
Keep the following information in mind while searching for Florida to Chicago flight deals. Data was last updated August 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $133 (Kiwi.com) |
One-way from | $68 (Trip.com) |
Popular in | June |
Cheapest in | September |
Average price | $193 |
Good round-trip deal | $138 or less |
Good one-way deal | $64 or less |
Fly from
Fly to
Route
Depart
Return
MiamiChicago
MIA - ORD
MIAORD
Miami
Sat 8/29
3:57 pm-6:30 pm
Nonstop3h 33m
Chicago O'Hare Intl
Tue 9/1
7:30 am-11:54 am
Nonstop3h 24m
MiamiChicago
MIA - MDW
MIAMDW
Miami
Thu 9/17
7:15 am-9:20 am
Nonstop3h 05m
Chicago Midway
Mon 9/21
8:00 am-12:10 pm
Nonstop3h 10m
MiamiChicago
MIA - ORD
MIAORD
Miami
Sat 9/26
12:29 pm-3:00 pm
Nonstop3h 31m
Chicago O'Hare Intl
Tue 9/29
10:38 am-2:59 pm
Nonstop3h 21m
Fort LauderdaleChicago
FLL - ORD
FLLORD
Fort Lauderdale
Wed 9/16
6:00 pm-8:36 pm
Nonstop3h 36m
Chicago O'Hare Intl
Mon 9/21
5:30 pm-9:42 pm
Nonstop3h 12m
MiamiChicago
MIA - MDW
MIAMDW
Miami
Thu 9/24
7:15 am-9:20 am
Nonstop3h 05m
Chicago Midway
Mon 9/28
5:30 am-2:40 pm
1 stop8h 10m
MiamiChicago
MIA - MDW
MIAMDW
Miami
Thu 8/27
7:15 am-9:20 am
Nonstop3h 05m
Chicago Midway
Sat 8/29
5:55 am-1:35 pm
1 stop6h 40m
MiamiChicago
MIA - ORD
MIAORD
Miami
Thu 9/17
5:37 pm-12:28 am
1 stop7h 51m
Chicago O'Hare Intl
Mon 9/21
10:30 am-2:51 pm
Nonstop3h 21m
MiamiChicago
MIA - MDW
MIAMDW
Miami
Mon 9/14
7:15 am-9:20 am
Nonstop3h 05m
Chicago Midway
Mon 9/21
7:25 am-3:20 pm
1 stop6h 55m
MiamiChicago
MIA - ORD
MIAORD
Miami
Tue 9/29
5:00 pm-12:23 am
1 stop8h 23m
Chicago O'Hare Intl
Wed 9/30
7:30 am-11:55 am
Nonstop3h 25m
MiamiChicago
MIA - MDW
MIAMDW
Miami
Fri 9/11
4:00 pm-10:55 pm
1 stop7h 55m
Chicago Midway
Mon 9/14
5:30 am-3:20 pm
1 stop8h 50m
Everything you need to know about your flight from Florida to Chicago
If you fly into Chicago O’Hare International Airport you’ll be about 14 miles from the central Loop business district in the city. This airport took over as the primary one for the city some time ago. It used to be Midway. The airport serves more than 83 million travelers in a year, making it the sixth busiest one in the world.
The other place you might fly into is Midway International Airport. This one is closer to the Loop district at only eight miles away. The airport handles over 22 million passengers per year and is the second busiest airport in Illinois. The majority of flights going into Midway are operated by Southwest Airlines.
Southwest flies into Midway with stopovers in Baltimore, Atlanta, Birmingham, and Kansas City. You might also stop in Dallas, St. Louis, or Manchester in New Hampshire. None of the stopovers are much more than an hour and many of them are under that.
Find useful and relevant information for your journey from Florida to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$43 | Average$191 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$76 | Average$171 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$98 | Average$342 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$105 | Average$298 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$144 | Average$357 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$156 | Average$338 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$345 | FlexibilityNo cancel fee | On-time63% |