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Cheap flights from San José del Cabo to Chicago from $251

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 9/29. 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
1 adult, Economy, 0 bags

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
7:37 pm - 7:04 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
21h 27m2 stops Tijuana Rodriguez Guadalajara Miguel Hidal
Volaris Logo
8:23 pm - 11:29 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
17h 06m1 stop Guadalajara Miguel Hidal
$502Volaris
Sat, Aug 29 - Fri, Sep 4
Volaris Logo
7:37 pm - 7:04 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
21h 27m2 stops Tijuana Rodriguez Guadalajara Miguel Hidal
Volaris Logo
8:23 pm - 7:04 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
24h 41m2 stops Guadalajara Miguel Hidal Mexico City Benito Juarez
$520Volaris
Sat, Aug 29 - Fri, Sep 4
Volaris Logo
2:02 pm - 7:04 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
27h 02m3 stops Mexico City Felipe Ángeles Intl Tijuana Rodriguez Guadalajara Miguel Hidal
Volaris Logo
8:23 pm - 11:29 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
17h 06m1 stop Guadalajara Miguel Hidal
$597Volaris
Sun, Sep 13 - Mon, Sep 28
Delta Logo
12:12 pm - 10:44 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
8h 32m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 11:07 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
7h 02m1 stop Atlanta Hartsfield-Jackson
$649Delta
Sat, Sep 19 - Sat, Sep 26
Southwest Logo
2:05 pm - 12:30 amSJD  San José del Cabo Los Cabos-MDW Chicago Midway
8h 25m1 stop Phoenix Sky Harbor Intl
Southwest Logo
5:25 am - 9:45 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
6h 20m1 stop Houston Hobby
$705Southwest
Sun, Sep 13 - Mon, Sep 28
Southwest Logo
2:05 pm - 12:30 amSJD  San José del Cabo Los Cabos-MDW Chicago Midway
8h 25m1 stop Phoenix Sky Harbor Intl
Southwest Logo
5:30 am - 12:50 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
9h 20m2 stops Dallas Love Field Houston Hobby
$710Southwest
Sun, Sep 13 - Mon, Sep 28
Southwest Logo
11:35 am - 11:30 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
9h 55m2 stops Phoenix Sky Harbor Intl Las Vegas Harry Reid Intl
Southwest Logo
6:35 am - 12:15 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
7h 40m2 stops Lambert-St Louis Houston Hobby
$744Southwest
Sat, Sep 19 - Sat, Sep 26
Delta Logo
9:17 am - 10:44 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
11h 27m2 stops Mexico City Benito Juarez Atlanta Hartsfield-Jackson
Delta Logo
1:00 pm - 10:30 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
11h 30m2 stops Atlanta Hartsfield-Jackson Mexico City Benito Juarez
$855Delta
Thu, Sep 10 - Thu, Sep 17
Southwest Logo
1:45 pm - 10:20 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
6h 35m1 stop Houston Hobby
Southwest Logo
5:25 am - 9:45 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
6h 20m1 stop Houston Hobby
$882Southwest
Thu, Sep 10 - Thu, Sep 17
Delta Logo
12:12 pm - 10:36 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
8h 24m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 11:07 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
7h 02m1 stop Atlanta Hartsfield-Jackson
$927Delta
Sat, Aug 29 - Fri, Sep 4

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Volaris flights from San José del Cabo to Chicago Midway Airport

Our best Volaris deals on San José del Cabo to Chicago Midway Airport flight tickets
Volaris
Aug 29
SJD7:37 pmSan José del Cabo Los Cabos
21h 27m
2 stops
MDW7:04 pmChicago Midway
Sep 4
MDW8:23 pmChicago Midway
17h 06m
1 stop
SJD11:29 amSan José del Cabo Los Cabos
$502
Volaris
Aug 29
SJD7:37 pmSan José del Cabo Los Cabos
21h 27m
2 stops
MDW7:04 pmChicago Midway
Sep 4
MDW8:23 pmChicago Midway
24h 41m
2 stops
SJD7:04 pmSan José del Cabo Los Cabos
$520
Volaris
Sep 13
SJD2:02 pmSan José del Cabo Los Cabos
27h 02m
3 stops
MDW7:04 pmChicago Midway
Sep 28
MDW8:23 pmChicago Midway
17h 06m
1 stop
SJD11:29 amSan José del Cabo Los Cabos
$597

Delta flights from San José del Cabo to Chicago Midway Airport

Our best Delta deals on San José del Cabo to Chicago Midway Airport flight tickets
Delta
Sep 19
SJD12:12 pmSan José del Cabo Los Cabos
8h 32m
1 stop
MDW10:44 pmChicago Midway
Sep 26
MDW6:05 amChicago Midway
7h 02m
1 stop
SJD11:07 amSan José del Cabo Los Cabos
$649
Delta
Aug 7
SJD2:24 pmSan José del Cabo Los Cabos
20h 15m
2 stops
MDW12:39 pmChicago Midway
Aug 31
MDW6:05 amChicago Midway
7h 02m
1 stop
SJD11:07 amSan José del Cabo Los Cabos
$757
Delta
Sep 10
SJD9:17 amSan José del Cabo Los Cabos
11h 27m
2 stops
MDW10:44 pmChicago Midway
Sep 17
MDW1:00 pmChicago Midway
11h 30m
2 stops
SJD10:30 pmSan José del Cabo Los Cabos
$855

momondo Fare Finder

 
Customize your flight search to find flights from San José del Cabo to Chicago Midway Airport 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 August 6, 2026.
Use the filters below to find and compare flights from San José del Cabo to Chicago Midway Airport 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 - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Sat 8/29

7:37 pm-7:04 pm

2 stops21h 27m

Chicago Midway

Fri 9/4

8:23 pm-11:29 am

1 stop17h 06m

$502

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Sat 8/29

7:37 pm-7:04 pm

2 stops21h 27m

Chicago Midway

Fri 9/4

8:23 pm-7:04 pm

2 stops24h 41m

$520

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Sun 9/13

2:02 pm-7:04 pm

3 stops27h 02m

Chicago Midway

Mon 9/28

8:23 pm-11:29 am

1 stop17h 06m

$597

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Sat 9/19

12:12 pm-10:44 pm

1 stop8h 32m

Chicago Midway

Sat 9/26

6:05 am-11:07 am

1 stop7h 02m

$649

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Sun 9/13

2:05 pm-12:30 am

1 stop8h 25m

Chicago Midway

Mon 9/28

5:25 am-9:45 am

1 stop6h 20m

$705

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Sun 9/13

2:05 pm-12:30 am

1 stop8h 25m

Chicago Midway

Mon 9/28

5:30 am-12:50 pm

2 stops9h 20m

$710

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Sat 9/19

11:35 am-11:30 pm

2 stops9h 55m

Chicago Midway

Sat 9/26

6:35 am-12:15 pm

2 stops7h 40m

$744

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Thu 9/10

9:17 am-10:44 pm

2 stops11h 27m

Chicago Midway

Thu 9/17

1:00 pm-10:30 pm

2 stops11h 30m

$855
Quickest round-trip

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Thu 9/10

1:45 pm-10:20 pm

1 stop6h 35m

Chicago Midway

Thu 9/17

5:25 am-9:45 am

1 stop6h 20m

$882

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Sat 8/29

12:12 pm-10:36 pm

1 stop8h 24m

Chicago Midway

Fri 9/4

6:05 am-11:07 am

1 stop7h 02m

$927

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 Midway Airport

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

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

You could potentially save up to 40% on your flight if you consider stops on a San José del Cabo to Chicago Midway Airport flight.

When to book flights from San José del Cabo to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San José del Cabo to Chicago Midway Airport 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 Midway Airport (SJD to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San José del Cabo to Chicago Midway Airport

Fastest flight time

8h 32m

Direct flights

None
The fastest flight from San José del Cabo to Chicago Midway Airport takes 8h 32m
There are no direct flights from San José del Cabo to Chicago Midway Airport. There are no popular flight routes from San José del Cabo to Chicago Midway Airport.
Search flight deals

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

  • How far is San José del Cabo Los Cabos to Chicago Midway by plane?

    The straight-line distance from San José del Cabo Los Cabos to Chicago Midway is 1808.5 mi. Typically, this will take 8h 32m by plane in normal conditions.

  • When did momondo last update prices for flights from San José del Cabo Los Cabos Airport to Chicago Midway Airport?

    Prices for flights from San José del Cabo Los Cabos Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from San José del Cabo Los Cabos Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from San José del Cabo Los Cabos Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport 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 Midway Airport. 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 Midway Airport?

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
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?

It is quick and easy to find San José del Cabo to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from San José del Cabo to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from San José del Cabo with this policy.

How can momondo help me find flights from San José del Cabo to Chicago?

Once all potential San José del Cabo to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from San José del Cabo to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of San José del Cabo to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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