Cheap Flights from San Jose Cabo (SJD) to Chicago (CHIA)

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Compare Los Cabos International to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Los Cabos International to Chicago

Looking for a cheap last-minute deal or the best return flight from Los Cabos International to Chicago? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Los Cabos International to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Los Cabos International to Chicago flights are currently cheapest in September.

Direct flights from Los Cabos International to Chicago

Alternative Los Cabos International to Chicago routes

Looking for the cheapest, fastest or easiest route from Los Cabos International to Chicago? You could fly into the following airports instead.

San Jose Cabo to Chicago: Flight information

The things to know before you go.
Cheapest flight found$474
Cheapest month to flySeptember
Average flight time4 hrs, 11 mins
Most popular airlineQatar Airways
Average flights per week30

Finding cheap flights from Los Cabos International to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Los Cabos International to Chicago is $474. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 11 minutes is the average flight time from Los Cabos International to Chicago.
Qatar Airways, American Airlines and United fly direct from Los Cabos International to Chicago.
As of June 2025, there are 30 flights per week flying from Los Cabos International to Chicago.
The cheapest month to fly from Los Cabos International to Chicago is usually June 2025.
If you're flying from Los Cabos International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $474.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Los Cabos International Airport to Chicago on Wednesday, 10 September 2025.
Yes – the average flight time is 4 hours and 11 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In June, the average temperature is usually around 19°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Delta and United offer the cheapest flight tickets to Chicago.

Flying from Los Cabos International Airport (SJD) to Chicago: what you need to know

  • Expect to be in the air for 4 hours 50 minutes. That's the average journey time for a direct flight from Los Cabos International Airport to Chicago.

  • The timezone in Chicago is UTC-5. The city is two hours ahead of San Jose Cabo, where Los Cabos International Airport is located.

  • With 14 flights a week between the two airports, Los Cabos International Airport (SJD) to O'Hare International Airport (ORD) is the most popular route. American Airlines operates the earliest flight at 10:50. If you'd like to get more out of your day before jetting off, the last flight from SJD to ORD is with American Airlines at 13:56.

  • Leave plenty of time to make your SJD to Chicago flight. Generally, it's best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Delays at security and check-in are likely if you're flying during high season, so give yourself some extra wiggle room. A good general rule for peak times? Get there up to four hours early for international flights and two hours for domestic departures.

  • You can book a direct Los Cabos International Airport to Chicago ticket. Begin your journey at SJD and land at O'Hare International Airport (ORD).

  • You'll have your choice of airlines that offer direct flights from Los Cabos International Airport to Chicago. Book your ticket with one of these:

  • Consider adding a stopover to potentially find a cheaper flight ticket from SJD to Chicago. Just deselect 'Direct flights only' during your search. Give yourself a breather (and maybe even a better deal) by stopping at one of these popular options:

    • Dallas/Fort Worth International Airport (DFW)

    • Denver International Airport (DEN)

    • Los Angeles International Airport (LAX)

  • To get to SJD from central San Jose Cabo, it takes around 20 minutes if you're travelling by car. It's roughly 11 kilometres from the airport to the city centre.

  • In search of a hotel near SJD? If you're boarding an early flight from Los Cabos International Airport to Chicago, these accommodation options will put you moments from your departure gate:

  • When it comes to the on-time performance of Los Cabos International Airport, data shows 73.83% of flights arrive within the scheduled time frame.

How to find the cheapest flights from Los Cabos International Airport (SJD) to Chicago

  • The lowest price we've seen for a one-way Los Cabos International Airport to Chicago flight is $294. The cheapest price for a return flight is $474. Remember fares may change due to demand at the time of booking.

  • Book seven months before you want to travel. Pricing trends suggest that this is the ideal window for finding cheap flights from SJD to Chicago.

  • Plan your trip for November. That's the best month for landing an epic deal on Los Cabos International Airport to Chicago tickets. If you're open to different travel dates, use the 'Whole month' tool to access the cheapest price across every month.

  • There's no need to keep looking every day to see if fares have dropped when you create a Price Alert. We'll update you when there's an extra saving on cheap flights from SJD to Chicago.

  • Save money on your flight from Los Cabos International Airport to Chicago with the help of our filters. Select your preferred times, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to central Chicago takes around 35 minutes to reach by car. The centre is roughly 40 kilometres away.

  • Travelling to the centre on public transport will take you around 55 minutes.

  • Consider staying in a hotel close to ORD if you have a late flight from Los Cabos International Airport to Chicago. Settle into one of these accommodation options and make your first night all about catching up on rest:

  • Go where the road takes you with an O'Hare International Airport rental car. Pick up your wheels from Routes Car Rentals, Dollar or Budget and chase adventure across Chicago and beyond.

  • To lock in the lowest price, book your vehicle from O'Hare International Airport about four weeks in advance of your flight from SJD to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is roughly 19 kilometres from central Chicago. Following your flight from Los Cabos International Airport to Chicago, it'll take you around 20 minutes to get to the heart of the city in a cab or ride-share.

  • You can expect the journey to take about 45 minutes on public transport.

  • After stepping off your SJD to Chicago flight, rest your head at a hotel near MDW. These are some comfortable options that'll help you get into relaxation mode:

  • No need to worry about public transport schedules or waiting forever for a cab. Pick up a Chicago Midway International Airport rental car and go in any direction that inspires you. Compare rates and availability from Dollar, Hertz and Budget.

  • Lock in the lowest price by reserving your ride from MDW four weeks ahead of time. You can also expect to have a greater selection of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Los Cabos International Airport to Chicago and head for your hotel or jump right into exploring. The centre of Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to reach by car.

  • If you use public transport, the journey takes around 4 hours 15 minutes.

  • Enjoy an unhurried start to your trip by choosing a hotel near RFD after your SJD to Chicago flight. Take a load off after a long travel day or just give yourself time to get your bearings in a new city at:

  • Whether you'd like a zippy mini for a solo getaway or a roomy SUV to fit the family, you'll find the right Chicago Rockford International Airport rental car for your needs. Explore the types of wheels available here from providers such as Budget, Alamo and National.

  • Booking at least a few weeks ahead of your flight from Los Cabos International Airport to Chicago is smart. Along with better deals, you'll be able to choose the vehicle make and model you prefer at RFD.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Plan your trip to Chicago during peak season if you want a bustling atmosphere, but remember that prices tend to be higher. Alternatively, book your flights from Los Cabos International Airport to Chicago in the low season when prices are cheaper and crowds are smaller.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your Los Cabos International Airport to Chicago flight ticket then if that's your definition of good weather.

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for a cheap ticket from SJD to Chicago around that time if you want to travel when it's cooler.

More about Chicago

Explore more of United States

  • Chicago has loads to offer, but there are so many other parts of United States waiting to be explored. About 451 kilometres south-east of Chicago, a visit to Columbus will keep you on the move. Start with leading attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another favourite destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without visiting The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.