12 days before departure is when Chicago to Florida ticket prices start increasing. They can rise up to around $233 to fly last minute to Florida (an increase of 50). If you are flexible within the next 14 days, prices are around $132.
Priceline flight searches for January show the best prices for flights to Florida from Chicago. Prices at this time are around $220, but we have found deals as low as $64.
Ticket prices will remain the same regardless of what time you plan to fly to Florida from Chicago. With this in mind, we recommend booking flights for whatever time is available and fits your travel schedule.
Fly from
Fly to
Budget
$37 - $64
Route
Depart
Return
Price
Chicago MidwayMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 5/29
Nonstop3h 11m
Miami
Wed 6/5
Nonstop3h 12m
Chicago O'Hare IntlFort Myers SW Florida Intl
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Tue 5/28
Nonstop2h 54m
Fort Myers SW Florida Intl
Tue 6/4
Nonstop3h 11m
Chicago MidwayMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 5/29
Nonstop3h 11m
Miami
Wed 6/5
Nonstop3h 12m
Chicago MidwayMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 5/14
Nonstop3h 17m
Miami
Wed 5/22
Nonstop3h 15m
Chicago O'Hare IntlFort Myers SW Florida Intl
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Thu 5/30
Nonstop2h 54m
Fort Myers SW Florida Intl
Tue 6/4
Nonstop3h 11m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 5/29
Nonstop2h 49m
Orlando
Wed 6/5
1 stop5h 08m
Chicago MidwayMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/11
Nonstop3h 14m
Miami
Wed 5/15
Nonstop3h 32m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 5/29
Nonstop2h 58m
Orlando
Wed 6/5
1 stop5h 08m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 5/29
Nonstop2h 49m
Orlando
Wed 6/5
Nonstop3h 09m
No data available for this route at this time. Please check back soon.
6%of flight departures | Early morningMidnight to 6 am |
---|---|
47%of flight departures | Morning6 am to noon |
38%of flight departures | AfternoonNoon to 6 pm |
9%of flight departures | Evening6 pm to midnight |