$106 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 5/26. 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

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Everything you should know

Cheapest round-trip
$371
Typical prices: $745-$543
Volaris, Viva
Tue 5/26Tue 6/2
ORD - SJD • 1 stop
Cheapest non-stop
$510
Typical prices: $732-$576
American Airlines
Mon 5/18Thu 5/21
ORD - SJD • Non-stop
Arrival airport
You can't fly directly to Cabo San Lucas. It is served by San José del Cabo (SJD), located 21.7 miles from Cabo San Lucas.
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Flight Deals
Useful Info
Flight Deals

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

Tue, May 26 - Tue, Jun 2
Multiple Airlines Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Multiple Airlines Logo
1:10 pm - 11:55 pm
SJD
-
ORD
8h 45m
1 stop
$371Multiple Airlines
Sun, Jul 12 - Sat, Jul 18
Volaris Logo
6:21 am - 2:51 pm
ORD
-
SJD
10h 30m
1 stop
Volaris Logo
12:02 pm - 11:47 pm
SJD
-
ORD
9h 45m
1 stop
$374Volaris
Sat, May 16 - Fri, May 22
Multiple Airlines Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Multiple Airlines Logo
8:40 am - 12:45 am
SJD
-
ORD
14h 05m
1 stop
$376Multiple Airlines
Fri, Oct 23 - Sat, Oct 31
Volaris Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
Volaris Logo
3:36 pm - 12:55 am
SJD
-
ORD
7h 19m
1 stop
$379Volaris
Wed, May 20 - Wed, May 27
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Volaris Logo
12:02 pm - 11:47 pm
SJD
-
ORD
9h 45m
1 stop
$380Volaris
Tue, Jun 16 - Sun, Jun 21
Volaris Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
Volaris Logo
3:36 pm - 12:55 am
SJD
-
ORD
7h 19m
1 stop
$381Volaris
Sat, May 30 - Tue, Jun 2
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Volaris Logo
12:06 pm - 12:55 am
SJD
-
ORD
10h 49m
1 stop
$382Volaris
Wed, May 27 - Mon, Jun 1
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
$383Volaris
Tue, Jun 16 - Sun, Jun 21
Volaris Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
Volaris Logo
3:36 pm - 12:55 am
SJD
-
ORD
7h 19m
1 stop
$384Volaris
Tue, Aug 11 - Tue, Sep 1
Delta Logo
6:00 am - 11:22 am
MDW
-
SJD
7h 22m
1 stop
Delta Logo
6:04 am - 9:46 pm
SJD
-
MDW
13h 42m
2 stops
$478Delta
Useful Info

Good to know

Low seasonAugust
Cheapest flight$106
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 21% 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 33m.

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

    1 direct flights run between Chicago and Cabo San Lucas on a daily basis. On average, there are about 9 departures each week.

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

    Consider leaving on a Wednesday and avoid Mondays 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 $119. Delta offered a round-trip connection from $184 and Volaris from $185.

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 41 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 February, March and April. 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 4314 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

4.0 OkayCrystal, Apr 2026
MSY - MDW
Read more Southwest reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Everything was great. The only issue is unfixable. Seats are too small. 😁🤪

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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

The flights were on time, the ground crew and on board crews were kind and efficient. The free snacks for Premium+ were good, similar to US First Class snacks. The plane were clean and bright! Complaints? The seats were worn and the seat-back pockets were missing. Overall, I'll book again with Volaris. Ignore the negative social media posts, understand what your fare includes, buy the add ons you need. We had no problems with our personal items and carryons.

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.

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

Complete your trip to Cabo San Lucas with a hotel stay or car rental