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

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This Weekend's Flight Deals from Cabo San Lucas to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Sep 6 - Sat, Jan 10
SJD
Los Cabos Intl.
ORD
O'Hare Intl.
$431 Roundtrip, found 1 day ago
$431
Roundtrip
found 1 day ago
Select Volaris flight, departing Sat, Sep 6 from Los Cabos Intl. to O'Hare Intl., returning Sat, Jan 10, priced at $431 found 1 day ago

Airfares from $196 One Way, $362 Round Trip from Cabo San Lucas to Chicago

Prices starting at $362 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, Mar 13 - Mon, Mar 23
SJD
San José del Cabo
ORD
Chicago
$362 Roundtrip, found 4 days ago
$362
Roundtrip
found 4 days ago
Select Volaris flight, departing Fri, Mar 13 from San José del Cabo to Chicago, returning Mon, Mar 23, priced at $362 found 4 days ago
Fri, Oct 31 - Sun, Nov 9
SJD
San José del Cabo
ORD
Chicago
$401 Roundtrip, found 5 days ago
$401
Roundtrip
found 5 days ago
Select Aeromexico flight, departing Fri, Oct 31 from San José del Cabo to Chicago, returning Sun, Nov 9, priced at $401 found 5 days ago
Fri, Oct 17 - Mon, Oct 20
SJD
San José del Cabo
ORD
Chicago
$415 Roundtrip, found 2 days ago
$415
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Fri, Oct 17 from San José del Cabo to Chicago, returning Mon, Oct 20, priced at $415 found 2 days ago
Fri, Mar 13 - Mon, Mar 23
SJD
San José del Cabo
ORD
Chicago
$417 Roundtrip, found 4 days ago
$417
Roundtrip
found 4 days ago
Select Viva flight, departing Fri, Mar 13 from San José del Cabo to Chicago, returning Mon, Mar 23, priced at $417 found 4 days ago
Sat, Sep 13 - Mon, Sep 29
SJD
San José del Cabo
ORD
Chicago
$462 Roundtrip, found 4 days ago
$462
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Sep 13 from San José del Cabo to Chicago, returning Mon, Sep 29, priced at $462 found 4 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

9/10 Wonderful! (1,975 reviews)

Oct 16 - Oct 20

4 night stay

San José del Cabo (SJD) to Chicago (ORD)

Southwest Airlines • Non-stop • Coach

Chicago (ORD) to San José del Cabo (SJD)

Aeromexico • Non-stop • Coach
Price was $1,064, price is now $857 per person
$857
per person
found 4 hours ago
Attitude of the people was outstanding!! Very friendly and helpful.

Reviewed on Jun 13, 2025

The Emily Hotel
4.0-star property

The Emily Hotel

9.2/10 Wonderful! (1,192 reviews)

Oct 16 - Oct 20

4 night stay

San José del Cabo (SJD) to Chicago (ORD)

Southwest Airlines • Non-stop • Coach

Chicago (ORD) to San José del Cabo (SJD)

Aeromexico • Non-stop • Coach
Price was $1,725, price is now $1,333 per person
$1,333
per person
found 4 hours ago
Cute and trendy hotwl but there was a loud party on-site which ruined experience. It felt clean but our mini fridge had takeout left from former guest, so maid service obviously missed that.

Reviewed on Jul 26, 2025

Hilton Chicago/Magnificent Mile Suites
3.5-star property

Hilton Chicago/Magnificent Mile Suites

8.8/10 Excellent! (2,714 reviews)

Oct 16 - Oct 20

4 night stay

San José del Cabo (SJD) to Chicago (ORD)

Southwest Airlines • Non-stop • Coach

Chicago (ORD) to San José del Cabo (SJD)

Aeromexico • Non-stop • Coach
Price was $1,125, price is now $912 per person
$912
per person
found 4 hours ago
Very nice stay in the downtown area Great location and a lot of parking options around Very good facility and very clean

Reviewed on Aug 22, 2025

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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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Cabo San Lucas to Chicago

Orbitz combines guaranteed low prices with cutting-edge mobile tools for travel from Cabo San Lucas to Chicago to give you a travel experience that is second to none.

Bargain Travel at Your Fingertips

Orbitz provides the cheapest fares from Cabo San Lucas to Chicago. When reserving your flight you can mix and match a range of low cost airlines for you departing and returning domestic or international flights. This way you can travel on a budget while selecting the flights that suit your schedule.

Modern Tools for Fast-Paced Travel

Orbitz makes use of the latest technology to ensure that you are always kept up-to-date on the status of your Cabo San Lucas to Chicago flights. Through easy-to-use mobile Android and iPhone apps you can book low cost flights from Cabo San Lucas to Chicago and choose a range of cheap hotels to stay in.

Enjoy Stress-Free Travel with Flight Alerts

Once you have booked your flights from Cabo San Lucas to Chicago on Orbitz you will always be kept informed of any changes to your flight. When you opt into Orbitz’s free email and SMS alerts on your Cabo San Lucas to Chicago flights you can ask Orbitz to send the flight details to up to 6 other contacts, so keeping your family and business team informed is a cinch.

Frequent Flyer Program

For loyal Orbitz customers who fly from Cabo San Lucas to Chicago the chance to join our frequent flyer program is an added bonus. Simply log-on to your online account and input your frequent flyer number for future flights.

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.