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Find cheap flights from Los Cabos to Chicago from $182

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 6/3. 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
0 bags
mer. 6/5
mer. 6/12

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Good to know

Low season

January

High season

May

Cheapest flight

$182
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 14% 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.

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, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 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, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Los Cabos

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 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, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

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 11118 reviews
8.1Crew
7.1Entertainment
6.7Food
7.2Comfort
7.7Boarding
Airline reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

8.0 ExcellentAnonymous, Apr 2024YUL - ORD
Read more about United Airlines reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

The CX617 from HK to BKK was delayed more than 1.5 hours.

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Book cheap flights from Los Cabos to Chicago

Recent round-trip flight deals

9/6ven.
1 stopUnited Airlines
7h 40mSJD-ORD
9/10mar.
1 stopUnited Airlines
15h 21mORD-SJD
$362
9/6ven.
1 stopDelta
9h 47mSJD-ORD
9/10mar.
2 stopsDelta
12h 32mORD-SJD
$365
9/6ven.
2 stopsAeromexico
15h 58mSJD-ORD
9/10mar.
1 stopAeromexico
7h 07mORD-SJD
$378
9/6ven.
1 stopAeromexico
16h 09mSJD-ORD
9/9lun.
1 stopAeromexico
10h 08mORD-SJD
$391
6/28ven.
1 stopAmerican Airlines
8h 08mSJD-ORD
7/3mer.
1 stopAmerican Airlines
10h 14mORD-SJD
$413
10/9mer.
1 stopVivaAerobus
14h 55mSJD-ORD
10/15mar.
1 stopVivaAerobus
16h 15mORD-SJD
$421
6/28ven.
1 stopAmerican Airlines
8h 08mSJD-ORD
7/4jeu.
1 stopAmerican Airlines
24h 09mORD-SJD
$439
10/9mer.
1 stopVivaAerobus
14h 55mSJD-ORD
10/16mer.
1 stopVivaAerobus
11h 10mORD-SJD
$449
6/28ven.
1 stopVolaris
14h 12mSJD-MDW
7/3mer.
1 stopVolaris
22h 04mMDW-SJD
$718
6/28ven.
1 stopVolaris
14h 12mSJD-MDW
7/3mer.
2 stopsVolaris
17h 22mMDW-SJD
$743

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Recent one-way flight deals

6/3lun.
1 stopVolaris
11h 53mSJD-ORD
$182
6/27jeu.
1 stopVolaris
11h 53mSJD-ORD
$198
5/31ven.
1 stopVivaAerobus
9h 25mSJD-ORD
$201
5/10ven.
1 stopVivaAerobus
15h 10mSJD-ORD
$218
5/31ven.
2 stopsDelta
13h 08mSJD-MDW
$227
5/31ven.
2 stopsDelta
12h 02mSJD-ORD
$227
6/27jeu.
nonstopAmerican Airlines
4h 20mSJD-ORD
$256
7/1lun.
1 stopAmerican Airlines
11h 29mSJD-ORD
$273
6/29sam.
nonstopUnited Airlines
4h 19mSJD-ORD
$408
5/14mar.
1 stopUnited Airlines
7h 24mSJD-ORD
$497

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Flights to Chicago

Return flight deals:

Chicago - Los Cabos

Cabin classes:

$333
$301
$219
$38