$160 Find Cheap Flights from Los Cabos to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 3/5. 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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Cheap Flight Deals from Los Cabos to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Los Cabos to Chicago 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.

Recent round-trip flight deals from Los Cabos to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Los Cabos to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:20 pm - 6:15 pmSJD-ORD
24h 55m1 stop
6:35 am - 2:50 pmORD-SJD
10h 15m1 stop
$289Viva
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Thu, May 8 - Tue, May 13
8:22 am - 6:15 pmSJD-ORD
7h 53m1 stop
1:40 am - 10:09 amORD-SJD
10h 29m1 stop
Thu, May 8 - Mon, May 12
3:32 pm - 12:15 amSJD-ORD
6h 43m1 stop
1:55 am - 2:50 pmORD-SJD
14h 55m1 stop
Wed, Jul 9 - Tue, Jul 15
6:41 pm - 4:51 amSJD-ORD
8h 10m1 stop
7:25 am - 8:04 pmORD-SJD
14h 39m1 stop
$396Volaris
Find Deal
Wed, Jul 9 - Wed, Jul 16
11:55 am - 12:15 amSJD-ORD
10h 20m1 stop
7:25 am - 8:04 pmORD-SJD
14h 39m1 stop
$402Volaris
Find Deal
Wed, Jul 23 - Wed, Jul 30
12:25 pm - 6:50 pmSJD-ORD
4h 25mnonstop
8:05 am - 10:25 amORD-SJD
4h 20mnonstop
$502American Airlines
Find Deal
Wed, Jul 9 - Wed, Jul 16
11:52 am - 6:10 pmSJD-ORD
4h 18mnonstop
7:45 am - 12:50 pmORD-SJD
7h 05m1 stop
$504United Airlines
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Thu, Apr 17 - Tue, Apr 22
12:25 pm - 6:50 pmSJD-ORD
4h 25mnonstop
7:14 am - 12:14 pmORD-SJD
7h 00m1 stop
$506American Airlines
Find Deal
Wed, Jul 9 - Wed, Jul 16
2:10 pm - 11:59 pmSJD-ORD
7h 49m1 stop
7:05 am - 9:17 pmORD-SJD
16h 12m2 stops
$509Aeromexico
Find Deal
Thu, Apr 17 - Tue, Apr 22
6:01 am - 11:59 pmSJD-ORD
15h 58m2 stops
7:05 am - 9:17 pmORD-SJD
16h 12m2 stops
$535Aeromexico
Find Deal
Thu, Apr 17 - Tue, Apr 22

Good to know

Low season

March

High season

July

Cheapest flight

$160
Best time to beat the crowds but there is an average 83% increase in price.
Most popular time to fly with an average 39% increase in price.
Flight from San José del Cabo to Chicago O'Hare Airport

FAQs for booking flights from Los Cabos to Chicago

  • How does KAYAK find such low prices on flights from Los Cabos to Chicago?

    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 Los Cabos to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Los Cabos 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 Los Cabos to Chicago?

    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 Chicago with an airline and back to Los Cabos with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Los Cabos to Chicago?

    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 Chicago from Los Cabos up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airlines flying from Los Cabos to Chicago

Need help choosing which airline to fly with from Los Cabos to Chicago? 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.
7.4
United AirlinesOverall score based on 8765 reviews
7.3Comfort
8.1Crew
7.7Boarding
6.7Food
7.1Entertainment
Airline reviews

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

10.0 ExcellentSam, Feb 2025GRU - ORD
Read more United Airlines reviews

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

Did not even get on board. Was told I needed an esta agreement. Was not aware of this when I booked the fare and not told about them

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Los Cabos

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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