1 stop24h 36m

$381

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 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 $379. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from San José del Cabo to Chicago for around $679.

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.

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

As of March 2026, prices for San José del Cabo to Chicago flights are approximately 12% cheaper 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

$274

Fastest flight time

3h 55m

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 $274. The best round-trip flight deal from San José del Cabo to Chicago found on momondo in the last 72 hours is $470.
The fastest flight from San José del Cabo to Chicago takes 3h 55m
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. 3h 55m 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
9,375 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 7 flights on this route every week with an average price of $420. 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
Valparaiso
Schererville
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.

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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