Find a great deal and save up to 50% by booking at least 12 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 $132.
January can be a great time to fly to Florida from Chicago with a flight ticket averaging about $220. Cheapflights users have found deals in the month of January for as cheap as $64. 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
$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.
Boarding
Entertainment
Overall
Crew
Food
Comfort
Reviews
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
Boarding
Entertainment
Overall
Crew
Food
Comfort
Reviews
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
Boarding
Entertainment
Overall
Crew
Food
Comfort
Reviews
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
Boarding
Entertainment
Overall
Crew
Food
Comfort
Reviews
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
Boarding
Entertainment
Overall
Crew
Food
Comfort
Reviews
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
Boarding
Entertainment
Overall
Crew
Food
Comfort
Reviews
I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.
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.
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 |
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