$167 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 11/12. 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

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Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Los Cabos to Chicago

Wed, Nov 26 - Sun, Nov 30
United Airlines Logo
12:50 pm - 6:03 pmSJD-ORD
4h 13mnonstop
United Airlines Logo
9:05 am - 1:03 pmORD-SJD
4h 58mnonstop
$355United Airlines
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Wed, Nov 26 - Sun, Nov 30
United Airlines Logo
3:46 pm - 11:59 pmSJD-ORD
7h 13m1 stop
United Airlines Logo
9:05 am - 1:03 pmORD-SJD
4h 58mnonstop
$361United Airlines
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Thu, Oct 30 - Thu, Nov 6
Volaris Logo
11:53 am - 12:15 amSJD-ORD
10h 22m1 stop
Volaris Logo
6:23 am - 3:25 pmORD-SJD
10h 02m1 stop
$362Volaris
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Fri, Oct 31 - Thu, Nov 6
Volaris Logo
11:53 am - 12:15 amSJD-ORD
10h 22m1 stop
Volaris Logo
6:23 am - 3:25 pmORD-SJD
10h 02m1 stop
$373Volaris
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Fri, Feb 13 - Mon, Feb 16
Aeromexico Logo
10:54 am - 11:18 pmSJD-ORD
11h 24m1 stop
Aeromexico Logo
1:00 am - 10:04 amORD-SJD
10h 04m1 stop
$383Aeromexico
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Fri, Feb 13 - Mon, Feb 16
Aeromexico Logo
10:54 am - 11:18 pmSJD-ORD
11h 24m1 stop
Aeromexico Logo
1:00 am - 2:40 pmORD-SJD
14h 40m1 stop
$384Aeromexico
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Thu, Oct 30 - Wed, Nov 5
Multiple Airlines Logo
7:00 pm - 2:12 pmSJD-ORD
17h 12m1 stop
Multiple Airlines Logo
12:55 am - 4:35 pmORD-SJD
16h 40m1 stop
$395Multiple Airlines
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Fri, Oct 31 - Thu, Nov 6
Multiple Airlines Logo
2:15 pm - 11:30 pmSJD-ORD
31h 15m2 stops
Multiple Airlines Logo
11:59 pm - 2:56 pmORD-SJD
15h 57m1 stop
$396Multiple Airlines
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Wed, Nov 26 - Sun, Nov 30
American Airlines Logo
5:26 pm - 8:44 amSJD-ORD
14h 18m1 stop
American Airlines Logo
5:00 am - 3:23 pmORD-SJD
11h 23m1 stop
$413American Airlines
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Sat, Nov 1 - Sat, Nov 15
American Airlines Logo
12:45 pm - 7:10 pmSJD-ORD
4h 25mnonstop
American Airlines Logo
8:50 pm - 11:43 amORD-SJD
15h 53m1 stop
$449American Airlines
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Everything you should know

Cheapest round-trip
$355
Typical prices: $411-580
United Airlines
Wed 11/26Sun 11/30
SJD - ORD • Non-stop
Cheapest one-way
$167
Typical prices: $286-365
Viva
Wed 11/12
SJD - ORD • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$167
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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.

Reviews of the top airline 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 8929 reviews
7.1Entertainment
8.1Crew
7.7Boarding
6.6Food
7.3Comfort
Airline reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

8.0 ExcellentAnonymous, Aug 2025YOW - ORD
Read more United Airlines reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Valparaiso
Lansing
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

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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