$196 Cheap flight deals from Cabo San Lucas (SJD) to Chicago (CHI)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Airfares from $196 One Way, $358 Round Trip from Cabo San Lucas to Chicago

Prices starting at $358 for return flights and $196 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Feb 13 - Tue, Feb 17
SJD
San José del Cabo
ORD
Chicago
$358 Roundtrip, found 1 day ago
$358
Roundtrip
found 1 day ago
Select Volaris flight, departing Fri, Feb 13 from San José del Cabo to Chicago, returning Tue, Feb 17, priced at $358 found 1 day ago
Thu, Oct 16 - Mon, Oct 20
SJD
San José del Cabo
ORD
Chicago
$384 Roundtrip, found 6 days ago
$384
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Thu, Oct 16 from San José del Cabo to Chicago, returning Mon, Oct 20, priced at $384 found 6 days ago
Fri, Nov 14 - Mon, Nov 17
SJD
San José del Cabo
ORD
Chicago
$392 Roundtrip, found 3 days ago
$392
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Fri, Nov 14 from San José del Cabo to Chicago, returning Mon, Nov 17, priced at $392 found 3 days ago
Thu, Aug 21 - Sun, Aug 24
SJD
San José del Cabo
ORD
Chicago
$399 Roundtrip, found 5 days ago
$399
Roundtrip
found 5 days ago
Select Aeromexico flight, departing Thu, Aug 21 from San José del Cabo to Chicago, returning Sun, Aug 24, priced at $399 found 5 days ago
Tue, Oct 14 - Mon, Oct 20
SJD
San José del Cabo
ORD
Chicago
$399 Roundtrip, found 6 days ago
$399
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Oct 14 from San José del Cabo to Chicago, returning Mon, Oct 20, priced at $399 found 6 days ago

More About Flying To Chicago from Cabo San Lucas

Route Information for Flights from Cabo San Lucas to Chicago

Origin Airport IATA Code
SJD
Destination Airport IATA Code
CHI
Distance
1806 mi
Direct Flight Airlines
American Airlines
Earliest Flight Arrival
1:10AM UTC
Latest Flight Arrival
1:10AM UTC

Cabo San Lucas to Chicago

For guaranteed low prices on flights from Cabo San Lucas to Chicago, search no further than Orbitz. Planning the perfect trip is simple with Orbitz; our range of bargain holiday packages and cutting edge mobile tools makes it quick and easy.

Mobile Movers

Never miss out on bargain prices on Cabo San Lucas to Chicago flights with free mobile apps for Android and iPhone. On the road? Not a problem – just use m.orbitz.com in your mobile browser to book flights from Cabo San Lucas to Chicago or check the latest details of your flights.

All-in-One

With Orbitz’s Display Matrix, it is so easy to book your perfect vacation package. Just add in flights from Cabo San Lucas to Chicago, decide if you want hotels and car rental included and click the button! Orbitz’s Display Matrix clearly shows all the deals and great savings available, including extra discounts, such as free nights.

Cheap Flights Equals Extra Miles

Enjoy great deals on Cabo San Lucas to Chicago flights and rack up those air miles at the same time! With Orbitz you just add in your frequent flyer number when asked and your qualifying miles are instant. Store your number to your account profile and next time you book your miles will be automatically added.

Safeguard with our Low Price Guarantee

Feel confident when you book your Cabo San Lucas to Chicago flights, a great hotel or a full vacation package that you are getting the best deal around. Orbitz’s low price guarantee assures you of peace of mind.

Frequently asked questions

Are there non-stop flights from Cabo San Lucas to Chicago?
United Airlines and American Airlines offer nonstop flights from San Jose del Cabo, Baja California Sur (SJD-Los Cabos Intl.) to ORD, which means you won't need to worry about swapping planes or waiting around during a stopover.
What is the shortest flight from Cabo San Lucas to Chicago?
Traveling from Los Cabos Airport to O'Hare Airport will take a minimum of 4 hours and 50 minutes. Treat yourself to a wine and watch a movie or two --- here's your chance to take some time out.
What airlines fly from Cabo San Lucas to Chicago most frequently?
The airlines that fly frequently between San Jose del Cabo, Baja California Sur (SJD-Los Cabos Intl.) and ORD include United Airlines (UA). This well-known option operates 17 flights on the route every month. American Airlines (AA) also services the route from Cabo San Lucas to Chicago. It's another excellent choice and offers 13 flights each month.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.