HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$172+ Cheap flights from San José (SJO) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Nov 19 — Nov 261
1 adult
Tue 11/19
Tue 11/26
We work with more than 300 partners to bring you better travel deals

...and more

Find cheap flights from San José to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from San José to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 14, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

February

Cheapest in

September

Round-trip from

$478
(Kiwi.com)

One-way from

$172
(FlightHub)
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago Midway flights.
Search Deals
High demand for flights, 40% potential price rise
Search Deals
Best time to find cheap flights, 32% potential price drop
Search Deals
From San José Juan Santamaria Intl to Chicago Midway
Search Deals
One-way flight from San José Juan Santamaria Intl to Chicago Midway
Search Deals

Find flight deals from San José to Midway

Cheapest flights from San José to Midway
Explore the most affordable flight options available from San José to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 14, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/245:20 pmSJO - MDW
2 stops15h 01mMultiple Airlines
Tue 12/316:49 pmMDW - SJO
1 stop16h 52mMultiple Airlines
Deal found 11/14$478
This Southwest deal was found by Cheapflights users on 11/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/232:40 pmSJO - MDW
1 stop8h 30mSouthwest
Sat 11/309:30 amMDW - SJO
1 stop11h 10mSouthwest
Deal found 11/13$574
This Delta deal was found by Cheapflights users on 11/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/77:00 amSJO - MDW
2 stops10h 01mDelta
Thu 2/271:05 pmMDW - SJO
1 stop9h 21mDelta
Deal found 11/13$628

Find flights from San José to Midway within your budget

Customize your flight search to find flights from San José to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,752,363 searches. Data last updated November 14, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 1/12

1:57 am-10:45 pm

2 stops20h 48m

Chicago Midway

Mon 1/20

7:45 am-12:26 pm

1 stop28h 41m

$454

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 3/4

9:55 am-6:50 pm

2 stops8h 55m

Chicago Midway

Tue 3/11

12:30 pm-7:40 pm

1 stop8h 10m

$543

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 12/7

2:13 pm-10:06 pm

1 stop7h 53m

Chicago Midway

Thu 2/27

1:05 pm-10:26 pm

1 stop9h 21m

$628

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 4/13

9:40 am-8:49 pm

1 stop10h 09m

Chicago Midway

Sat 4/19

9:44 pm-8:25 am

1 stop11h 41m

$1,053

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 11/19

12:26 pm-10:52 pm

2 stops34h 26m

$219

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 4/29

8:45 am-6:25 pm

1 stop8h 40m

$324

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 12/7

7:00 am-4:12 pm

1 stop9h 12m

$341

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/18

5:00 pm-10:20 pm

2 stops29h 20m

$1,117

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

  • Most accurate provider: When it comes to deals on San José, San José Province-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José, San José Province-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José, San José Province-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San José, San José Province-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San José, San José Province-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from San José to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San José with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from San José to Midway

Get recent, data-driven insights about flights from San José to Midway including ideal travel times, pricing trends, and more.

What is the cheapest time of day to fly from SJO to MDW?

Find hourly flight availability from San José to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 14, 2024.

When flying from San José, San José Province to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 32% versus a flight at noon.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated November 14, 2024.
Southwest
8.1
Very good
5,045 reviews

Crew

8.7

Overall

8.1

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,045 reviews
Southwest
8.1
Very good
5,045 reviews

Crew

8.7

Overall

8.1

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,788 reviews
Southwest
8.1
Very good
5,045 reviews

Crew

8.7

Overall

8.1

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

LATAM Airlines
7.5
Good
1,948 reviews
Southwest
8.1
Very good
5,045 reviews

Crew

8.7

Overall

8.1

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,551 reviews
Southwest
8.1
Very good
5,045 reviews

Crew

8.7

Overall

8.1

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

Find useful and relevant information for your journey from San José to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San José to Chicago Midway?

    San José Juan Santamaria Intl (SJO), located 8.8 mi from the city center, is the airport you fly out of when you book flights from San José to Chicago Midway. 0 airlines have flights from Juan Santamaria Intl to Chicago Midway on a regular basis. Booking flights from San José Juan Santamaria Intl to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • What are the cheapest airlines flying from San José, San José Province to Chicago Midway Airport round-trip?

    Currently priced at $543, Southwest will fly you from San José, San José Province to Chicago Midway Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and Frontier - these airlines can fly you to your destination from $628 and $1,053, respectively. Users have found that Southwest is 40% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from San José, San José Province to Chicago Midway Airport one-way?

    $172 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $324 and $341, respectively.

  • Can I find deals for flights from San José to Midway that include hotel bookings?

    Yes. In addition to deals on San José to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San José to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José to Midway.

  • Can I find deals for business class flights from San José to Midway?

    Yes. Cheapflights offers flight deals from San José to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San José, San José Province to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from San José, San José Province to Chicago Midway Airport (average of $159). Flying from San José, San José Province to Chicago Midway Airport in July is currently the most expensive (average of $231). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for San José to Midway

See prices for flight routes from nearby airports that may be better suited for you.
San José to O'Hare Intl flights
Liberia to O'Hare Intl flights
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines