$204 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 6/25. 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, 0 bags

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 24% 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.

Flight Deals
Useful Info
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

Thu, Jun 18 - Sun, Jun 21
Volaris Logo
12:06 pm - 12:55 am
SJD
-
ORD
10h 49m
1 stop
Volaris Logo
2:53 am - 8:16 am
ORD
-
SJD
7h 23m
1 stop
$348Volaris
Wed, Sep 9 - Wed, Sep 16
Volaris Logo
12:02 pm - 11:47 pm
SJD
-
ORD
9h 45m
1 stop
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
$359Volaris
Wed, Jun 3 - Sun, Jun 7
Viva Logo
8:20 am - 11:55 pm
SJD
-
ORD
13h 35m
1 stop
Viva Logo
1:30 am - 7:30 am
ORD
-
SJD
8h 00m
1 stop
$381Viva
Fri, May 22 - Sat, Jun 6
Viva Logo
8:40 am - 12:45 am
SJD
-
ORD
14h 05m
1 stop
Viva Logo
8:40 pm - 12:30 pm
ORD
-
SJD
17h 50m
1 stop
$386Viva
Thu, Jun 18 - Fri, Jun 19
Multiple Airlines Logo
8:20 am - 11:55 pm
SJD
-
ORD
13h 35m
1 stop
Multiple Airlines Logo
2:53 am - 11:29 am
ORD
-
SJD
10h 36m
1 stop
$393Multiple Airlines
Fri, May 22 - Sat, Jun 6
Multiple Airlines Logo
8:40 am - 12:45 am
SJD
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
2:53 am - 8:16 am
ORD
-
SJD
7h 23m
1 stop
$394Multiple Airlines
Tue, Jun 16 - Sat, Jun 20
Delta Logo
6:07 am - 10:17 pm
SJD
-
MDW
14h 10m
2 stops
Delta Logo
6:00 am - 12:30 pm
MDW
-
SJD
8h 30m
1 stop
$601Delta
Tue, Jun 16 - Fri, Jun 19
Delta Logo
12:30 pm - 10:17 pm
SJD
-
MDW
7h 47m
1 stop
Delta Logo
6:00 am - 11:25 am
MDW
-
SJD
7h 25m
1 stop
$622Delta
Fri, May 22 - Mon, May 25
Southwest Logo
12:25 pm - 10:20 pm
SJD
-
MDW
7h 55m
1 stop
Southwest Logo
6:55 am - 1:25 pm
MDW
-
SJD
8h 30m
1 stop
$623Southwest
Thu, Jun 18 - Mon, Jun 22
Southwest Logo
11:15 am - 12:35 am
SJD
-
MDW
11h 20m
1 stop
Southwest Logo
5:45 am - 11:00 am
MDW
-
SJD
7h 15m
1 stop
$633Southwest
Useful Info

Good to know

Low seasonMarch
Cheapest flight$204
Best time to beat the crowds with an average 22% drop 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.

Reviews of the 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 9678 reviews
7.7Boarding
7.3Comfort
8.1Crew
6.6Food
7.1Entertainment
Airline reviews

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

8.0 ExcellentAnonymous, Apr 2026
ZRH - ORD
Read more United Airlines reviews

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Traveling to a place near Chicago?

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