$170 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 1/18. 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.
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Good to know

Low season

February

High season

July

Cheapest flight

$170
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 44% 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

Prefer to fly non-stop from Los Cabos to Chicago?

Find which airlines fly direct from Los Cabos to Chicago, which days they fly and book direct flights.

Nonstop departures

Los Cabos to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Los Cabos

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

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.
7.2
American AirlinesOverall score based on 10000 reviews
7.2Comfort
7.6Boarding
7.0Entertainment
6.6Food
8.0Crew
Airline reviews

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.

8.0 ExcellentAnonymous, Nov 2024SFO - ORD
Read more American Airlines reviews

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

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

Fantastic. I am low vision and was impressed with how helpful and accommodating the service tam was. It was super appreciated! I was pleasantly surprised about how delicious the food was. Like, “I wish I had more even though I’m no longer hungry” delicious. 100% enjoyable trip.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

Flights were on time both ways, such a big plus! Staff was very accommodating and friendly. Question the choice of snacks that, which on both flights was dairy based. Appreciated using bottled water.

This flight was fine but had no time to breathe as the connection was late from Sea to ORD.. Super stressful. If we checked bags, the trip would have been very distressed.

Book cheap flights from Los Cabos to Chicago

Recent round-trip flight deals

5/14Wed
1 stopViva
29h 00mSJD-ORD
5/28Wed
1 stopViva
10h 15mORD-SJD
$293
5/13Tue
1 stopViva
29h 00mSJD-ORD
5/28Wed
1 stopViva
10h 15mORD-SJD
$314
5/13Tue
2 stops
12h 24mSJD-ORD
5/28Wed
2 stops
22h 11mORD-SJD
$319
5/13Tue
2 stops
12h 24mSJD-ORD
5/28Wed
3 stops
22h 11mORD-SJD
$357
12/17Tue
1 stopUnited Airlines
20h 12mSJD-ORD
12/31Tue
nonstopUnited Airlines
4h 53mORD-SJD
$449
12/18Wed
1 stopDelta
7h 31mSJD-MDW
12/31Tue
1 stopDelta
9h 02mMDW-SJD
$457
5/14Wed
1 stopDelta
11h 35mSJD-ORD
5/28Wed
2 stopsDelta
14h 01mORD-SJD
$466
12/18Wed
nonstopUnited Airlines
4h 09mSJD-ORD
12/31Tue
1 stopUnited Airlines
15h 39mORD-SJD
$483
5/14Wed
nonstopAmerican Airlines
4h 15mSJD-ORD
5/28Wed
nonstopAmerican Airlines
4h 30mORD-SJD
$503
5/14Wed
nonstopAmerican Airlines
4h 15mSJD-ORD
5/28Wed
1 stopAmerican Airlines
11h 10mORD-SJD
$507

Search by stops

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Recent one-way flight deals

1/18Sat
2 stopsViva
25h 00mSJD-ORD
$170
1/30Thu
1 stopViva
21h 20mSJD-ORD
$174
1/20Mon
1 stopVolaris
11h 58mSJD-ORD
$185
1/15Wed
1 stopVolaris
6h 54mSJD-ORD
$186
1/21Tue
1 stop
23h 00mSJD-ORD
$196
1/14Tue
2 stops
16h 10mSJD-ORD
$197
1/11Sat
2 stopsFrontier
33h 37mSJD-MDW
$222
12/28Sat
1 stopFrontier
9h 57mSJD-ORD
$241
1/10Fri
nonstopAmerican Airlines
4h 20mSJD-ORD
$257
12/19Thu
nonstopAmerican Airlines
4h 20mSJD-ORD
$263

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Last minute flights from Los Cabos to Chicago

Last minute flight, train and bus deals

11/22Fri
multi-stopViva
9h 55mSJD-ORD
11/25Mon
multi-stopViva
18h 35mORD-SJD
$293
11/22Fri
multi-stopViva
9h 55mSJD-ORD
11/24Sun
multi-stopViva
9h 05mORD-SJD
$312
11/22Fri
multi-stop
10h 49mSJD-ORD
11/25Mon
multi-stop
27h 47mORD-SJD
$349
11/22Fri
multi-stop
9h 55mSJD-ORD
11/25Mon
multi-stop
16h 40mORD-SJD
$357
11/22Fri
multi-stopVolaris
7h 18mSJD-ORD
11/25Mon
multi-stopVolaris
27h 47mORD-SJD
$360
11/22Fri
multi-stopVolaris
7h 18mSJD-ORD
11/25Mon
multi-stopVolaris
27h 47mORD-SJD
$363
11/22Fri
nonstopUnited Airlines
4h 09mSJD-ORD
12/1Sun
nonstopUnited Airlines
4h 53mORD-SJD
$722
11/22Fri
nonstopUnited Airlines
4h 09mSJD-ORD
11/25Mon
multi-stopUnited Airlines
18h 15mORD-SJD
$753
11/22Fri
multi-stopDelta
14h 11mSJD-ORD
12/1Sun
multi-stopDelta
14h 11mORD-SJD
$811
11/22Fri
multi-stopDelta
7h 11mSJD-MDW
11/25Mon
multi-stopDelta
7h 30mMDW-SJD
$853

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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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