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
$403 - $636
Route
Depart
Return
Price
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 7/25
1 stop28h 27m
Chicago Midway
Sat 8/3
1 stop19h 02m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Mon 6/17
2 stops33h 59m
Chicago Midway
Thu 6/27
2 stops15h 11m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 6/14
1 stop17h 13m
Chicago Midway
Sun 6/16
1 stop16h 52m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 7/23
2 stops10h 45m
Chicago Midway
Sun 7/28
1 stop16h 41m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 8/29
1 stop10h 09m
Chicago Midway
Sat 9/7
1 stop11h 41m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 7/16
2 stops10h 45m
Chicago Midway
Sun 7/21
1 stop16h 41m
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
Sat 7/20
1 stop19h 05m
Chicago Midway
Sat 7/27
2 stops10h 24m
San José Juan Santamaria IntlChicago Midway
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 10/1
1 stop7h 31m
Chicago Midway
Tue 10/8
1 stop6h 53m
No data available for this route at this time. Please check back soon.
Comfort
Overall
Boarding
Crew
Entertainment
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.
Comfort
Overall
Boarding
Crew
Entertainment
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.
Comfort
Overall
Boarding
Crew
Entertainment
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.