When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 27 days in advance, which can save you up to 81% on flights from Costa Rica to Chicago Midway Airport compared to booking the week you need them. Waiting 27 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $413. For sooner than that we have options available in the next 3 days from $534.
Our data shows that August tends to be the cheapest month to fly to Chicago Midway Airport from Costa Rica. Users have commonly found prices around $414 for the month, but tickets can be as low as $269. Due to multiple factors, prepare for potentially higher prices in March.
When flying from Costa Rica to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$397 - $954
Route
Depart
Return
Price
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 6/14
1 stop17h 13m
Chicago Midway
Mon 6/17
1 stop25h 39m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Mon 6/3
1 stop29h 01m
Chicago Midway
Sun 6/9
1 stop16h 52m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 6/14
1 stop17h 13m
Chicago Midway
Mon 6/17
2 stops17h 39m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Mon 6/3
2 stops20h 25m
Chicago Midway
Sun 6/9
1 stop16h 52m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sun 8/25
1 stop10h 09m
Chicago Midway
Sat 8/31
1 stop27h 25m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 10/10
1 stop10h 09m
Chicago Midway
Wed 10/16
1 stop23h 25m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 10/10
1 stop10h 09m
Chicago Midway
Wed 10/16
1 stop11h 41m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sat 9/7
1 stop7h 34m
Chicago Midway
Tue 9/10
1 stop6h 53m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 6/20
1 stop9h 59m
Chicago Midway
Fri 7/5
1 stop10h 46m
No data available for this route at this time. Please check back soon.
Entertainment
Comfort
Boarding
Overall
Crew
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Entertainment
Comfort
Boarding
Overall
Crew
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Entertainment
Comfort
Boarding
Overall
Crew
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Entertainment
Comfort
Boarding
Overall
Crew
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
When you search for this flight from Costa Rica to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Costa Rica to Midway.
Certainly. Search results for flights to Midway from Costa Rica shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Yes, Cheapflights offers price alerts on Costa Rica to Midway flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.