
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $92 (Frontier) |
One-way from | $58 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $222 |
Good round-trip deal | $93 or less |
Good one-way deal | $42 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 7/15
8:10 pm-11:45 pm
Nonstop2h 35m
Orlando
Tue 7/21
8:10 pm-10:00 pm
Nonstop2h 50m
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Tue 5/26
2:00 pm-5:57 pm
Nonstop2h 57m
Orlando
Sat 5/30
12:34 pm-2:42 pm
Nonstop3h 08m
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 6/17
5:30 pm-11:35 pm
1 stop5h 05m
Orlando
Wed 6/24
10:20 am-2:10 pm
1 stop4h 50m
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 6/3
8:40 am-2:58 pm
1 stop5h 18m
Orlando
Wed 6/10
7:13 am-9:22 am
Nonstop3h 09m
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 8/5
7:40 am-2:50 pm
2 stops6h 10m
Tampa
Wed 8/12
7:00 pm-10:20 pm
1 stop4h 20m
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Tue 6/2
12:55 pm-7:55 pm
1 stop6h 00m
Orlando
Sat 6/6
8:15 am-12:35 pm
1 stop5h 20m
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Wed 8/5
5:28 am-11:29 am
1 stop5h 01m
Tampa
Wed 8/12
12:34 pm-4:54 pm
1 stop5h 20m
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Fri 5/29
8:35 pm-12:10 am
Nonstop2h 35m
Orlando
Wed 6/3
8:55 am-12:00 pm
1 stop4h 05m
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Thu 6/4
7:45 am-12:50 pm
1 stop4h 05m
Tampa
Wed 6/10
7:25 pm-11:50 pm
1 stop5h 25m
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Thu 5/28
11:26 am-6:51 pm
1 stop6h 25m
Tampa
Tue 6/2
5:46 pm-10:27 pm
1 stop5h 41m
The price you pay for your flight from Chicago to Florida may vary depending on when you book. For the best chance of a lower fare, look to book 29 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, September is the cheapest month in which you can book a flight from Chicago to Florida (average of $209). Flying from Chicago to Florida in March is currently the most expensive (average of $344). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
When flying from Chicago to Florida, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 4% versus a flight in the evening.
Travelers seeking maximum savings on their Chicago to Florida flight should consider departing on Wednesday at noon when fares are most often at their lowest. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to USFL are scheduled on a Friday (54 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (38 on average).
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
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.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$191 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$65 | Average$204 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$83 | Average$347 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$84 | Average$201 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$283 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$360 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$155 | Average$352 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$156 | Average$342 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$249 | FlexibilityNo cancel fee | On-time75% |