Midway

$286+ Cheap flights from San José del Cabo (SJD) to Midway (MDW)

SJD — MDW
Sep 25 — Oct 21
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Cheap flight deals from San José del Cabo to Midway

Cheapest flights from San José del Cabo to Midway

Fri 10/212:12 pm -
1 stop8h 32m
Mon 10/56:05 am -
1 stop7h 02m
Deal found 8/24$515
Thu 10/11:30 pm -
1 stop6h 50m
Sun 10/45:25 am -
1 stop7h 40m
Deal found 8/22$553
Sat 9/121:12 pm -
1 stop27h 52m
Wed 9/168:23 pm -
1 stop18h 03m
Deal found 8/26$572
Thu 10/11:30 pm -
1 stop6h 50m
Mon 10/55:25 am -
1 stop10h 15m
Deal found 8/22$576
Tue 10/271:30 pm -
1 stop7h 40m
Fri 10/305:15 am -
2 stops10h 25m
Deal found 8/24$585
Sun 9/131:12 pm -
1 stop27h 52m
Wed 9/168:23 pm -
1 stop18h 03m
Deal found 8/26$588
Fri 10/92:15 pm -
1 stop8h 55m
Sat 10/175:10 am -
1 stop7h 30m
Deal found 8/25$596

Find flight deals from San José del Cabo to Midway

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$515
(Delta)

One-way from

$286
(Kiwi.com)

Popular in

August

Cheapest in

December

Average price

$795
Provider with most accurate pricing for San José del Cabo Los Cabos-Chicago Midway flight deals.
Provider most trusted by Cheapflights users for San José del Cabo Los Cabos-Chicago Midway flights.
From San José del Cabo Los Cabos to Chicago Midway
One-way flight from San José del Cabo Los Cabos to Chicago Midway
Highest demand for flights based on searches. 13% potential increase in price ($76 potential increase over avg. RT price).
Cheapest flight prices on average. 7% potential price decrease ($35 potential savings vs. average RT price).
Average for round-trip flights in August 2026

Cheapflights Fare Finder

 
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

Fri 10/2

12:12 pm-10:44 pm

1 stop8h 32m

Chicago Midway

Mon 10/5

6:05 am-11:07 am

1 stop7h 02m

$515
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 10/1

1:30 pm-10:20 pm

1 stop6h 50m

Chicago Midway

Sun 10/4

5:25 am-11:05 am

1 stop7h 40m

$553

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Thu 10/1

1:30 pm-10:20 pm

1 stop6h 50m

Chicago Midway

Mon 10/5

5:25 am-1:40 pm

1 stop10h 15m

$576

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Tue 10/27

1:30 pm-11:10 pm

1 stop7h 40m

Chicago Midway

Fri 10/30

5:15 am-1:40 pm

2 stops10h 25m

$585

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Fri 10/2

10:45 am-11:05 pm

2 stops10h 20m

Chicago Midway

Mon 10/5

10:55 pm-11:20 am

2 stops14h 25m

$592

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Tue 9/29

12:12 pm-10:44 pm

1 stop8h 32m

Chicago Midway

Fri 10/2

12:35 pm-10:30 pm

2 stops11h 55m

$605

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Sat 9/12

9:04 am-6:05 pm

3 stops31h 01m

Chicago Midway

Wed 9/16

8:23 pm-12:26 pm

1 stop18h 03m

$630

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Sat 9/12

3:10 pm-7:04 pm

3 stops25h 54m

Chicago Midway

Wed 9/16

8:23 pm-3:59 pm

2 stops21h 36m

$673

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Fri 11/27

7:27 am-4:47 pm

1 stop8h 20m

Chicago Midway

Tue 12/1

6:20 pm-4:08 pm

2 stops22h 48m

$688
Cheapest one-way
Quickest one-way

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Wed 2/17

1:30 pm-10:10 pm

1 stop7h 40m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/21

Showing 1-10 of 18 resultsSorted by cheapest first
1
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  • Most accurate provider: When it comes to deals on San José del Cabo-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José del Cabo-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José del Cabo-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San José del Cabo-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San José del Cabo-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from San José del Cabo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San José del Cabo with our price prediction graph.
Estimated round-trip price

Related info for your journey

  • What airport do you fly from for flights from San José del Cabo to Chicago Midway?

    For a flight from San José del Cabo to Chicago Midway, you will be flying from Los Cabos. San José del Cabo Los Cabos (SJD) is just 6.6 mi from the center of the city. Los Cabos is the only San José del Cabo airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from San José del Cabo Los Cabos on a regular basis.

  • How long is the flight from San José del Cabo to Chicago Midway Airport?

    Delta and Southwest can get you from San José del Cabo to Chicago Midway Airport in just under 6h 50m. Your travel time can differ by up to 1h 42m. There are 1804 mi between San José del Cabo and Chicago Midway Airport. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from San José del Cabo to Midway that include hotel bookings?

    Yes. In addition to deals on San José del Cabo to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San José del Cabo to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José del Cabo to Midway.

  • Can I find deals for business class flights from San José del Cabo to Midway?

    Yes. Cheapflights offers flight deals from San José del Cabo to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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