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Cheap flights from Chicago Midway Airport to Los Cabos from $157

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Los Cabos departing on 10/24. 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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Find the cheapest flights from Chicago Midway Airport to Los Cabos

Cheap round-trip flights

Southwest Logo
7:50 am - 12:50 pmMDW-SJD
7h 00m1 stop
Southwest Logo
1:45 pm - 11:40 pmSJD-MDW
7h 55m1 stop
$437Southwest
Find Deal
lun., sep. 15 - vie., sep. 19
Southwest Logo
7:00 am - 1:10 pmMDW-SJD
7h 10m1 stop
Southwest Logo
11:50 am - 10:10 pmSJD-MDW
9h 20m1 stop
$442Southwest
Find Deal
mié., nov. 19 - mar., dic. 2
Southwest Logo
5:00 am - 1:10 pmMDW-SJD
9h 10m2 stops
Southwest Logo
2:40 pm - 10:55 pmSJD-MDW
7h 15m1 stop
$447Southwest
Find Deal
mié., dic. 3 - mar., dic. 9
Southwest Logo
6:50 am - 1:25 pmMDW-SJD
8h 35m1 stop
Southwest Logo
1:35 pm - 10:25 pmSJD-MDW
6h 50m1 stop
$452Southwest
Find Deal
lun., oct. 6 - sáb., oct. 11
Delta Logo
5:34 pm - 3:29 pmMDW-SJD
22h 55m2 stops
Delta Logo
1:17 pm - 11:32 pmSJD-MDW
9h 15m1 stop
$457Delta
Find Deal
vie., nov. 14 - jue., nov. 20
Aeromexico Logo
6:00 am - 11:25 amMDW-SJD
7h 25m1 stop
Aeromexico Logo
6:05 am - 9:36 pmSJD-MDW
13h 31m2 stops
$497Aeromexico
Find Deal
jue., oct. 2 - dom., oct. 5
Delta Logo
1:14 pm - 12:12 pmMDW-SJD
23h 58m2 stops
Delta Logo
1:17 pm - 12:32 pmSJD-MDW
22h 15m2 stops
$511Delta
Find Deal
dom., nov. 16 - mié., dic. 3
Delta Logo
6:00 am - 7:23 pmMDW-SJD
15h 23m2 stops
Delta Logo
6:00 am - 9:36 pmSJD-MDW
13h 36m2 stops
$527Delta
Find Deal
mié., sep. 24 - mié., oct. 1
Aeromexico Logo
6:00 am - 10:30 pmMDW-SJD
17h 30m2 stops
Aeromexico Logo
1:17 pm - 9:44 pmSJD-MDW
7h 27m1 stop
$601Aeromexico
Find Deal
vie., nov. 28 - sáb., dic. 6
Aeromexico Logo
6:00 am - 11:42 amMDW-SJD
7h 42m1 stop
Aeromexico Logo
12:47 pm - 10:14 pmSJD-MDW
7h 27m1 stop
$617Aeromexico
Find Deal
mar., oct. 7 - sáb., oct. 11

Delta flights from Chicago Midway Airport to Los Cabos

Our best Delta deals on Chicago Midway Airport to Los Cabos flight tickets
Delta
Nov 14
MDW5:34 pmChicago Midway
22h 55m
2 stops
SJD3:29 pmSan José del Cabo Los Cabos
Nov 20
SJD1:17 pmSan José del Cabo Los Cabos
9h 15m
1 stop
MDW11:32 pmChicago Midway
$457
Find similar
Delta
Nov 16
MDW1:14 pmChicago Midway
23h 58m
2 stops
SJD12:12 pmSan José del Cabo Los Cabos
Dec 3
SJD1:17 pmSan José del Cabo Los Cabos
22h 15m
2 stops
MDW12:32 pmChicago Midway
$511
Find similar
Delta
Sep 24
MDW6:00 amChicago Midway
15h 23m
2 stops
SJD7:23 pmSan José del Cabo Los Cabos
Oct 1
SJD6:00 amSan José del Cabo Los Cabos
13h 36m
2 stops
MDW9:36 pmChicago Midway
$527
Find similar

Aeromexico flights from Chicago Midway Airport to Los Cabos

Our best Aeromexico deals on Chicago Midway Airport to Los Cabos flight tickets
Aeromexico
Oct 2
MDW6:00 amChicago Midway
7h 25m
1 stop
SJD11:25 amSan José del Cabo Los Cabos
Oct 5
SJD6:05 amSan José del Cabo Los Cabos
13h 31m
2 stops
MDW9:36 pmChicago Midway
$497
Find similar
Aeromexico
Nov 28
MDW6:00 amChicago Midway
17h 30m
2 stops
SJD10:30 pmSan José del Cabo Los Cabos
Dec 6
SJD1:17 pmSan José del Cabo Los Cabos
7h 27m
1 stop
MDW9:44 pmChicago Midway
$601
Find similar
Aeromexico
Oct 7
MDW6:00 amChicago Midway
7h 42m
1 stop
SJD11:42 amSan José del Cabo Los Cabos
Oct 11
SJD12:47 pmSan José del Cabo Los Cabos
7h 27m
1 stop
MDW10:14 pmChicago Midway
$617
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Los Cabos 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 agosto 26, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Los Cabos that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 9/15

7:50 am-12:50 pm

1 stop7h 00m

San José del Cabo Los Cabos

vie. 9/19

1:45 pm-11:40 pm

1 stop7h 55m

$437

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 11/19

7:00 am-1:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

mar. 12/2

11:50 am-10:10 pm

1 stop9h 20m

$442

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 12/3

5:00 am-1:10 pm

2 stops9h 10m

San José del Cabo Los Cabos

mar. 12/9

2:40 pm-10:55 pm

1 stop7h 15m

$447

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 10/6

6:50 am-1:25 pm

1 stop8h 35m

San José del Cabo Los Cabos

sáb. 10/11

1:35 pm-10:25 pm

1 stop6h 50m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 11/14

5:34 pm-3:29 pm

2 stops22h 55m

San José del Cabo Los Cabos

jue. 11/20

1:17 pm-11:32 pm

1 stop9h 15m

$457

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

jue. 10/2

6:00 am-11:25 am

1 stop7h 25m

San José del Cabo Los Cabos

dom. 10/5

6:05 am-9:36 pm

2 stops13h 31m

$497

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 11/16

1:14 pm-12:12 pm

2 stops23h 58m

San José del Cabo Los Cabos

mié. 12/3

1:17 pm-12:32 pm

2 stops22h 15m

$511

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 9/24

6:00 am-7:23 pm

2 stops15h 23m

San José del Cabo Los Cabos

mié. 10/1

6:00 am-9:36 pm

2 stops13h 36m

$527

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 11/28

6:00 am-10:30 pm

2 stops17h 30m

San José del Cabo Los Cabos

sáb. 12/6

1:17 pm-9:44 pm

1 stop7h 27m

$601

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mar. 10/7

6:00 am-11:42 am

1 stop7h 42m

San José del Cabo Los Cabos

sáb. 10/11

12:47 pm-10:14 pm

1 stop7h 27m

$617

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 Los Cabos from

How to get the cheapest flight ticket from Chicago Midway Airport to Los Cabos

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 Los Cabos?

The month of October is, on average, the cheapest month to fly to Los Cabos from Chicago Midway Airport, with most prices found around $505. The month of August is another great option to travel to Los Cabos, with average flight prices from Chicago Midway Airport averaging around $548.

What is the cheapest day to depart on your flight to Los Cabos?

The cheapest day to depart from Chicago Midway Airport to Los Cabos is on a Tuesday. Travelers who choose to depart for Los Cabos on a Tuesday will often find tickets for as low as $627. On the other hand, Saturday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,172.

What is the cheapest Chicago Midway to Los Cabos flight route?

Fly from Chicago Midway to San José del Cabo Los Cabos for the best Chicago Midway - Los Cabos flight prices

What cabin class options are available on Chicago Midway to Los Cabos flights?

There is only 1 cabin class available to choose from on Chicago Midway to Los Cabos 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 Chicago Midway Airport to Los Cabos flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Los Cabos.

Cheap Chicago Midway Airport to Los Cabos flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Los Cabos

Fastest flight time

4h 50m

Direct flights

Sun

Airports in Los Cabos

1 airport
The fastest flight from Chicago Midway Airport to Los Cabos takes 4h 50m
Direct flights go from Chicago Midway Airport to Los Cabos on Sunday. There are no airlines offering direct flights.
There is 1 airport near Los Cabos: San José del Cabo Los Cabos (SJD)
Search flight deals

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

    Prices for flights from Chicago Midway Airport to Los Cabos were last updated today.

  • How many operators does momondo search for flights from Chicago Midway Airport to Los Cabos?

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Los Cabos.

  • What documentation or ID do you need to fly to Los Cabos?

    The necessary travel and health documents for your Los Cabos trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Los Cabos?

Best airlines flying from Chicago Midway Airport to Los Cabos

Compare and see reviews for airlines that fly from Chicago Midway Airport to Los Cabos with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $545Free CancellationRating
8.0
4,243 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Los Cabos?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Los Cabos. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Los Cabos with flexible booking policies on momondo?

All flight searches from Chicago to Los Cabos on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Los Cabos?

Once you have performed a search for Chicago to Los Cabos 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 Chicago to Los Cabos right now. Can momondo alert me if prices change?

Price alerts on flights to Los Cabos from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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