$109 Find Cheap Flights from Chicago to Cabo San Lucas

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 Cabo San Lucas departing on 9/4. 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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Cheap Flights from Chicago to Cabo San Lucas (CHI-SJD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Cabo San Lucas 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 Cabo San Lucas

Mon, Sep 29 - Sat, Oct 4
Volaris Logo
7:25 am - 7:54 pmORD-SJD
14h 29m1 stop
Volaris Logo
11:53 am - 12:15 amSJD-ORD
10h 22m1 stop
$303Volaris
Find Deal
Thu, Sep 11 - Mon, Sep 15
Volaris Logo
7:25 am - 7:54 pmORD-SJD
14h 29m1 stop
Volaris Logo
11:07 am - 11:32 pmSJD-ORD
10h 25m1 stop
$311Volaris
Find Deal
Fri, Sep 5 - Wed, Sep 10
 Logo
7:25 am - 7:54 pmORD-SJD
14h 29m1 stop
 Logo
8:30 am - 11:50 pmSJD-ORD
13h 20m1 stop
Thu, Sep 11 - Mon, Sep 15
 Logo
7:25 am - 7:54 pmORD-SJD
14h 29m1 stop
 Logo
8:30 am - 11:50 pmSJD-ORD
13h 20m1 stop
Sat, Aug 23 - Wed, Aug 27
Viva Logo
12:25 pm - 9:05 pmORD-SJD
10h 40m1 stop
Viva Logo
8:30 am - 11:50 pmSJD-ORD
13h 20m1 stop
$343Viva
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Sat, Nov 1 - Fri, Nov 7
Viva Logo
2:55 am - 4:35 pmORD-SJD
14h 40m1 stop
Viva Logo
9:55 pm - 3:00 pmSJD-ORD
16h 05m1 stop
$346Viva
Find Deal
Mon, Aug 25 - Thu, Aug 28
Southwest Logo
5:45 am - 9:45 amMDW-SJD
6h 00m1 stop
Southwest Logo
1:45 pm - 11:40 pmSJD-MDW
7h 55m1 stop
$401Southwest
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Sun, Aug 31 - Thu, Sep 4
Delta Logo
6:00 am - 4:40 pmMDW-SJD
12h 40m2 stops
Delta Logo
6:01 am - 9:26 pmSJD-MDW
13h 25m2 stops
$406Delta
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Mon, Sep 29 - Wed, Oct 8
Delta Logo
6:30 pm - 1:13 pmMDW-SJD
20h 43m2 stops
Delta Logo
2:23 pm - 8:55 amSJD-MDW
16h 32m2 stops
$410Delta
Find Deal
Sun, Nov 2 - Fri, Nov 7
Southwest Logo
5:15 am - 1:10 pmMDW-SJD
8h 55m1 stop
Southwest Logo
2:05 pm - 9:55 pmSJD-MDW
6h 50m1 stop
$454Southwest
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Useful Info

Good to know

Low seasonAugust
Cheapest flight$109
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Chicago O'Hare Airport to San José del Cabo

When to book flights from Chicago to Cabo San Lucas

Are your dates flexible? Find out the best times to travel from Chicago to Cabo San Lucas based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Cabo San Lucas

  • Which airports will I be using when flying from Chicago to Cabo San Lucas?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Cabo San Lucas does not have its own airport so you’ll be flying into nearby San José del Cabo Los Cabos airport, which is 21.7 mi away.

  • How long does a flight from Chicago to Cabo San Lucas take?

    Direct flights cover the 1,813 miles separating Chicago and Cabo San Lucas in about 9h 59m.

  • What’s the cheapest day of the week to fly between Chicago and Cabo San Lucas?

    Consider leaving on a Monday and avoid Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Sundays and the most expensive ones on Tuesdays.

  • How does KAYAK find such low prices on flights from Chicago to Cabo San Lucas?

    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 Cabo San Lucas.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Cabo San Lucas from Chicago 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 Cabo San Lucas?

    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 to Cabo San Lucas with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Cabo San Lucas?

    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 to Cabo San Lucas from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Cabo San Lucas?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Cabo San Lucas found on KAYAK was with Volaris for $109. Volaris offered a round-trip connection from $303 and Viva from $343.

Top tips for finding cheap flights from Chicago to Cabo San Lucas

  • There is no airport in Cabo San Lucas. Instead, you’ll be flying into Los Cabos Airport when flying between Chicago and Cabo San Lucas.
  • The cheapest flight from Chicago to Cabo San Lucas was found 49 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is September.

Reviews of the top 5 airlines serving Chicago to Cabo San Lucas

 
Need help choosing which airline to fly with from Chicago to Cabo San Lucas? 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 4246 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

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!

They no longer offer anything free to eat or drink, everything is sold, not even a bottle of water is offered for free.

I paid for Viva play and most of the time didn’t work and also I order some drinks and the price was to expensive.

The terminal and gate was never the right one announced in the Viva App, neither in screens, moved from one terminal to another

The smart/express line to check in was a mess, employees not doing the process smooth and quick, using their mobile phones, talking to their coworkers

My flight was changed 4 tienes , delaying my arrival lore than 5 hours

Everything was okay, but boarding begins late and when I was returning there was a gate change. The app never showed the change.

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

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.

Liked on time, rear entry and exit from plane Dislike the use of duct tape to repair seat rests

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

They check you everything before entering to waiting room, if you have any liquid they take it away even if you buy it inside the airport, no recommend volaris, for mi know Alaska airline is better

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

The worst. Kayak sent notification at 2am and 10am regarding the delay. Then sends a notification an hour before original depart time that it will depart on time. I had to wait 8 hours at the airport. My family had to pay for lodging in Guadalajara where I was landing for pick up.

The flight was delayed an hour and a half, and they would not update the board on when the flight was supposed to take off. Once the plane arrived, they started the boarding process before the plane was even ready for the passengers so we had to wait another 45 minutes on the tarmac while we waited for the plane to be ready for us. In my opinion, there is no point in starting the boarding process when you are not ready to board the plane. This just causes a crowded gate with everyone from zone one and zone two standing up going nowhere.

They were only able to give me a seat and not my travel companion, she had to fly on a different airline. unacceptable

Everything you need to know for your flight from Chicago to Cabo San Lucas

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