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Cheap flights from San José del Cabo to Chicago from $202

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
7:47 pm - 5:52 amSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
8h 05m1 stop Mexico City Benito Juarez
Volaris Logo
7:35 am - 7:04 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
13h 29m1 stop Mexico City Benito Juarez
$347Volaris
Sat, Oct 3 - Tue, Oct 6
Viva Logo
7:51 pm - 1:10 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
15h 19m1 stop Monterrey Gen Mariano Escobedo
Viva Logo
5:20 pm - 7:43 amORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
16h 23m1 stop Monterrey Gen Mariano Escobedo
$351Viva
Fri, Oct 2 - Mon, Oct 5
Viva Logo
8:25 am - 1:10 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
26h 45m1 stop Monterrey Gen Mariano Escobedo
Viva Logo
2:40 pm - 7:43 amORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
19h 03m1 stop Monterrey Gen Mariano Escobedo
$362Viva
Fri, Oct 9 - Sat, Oct 17
Volaris Logo
7:47 pm - 5:52 amSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
8h 05m1 stop Mexico City Benito Juarez
Volaris Logo
7:35 am - 7:04 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
13h 29m1 stop Mexico City Benito Juarez
$374Volaris
Thu, Oct 1 - Mon, Oct 5
Volaris Logo
12:06 pm - 12:55 amSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
10h 49m1 stop Guadalajara Miguel Hidal
Volaris Logo
7:35 am - 7:04 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
13h 29m1 stop Mexico City Benito Juarez
$377Volaris
Tue, Sep 29 - Fri, Oct 2
Volaris Logo
12:06 pm - 12:55 amSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
10h 49m1 stop Guadalajara Miguel Hidal
Volaris Logo
7:35 am - 7:04 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
13h 29m1 stop Mexico City Benito Juarez
$384Volaris
Thu, Oct 1 - Sun, Oct 4
Multiple Airlines Logo
7:52 pm - 1:10 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
15h 18m2 stops Culiacán Fedl De Bachigualato Monterrey Gen Mariano Escobedo
Multiple Airlines Logo
7:35 am - 7:04 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
13h 29m1 stop Mexico City Benito Juarez
$387Multiple Airlines
Fri, Oct 9 - Sat, Oct 17
Viva Logo
8:25 am - 1:10 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
26h 45m1 stop Monterrey Gen Mariano Escobedo
Viva Logo
2:40 pm - 7:43 amORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
19h 03m1 stop Monterrey Gen Mariano Escobedo
$390Viva
Fri, Oct 2 - Sat, Oct 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
7:29 am - 2:32 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
8h 03m1 stop Houston George Bush Intcntl
$486United Airlines
Tue, Nov 24 - Mon, Nov 30
United Airlines Logo
11:52 am - 6:07 pmSJD  San José del Cabo Los Cabos-ORD Chicago O'Hare Intl
4h 15mnonstop
United Airlines Logo
10:00 pm - 12:05 pmORD  Chicago O'Hare Intl-SJD San José del Cabo Los Cabos
16h 05m1 stop Denver Intl
$487United Airlines
Thu, Oct 1 - Mon, Oct 5

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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
Nov 24
SJD12:55 pmSan José del Cabo Los Cabos
4h 16m
ORD6:11 pmChicago O'Hare Intl
Nov 30
ORD7:29 amChicago O'Hare Intl
8h 03m
1 stop
SJD2:32 pmSan José del Cabo Los Cabos
$486
United Airlines
Oct 1
SJD11:52 amSan José del Cabo Los Cabos
4h 15m
ORD6:07 pmChicago O'Hare Intl
Oct 4
ORD10:00 pmChicago O'Hare Intl
17h 43m
1 stop
SJD1:43 pmSan José del Cabo Los Cabos
$487
United Airlines
Sep 19
SJD11:52 amSan José del Cabo Los Cabos
4h 15m
ORD6:07 pmChicago O'Hare Intl
Sep 22
ORD5:30 amChicago O'Hare Intl
7h 00m
1 stop
SJD10:30 amSan José del Cabo Los Cabos
$516

Viva flights from San José del Cabo to Chicago

Our best Viva deals on San José del Cabo to Chicago flight tickets
Viva
Oct 2
SJD7:51 pmSan José del Cabo Los Cabos
15h 19m
1 stop
ORD1:10 pmChicago O'Hare Intl
Oct 5
ORD5:20 pmChicago O'Hare Intl
16h 23m
1 stop
SJD7:43 amSan José del Cabo Los Cabos
$351
Viva
Oct 9
SJD8:25 amSan José del Cabo Los Cabos
26h 45m
1 stop
ORD1:10 pmChicago O'Hare Intl
Oct 17
ORD2:40 pmChicago O'Hare Intl
19h 03m
1 stop
SJD7:43 amSan José del Cabo Los Cabos
$362
Viva
Oct 2
SJD8:25 amSan José del Cabo Los Cabos
26h 45m
1 stop
ORD1:10 pmChicago O'Hare Intl
Oct 17
ORD2:40 pmChicago O'Hare Intl
19h 03m
1 stop
SJD7:43 amSan José del Cabo Los Cabos
$390

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

Sat 10/3

7:47 pm-5:52 am

1 stop8h 05m

Chicago O'Hare Intl

Tue 10/6

7:35 am-7:04 pm

1 stop13h 29m

$347

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Fri 10/2

7:51 pm-1:10 pm

1 stop15h 19m

Chicago O'Hare Intl

Mon 10/5

5:20 pm-7:43 am

1 stop16h 23m

$351

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Fri 10/9

8:25 am-1:10 pm

1 stop26h 45m

Chicago O'Hare Intl

Sat 10/17

2:40 pm-7:43 am

1 stop19h 03m

$362

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Thu 10/1

7:47 pm-5:52 am

1 stop8h 05m

Chicago O'Hare Intl

Mon 10/5

7:35 am-7:04 pm

1 stop13h 29m

$374

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Tue 9/29

12:06 pm-12:55 am

1 stop10h 49m

Chicago O'Hare Intl

Fri 10/2

7:35 am-7:04 pm

1 stop13h 29m

$377

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Thu 10/1

12:06 pm-12:55 am

1 stop10h 49m

Chicago O'Hare Intl

Sun 10/4

7:35 am-7:04 pm

1 stop13h 29m

$384

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Fri 10/9

7:52 pm-1:10 pm

2 stops15h 18m

Chicago O'Hare Intl

Sat 10/17

7:35 am-7:04 pm

1 stop13h 29m

$387

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Fri 10/2

8:25 am-1:10 pm

1 stop26h 45m

Chicago O'Hare Intl

Sat 10/17

2:40 pm-7:43 am

1 stop19h 03m

$390
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

Tue 11/24

12:55 pm-6:11 pm

Nonstop4h 16m

Chicago O'Hare Intl

Mon 11/30

7:29 am-2:32 pm

1 stop8h 03m

$486

San José del CaboChicago

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

SJDORD

San José del Cabo Los Cabos

Thu 10/1

11:52 am-6:07 pm

Nonstop4h 15m

Chicago O'Hare Intl

Mon 10/5

10:00 pm-12:05 pm

1 stop16h 05m

$487

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 month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from San José del Cabo, with most prices found around $353. If you’re not able to fly to Chicago in September, then December is your next best option. Flight prices from San José del Cabo to Chicago during December average around $411.

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 $469. 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 $616.

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.

Can stopping save me money on San José del Cabo to Chicago flights?

No. A direct flight is the cheapest option for a flight between San José del Cabo to Chicago.

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

As of August 2026, prices for San José del Cabo to Chicago flights are approximately 23% 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

$202

Fastest flight time

4h 15m

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 $202. The best round-trip flight deal from San José del Cabo to Chicago found on momondo in the last 72 hours is $347.
The fastest flight from San José del Cabo to Chicago takes 4h 15m
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).
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 15m 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?

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
7.4
10,127 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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