$69 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 4/13. 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.
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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

Fri, Apr 24 - Tue, Apr 28
Alaska Airlines Logo
3:52 pm - 11:29 am
ORD
-
SJD
21h 37m
2 stops
Alaska Airlines Logo
2:49 pm - 11:59 pm
SJD
-
ORD
31h 10m
1 stop
$429Alaska Airlines
Tue, Apr 21 - Mon, Apr 27
Multiple Airlines Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
Multiple Airlines Logo
12:02 pm - 12:45 am
SJD
-
ORD
10h 43m
2 stops
$430Multiple Airlines
Wed, Apr 29 - Sun, May 3
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
$431Volaris
Tue, Jun 2 - Mon, Jun 8
Volaris Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
$432Volaris
Thu, Apr 23 - Sun, Apr 26
Volaris Logo
7:35 am - 10:53 am
ORD
-
SJD
29h 18m
3 stops
Volaris Logo
7:47 pm - 12:55 am
SJD
-
ORD
27h 08m
3 stops
$433Volaris
Sun, May 3 - Thu, May 7
Aeromexico Logo
2:01 am - 9:01 am
ORD
-
SJD
9h 00m
1 stop
Aeromexico Logo
6:44 pm - 12:00 pm
SJD
-
ORD
15h 16m
2 stops
$439Aeromexico
Wed, May 6 - Wed, May 13
Delta Logo
12:52 pm - 10:18 pm
MDW
-
SJD
11h 26m
2 stops
Delta Logo
6:07 am - 9:09 pm
SJD
-
MDW
13h 02m
2 stops
$454Delta
Mon, Apr 27 - Fri, May 1
Southwest Logo
8:35 am - 1:25 pm
MDW
-
SJD
6h 50m
1 stop
Southwest Logo
2:20 pm - 5:45 am
SJD
-
MDW
13h 25m
1 stop
$465Southwest
Wed, Apr 15 - Wed, Apr 22
Delta Logo
6:00 am - 11:31 am
MDW
-
SJD
7h 31m
1 stop
Delta Logo
6:01 am - 10:28 pm
SJD
-
MDW
14h 27m
2 stops
$476Delta
Wed, May 13 - Wed, May 13
Southwest Logo
7:25 am - 12:10 pm
MDW
-
SJD
6h 45m
1 stop
Southwest Logo
2:20 pm - 11:20 pm
SJD
-
MDW
7h 00m
1 stop
$486Southwest
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 $454 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 $454.

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

The average price for all round-trip flights from Chicago 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 $623 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 $623.

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 $419, 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 $485 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $726 and $695 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 Tuesdays 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 3 weeks before departure, which saves you about 15% 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$69
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 22% 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.

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 4317 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

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. :/

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

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.