$117 Find Cheap Flights from Chicago to Cabo San Lucas - Compare and Save

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 1/22. 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
$348
Typical prices: $456-$690
Volaris
Sun 10/4Fri 10/23
ORD - SJD • 1 stop
Cheapest non-stop
$483
Typical prices: $502-$663
United Airlines
Mon 9/28Thu 10/1
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

Sun, Oct 4 - Fri, Oct 23
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
$348Volaris
Mon, Aug 24 - Mon, Aug 31
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
$348Volaris
Wed, Oct 21 - Wed, Oct 28
Multiple Airlines Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Multiple Airlines Logo
12:36 pm - 11:59 pm
SJD
-
ORD
33h 23m
2 stops
$348Multiple Airlines
Tue, Oct 20 - Sat, Oct 24
Multiple Airlines Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
Multiple Airlines Logo
12:36 pm - 11:59 pm
SJD
-
ORD
33h 23m
2 stops
$348Multiple Airlines
Sat, Oct 17 - Sat, Oct 24
American Airlines Logo
10:35 pm - 12:23 pm
ORD
-
SJD
15h 48m
1 stop
American Airlines Logo
12:41 pm - 7:15 pm
SJD
-
ORD
4h 34mnonstop
$476American Airlines
Sun, Oct 25 - Fri, Oct 30
American Airlines Logo
9:00 am - 11:41 am
ORD
-
SJD
4h 41mnonstop
American Airlines Logo
12:41 pm - 7:15 pm
SJD
-
ORD
4h 34mnonstop
$483American Airlines
Wed, Sep 30 - Wed, Oct 7
United Airlines Logo
8:52 am - 11:25 am
ORD
-
SJD
4h 33mnonstop
United Airlines Logo
11:52 am - 6:07 pm
SJD
-
ORD
4h 15mnonstop
$483United Airlines
Mon, Sep 28 - Thu, Oct 1
United Airlines Logo
8:52 am - 11:25 am
ORD
-
SJD
4h 33mnonstop
United Airlines Logo
11:52 am - 6:07 pm
SJD
-
ORD
4h 15mnonstop
$483United Airlines
Sun, Oct 18 - Fri, Oct 23
Southwest Logo
6:30 am - 1:30 pm
MDW
-
SJD
9h 00m
1 stop
Southwest Logo
12:25 pm - 12:55 am
SJD
-
MDW
10h 30m
1 stop
$498Southwest
Mon, Nov 16 - Fri, Nov 20
Southwest Logo
5:45 am - 12:10 pm
MDW
-
SJD
7h 25m
1 stop
Southwest Logo
2:45 pm - 11:45 pm
SJD
-
MDW
8h 00m
1 stop
$498Southwest
Useful Info

Good to know

Low season

August

Cheapest flight

$117
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 20% 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 27m.

  • 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 5 days, the cheapest one-way ticket between Chicago and Cabo San Lucas found on KAYAK was with Volaris for $121. Volaris offered a round-trip connection from $185 and United Airlines from $417.

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 11 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 4228 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

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

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

All planes flying to Mexico City are very old. Seats don’t even have power outlets.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

With a business flight, having a designated seat in the aircraft, I was denied boarding at the gate at last minute without any genuine explanation. The staff used profane language when asked for reasons. Viva overbooked and passenger had to pay for it. The food voucher that was provided did not even cover the the full meal and water for a single person. It should not be running in service.

Super BAD Everyone Behind the counters in Cancun Not Helpful At All And then on the second flight I Had to purchase Cancun - Guadalajara one of the flight Attendants Kick Out a Couple Out of the Plane and that Flight Attendant Had a Mask So People wouldn’t take pics of her and she was kind of Mean ! I Would NEVER Flight VIVA EVER THEY ARE NOT FRIENDLY AT ALL ! People think They Are Cheap but They Arent!!!

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.

THE AIRLINE FUCKEN SUCKS... NO DAMN PROFESIONALS.. NO CURTESY THEY CANCEL THE DAMN FLIGHT AS ITS ABOUT TO TAKE OFF

They need to have enough immigration forms for every one. They should offer free water to everyone, unless some one needs bottled water

They cancel the fly and don’t give a money refund.

The air conditioner was poor and we were delayed 1 hour for no apparent reasons and no information provided

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

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

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.

The app doesn’t work. I am having a lot of trouble checking in for flight tomorrow. Very disconcerting. Then they es t to charge extra for checking in at the airport;(

Overall good but we had a minor scare when a wind shear caused the plane to re take off on the first landing attempt. The crew handled it well and we landed safely on the second attempt

To many extra fees, poor customer service and very uncomfortable flight. No leg room and seat wont recline.

The whole experience was good. We left a little late but that seems pretty normal we it’s anybairline these days. No free snacks or drinks provided.

We paid for Premium seats and no one, EVER asked us for a drink or snack! No one

The flight was 3 hrs delayed and no remorse from airline

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

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