$106 Find Cheap Flights from Chicago to Todos Santos - 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 Todos Santos departing on 7/18. 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
$364
Typical prices: $420-$587
Volaris, Viva
Sat 9/5Sat 9/12
ORD - SJD • 1 stop
Cheapest non-stop
$483
Typical prices: $477-$679
United Airlines
Mon 10/5Fri 10/9
ORD - SJD • Non-stop
Arrival airport
You can't fly directly to Todos Santos. It is served by San José del Cabo (SJD), located 37.8 miles from Todos Santos.
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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

Sat, Sep 5 - Sat, Sep 12
Multiple Airlines Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Multiple Airlines Logo
8:05 am - 11:59 pm
SJD
-
ORD
37h 54m
2 stops
$364Multiple Airlines
Sun, Nov 8 - Mon, Nov 16
Volaris Logo
6:23 am - 3:35 pm
ORD
-
SJD
10h 12m
1 stop
Volaris Logo
3:36 pm - 11:39 pm
SJD
-
ORD
7h 03m
1 stop
$368Volaris
Fri, Jul 10 - Sat, Jul 18
Volaris Logo
2:53 am - 8:16 am
ORD
-
SJD
7h 23m
1 stop
Volaris Logo
3:36 pm - 12:55 am
SJD
-
ORD
7h 19m
1 stop
$369Volaris
Mon, Oct 5 - Fri, Oct 9
Multiple Airlines Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Multiple Airlines Logo
9:02 am - 2:50 pm
SJD
-
ORD
27h 48m
2 stops
$370Multiple Airlines
Sun, Sep 27 - Sat, Oct 3
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
$371Volaris
Wed, Nov 18 - Sun, Nov 22
Volaris Logo
6:23 am - 3:35 pm
ORD
-
SJD
10h 12m
1 stop
Volaris Logo
11:16 am - 11:39 pm
SJD
-
ORD
11h 23m
1 stop
$372Volaris
Sun, Sep 13 - Tue, Sep 15
Delta Logo
6:05 am - 10:27 pm
MDW
-
SJD
18h 22m
2 stops
Delta Logo
9:14 am - 9:50 am
SJD
-
MDW
22h 36m
2 stops
$498Delta
Tue, Aug 4 - Fri, Aug 7
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
Delta Logo
1:12 pm - 1:10 pm
SJD
-
MDW
21h 58m
2 stops
$502Delta
Mon, Oct 5 - Fri, Oct 9
Southwest Logo
5:10 am - 1:40 pm
MDW
-
SJD
10h 30m
2 stops
Southwest Logo
1:30 pm - 12:45 am
SJD
-
MDW
9h 15m
2 stops
$535Southwest
Mon, Sep 14 - Fri, Sep 18
Southwest Logo
5:30 am - 12:50 pm
MDW
-
SJD
9h 20m
2 stops
Southwest Logo
10:40 am - 11:20 pm
SJD
-
MDW
10h 40m
2 stops
$546Southwest
Useful Info

Good to know

Low seasonAugust
Cheapest flight$106
Best time to beat the crowds with an average 7% 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 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 29m.

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

    1 direct flights run between Chicago and Todos Santos 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 Todos Santos?

    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 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 5 days, the cheapest one-way ticket between Chicago and Todos Santos found on KAYAK was with Volaris for $121. Volaris offered a round-trip connection from $185 and Viva from $223.

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 6 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 June.

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.
7.9
SouthwestOverall score based on 4248 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

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.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

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.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

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.

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.

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.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

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.

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.

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 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 Todos Santos

Complete your trip to Todos Santos with a hotel stay or car rental