Cheap Flights from Chicago to Los Cabos International

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Flight deals from Chicago to Los Cabos International

Looking for a cheap last-minute deal or the best return flight from Chicago to Los Cabos International Airport? If you want to travel next month, return fares start from $897. Find the lowest prices on one-way and return tickets right here.

San Jose del Cabo.$313 per passenger.Departing Fri, 29 Jan, returning Sat, 20 Feb.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Fri, 29 Jan, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sat, 20 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From $313, select.

San Jose del Cabo.$384 per passenger.Departing Fri, 19 Feb, returning Fri, 26 Feb.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Fri, 19 Feb, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Fri, 26 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From $384, select.

San Jose del Cabo.$451 per passenger.Departing Fri, 15 Jan, returning Sat, 30 Jan.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Fri, 15 Jan, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sat, 30 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From $451, select.

San Jose del Cabo.$488 per passenger.Departing Tue, 1 Sep, returning Thu, 3 Sep.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Tue, 1 Sep, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Thu, 3 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $488, select.

San Jose del Cabo.$509 per passenger.Departing Sun, 8 Nov, returning Sat, 21 Nov.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sun, 8 Nov, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sat, 21 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $509, select.

San Jose del Cabo.$558 per passenger.Departing Thu, 3 Dec, returning Sat, 5 Dec.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Thu, 3 Dec, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sat, 5 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From $558, select.

San Jose del Cabo.$560 per passenger.Departing Mon, 14 Sep, returning Sat, 3 Oct.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Mon, 14 Sep, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sat, 3 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $560, select.

San Jose del Cabo.$567 per passenger.Departing Sat, 24 Oct, returning Wed, 11 Nov.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sat, 24 Oct, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Wed, 11 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $567, select.

San Jose del Cabo.$577 per passenger.Departing Tue, 17 Nov, returning Sat, 5 Dec.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Tue, 17 Nov, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sat, 5 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From $577, select.

San Jose del Cabo.$579 per passenger.Departing Sat, 17 Oct, returning Tue, 20 Oct.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sat, 17 Oct, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Tue, 20 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $579, select.

San Jose del Cabo.$584 per passenger.Departing Mon, 31 Aug, returning Thu, 3 Sep.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Mon, 31 Aug, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Thu, 3 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $584, select.

San Jose del Cabo.$633 per passenger.Departing Mon, 24 Aug, returning Fri, 28 Aug.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Mon, 24 Aug, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Fri, 28 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $633, select.

San Jose del Cabo.$669 per passenger.Departing Fri, 3 Jul, returning Sun, 21 Feb.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Fri, 3 Jul, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sun, 21 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From $669, select.

San Jose del Cabo.$778 per passenger.Departing Sat, 20 Jun, returning Sat, 27 Jun.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sat, 20 Jun, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sat, 27 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $778, select.

San Jose del Cabo.$839 per passenger.Departing Sun, 28 Feb, returning Sun, 7 Mar.Return flight with Alaska Airlines and Volaris.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Sun, 28 Feb, arriving in Los Cabos International.Inbound indirect flight with Volaris, departs from Los Cabos International on Sun, 7 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From $839, select.

San Jose del Cabo.$862 per passenger.Departing Sat, 20 Jun, returning Tue, 7 Jul.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sat, 20 Jun, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Tue, 7 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $862, select.

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

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

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Direct flights from Chicago to Los Cabos International

Chicago to Los Cabos International: Alternative routes

Compare routes from Chicago to San Jose del Cabo below. You may find an airport to fly into that's cheaper, faster, or easier than Los Cabos International.

Los Cabos International

12km from central San Jose del Cabo

ClosestCheapest

from $313

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Chicago to San Jose del Cabo: Flight information

The things to know before you go.

Cheapest flight found	$313
Cheapest month to fly	January
Average flight time	4 hrs, 49 mins
Most popular airline	American Airlines
Average flights per week	24

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

How much are return flights from Chicago to Los Cabos International?

The best price we found for a return flight from Chicago to Los Cabos International is $313. 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.

How long does it take to fly from Chicago to Los Cabos International?

4 hours and 49 minutes is the average flight time from Chicago to Los Cabos International.

Which airlines fly direct from Chicago to Los Cabos International?

American Airlines, United and Emirates fly direct from Chicago to Los Cabos International.

How many flights are there a week from Chicago to Los Cabos International?

As of June 2026, there are 24 flights per week flying from Chicago to Los Cabos International.

When is the cheapest time to fly from Chicago to Los Cabos International?

The cheapest month to fly from Chicago to Los Cabos International is usually January.

Which upcoming date is cheapest to fly from Chicago to Los Cabos International Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Los Cabos International Airport on Friday, 29 January 2027.

Can I get a direct flight from Chicago to Los Cabos International Airport?

Yes – the average flight time is 4 hours and 49 minutes.

How can I find the best flight deal to Los Cabos International?

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 Los Cabos International 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.

When is the best time to book flights to San Jose del Cabo?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to San Jose del Cabo is around 40 days in advance, so don’t leave your flight to the last minute.

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

Start your travel planning by working out where you'll take off for your flight from Chicago to Los Cabos International Airport (SJD). Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the main airports in Chicago.
4 hours 50 minutes is the average travel time for a direct Chicago to Los Cabos International Airport flight.
San Jose del Cabo is one hour behind Chicago. Los Cabos International Airport is located in San Jose del Cabo, which follows the UTC-7 timezone.
Chicago O'Hare International Airport (ORD) to Los Cabos International Airport (SJD) is the most popular route. There are 14 direct flights a week to pick from. If you prefer to head out later, hop on the last flight with United Airlines at 11:20am. Choose the first ORD to SJD departure operated by United Airlines at 7:30am if you'd rather get going earlier.
Give yourself enough time to get on your flight from Chicago to SJD. Generally, it's best to arrive at least two hours before international departures and an hour ahead for domestic flights.
If you're going away during a popular month like July, get to the airport even earlier. It's smart to arrive up to four hours before an international flight and two hours ahead of a domestic departure. Expect lines to be longer during peak periods like Christmas and New Year.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

You can jump on a direct flight from Chicago to Los Cabos International Airport (SJD) departing from Chicago O'Hare International Airport (ORD).
When departing from ORD, you can catch a direct flight from Chicago to Los Cabos International Airport with American Airlines.
American Airlines ranks first in bookings for flights from ORD to SJD.
Among carriers on this route, United has the highest rate of on-time arrivals.
A stopover is the perfect opportunity to take a travel break and possibly even visit a new city. When browsing cheap flights from Chicago to SJD departing from Chicago O'Hare International Airport (ORD), deselect the 'Direct flights only' box to find out where you can stop along the way. Your journey might pause in:
- Dallas Fort Worth International Airport (DFW)
- St Louis Lambert International Airport (STL)
- Miguel Hidalgo y Costilla Guadalajara Intl Airport (GDL)
ORD is around 27 kilometres from central Chicago. If you're driving, ride-sharing or catching a taxi from the centre, it'll take you 30 minutes or so to get there, depending on the traffic. If you're using public transport, expect the journey time to be around 45 minutes.
Want an easy start to your trip? Stay near Chicago O'Hare International Airport. Whether you're boarding an early flight from Chicago to Los Cabos International Airport or just don't want to be rushed, these hotels are the answer:
70% of flights that depart Chicago O'Hare International Airport arrive at their destination on schedule.
ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

You can book a direct Chicago to Los Cabos International Airport (SJD) plane ticket with departures from Chicago Midway International Airport (MDW). Decide if leaving from MDW is a better fit for your trip.
Southwest Airlines operates direct flights from Chicago to SJD departing from MDW. Book your favourite window (or aisle) seat and reach your destination in a single stretch.
On the MDW to SJD route, Southwest Airlines is the preferred choice for many passengers.
If you're looking for a consistently punctual carrier, go with Southwest Airlines. It has an exceptional on-time performance of 100.0% for flights between Chicago Midway International Airport and Los Cabos International Airport.
Turn your flight into part of the adventure with a stopover on your flight from Chicago to Los Cabos International Airport. Here's where you can connect between Chicago Midway International Airport and SJD:
- Denver International Airport (DEN)
- Phoenix Sky Harbour International Airport (PHX)
- Houston Hobby Airport (HOU)
You can get to MDW from central Chicago in approximately 25 minutes by car (depending on traffic conditions). The journey by public transport takes roughly 30 minutes to cover the 16 kilometres or so.
Want to treat yourself to an extra night away before boarding your Chicago to SJD flight? Check in to a hotel near Chicago Midway International Airport before your trip officially begins. Here's where you can stay:
When it comes to keeping flights on track, Chicago Midway International Airport has an on-time arrival performance of 76%.
The address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

You can book a plane ticket from Chicago to Los Cabos International Airport (SJD) leaving from Chicago Rockford International Airport (RFD) with a stopover. Los Angeles International Airport (LAX) is a popular transfer point.
The journey time to RFD from the centre of Chicago is around 2 hours by public transport. If you're planning to travel by car, it'll take you roughly 1 hour 40 minutes to cover the 145 kilometres or so.
Take the uncertainty out of departure day — stay close to Chicago Rockford International Airport and know you'll make it to your boarding gate with time to spare. Check in to one of these hotels the day before if you're catching an early Chicago to Los Cabos International Airport flight:
Airports have an on-time performance rating that monitors how often flights touch down as expected. At RFD, that rate is 71%.
The address of Chicago Rockford International Airport is 2 Airport Cir.

About Los Cabos International Airport (SJD)

The last thing you want is a long journey to your hotel if you're getting in late on a flight from Chicago to Los Cabos International Airport. Book one of these accommodation options near SJD instead:
For the lowest price, book your vehicle around two weeks ahead of your Chicago to Los Cabos International Airport flight.

Getting from Los Cabos International Airport (SJD) to central San Jose del Cabo

Central San Jose del Cabo is around 8 kilometres from Los Cabos International Airport and takes about 15 minutes to reach by car. See what your options are for heading into the city, whether that's with a taxi, car hire or ride-share.
If you're taking public transport, expect a journey time of roughly 25 minutes.

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

Currently, $171 is the lowest price we've found for a one-way ticket from Chicago to Los Cabos International Airport. The cheapest price for a return flight is $313. Remember fares can change due to demand at the time of booking.
Lock in cheap flights from Chicago to SJD by booking five months ahead. Based on our research, that's the ideal time frame for bagging a bargain.
Schedule your trip for October. That's the best month for scoring the biggest deals on Chicago to Los Cabos International Airport tickets. If you have flexibility with your dates, use the 'Whole month' tool to find the lowest price across each month.
You don't need to check every day to find out if fares have dropped when you set up a Price Alert. We'll let you know when a lower fare pops up on plane tickets from Chicago to SJD.
Filters make it easier to scoop up a deal on your flight from Chicago to Los Cabos International Airport. Pick the airlines, flight times and stops that look good to you. Then sort the results by 'Cheapest' to find the best price quickly.

The best time to fly from Chicago to Los Cabos International Airport (SJD)

December is the quietest month for flights from Chicago to Los Cabos International Airport (SJD), while March is the most popular. Work out the best time to visit San Jose del Cabo based on whether you like a laid-back vibe or a lively atmosphere.
Before locking in your Chicago to SJD plane ticket, consider what kind of weather works for you. August is the warmest month in San Jose del Cabo, with temperatures ranging from 23ºC to 35ºC.
If you'd rather travel in cooler conditions, search for a cheap ticket from Chicago to Los Cabos International Airport in January when temperatures are between 11ºC and 26ºC.

More about San Jose del Cabo

Start your San Jose del Cabo trip off on the right foot by choosing the perfect place to stay. As soon as you've booked your flight from Chicago to Los Cabos International Airport, check out our selection of accommodation options including:
Every great holiday has to include some sightseeing. Costa Azul Beach, Playa Las Palmas and Plaza Mijares are essential stops on your San Jose del Cabo itinerary.

Explore more of Mexico

San Jose del Cabo will leave a lasting impression, but there are so many other corners of Mexico waiting to be discovered. About 129 kilometres northwest of San Jose del Cabo, a visit to La Paz will keep your itinerary busy. Start with attractions like Balandra Beach, Malecon and Playa Pichilingue (Pichilingue Beach).
Journey 290 kilometres northwest from San Jose del Cabo and you'll reach Ciudad Constitucion, another standout destination in Mexico. Don't leave without exploring Museo Municipal Casa Amarilla and Plaza De Armas Del General Ignacio Zaragoza.