
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $135 (Kiwi.com) |
One-way from | $72 (Super.com) |
Popular in | June |
Cheapest in | September |
Average price | $318 |
Good round-trip deal | $98 or less |
Good one-way deal | $57 or less |
Fly from
Fly to
Route
Depart
Return
MiamiChicago
MIA - MDW
MIAMDW
Miami
Wed 7/8
11:45 am-3:55 pm
1 stop5h 10m
Chicago Midway
Wed 7/15
1:00 pm-10:15 pm
2 stops8h 15m
MiamiChicago
MIA - MDW
MIAMDW
Miami
Tue 9/8
12:50 pm-4:50 pm
1 stop5h 00m
Chicago Midway
Tue 9/22
1:00 pm-8:10 pm
2 stops6h 10m
Fort LauderdaleChicago
FLL - MDW
FLLMDW
Fort Lauderdale
Tue 9/8
2:55 pm-8:45 pm
1 stop6h 50m
Chicago Midway
Tue 9/22
1:00 pm-8:25 pm
2 stops6h 25m
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Sat 7/11
7:00 am-12:49 am
1 stop18h 49m
Chicago O'Hare Intl
Tue 7/14
5:13 pm-9:25 pm
Nonstop3h 12m
Fort LauderdaleChicago
FLL - MDW
FLLMDW
Fort Lauderdale
Fri 7/17
5:55 am-7:55 am
Nonstop3h 00m
Chicago Midway
Mon 7/20
7:35 pm-11:35 pm
Nonstop3h 00m
MiamiChicago
MIA - ORD
MIAORD
Miami
Thu 9/17
3:57 pm-6:30 pm
Nonstop3h 33m
Chicago O'Hare Intl
Mon 9/21
5:50 am-2:47 pm
1 stop7h 57m
Fort LauderdaleChicago
FLL - ORD
FLLORD
Fort Lauderdale
Thu 9/3
12:20 pm-2:48 pm
Nonstop3h 28m
Chicago O'Hare Intl
Sun 9/6
10:50 am-3:07 pm
Nonstop3h 17m
Fort LauderdaleChicago
FLL - ORD
FLLORD
Fort Lauderdale
Fri 9/4
11:58 am-6:48 pm
1 stop7h 50m
Chicago O'Hare Intl
Mon 9/7
7:00 am-11:14 am
Nonstop3h 14m
MiamiChicago
MIA - MDW
MIAMDW
Miami
Tue 7/28
6:00 am-10:05 am
1 stop5h 05m
Chicago Midway
Tue 8/4
9:24 am-5:37 pm
1 stop7h 13m
Fort LauderdaleChicago
FLL - ORD
FLLORD
Fort Lauderdale
Tue 7/28
3:32 pm-8:33 pm
1 stop6h 01m
Chicago O'Hare Intl
Tue 8/4
6:40 am-12:21 pm
1 stop4h 41m
Currently, January is the cheapest month in which you can book a flight from Florida to Illinois (average of $180). Flying from Florida to Illinois in June is currently the most expensive (average of $338). 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.
It’s typically best to fly out from Florida to Illinois in the morning. Doing so could potentially save you 13% on the flight price compared to flying at noon, which is usually more expensive.
The most flights from USFL to USIL are scheduled on a Friday (56 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (38 on average).
The best time to book flights from Florida to Illinois is 47 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Travelers seeking maximum savings on their Florida to Illinois flight should consider departing on Saturday evenings when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Entertainment
Overall
Boarding
Comfort
Crew
Food
Reviews
Reza,Jun 2026
TPA - MDW
Entertainment
Overall
Boarding
Comfort
Crew
Food
Reviews
Reza,Jun 2026
TPA - MDW
Entertainment
Overall
Boarding
Comfort
Crew
Food
Reviews
Reza,Jun 2026
TPA - MDW
Entertainment
Overall
Boarding
Comfort
Crew
Food
Reviews
Reza,Jun 2026
TPA - MDW
Entertainment
Overall
Boarding
Comfort
Crew
Food
Reviews
Reza,Jun 2026
TPA - MDW
Entertainment
Overall
Boarding
Comfort
Crew
Food
Reviews
Reza,Jun 2026
TPA - MDW
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$43 | Average$172 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$76 | Average$176 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$105 | Average$292 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$121 | Average$372 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$182 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$133 | Average$353 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$149 | Average$339 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$369 | FlexibilityNo cancel fee | On-time71% |