$105 Find Cheap Flights from Chicago to Todos Santos

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 Todos Santos departing on 1/18. 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
$388
Overall average: $636
Volaris
Thu 4/9Thu 4/16
ORD - SJD • 1 stop
Cheapest non-stop
$415
Typical prices: $522-$735
American Airlines
Mon 1/26Thu 1/29
ORD - SJD • Non-stop
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Todos Santos (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 Todos Santos 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 Todos Santos

Thu, Apr 9 - Thu, Apr 16
Volaris Logo
7:40 am - 7:04 pm
ORD
-
SJD
13h 24m1 stop
Volaris Logo
3:36 pm - 12:39 am
SJD
-
ORD
7h 03m1 stop
$388Volaris
Sun, Mar 15 - Thu, Mar 19
Multiple Airlines Logo
12:59 pm - 11:30 am
ORD
-
SJD
24h 31m1 stop
Multiple Airlines Logo
8:20 pm - 12:45 am
SJD
-
ORD
26h 25m2 stops
$389Multiple Airlines
Sat, Jan 31 - Sat, Feb 7
Multiple Airlines Logo
11:59 pm - 7:15 am
ORD
-
SJD
8h 16m1 stop
Multiple Airlines Logo
2:15 pm - 11:50 pm
SJD
-
ORD
32h 35m2 stops
$390Multiple Airlines
Sun, Feb 8 - Sun, Feb 15
Viva Logo
1:20 am - 4:30 pm
ORD
-
SJD
40h 10m2 stops
Viva Logo
9:00 am - 11:50 pm
SJD
-
ORD
13h 50m2 stops
$391Viva
Fri, Mar 13 - Mon, Mar 16
Volaris Logo
11:59 pm - 11:30 am
ORD
-
SJD
13h 31m1 stop
Volaris Logo
4:08 pm - 5:36 am
SJD
-
ORD
11h 28m1 stop
$392Volaris
Mon, Feb 23 - Thu, Feb 26
Alaska Airlines Logo
7:00 am - 4:10 pm
ORD
-
SJD
10h 10m1 stop
Alaska Airlines Logo
12:21 pm - 11:59 pm
SJD
-
ORD
10h 38m1 stop
$398Alaska Airlines
Sun, Jan 18 - Thu, Jan 22
Aeromexico Logo
6:45 am - 2:09 pm
MDW
-
SJD
8h 24m1 stop
Aeromexico Logo
1:45 pm - 10:22 pm
SJD
-
MDW
7h 37m1 stop
$403Aeromexico
Tue, Feb 3 - Tue, Feb 10
Aeromexico Logo
6:00 am - 12:40 pm
MDW
-
SJD
7h 40m1 stop
Aeromexico Logo
6:25 pm - 10:22 pm
SJD
-
MDW
26h 57m2 stops
$430Aeromexico
Sat, Feb 7 - Wed, Feb 11
Delta Logo
10:53 am - 8:40 am
MDW
-
SJD
22h 47m2 stops
Delta Logo
1:45 pm - 10:22 pm
SJD
-
MDW
7h 37m1 stop
$435Delta
Tue, Mar 3 - Fri, Mar 6
Delta Logo
6:00 am - 5:37 pm
MDW
-
SJD
12h 37m2 stops
Delta Logo
6:05 am - 10:31 pm
SJD
-
MDW
15h 26m2 stops
$454Delta
Useful Info

Good to know

Low seasonAugust
Cheapest flight$105
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Chicago O'Hare Airport to San José del Cabo

When to book flights from Chicago to Todos Santos

Are your dates flexible? Find out the best times to travel from Chicago to Todos Santos 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 Todos Santos

  • Which airports will I be using when flying from Chicago to Todos Santos?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Todos Santos does not have its own airport so you’ll be flying into nearby San José del Cabo Los Cabos airport, which is 37.8 mi away.

  • How long does a flight from Chicago to Todos Santos take?

    Direct flights cover the 1,813 miles separating Chicago and Todos Santos in about 4h 42m.

  • How many flights are there between Chicago and Todos Santos?

    6 direct flights run between Chicago and Todos Santos on a daily basis. On average, there are about 47 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Todos Santos?

    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 Todos Santos?

    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 Todos Santos.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Todos Santos 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 Todos Santos?

    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 Todos Santos 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 Todos Santos?

    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 Todos Santos 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 Todos Santos?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Todos Santos found on KAYAK was with Viva for $88. Viva offered a round-trip connection from $266 and Delta from $278.

Top tips for finding cheap flights from Chicago to Todos Santos

  • There is no airport in Todos Santos. Instead, you’ll be flying into Los Cabos Airport when flying between Chicago and Todos Santos.
  • The cheapest flight from Chicago to Todos Santos was found 2 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 Todos Santos

 
Need help choosing which airline to fly with from Chicago to Todos Santos? 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 4258 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

10.0 ExcellentAnonymous, Dec 2025
DAL - CHS
Read more Southwest reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

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.

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!

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

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

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.

Better communication about delayed flight. I am thankful for a small credit for late flight.

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.

Everything you need to know for your flight from Chicago to Todos Santos

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