$114 Find Cheap Flights from Chicago O'Hare Airport to Los Cabos - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Los Cabos departing on 11/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Book Cheap O'Hare Intl to Los Cabos Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Los Cabos that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Los Cabos

Sun, Jan 24 - Tue, Feb 2
Volaris Logo
1:19 am - 10:35 am
ORD
-
SJD
10h 16m
1 stop
Volaris Logo
3:36 pm - 11:39 pm
SJD
-
ORD
7h 03m
1 stop
$347Volaris
Thu, Sep 10 - Tue, Sep 15
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
$348Volaris
Wed, Oct 21 - Wed, Oct 28
Multiple Airlines Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Multiple Airlines Logo
12:36 pm - 11:59 pm
SJD
-
ORD
33h 23m
2 stops
$348Multiple Airlines
Tue, Oct 20 - Sat, Oct 24
Multiple Airlines Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
Multiple Airlines Logo
12:36 pm - 11:59 pm
SJD
-
ORD
33h 23m
2 stops
$348Multiple Airlines
Fri, Oct 9 - Sun, Oct 18
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
$348Volaris
Sun, Oct 18 - Sat, Oct 24
Multiple Airlines Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Multiple Airlines Logo
12:36 pm - 11:59 pm
SJD
-
ORD
33h 23m
2 stops
$349Multiple Airlines
Sat, Oct 17 - Sat, Oct 24
American Airlines Logo
10:35 pm - 12:23 pm
ORD
-
SJD
15h 48m
1 stop
American Airlines Logo
12:41 pm - 7:15 pm
SJD
-
ORD
4h 34mnonstop
$476American Airlines
Mon, Oct 5 - Fri, Oct 9
American Airlines Logo
9:00 am - 11:41 am
ORD
-
SJD
4h 41mnonstop
American Airlines Logo
12:41 pm - 7:15 pm
SJD
-
ORD
4h 34mnonstop
$483American Airlines
Mon, Sep 28 - Fri, Oct 2
United Airlines Logo
8:52 am - 11:25 am
ORD
-
SJD
4h 33mnonstop
United Airlines Logo
11:52 am - 6:07 pm
SJD
-
ORD
4h 15mnonstop
$483United Airlines
Mon, Oct 5 - Fri, Oct 9
United Airlines Logo
8:52 am - 11:25 am
ORD
-
SJD
4h 33mnonstop
United Airlines Logo
11:52 am - 6:07 pm
SJD
-
ORD
4h 15mnonstop
$483United Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Los Cabos flights

Get data-powered insights and trends into flights from O'Hare Intl to Los Cabos to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to Los Cabos flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Los Cabos from Chicago O'Hare Intl Airport found in the last 5 days was to San José del Cabo, at $539 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to San José del Cabo (SJD), and the cheapest round-trip airline ticket found on this route in the last 5 days was $539.

What is the cheapest time of day to fly to Los Cabos?

The average price for all round-trip flights from Chicago O'Hare Intl Airport to Los Cabos depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Los Cabos is generally in the morning, when round-trip flights cost $651 on average. The most expensive time of day to fly to Los Cabos is generally in the morning, which is peak travel time and where the average cost of a ticket is $651.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Los Cabos?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $490, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Los Cabos?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Los Cabos, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Los Cabos is September, when tickets cost $478 (return) on average. On the other hand, the most expensive months are November and June, when the average cost of round-trip tickets is $701 and $663 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Los Cabos?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Los Cabos clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Los Cabos on a Tuesday and more expensive on a Thursday. On your return trip to Chicago O'Hare Airport, you should consider flying back on a Thursday, and avoid Saturdays for better deals.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Los Cabos?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Los Cabos, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Los Cabos, you should book around 2 weeks before departure, which saves you about 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low season

August

Cheapest flight

$114
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago O'Hare Airport to San José del Cabo

FAQs - booking Los Cabos flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Los Cabos?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Los Cabos.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Los Cabos?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Los Cabos is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Los Cabos?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago O'Hare Airport to Los Cabos with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Los Cabos?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago O'Hare Airport to Los Cabos up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between Chicago O'Hare Intl Airport and Los Cabos per day?

    Each day, there are between 1 and 2 nonstop flights that take off from Chicago O'Hare Intl Airport and land in Los Cabos, with an average flight time of 4h 36m. The most common departure time is 8:00 am and most flights take off in the morning, while the most flights land at San José del Cabo. Each week, there are 4 flights. The most frequent day of departure is Saturday, when 50% of all weekly flights depart. The fewest flights depart on a Monday.

Reviews of the top 3 airlines serving from O'Hare Intl to Los Cabos

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Los Cabos. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Los Cabos? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 10046 reviews
7.3Comfort
8.1Crew
7.7Boarding
7.1Entertainment
6.6Food
Airline reviews

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

8.0 ExcellentArmedrest, Jul 2026
ORD - PAH
Read more United Airlines reviews

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

All planes flying to Mexico City are very old. Seats don’t even have power outlets.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

Overall a good red eye. Crew chatted very loudly the whole time making it difficult to sleep.

The fly was 2 hours delayed and the plane was old and dirty. A very umcorfotable flight, which I won't recomend to anyone

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

The app doesn’t work. I am having a lot of trouble checking in for flight tomorrow. Very disconcerting. Then they es t to charge extra for checking in at the airport;(

Overall good but we had a minor scare when a wind shear caused the plane to re take off on the first landing attempt. The crew handled it well and we landed safely on the second attempt

To many extra fees, poor customer service and very uncomfortable flight. No leg room and seat wont recline.

The whole experience was good. We left a little late but that seems pretty normal we it’s anybairline these days. No free snacks or drinks provided.

We paid for Premium seats and no one, EVER asked us for a drink or snack! No one

The flight was 3 hrs delayed and no remorse from airline

Everything you need to know for your flight to Los Cabos

Information on your arrival and departure airports