$117 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 2/6. 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, Dec 29 - Wed, Jan 7
Southwest Logo
5:25 am - 1:45 pmMDW-SJD
9h 20m2 stops
Southwest Logo
2:20 pm - 5:05 amSJD-MDW
13h 45m2 stops
$437Southwest
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Fri, Oct 3 - Tue, Oct 7
Volaris Logo
6:31 am - 6:00 pmORD-SJD
13h 29m1 stop
Volaris Logo
2:57 pm - 12:15 amSJD-ORD
7h 18m1 stop
$439Volaris
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Fri, Oct 31 - Fri, Nov 7
United Airlines Logo
7:10 am - 1:32 pmORD-SJD
8h 22m1 stop
United Airlines Logo
12:50 pm - 6:03 pmSJD-ORD
4h 13mnonstop
$440United Airlines
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Mon, Nov 17 - Mon, Nov 24
Delta Logo
12:33 am - 8:42 amORD-SJD
9h 09m1 stop
Delta Logo
1:17 pm - 12:02 amSJD-ORD
9h 45m1 stop
$446Delta
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Tue, Oct 14 - Tue, Oct 21
United Airlines Logo
5:01 am - 12:10 pmORD-SJD
9h 09m1 stop
United Airlines Logo
2:50 pm - 11:59 pmSJD-ORD
7h 09m1 stop
$447United Airlines
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Sun, Nov 16 - Sun, Nov 23
Delta Logo
5:32 am - 3:59 pmORD-SJD
11h 27m2 stops
Delta Logo
10:17 am - 12:02 amSJD-ORD
12h 45m2 stops
$450Delta
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Sun, Dec 14 - Sun, Dec 21
American Airlines Logo
8:25 am - 12:17 pmORD-SJD
4h 52mnonstop
American Airlines Logo
3:34 pm - 9:09 pmSJD-ORD
4h 35mnonstop
$452American Airlines
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Wed, Dec 3 - Sun, Dec 7
American Airlines Logo
5:00 am - 11:46 amORD-SJD
7h 46m1 stop
American Airlines Logo
5:27 pm - 8:39 amSJD-ORD
14h 12m1 stop
$455American Airlines
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Sat, Nov 1 - Mon, Nov 10
Viva Logo
1:05 am - 7:50 amORD-SJD
8h 45m1 stop
Viva Logo
5:05 pm - 11:20 amSJD-ORD
17h 15m1 stop
$460Viva
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Sat, Nov 1 - Tue, Dec 2
Viva Logo
1:05 am - 9:20 pmORD-SJD
22h 15m1 stop
Viva Logo
5:05 pm - 6:00 pmSJD-ORD
23h 55m1 stop
$461Viva
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Useful Info

Good to know

Low seasonAugust
Cheapest flight$117
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 16% 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 4h 52m.

  • How many flights are there between Chicago and Cabo San Lucas?

    3 direct flights run between Chicago and Cabo San Lucas on a daily basis. On average, there are about 23 departures each week.

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

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

  • 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 $117. Southwest offered a round-trip connection from $437 and Volaris from $439.

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 17 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 4242 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

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!

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

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

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.

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

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.

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

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