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 $420. 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
$319 - $923
Route
Depart
Return
Price
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sun 9/22
1 stop10h 09m
Chicago Midway
Sat 9/28
1 stop23h 25m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sun 9/22
1 stop10h 09m
Chicago Midway
Sat 9/28
1 stop11h 41m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 9/19
1 stop10h 09m
Chicago Midway
Mon 9/23
2 stops21h 05m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sun 8/11
1 stop28h 27m
Chicago Midway
Wed 8/14
1 stop25h 58m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sun 8/25
1 stop24h 15m
Chicago Midway
Sat 8/31
1 stop27h 25m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 9/19
1 stop10h 09m
Chicago Midway
Mon 9/23
1 stop26h 02m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 10/17
1 stop10h 09m
Chicago Midway
Thu 10/24
2 stops12h 02m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Mon 10/7
1 stop7h 31m
Chicago Midway
Sat 10/19
1 stop6h 53m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 7/23
1 stop10h 05m
Chicago Midway
Mon 7/29
1 stop17h 48m
No data available for this route at this time. Please check back soon.
Food
Crew
Boarding
Entertainment
Overall
Comfort
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.
Food
Crew
Boarding
Entertainment
Overall
Comfort
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.
Food
Crew
Boarding
Entertainment
Overall
Comfort
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.
Food
Crew
Boarding
Entertainment
Overall
Comfort
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.