$156 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 5/7. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Los Cabos to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
 Logo
8:25 am - 5:00 pmSJD-ORD
6h 35m1 stop
 Logo
6:34 pm - 8:25 amORD-SJD
15h 51m2 stops
Thu, Jun 19 - Tue, Jun 24
Volaris Logo
11:53 am - 12:15 amSJD-ORD
10h 22m1 stop
Volaris Logo
7:25 am - 8:04 pmORD-SJD
14h 39m1 stop
$367Volaris
Find Deal
Thu, Jun 19 - Tue, Jun 24
Volaris Logo
6:41 pm - 4:51 amSJD-ORD
8h 10m1 stop
Volaris Logo
1:55 am - 11:11 amORD-SJD
11h 16m1 stop
$383Volaris
Find Deal
Wed, Jul 23 - Tue, Jul 29
Volaris Logo
6:41 pm - 4:51 amSJD-ORD
8h 10m1 stop
Volaris Logo
7:25 am - 8:04 pmORD-SJD
14h 39m1 stop
$411Volaris
Find Deal
Wed, Jul 9 - Wed, Jul 16
Volaris Logo
11:53 am - 12:15 amSJD-ORD
10h 22m1 stop
Volaris Logo
7:25 am - 8:04 pmORD-SJD
14h 39m1 stop
$420Volaris
Find Deal
Tue, Jul 1 - Mon, Aug 4
American Airlines Logo
12:55 pm - 7:20 pmSJD-ORD
4h 25mnonstop
American Airlines Logo
9:15 am - 11:55 amORD-SJD
4h 40mnonstop
$439American Airlines
Find Deal
Wed, Jul 9 - Wed, Jul 16
Delta Logo
1:42 pm - 12:15 amSJD-ORD
8h 33m1 stop
Delta Logo
10:35 am - 10:00 pmORD-SJD
13h 25m2 stops
$440Delta
Find Deal
Wed, Jul 9 - Wed, Jul 16
American Airlines Logo
12:55 pm - 7:20 pmSJD-ORD
4h 25mnonstop
American Airlines Logo
5:00 am - 1:30 pmORD-SJD
10h 30m1 stop
$444American Airlines
Find Deal
Wed, Jul 9 - Wed, Jul 16
Delta Logo
6:03 am - 9:38 pmSJD-MDW
13h 35m2 stops
Delta Logo
10:39 am - 9:37 pmMDW-SJD
12h 58m2 stops
$446Delta
Find Deal
Thu, Jun 19 - Tue, Jun 24
Southwest Logo
11:55 am - 12:10 amSJD-MDW
10h 15m1 stop
Southwest Logo
6:15 am - 10:20 amMDW-SJD
6h 05m1 stop
$575Southwest
Find Deal
Thu, Jun 19 - Tue, Jun 24

Good to know

Low season

February

High season

July

Cheapest flight

$156
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 38% 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 8615 reviews
7.3Comfort
7.0Entertainment
7.7Boarding
8.1Crew
6.6Food
Airline reviews

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

2.0 MediocreJ.C., Mar 2025COS - ORD
Read more United Airlines reviews

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

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.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

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.

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.