$109 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 1/15. 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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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

Sun, Mar 15 - Sun, Mar 22
Volaris Logo
12:49 pm - 2:22 pmORD-SJD
27h 33m3 stops
Volaris Logo
4:43 pm - 5:36 amSJD-ORD
10h 53m1 stop
$412Volaris
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Fri, Jan 23 - Mon, Feb 2
American Airlines Logo
10:19 am - 2:16 pmORD-SJD
4h 57mnonstop
American Airlines Logo
1:52 pm - 7:15 pmSJD-ORD
4h 23mnonstop
$413American Airlines
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Fri, Dec 5 - Mon, Dec 8
American Airlines Logo
10:04 am - 2:00 pmORD-SJD
4h 56mnonstop
American Airlines Logo
3:00 pm - 6:46 amSJD-ORD
14h 46m1 stop
$414American Airlines
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Sun, Dec 21 - Wed, Dec 31
Delta Logo
7:05 pm - 11:16 amORD-SJD
17h 11m1 stop
Delta Logo
3:15 pm - 9:36 amSJD-ORD
17h 21m1 stop
$416Delta
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Tue, Dec 9 - Thu, Dec 11
Delta Logo
6:00 am - 12:10 pmMDW-SJD
7h 10m1 stop
Delta Logo
1:15 pm - 11:47 pmSJD-MDW
9h 32m1 stop
$416Delta
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Fri, Jan 9 - Sat, Jan 31
Volaris Logo
2:12 am - 11:30 amORD-SJD
10h 18m1 stop
Volaris Logo
12:11 pm - 10:29 pmSJD-ORD
9h 18m1 stop
$424Volaris
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Wed, Feb 4 - Mon, Feb 9
Viva Logo
12:55 am - 4:30 pmORD-SJD
16h 35m1 stop
Viva Logo
8:30 am - 11:50 pmSJD-ORD
14h 20m1 stop
$425Viva
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Wed, Feb 11 - Sat, Feb 14
Southwest Logo
6:15 am - 1:10 pmMDW-SJD
7h 55m1 stop
Southwest Logo
12:00 pm - 9:20 pmSJD-MDW
8h 20m1 stop
$427Southwest
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Tue, Feb 24 - Mon, Mar 2
Viva Logo
12:55 am - 4:30 pmORD-SJD
16h 35m1 stop
Viva Logo
9:00 am - 11:45 pmSJD-ORD
13h 45m2 stops
$430Viva
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Wed, Jan 7 - Sat, Jan 10
Southwest Logo
6:15 am - 1:10 pmMDW-SJD
7h 55m1 stop
Southwest Logo
12:55 pm - 8:25 pmSJD-MDW
6h 30m1 stop
$467Southwest
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Everything you should know

Cheapest round-trip
$412
Overall average: $669
Volaris
Sun 3/15Sun 3/22
ORD - SJD • 3 stops
Cheapest non-stop
$413
Typical prices: $555-$785
American Airlines
Fri 1/23Mon 2/2
ORD - SJD • Non-stop
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We hope you love your trip to Todos Santos!
Useful Info

Good to know

Low seasonAugust
Cheapest flight$109
Best time to beat the crowds with an average 10% 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 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 51m.

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

    5 direct flights run between Chicago and Todos Santos on a daily basis. On average, there are about 37 departures each week.

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

    Consider leaving on a Sunday 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 Mondays.

  • 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 Volaris for $109. Volaris offered a round-trip connection from $412 and American Airlines from $413.

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 33 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 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 4240 reviews
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

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.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

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.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

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.

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.

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

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

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

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.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

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.

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

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