
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $188 (Frontier) |
One-way from | $95 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $324 |
Fly from
Fly to
Route
Depart
Return
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 7/15
5:35 am-3:10 pm
1 stop8h 35m
Miami
Wed 7/22
4:00 pm-6:10 pm
Nonstop3h 10m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 7/22
6:05 pm-10:27 pm
Nonstop3h 22m
Miami
Tue 7/28
4:53 pm-12:45 am
1 stop8h 52m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 9/1
7:30 am-3:55 pm
1 stop7h 25m
Miami
Sun 9/6
4:13 pm-6:46 pm
Nonstop3h 33m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 6/17
6:05 pm-10:27 pm
Nonstop3h 22m
Miami
Wed 6/24
4:06 pm-6:49 pm
Nonstop3h 43m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 7/8
3:00 pm-10:15 pm
2 stops6h 15m
Miami
Wed 7/22
11:25 am-7:05 pm
2 stops8h 40m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 7/8
3:00 pm-10:15 pm
2 stops6h 15m
Miami
Sat 7/11
7:15 am-5:05 pm
1 stop10h 50m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 7/10
11:00 am-4:25 pm
1 stop4h 25m
Miami
Tue 7/14
4:00 pm-6:10 pm
Nonstop3h 10m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 8/11
12:20 pm-8:00 pm
1 stop6h 40m
Miami
Fri 8/14
7:15 am-9:20 am
Nonstop3h 05m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 8/13
8:00 am-12:10 pm
Nonstop3h 10m
Miami
Fri 8/21
7:15 am-9:20 am
Nonstop3h 05m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 7/29
6:05 pm-10:27 pm
Nonstop3h 22m
Miami
Mon 8/3
4:53 pm-12:45 am
1 stop8h 52m
When flying from Chicago to Islamorada, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 13% versus a flight in the afternoon.
The most flights from CHI to I5L are scheduled on a Wednesday (50 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (15 on average).
Travelers seeking maximum savings on their Chicago to Islamorada flight should consider departing on Wednesday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Scott,Feb 2026
HOU - FLL
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Scott,Feb 2026
HOU - FLL
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Scott,Feb 2026
HOU - FLL
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Scott,Feb 2026
HOU - FLL
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Scott,Feb 2026
HOU - FLL
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Scott,Feb 2026
HOU - FLL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$199 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$84 | Average$136 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$391 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$155 | Average$327 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$377 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$367 | FlexibilityNo cancel fee | On-time63% |