$89 Find Cheap Flights from Chicago to Los Cabos

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Los Cabos departing on 4/27. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Los Cabos

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Los Cabos.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Los Cabos.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Book Cheap Chicago 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 Chicago 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 Chicago to Los Cabos

Thu, Apr 16 - Sun, Apr 26
Multiple Airlines Logo
8:53 pm - 3:04 pm
ORD
-
SJD
20h 11m
2 stops
Multiple Airlines Logo
4:49 pm - 12:09 pm
SJD
-
ORD
17h 20m
2 stops
$476Multiple Airlines
Tue, Feb 10 - Fri, Feb 13
Delta Logo
2:50 pm - 11:32 am
ORD
-
SJD
21h 42m
2 stops
Delta Logo
9:35 am - 9:01 pm
SJD
-
ORD
10h 26m
2 stops
$477Delta
Mon, Feb 23 - Sat, Feb 28
Delta Logo
6:00 am - 12:40 pm
MDW
-
SJD
7h 40m
1 stop
Delta Logo
1:45 pm - 10:31 pm
SJD
-
MDW
7h 46m
1 stop
$478Delta
Thu, Feb 19 - Tue, Feb 24
Delta Logo
2:54 pm - 10:27 pm
ORD
-
SJD
8h 33m
1 stop
Delta Logo
4:56 pm - 8:40 am
SJD
-
ORD
14h 44m
2 stops
$478Delta
Sat, May 2 - Tue, May 5
Aeromexico Logo
6:00 am - 11:31 am
MDW
-
SJD
7h 31m
1 stop
Aeromexico Logo
12:36 pm - 10:28 pm
SJD
-
MDW
7h 52m
1 stop
$479Aeromexico
Mon, Mar 9 - Fri, Mar 13
Southwest Logo
9:05 am - 12:00 pm
MDW
-
SJD
4h 55mnonstop
Southwest Logo
3:20 pm - 5:45 am
SJD
-
MDW
12h 25m
1 stop
$480Southwest
Tue, May 26 - Tue, Jun 2
Alaska Airlines Logo
9:00 am - 4:36 pm
ORD
-
SJD
9h 36m
1 stop
Alaska Airlines Logo
4:39 pm - 2:47 pm
SJD
-
ORD
20h 08m
2 stops
$480Alaska Airlines
Tue, May 12 - Fri, May 15
Aeromexico Logo
6:00 am - 5:50 pm
MDW
-
SJD
13h 50m
2 stops
Aeromexico Logo
6:55 pm - 9:45 pm
SJD
-
MDW
24h 50m
2 stops
$486Aeromexico
Wed, Feb 25 - Wed, Mar 4
Southwest Logo
5:05 am - 1:40 pm
MDW
-
SJD
9h 35m
1 stop
Southwest Logo
12:35 pm - 10:40 pm
SJD
-
MDW
9h 05m
2 stops
$489Southwest
Mon, Apr 20 - Sat, Apr 25
Volaris Logo
8:09 pm - 10:21 am
MDW
-
SJD
16h 12m
2 stops
Volaris Logo
7:37 pm - 12:46 pm
SJD
-
MDW
15h 09m
2 stops
$501Volaris
Booking Insights

KAYAK's insights & trends for Chicago to Los Cabos flights

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

What is the cheapest Chicago 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 found in the last 72 hours was to San José del Cabo, at $471 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 72 hours was $471.

Can I save money by flying with a layover from Chicago 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 $412, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago 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 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 to Los Cabos is September, when tickets cost $482 (return) on average. On the other hand, the most expensive months are March and February, when the average cost of round-trip tickets is $715 and $665 respectively.

What’s the cheapest day of the week to fly from Chicago to Los Cabos?

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

If you are looking for a flight deal from Chicago to Los Cabos, look for departures on Mondays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Los Cabos, Thursday is the cheapest day to fly and Tuesday is the most expensive.

How far in advance should I book a flight from Chicago 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 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 to Los Cabos, you should book around 4 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$89
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 19% 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 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 to Los Cabos.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 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 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 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 to Los Cabos up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

    The cheapest time of day to fly to Los Cabos is generally in the morning, when round-trip flights cost $626 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 $626.

Reviews of the top 5 airlines serving from Chicago 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 Chicago 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.
8.0
SouthwestOverall score based on 4267 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

It was cancelled at the last moment and the customer services seemed unnoticed to this change and hanged me off the phone the first time I called.

Staff especially Alan Hernandez was a great help with arrangements for my partner and me sit together. This made the trip do much more enjoyable. Thanks so much.

One of the flight was delayed an hour. We then boarded a new flight. We were told to unboard after some other time. To wait for the next flight for another hour. I paid for a short flight that turned in to half a day of travel.

No entertainment, charging, nor wifi on board but I napped for basically the entire time so it was alright. Was allowed to switch seats because the flight was not full but everyone was assigned to the back. Comfortable seats and we got moved to the emergency exit so the extra room was nice.

Painless trip. Only downside: No entertainment system (which we know with Viva & Volaris) and very small seat space. I'm petite and felt squizzed. I'm not sure how most overweight passengers do.

I was charge $90 for my bag more then the fight crazy!! And the plain hit a couple of birds on the take off bird strikes we returned back and had to change planes bad customer service everyone has an attitude problem!!! Bad experience!!!

The bad thing is they didnt send me the deatils about how much alowed bagage ehight 1 carryon or cheacking bag Also they just send in spanishlanfuage i couldnt understand emails

The boarding process was ridiculous. The boarded groups into a walkway just before the aerobridge (about 20 mins late), whilst we watch the crew stroll casually onto the plane, running late. And then they made us line up on then aerobridge with no aircon for 10 minutes before we boarded. Staff are just as ghetto as the customers. Wouldn’t fly again

They closed the gate over 25 minutes before departure and I didn’t get to board.

No empathy for my situation, arriving at the check-in counter 5 minutes after the deadline to deposit baggage due to a very delayed incoming intercontinental flight. The attendant simply stared past my shoulder and picked up the microphone to announce a "reminder that all passengers must arrive at least one hour before the flight" before speaking to the passenger behind me. I understand that there are rules above deadlines but at least show some damn empathy. It was Christmas morning and I'd been travelling for 20 hours for goodness sake!

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

It’s a 2 1/2 hour flight so good and comfort was not my real concern. Safety, easy, fast was what I was looking for. The crews were great, plane was clean, boarding from CBX was fantastic! Definitely traveling this way again.

The money you save flying volaris is not worth it

Is was a good short flight with some turbulence! I would fly Volaris again.

We had boarding passes for the next flight but we could not catch the flight in the small airport just because volaris closed the boarding at the counters an hour before for which we had to sepnd almost 3+ hours to catch next flight. There are hardly anyone who can speak english, but thank God, we have found an young man who could not only speak English but helped us book for the next flight. The air crafts are noisy and scary sometimes to hear that squeeking noises during the take off and during the flight. They do not even offer a cup of coffee for free in flight. The prices are super high and the services are zero. That’s pretty much for this airlines in summary.

Unfortunately it was not a good flight got canceled had to be at the airport all night long to get a different flight to another airport my first flight with Volaris was very bad. Poor services

The boarding , and it would be nice if they would let us know head of time about flight changes

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

The flight was delayed by two hours. I had paid for extended leg room. Due to the delay, the plane was different and I didn't end up having extended leg room. I finally was able to reach Volaris on Whats App and they gave me an airline credit. I wanted a refund to the credit card since I hardly ever fly Volaris. Other than that, it was a very comfortable flight.

In Mexico charges too much for my luggage and I ask for help and nothing one lady she just disappeared 😡😡😡😡😡never going to fly there

Everything you need to know for your flight to Los Cabos

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.