Travelers have found it’s best to book a flight 16 days in advance to save up to 85% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 16 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Puerto Rico to Chicago Midway Airport 1-2 weeks in advance for as low as $238, or $312 for flights within the next 24 hours.
January can be a great time to fly to Chicago Midway Airport from Puerto Rico with a flight ticket averaging about $269. Cheapflights users have found deals in the month of January for as cheap as $122. The most expensive prices can be found in the month of March.
When flying from Puerto Rico 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
$270 - $512
Route
Depart
Return
Price
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/8
2 stops17h 42m
Chicago Midway
Sat 8/17
1 stop12h 21m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 6/7
1 stop12h 58m
Chicago Midway
Fri 6/14
1 stop7h 47m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/6
2 stops11h 26m
Chicago Midway
Thu 6/13
1 stop11h 32m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 8/13
1 stop9h 44m
Chicago Midway
Wed 8/21
1 stop13h 20m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/6
1 stop23h 26m
Chicago Midway
Sun 6/9
1 stop28h 10m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 6/17
1 stop23h 00m
Chicago Midway
Mon 6/24
1 stop7h 45m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/6
2 stops11h 26m
Chicago Midway
Sun 6/9
1 stop28h 10m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/6
2 stops17h 11m
Chicago Midway
Mon 6/10
2 stops10h 31m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/27
1 stop9h 45m
Chicago Midway
Tue 7/2
1 stop9h 31m
No data available for this route at this time. Please check back soon.
Comfort
Entertainment
Crew
Overall
Boarding
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
Entertainment
Crew
Overall
Boarding
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
Entertainment
Crew
Overall
Boarding
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.
0%of flight departures | Early morningMidnight to 6 am |
---|---|
0%of flight departures | Morning6 am to noon |
100%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
Cheapflights helps you search for flights from Puerto Rico to Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Puerto Rico to Midway for you. Better yet — we are completely free to use.
Yes, we can. To see specific flights from Puerto Rico to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.
Of course! You can now track prices for flights from Puerto Rico to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.