$148 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 6/15. 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

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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

Fri, May 1 - Tue, May 5
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
$289Volaris
Fri, May 1 - Tue, May 5
Multiple Airlines Logo
12:02 pm - 12:45 am
SJD
-
ORD
10h 43m
2 stops
Multiple Airlines Logo
7:35 am - 7:25 am
ORD
-
SJD
25h 50m
1 stop
$319Multiple Airlines
Wed, Apr 29 - Wed, May 6
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
$326Volaris
Tue, Jun 23 - Mon, Jun 29
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
Volaris Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
$329Volaris
Thu, Apr 23 - Mon, Apr 27
Alaska Airlines Logo
3:50 pm - 7:03 pm
SJD
-
ORD
25h 13m
1 stop
Alaska Airlines Logo
7:59 pm - 11:37 am
ORD
-
SJD
17h 38m
1 stop
$351Alaska Airlines
Thu, Apr 23 - Mon, Apr 27
Alaska Airlines Logo
10:41 am - 11:43 pm
SJD
-
ORD
11h 02m
1 stop
Alaska Airlines Logo
7:59 pm - 1:39 pm
ORD
-
SJD
19h 40m
1 stop
$353Alaska Airlines
Fri, May 1 - Tue, May 5
Delta Logo
12:36 pm - 10:28 pm
SJD
-
MDW
7h 52m
1 stop
Delta Logo
6:00 am - 1:04 pm
MDW
-
SJD
9h 04m
1 stop
$390Delta
Fri, May 1 - Tue, May 5
Delta Logo
12:36 pm - 10:28 pm
SJD
-
MDW
7h 52m
1 stop
Delta Logo
6:00 am - 5:48 pm
MDW
-
SJD
13h 48m
2 stops
$406Delta
Mon, Apr 27 - Mon, May 4
Southwest Logo
1:55 pm - 4:35 am
SJD
-
MDW
12h 40m
1 stop
Southwest Logo
5:25 am - 10:45 am
MDW
-
SJD
7h 20m
1 stop
$538Southwest
Mon, Apr 27 - Mon, May 4
Southwest Logo
1:55 pm - 4:35 am
SJD
-
MDW
12h 40m
1 stop
Southwest Logo
5:30 am - 12:10 pm
MDW
-
SJD
8h 40m
2 stops
$597Southwest
Useful Info

Good to know

Cheapest flight$148
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 9435 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

6.0 GoodAnonymous, Mar 2026
FRA - ORD
Read more United Airlines reviews

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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.