Find a great deal and save up to 28% by booking at least 31 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Florida within the next two weeks, with the cheapest ticket starting at $149.
May can be a great time to fly to Florida from Chicago with a flight ticket averaging about $230. Cheapflights users have found deals in the month of May for as cheap as $60. The most expensive prices can be found in the month of March.
When flying from Chicago to Florida, 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
$63 - $172
Route
Depart
Return
Price
Chicago O'Hare IntlFort Myers SW Florida Intl
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Wed 5/29
Nonstop2h 54m
Fort Myers SW Florida Intl
Wed 6/5
Nonstop3h 09m
Chicago O'Hare IntlFort Myers SW Florida Intl
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Sat 6/1
Nonstop2h 54m
Fort Myers SW Florida Intl
Tue 6/11
Nonstop3h 12m
Chicago O'Hare IntlMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 6/1
Nonstop3h 17m
Miami
Sat 6/8
Nonstop3h 31m
Chicago O'Hare IntlTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Tue 5/28
1 stop13h 40m
Tampa
Tue 6/4
Nonstop2h 57m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 5/22
Nonstop2h 58m
Orlando
Tue 5/28
Nonstop3h 09m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Tue 5/21
Nonstop2h 58m
Orlando
Thu 5/23
Nonstop3h 09m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Sun 5/26
1 stop11h 42m
Orlando
Wed 5/29
Nonstop3h 09m
Chicago O'Hare IntlMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 5/15
1 stop12h 57m
Miami
Wed 5/22
1 stop9h 52m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Fri 6/21
1 stop13h 38m
Orlando
Mon 6/24
1 stop6h 11m
No data available for this route at this time. Please check back soon.
Crew
Entertainment
Comfort
Boarding
Food
Overall
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Crew
Entertainment
Comfort
Boarding
Food
Overall
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Crew
Entertainment
Comfort
Boarding
Food
Overall
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Crew
Entertainment
Comfort
Boarding
Food
Overall
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Crew
Entertainment
Comfort
Boarding
Food
Overall
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Crew
Entertainment
Comfort
Boarding
Food
Overall
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Florida often provides a refuge for residents in Chicago looking to get away from bitterly cold winters. The state is home to some of the most popular beaches and tourist destinations in the country, making it a great option for singles, couples and families looking for a getaway. Between Disney World, Miami Beach and the Florida Keys, there's no shortage of fun to be had in Florida.
Both Florida and Chicago are home to fun, hardworking locals who know how to enjoy the best that their hometowns have to offer. However, the climates couldn't be more different. Summers in Florida are hot and humid, much more so than Chicago summers, and winters in Florida tend to be mild and enjoyable. Native Chicagoans visiting Florida will feel right at home in the bustling metropolis that is Miami, and they can get the world-famous theme park experiences in Orlando/Kissimmee. The white sandy beaches of Florida's coastline provides plenty of space for visitors to relax, and Chicagoans will feel right at home, as they have plenty of access to beautiful beaches in their fair city too.
Put our convenient smart engine to use, and find cheap flights from Chicago to any of Florida's most popular destination cities for your next vacation getaway.
7%of flight departures | Early morningMidnight to 6 am |
---|---|
48%of flight departures | Morning6 am to noon |
38%of flight departures | AfternoonNoon to 6 pm |
7%of flight departures | Evening6 pm to midnight |
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