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Cheap flights from San José del Cabo to Chicago from $207

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.
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
1:24 am - 10:35 amORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
10h 11m1 stop Guadalajara Miguel Hidal
$385Volaris
Thu, Feb 11 - Sun, Feb 14
Viva Logo
8:45 am - 12:30 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
26h 45m2 stops Culiacán Fedl De Bachigualato Monterrey Gen Mariano Escobedo
Viva Logo
2:00 pm - 8:12 amORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
19h 12m2 stops Monterrey Gen Mariano Escobedo Culiacán Fedl De Bachigualato
$393Viva
Sat, Feb 6 - Thu, Feb 11
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 - 2:17 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
25h 17m1 stop Monterrey Gen Mariano Escobedo
$393Viva
Sat, Feb 6 - Thu, Feb 11
Viva Logo
8:45 am - 12:30 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
26h 45m2 stops Culiacán Fedl De Bachigualato Monterrey Gen Mariano Escobedo
Viva Logo
2:00 pm - 2:17 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
25h 17m1 stop Monterrey Gen Mariano Escobedo
$393Viva
Sat, Feb 6 - Thu, Feb 11
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
$394Volaris
Wed, Feb 10 - Mon, Feb 15
Viva 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
Viva Logo
1:05 am - 1:59 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
13h 54m1 stop Mexico City Benito Juarez
$398Viva
Fri, Nov 20 - Sat, Nov 28
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
12:35 am - 4:00 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
16h 25m1 stop Guadalajara Miguel Hidal
$404Viva
Sat, Feb 6 - Thu, Feb 11
Viva Logo
8:45 am - 12:30 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
26h 45m2 stops Culiacán Fedl De Bachigualato Monterrey Gen Mariano Escobedo
Viva 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
$404Viva
Sat, Feb 6 - Thu, Feb 11
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
$449United 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
9:25 pm - 11:43 amORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
15h 18m1 stop Houston George Bush Intcntl
$449United Airlines
Wed, Feb 10 - Mon, Feb 15

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Volaris flights from San José del Cabo to Chicago

Our best Volaris deals on San José del Cabo to Chicago flight tickets
Volaris
Feb 11
SJD3:38 pmSan José del Cabo Los Cabos
12h 05m
1 stop
ORD4:43 amChicago O'Hare Intl
Feb 14
ORD1:24 amChicago O'Hare Intl
10h 11m
1 stop
SJD10:35 amSan José del Cabo Los Cabos
$385
Volaris
Feb 10
SJD3:38 pmSan José del Cabo Los Cabos
12h 05m
1 stop
ORD4:43 amChicago O'Hare Intl
Feb 15
ORD6:29 amChicago O'Hare Intl
9h 31m
1 stop
SJD3:00 pmSan José del Cabo Los Cabos
$394
Volaris
Dec 22
SJD3:21 pmSan José del Cabo Los Cabos
7h 23m
1 stop
ORD11:44 pmChicago O'Hare Intl
Dec 31
ORD1:24 amChicago O'Hare Intl
10h 11m
1 stop
SJD10:35 amSan José del Cabo Los Cabos
$550

Viva flights from San José del Cabo to Chicago

Our best Viva deals on San José del Cabo to Chicago flight tickets
Viva
Feb 6
SJD8:45 amSan José del Cabo Los Cabos
26h 45m
2 stops
ORD12:30 pmChicago O'Hare Intl
Feb 11
ORD2:00 pmChicago O'Hare Intl
19h 12m
2 stops
SJD8:12 amSan José del Cabo Los Cabos
$393
Viva
Nov 20
SJD12:42 pmSan José del Cabo Los Cabos
9h 13m
1 stop
ORD10:55 pmChicago O'Hare Intl
Nov 28
ORD1:05 amChicago O'Hare Intl
13h 54m
1 stop
SJD1:59 pmSan José del Cabo Los Cabos
$398
Viva
Feb 6
SJD8:11 amSan José del Cabo Los Cabos
27h 19m
1 stop
ORD12:30 pmChicago O'Hare Intl
Feb 11
ORD12:35 amChicago O'Hare Intl
16h 25m
1 stop
SJD4:00 pmSan José del Cabo Los Cabos
$404

momondo Fare Finder

 
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

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 2/11

3:38 pm-4:43 am

1 stop12h 05m

Chicago O'Hare Intl

Sun 2/14

1:24 am-10:35 am

1 stop10h 11m

$385

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Sat 2/6

8:45 am-12:30 pm

2 stops26h 45m

Chicago O'Hare Intl

Thu 2/11

2:00 pm-8:12 am

2 stops19h 12m

$393

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Sat 2/6

8:11 am-12:30 pm

1 stop27h 19m

Chicago O'Hare Intl

Thu 2/11

2:00 pm-2:17 pm

1 stop25h 17m

$393

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Sat 2/6

8:45 am-12:30 pm

2 stops26h 45m

Chicago O'Hare Intl

Thu 2/11

2:00 pm-2:17 pm

1 stop25h 17m

$393

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

3:38 pm-4:43 am

1 stop12h 05m

Chicago O'Hare Intl

Mon 2/15

6:29 am-3:00 pm

1 stop9h 31m

$394

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Fri 11/20

12:42 pm-10:55 pm

1 stop9h 13m

Chicago O'Hare Intl

Sat 11/28

1:05 am-1:59 pm

1 stop13h 54m

$398

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Sat 2/6

8:11 am-12:30 pm

1 stop27h 19m

Chicago O'Hare Intl

Thu 2/11

12:35 am-4:00 pm

1 stop16h 25m

$404

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Sat 2/6

8:45 am-12:30 pm

2 stops26h 45m

Chicago O'Hare Intl

Thu 2/11

1:10 am-1:54 pm

1 stop13h 44m

$404
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

$449

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

Mon 2/15

9:25 pm-11:43 am

1 stop15h 18m

$449

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 typical price of a round-trip flight between San José del Cabo and Chicago?

Prices are currently low for flights on this route.

Typical prices usually range from $606 to $774.
The lowest price recently found on this route was $385.

What is the cheapest month to fly to Chicago?

The month of December is, on average, the cheapest month to fly to Chicago from San José del Cabo, with most prices found around $411. If you’re not able to fly to Chicago in December, then June is your next best option. Flight prices from San José del Cabo to Chicago during June average around $431.

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 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. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from San José del Cabo to Chicago for around $803.

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 to Chicago flights?

There are 2 cabin classes available to choose from on San José del Cabo 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 October 2026, prices for San José del Cabo to Chicago flights are approximately 24% 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

$207

Fastest flight time

4h 16m

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 $207. The best round-trip flight deal from San José del Cabo to Chicago found on momondo in the last 72 hours is $385.
The fastest flight from San José del Cabo to Chicago takes 4h 16m
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

Frequently asked questions about flying from San José del Cabo to Chicago

  • 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 16m 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 $329Free CancellationRating
7.3
10,436 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 $329. Generally, United Airlines has 2 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
Merrillville
New Buffalo
Hammond
Portage
Saint Joseph
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport