ORD - SJD

$121 Find Cheap Flights from Chicago O'Hare Airport to San José del Cabo

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to San José del Cabo departing on 5/30. 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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KAYAK searches hundreds of travel sites at once for deals on flights to San José del Cabo

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José del Cabo.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José del Cabo.
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Flights Deals

Cheap Flight Deals from O'Hare Intl to San José del Cabo (ORD-SJD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to San José del Cabo 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.

Recent round-trip flight deals from O'Hare Intl to San José del Cabo

KAYAK's recommended round-trip deals from the most popular airlines that fly from O'Hare Intl to San José del Cabo.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
6:34 pm - 7:25 pmORD-SJD
26h 51m2 stops
 Logo
9:15 am - 11:35 pmSJD-ORD
12h 20m2 stops
Sun, May 11 - Tue, May 13
 Logo
6:34 pm - 3:35 pmORD-SJD
23h 01m2 stops
 Logo
9:15 am - 11:35 pmSJD-ORD
12h 20m2 stops
Fri, May 16 - Sat, May 24
Volaris Logo
6:34 pm - 3:35 pmORD-SJD
23h 01m2 stops
Volaris Logo
11:53 am - 12:15 amSJD-ORD
10h 22m1 stop
$343Volaris
Find Deal
Fri, May 30 - Wed, Jun 4
Volaris Logo
6:31 am - 6:07 pmORD-SJD
13h 36m1 stop
Volaris Logo
11:53 am - 12:15 amSJD-ORD
10h 22m1 stop
$350Volaris
Find Deal
Fri, May 30 - Wed, Jun 4
Viva Logo
12:35 pm - 8:00 amORD-SJD
21h 25m1 stop
Viva Logo
8:30 am - 11:35 pmSJD-ORD
13h 05m1 stop
$373Viva
Find Deal
Sun, May 11 - Tue, May 13
Viva Logo
12:35 pm - 2:25 pmORD-SJD
27h 50m1 stop
Viva Logo
8:30 am - 11:35 pmSJD-ORD
13h 05m1 stop
$374Viva
Find Deal
Sat, May 10 - Tue, May 13
American Airlines Logo
8:25 am - 3:20 pmORD-SJD
8h 55m1 stop
American Airlines Logo
12:45 pm - 7:10 pmSJD-ORD
4h 25mnonstop
$380American Airlines
Find Deal
Wed, Jul 16 - Wed, Jul 30
American Airlines Logo
9:05 am - 11:45 amORD-SJD
4h 40mnonstop
American Airlines Logo
12:45 pm - 7:10 pmSJD-ORD
4h 25mnonstop
$415American Airlines
Find Deal
Sun, Jul 6 - Fri, Jul 11
United Airlines Logo
5:02 am - 12:10 pmORD-SJD
9h 08m1 stop
United Airlines Logo
11:52 am - 6:10 pmSJD-ORD
4h 18mnonstop
$507United Airlines
Find Deal
Sat, May 31 - Sat, Jun 7
United Airlines Logo
5:02 am - 1:43 pmORD-SJD
10h 41m1 stop
United Airlines Logo
11:52 am - 6:10 pmSJD-ORD
4h 18mnonstop
$510United Airlines
Find Deal
Mon, Jun 2 - Sat, Jun 7
Expert advice

Expert advice for your flight from O'Hare Intl to San José del Cabo

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Basic Economy offers carry-on only travel with late boarding; compare costs with Main Cabin fares.


Main Cabin Extra provides early boarding and complimentary drinks, ideal for longer flights.

United Airlines

United First offers ample legroom with recliners, perfect for comfort on medium-haul flights.


Economy Plus provides extra legroom, ideal for added comfort without premium cabin costs.

Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Useful Info

KAYAK's insights & trends for O'Hare Intl to San José del Cabo flights

Get data-powered insights and trends into flights from O'Hare Intl to San José del Cabo to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to San José del Cabo?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to San José del Cabo clicked on KAYAK for each day over the last 12 months.

For Chicago O'Hare Airport to San José del Cabo, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from San José del Cabo back to Chicago O'Hare Airport, the best deals are generally found on Saturday, with Sunday being the most expensive.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to San José del Cabo?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to San José del Cabo, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to San José del Cabo is November, where tickets cost $545 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $793 and $663 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to San José del Cabo?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $1,289 on average.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to San José del Cabo?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to San José del Cabo, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to San José del Cabo, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$121
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago O'Hare Airport to San José del Cabo

When to book flights from O'Hare Intl to San José del Cabo

Are your dates flexible? Find out the best times to travel from O'Hare Intl to San José del Cabo based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago O'Hare Airport to San José del Cabo flights

  • How can I catch the earliest flight from Chicago O'Hare Airport to San José del Cabo?

    If you want to conveniently catch up with the earliest flight from ORD to San José del Cabo, which departs at around 7 am, spend the night at the Holiday Inn Express Hotel & Suites. Apart from being near the airport, the hotel provides free airport shuttle services making transportation there simpler and more affordable.

  • Which airline can I use when flying from Chicago O'Hare Airport to San José del Cabo with my kids?

    Give the little ones a great flight experience by booking either American or United Airlines. They will certainly enjoy complimentary snacks offered on board. The carriers’ seats are comfy and spacious, allowing you to sit comfortably with your kids throughout the voyage.

  • How can I connect to San José del Cabo city center from SJD?

    When connecting to San José del Cabo's downtown, the majority of passengers arriving at SJD choose to take taxis. Taxis provide a quick means of transportation and are easily accessible right after the SJD baggage claim area.

  • Is it safe to arrive in San José del Cabo late at night?

    Yes. You can connect to one of the nearby hotels safely using the free airport shuttles provided by the respective hotels. Hyatt Place Los Cabos, and Hotel Aeropuerto Los Cabos, whose airport shuttles operate on a 24-hour basis, are good options in that case.

  • What is the cheapest flight from Chicago O'Hare Intl Airport to San José del Cabo?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to San José del Cabo was $121 for a one-way ticket and $337 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and San José del Cabo?

    Yes, you’ll need a passport to travel to San José del Cabo from Chicago O'Hare Airport.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to San José del Cabo?

    American Airlines, Delta, British Airways, Alaska Airlines, and Aeromexico offer inflight Wi-Fi service on the Chicago O'Hare Airport to San José del Cabo flight route.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to San José del Cabo?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago O'Hare Airport to San José del Cabo flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to San José del Cabo?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago O'Hare Airport and San José del Cabo, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago O'Hare Airport to San José del Cabo?

    There are nonstop flights from Chicago O'Hare Airport to San José del Cabo on a daily basis.

  • Which is the best airline for flights from Chicago to San José del Cabo, Delta or Aeromexico?

    The two airlines most popular with KAYAK users for flights from Chicago to San José del Cabo are Delta and Aeromexico. With an average price for the route of $649 and an overall rating of 8.0, Delta is the most popular choice. Aeromexico is also a great choice for the route, with an average price of $552 and an overall rating of 7.5.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to San José del Cabo?

    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 Chicago O'Hare Airport to San José del Cabo.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to San José del Cabo?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San José del Cabo from Chicago O'Hare Airport 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 Chicago O'Hare Airport to San José del Cabo?

    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 San José del Cabo with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and SJD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to San José del Cabo?

    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 San José del Cabo from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to San José del Cabo

  • Looking for a cheap flight? 25% of our users found flights on this route for $296 or less one-way and $545 or less round-trip.
  • There are various ways to get to Chicago O'Hare Airport (ORD) from downtown Chicago. The least expensive choice is the Blue Line "L" train, which takes about 45 minutes to reach the airport. The coach stops at all three terminals at ORD. The other quick and reliable mode of transportation is a taxi if you want to get there in under 30 minutes, however, it is one of the most expensive.
  • All flights departing from Chicago O'Hare Airport and arriving in San José del Cabo are friendly to people with reduced mobility. If you let the airport officials know in advance, you can request wheelchair transportation from a taxi to an aircraft when you arrive at Chicago O'Hare Airport.
  • The majority of passengers arriving from ORD choose to arrive through San Jose del Cabo Los Cabos International Airport (SJD). Arriving travelers can take pleasure in watching airplanes land and take off. On the third level, just beyond the terminal's eastern end, is the observation deck where you can snap those spectacular views to offer lasting memories.
  • For business travelers seeking to take the shortest time possible to arrive in San José del Cabo from Chicago O'Hare Airport, they should consider using American Airlines or United Airlines. These two are the only airlines that offer nonstop flights from Chicago O'Hare to San José del Cabo.
  • SJD serves a number of other cities, including Mexico City and Guadalajara. Car rentals offer the most convenient and flexible transport option for those who want to visit these nearby cities. Remember to book your car in advance to enjoy special rates.

Prefer to fly direct from Chicago O'Hare Airport to San José del Cabo?

Find which airlines fly direct from Chicago O'Hare Intl Airport to San José del Cabo Los Cabos Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to San José del Cabo Los Cabos

Monday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Tuesday

Emirates, United Airlines, American Airlines

Emirates, United Airlines, +1 more

Wednesday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Sunday

American Airlines

American Airlines

See more direct flights

Direct returns

San José del Cabo Los Cabos to Chicago O'Hare Intl

Monday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Tuesday

Emirates, United Airlines, American Airlines

Emirates, United Airlines, +1 more

Wednesday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Sunday

American Airlines

American Airlines

See more direct flights
See more direct flights

Top 5 airlines serving from O'Hare Intl to San José del Cabo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San José del Cabo. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to San José del Cabo? 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.
8.0
DeltaOverall score based on 7934 reviews
7.9Comfort
8.2Boarding
7.9Entertainment
7.3Food
8.5Crew
Airline reviews

Our bag was lost so that made unnecessary chaos On our trip

6.0 GoodBarbara, Apr 2025JFK - FCO
Read more Delta reviews

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

The boarding process was ridiculous. The boarded groups into a walkway just before the aerobridge (about 20 mins late), whilst we watch the crew stroll casually onto the plane, running late. And then they made us line up on then aerobridge with no aircon for 10 minutes before we boarded. Staff are just as ghetto as the customers. Wouldn’t fly again

They closed the gate over 25 minutes before departure and I didn’t get to board.

No empathy for my situation, arriving at the check-in counter 5 minutes after the deadline to deposit baggage due to a very delayed incoming intercontinental flight. The attendant simply stared past my shoulder and picked up the microphone to announce a "reminder that all passengers must arrive at least one hour before the flight" before speaking to the passenger behind me. I understand that there are rules above deadlines but at least show some damn empathy. It was Christmas morning and I'd been travelling for 20 hours for goodness sake!

They no longer offer anything free to eat or drink, everything is sold, not even a bottle of water is offered for free.

I paid for Viva play and most of the time didn’t work and also I order some drinks and the price was to expensive.

The terminal and gate was never the right one announced in the Viva App, neither in screens, moved from one terminal to another

The smart/express line to check in was a mess, employees not doing the process smooth and quick, using their mobile phones, talking to their coworkers

My flight was changed 4 tienes , delaying my arrival lore than 5 hours

Everything was okay, but boarding begins late and when I was returning there was a gate change. The app never showed the change.

Flights were delayed both ways, with no communication provided by the boarding desk. Delay time kept changing and the boarding process is a pain, as it is so disorganized. Would not recommend.

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

Better communication about delayed flight. I am thankful for a small credit for late flight.

Liked on time, rear entry and exit from plane Dislike the use of duct tape to repair seat rests

They check you everything before entering to waiting room, if you have any liquid they take it away even if you buy it inside the airport, no recommend volaris, for mi know Alaska airline is better

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

The worst. Kayak sent notification at 2am and 10am regarding the delay. Then sends a notification an hour before original depart time that it will depart on time. I had to wait 8 hours at the airport. My family had to pay for lodging in Guadalajara where I was landing for pick up.

The flight was delayed an hour and a half, and they would not update the board on when the flight was supposed to take off. Once the plane arrived, they started the boarding process before the plane was even ready for the passengers so we had to wait another 45 minutes on the tarmac while we waited for the plane to be ready for us. In my opinion, there is no point in starting the boarding process when you are not ready to board the plane. This just causes a crowded gate with everyone from zone one and zone two standing up going nowhere.

They were only able to give me a seat and not my travel companion, she had to fly on a different airline. unacceptable

Everything you need to know for your flight from O'Hare Intl to San José del Cabo

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