flıghtmap
SkyView
Hotels
FlightsGuidesMoreMembership
Log In

Direct flights from Chicago to San Jose del Cabo

Did you mean Flights from San Jose del Cabo to Chicago?

Flightmap/Flights from MDW/MDW to SJD

Chicago

United States

MDW

Chicago Midway International Airport

San Jose del Cabo

Mexico

SJD

Los Cabos International Airport

Route
Nonstop service available
Distance
1,805 miles
Marketing airlines
1 airline
Aircraft
2 aircraft types
Dates
Mar 11 – Apr 5, 2027

Observed award fares

A sample of one-way prices for one traveler from Roame’s fare cache. Points, fees, and seats describe the same observation. Availability can change; confirm with the loyalty program before transferring points.

Departure window: 2026-10-23 – 2026-11-21.

No recent fares appear in this limited preview. This does not mean the route is sold out. Use the search controls to check other dates and routes.

Explore flight routesCompare transfer partnersLearn how to book with points

Explore these airports and cities

  • Flights from MDW
  • Flights to SJD
  • Award flights to Chicago

Chicago to San Jose del Cabo route overview

Chicago Midway International Airport (MDW) serves Chicago; Los Cabos International Airport (SJD) serves San Jose del Cabo.

The airports are 1,805 miles apart by great-circle distance.

Roame's current schedule feed shows nonstop service from MDW to SJD.

Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.

Published schedule dates span Mar 11 – Apr 5, 2027.

Marketing airlines on the Chicago to San Jose del Cabo route

These are marketing airlines, including codeshare sellers. This list does not identify the operating airline for each flight; check the flight details before booking.

Aircraft flying from MDW to SJD

Frequently asked questions

Which airports serve the Chicago to San Jose del Cabo route?

Chicago Midway International Airport (MDW) is the origin airport and Los Cabos International Airport (SJD) is the destination airport.

How far is San Jose del Cabo from Chicago?

MDW and SJD are approximately 1,805 miles apart by great-circle distance.

Are there direct flights from MDW to SJD?

Yes. Roame's current schedule feed shows nonstop service from MDW to SJD.

Which airlines market flights from MDW to SJD?

Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.

Which aircraft fly from MDW to SJD?

Aircraft listed in the current schedule include Boeing 737 MAX 8 (7M8) and 7S7.

More routes from Chicago

  • ATLAtlantaUnited States
  • MSPMinneapolisUnited States
  • MCOOrlandoUnited States
  • LASLas VegasUnited States
  • DTWDetroitUnited States
  • PHXPhoenixUnited States
  • BWIBaltimoreUnited States
  • DENDenverUnited States
  • DALDallasUnited States
  • LGANew YorkUnited States
  • BNANashvilleUnited States
  • TPATampaUnited States
Get the app
Download on the App Store
Flights
SearchDiscoverSkyViewFlightMapsNEW
Hotels
SearchDeals on Stays
About
MembershipAbout usGift CardsGiveawaysHow it works
Resources
Credit CardsGuidesNewsletterRSS FeedAdvertise with usBecome an affiliate
Support
FAQDirectoryHelp centerContact usTerms of servicePrivacy policy
Get the app
Download on the App Store
Follow us
®

The fastest search engine for points travel.

© Copyright 2026 Roame Holdings, Inc. All Rights Reserved.
Sign Up
SearchGuides