$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.

Fri, Jun 5 - Mon, Jun 8
SJD
Los Cabos Intl.
ORD
O'Hare Intl.
$543 Roundtrip, found 5 days ago
$543
Roundtrip
found 5 days ago
Select Volaris flight, departing Fri, Jun 5 from Los Cabos Intl. to O'Hare Intl., returning Mon, Jun 8, priced at $543 found 5 days ago
Sun, Jun 7 - Mon, Jun 8
SJD
Los Cabos Intl.
MDW
Midway Intl.
$865 Roundtrip, found 4 days ago
$865
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sun, Jun 7 from Los Cabos Intl. to Midway Intl., returning Mon, Jun 8, priced at $865 found 4 days ago

Airfares from $196 One Way, $365 Round Trip from Cabo San Lucas to Chicago

Prices starting at $365 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.

Sat, Sep 5 - Mon, Sep 14
SJD
San José del Cabo
ORD
Chicago
$365 Roundtrip, found 4 days ago
$365
Roundtrip
found 4 days ago
Select Volaris flight, departing Sat, Sep 5 from San José del Cabo to Chicago, returning Mon, Sep 14, priced at $365 found 4 days ago
Sat, Sep 5 - Mon, Sep 14
SJD
San José del Cabo
ORD
Chicago
$376 Roundtrip, found 4 days ago
$376
Roundtrip
found 4 days ago
Select Volaris flight, departing Sat, Sep 5 from San José del Cabo to Chicago, returning Mon, Sep 14, priced at $376 found 4 days ago
Thu, Jul 9 - Tue, Jul 21
SJD
San José del Cabo
ORD
Chicago
$611 Roundtrip, found 1 day ago
$611
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Thu, Jul 9 from San José del Cabo to Chicago, returning Tue, Jul 21, priced at $611 found 1 day ago
Thu, Jul 9 - Tue, Jul 21
SJD
San José del Cabo
ORD
Chicago
$637 Roundtrip, found 1 day ago
$637
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jul 9 from San José del Cabo to Chicago, returning Tue, Jul 21, priced at $637 found 1 day ago
Wed, Jun 17 - Tue, Jun 30
SJD
San José del Cabo
ORD
Chicago
$649 Roundtrip, found 6 days ago
$649
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jun 17 from San José del Cabo to Chicago, returning Tue, Jun 30, priced at $649 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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Cabo San Lucas to Chicago

Whether you want to book cheap flights from Cabo San Lucas to Chicago or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Cabo San Lucas to Chicago flights.

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Planning on the Go

Book your flights from Cabo San Lucas to Chicago wherever you are with the Orbitz app for Android and iPhone. Or simply use m.orbitz.com on your mobile browser to search and book the Cabo San Lucas to Chicago flights that you want. And if you’re running late, you check your flight status and baggage claim information on your mobile device too too.

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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.

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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.