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 $309 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 $270. 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
$140 - $455
Route
Depart
Return
Price
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 5/18
1 stop9h 36m
Chicago Midway
Tue 5/21
1 stop12h 38m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 5/15
1 stop9h 53m
Chicago Midway
Sun 5/19
1 stop29h 02m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 5/17
1 stop10h 03m
Chicago Midway
Mon 5/20
1 stop6h 28m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 5/17
1 stop10h 03m
Chicago Midway
Tue 5/21
1 stop12h 38m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 5/14
1 stop28h 46m
Chicago Midway
Sun 5/19
1 stop12h 07m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 8/20
1 stop8h 58m
Chicago Midway
Sat 9/7
1 stop10h 18m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 5/17
1 stop15h 48m
Chicago Midway
Sun 5/19
1 stop12h 07m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 5/19
1 stop18h 03m
Chicago Midway
Fri 6/7
1 stop12h 21m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 10/22
1 stop8h 19m
Chicago Midway
Sat 10/26
1 stop10h 52m
No data available for this route at this time. Please check back soon.
Food
Overall
Boarding
Entertainment
Comfort
Crew
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
Overall
Boarding
Entertainment
Comfort
Crew
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
Overall
Boarding
Entertainment
Comfort
Crew
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.
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