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Cheap flights from San José del Cabo to Chicago from $179

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 1/10. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
12:50 pm - 6:03 pmSJD-ORD
4h 13mnonstop
United Airlines Logo
9:05 am - 1:03 pmORD-SJD
4h 58mnonstop
$324United Airlines
Find Deal
jue., nov. 13 - mar., nov. 18
Delta Logo
4:35 pm - 8:30 amSJD-ORD
14h 55m2 stops
Delta Logo
6:45 am - 1:35 pmORD-SJD
7h 50m1 stop
$330Delta
Find Deal
sáb., nov. 22 - sáb., nov. 29
Volaris Logo
12:11 pm - 10:29 pmSJD-ORD
9h 18m1 stop
Volaris Logo
7:23 am - 3:25 pmORD-SJD
10h 02m1 stop
$337Volaris
Find Deal
mar., mar. 3 - mar., mar. 17
Volaris Logo
12:59 pm - 11:19 amSJD-ORD
21h 20m2 stops
Volaris Logo
7:23 am - 3:25 pmORD-SJD
10h 02m1 stop
$376Volaris
Find Deal
mar., mar. 3 - mar., mar. 17
Aeromexico Logo
6:00 am - 12:01 amSJD-ORD
17h 01m2 stops
Aeromexico Logo
5:23 am - 12:10 pmORD-SJD
7h 47m1 stop
$383Aeromexico
Find Deal
jue., nov. 13 - dom., nov. 16
Aeromexico Logo
6:00 am - 10:30 pmSJD-ORD
15h 30m2 stops
Aeromexico Logo
5:23 am - 1:35 pmORD-SJD
9h 12m1 stop
$385Aeromexico
Find Deal
sáb., nov. 22 - sáb., nov. 29
Southwest Logo
12:35 pm - 11:20 pmSJD-MDW
9h 45m1 stop
Southwest Logo
5:25 am - 12:10 pmMDW-SJD
7h 45m1 stop
$386Southwest
Find Deal
jue., nov. 13 - mar., nov. 18
Multiple Airlines Logo
6:00 am - 10:41 pmSJD-ORD
15h 41m1 stop
Multiple Airlines Logo
9:20 am - 4:20 pmORD-SJD
8h 00m1 stop
$394Multiple Airlines
Find Deal
jue., nov. 13 - dom., nov. 16
Multiple Airlines Logo
3:15 pm - 12:02 amSJD-ORD
7h 47m1 stop
Multiple Airlines Logo
8:39 am - 4:00 pmORD-SJD
8h 21m1 stop
$404Multiple Airlines
Find Deal
lun., dic. 29 - vie., ene. 2
Southwest Logo
11:50 am - 9:15 pmSJD-MDW
8h 25m2 stops
Southwest Logo
8:15 am - 2:50 pmMDW-SJD
7h 35m1 stop
$463Southwest
Find Deal
jue., nov. 13 - mar., nov. 18

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 13
SJD12:50 pmSan José del Cabo Los Cabos
4h 13m
ORD6:03 pmChicago O'Hare Intl
Nov 18
ORD9:05 amChicago O'Hare Intl
4h 58m
SJD1:03 pmSan José del Cabo Los Cabos
$324
Find similar
United Airlines
Dec 10
SJD2:22 pmSan José del Cabo Los Cabos
18h 18m
1 stop
ORD9:40 amChicago O'Hare Intl
Dec 17
ORD9:03 amChicago O'Hare Intl
5h 00m
SJD1:03 pmSan José del Cabo Los Cabos
$370
Find similar
United Airlines
Nov 13
SJD12:50 pmSan José del Cabo Los Cabos
4h 13m
ORD6:03 pmChicago O'Hare Intl
Nov 27
ORD9:05 amChicago O'Hare Intl
4h 58m
SJD1:03 pmSan José del Cabo Los Cabos
$371
Find similar

Delta flights from San José del Cabo to Chicago

Our best Delta deals on San José del Cabo to Chicago flight tickets
Delta
Nov 22
SJD4:35 pmSan José del Cabo Los Cabos
14h 55m
2 stops
ORD8:30 amChicago O'Hare Intl
Nov 29
ORD6:45 amChicago O'Hare Intl
7h 50m
1 stop
SJD1:35 pmSan José del Cabo Los Cabos
$330
Find similar
Delta
Nov 1
SJD2:04 pmSan José del Cabo Los Cabos
7h 54m
1 stop
ORD11:58 pmChicago O'Hare Intl
Nov 15
ORD5:23 amChicago O'Hare Intl
7h 47m
1 stop
SJD12:10 pmSan José del Cabo Los Cabos
$414
Find similar
Delta
Nov 1
SJD2:04 pmSan José del Cabo Los Cabos
7h 54m
1 stop
ORD11:58 pmChicago O'Hare Intl
Nov 15
ORD6:45 amChicago O'Hare Intl
7h 50m
1 stop
SJD1:35 pmSan José del Cabo Los Cabos
$415
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 octubre 29, 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

jue. 11/13

12:50 pm-6:03 pm

Nonstop4h 13m

Chicago O'Hare Intl

mar. 11/18

9:05 am-1:03 pm

Nonstop4h 58m

$324

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

sáb. 11/22

4:35 pm-8:30 am

2 stops14h 55m

Chicago O'Hare Intl

sáb. 11/29

6:45 am-1:35 pm

1 stop7h 50m

$330

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

mar. 3/3

12:11 pm-10:29 pm

1 stop9h 18m

Chicago O'Hare Intl

mar. 3/17

7:23 am-3:25 pm

1 stop10h 02m

$337

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

mar. 3/3

12:59 pm-11:19 am

2 stops21h 20m

Chicago O'Hare Intl

mar. 3/17

7:23 am-3:25 pm

1 stop10h 02m

$376

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

jue. 11/13

6:00 am-12:01 am

2 stops17h 01m

Chicago O'Hare Intl

dom. 11/16

5:23 am-12:10 pm

1 stop7h 47m

$383

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

sáb. 11/22

6:00 am-10:30 pm

2 stops15h 30m

Chicago O'Hare Intl

sáb. 11/29

5:23 am-1:35 pm

1 stop9h 12m

$385

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

jue. 11/13

12:35 pm-11:20 pm

1 stop9h 45m

Chicago Midway

mar. 11/18

5:25 am-12:10 pm

1 stop7h 45m

$386

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

jue. 11/13

6:00 am-10:41 pm

1 stop15h 41m

Chicago O'Hare Intl

dom. 11/16

9:20 am-4:20 pm

1 stop8h 00m

$394

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

lun. 12/29

3:15 pm-12:02 am

1 stop7h 47m

Chicago O'Hare Intl

vie. 1/2

8:39 am-4:00 pm

1 stop8h 21m

$404

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

jue. 11/13

11:50 am-9:15 pm

2 stops8h 25m

Chicago Midway

mar. 11/18

8:15 am-2:50 pm

1 stop7h 35m

$463

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 $469. 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 $774.

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 3% 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 October 2025, 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

$256

Fastest flight time

3h 55m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from San José del Cabo in the past 72 hours is $256. The best round-trip flight deal from San José del Cabo to Chicago found on momondo in the last 72 hours is $441.
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 2 airports near Chicago: 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 11m 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
8,999 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 6 flights on this route every week with an average price of $527. 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
Crown Point
Munster
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