To save up to 243% on this flight, we recommend booking at least 57 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Florida to Chicago from $112 1-2 weeks out and tickets from $248 for flights departing within the next 72 hours.
Our data shows that October tends to be the cheapest month to fly to Chicago from Florida. Users have commonly found prices around $152 for the month, but tickets can be as low as $43. Due to multiple factors, prepare for potentially higher prices in June.
When flying from Florida to Chicago, 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
$48 - $81
Route
Depart
Return
Price
TampaChicago Midway
TPA - MDW
TPAMDW
Tampa
Tue 9/3
Nonstop2h 43m
Chicago Midway
Tue 9/10
Nonstop2h 36m
TampaChicago Midway
TPA - MDW
TPAMDW
Tampa
Tue 9/3
Nonstop2h 43m
Chicago Midway
Wed 9/11
Nonstop2h 36m
MiamiChicago Midway
MIA - MDW
MIAMDW
Miami
Wed 9/4
Nonstop3h 10m
Chicago Midway
Mon 9/9
Nonstop3h 04m
MiamiChicago Midway
MIA - MDW
MIAMDW
Miami
Sat 8/17
Nonstop3h 10m
Chicago Midway
Wed 8/21
Nonstop3h 04m
Fort LauderdaleChicago O'Hare Intl
FLL - ORD
FLLORD
Fort Lauderdale
Sat 8/24
Nonstop3h 17m
Chicago O'Hare Intl
Tue 8/27
Nonstop3h 05m
TampaChicago Midway
TPA - MDW
TPAMDW
Tampa
Tue 8/27
Nonstop2h 43m
Chicago Midway
Sat 8/31
Nonstop2h 36m
MiamiChicago O'Hare Intl
MIA - ORD
MIAORD
Miami
Tue 8/20
Nonstop3h 23m
Chicago O'Hare Intl
Tue 8/27
Nonstop3h 16m
Fort LauderdaleChicago O'Hare Intl
FLL - ORD
FLLORD
Fort Lauderdale
Sat 8/24
Nonstop3h 20m
Chicago O'Hare Intl
Tue 8/27
Nonstop3h 05m
OrlandoChicago O'Hare Intl
MCO - ORD
MCOORD
Orlando
Wed 8/28
1 stop5h 52m
Chicago O'Hare Intl
Tue 9/3
Nonstop2h 58m
No data available for this route at this time. Please check back soon.
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
No tray tables for food or drink not convenient nor comfortable
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
No tray tables for food or drink not convenient nor comfortable
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
No tray tables for food or drink not convenient nor comfortable
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
No tray tables for food or drink not convenient nor comfortable
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
No tray tables for food or drink not convenient nor comfortable
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
No tray tables for food or drink not convenient nor comfortable
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.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Frontier | Cheapest$40 | Average$143 | FlexibilityNo cancel fee | On-time62% |
Spirit Airlines | Cheapest$42 | Average$148 | FlexibilityNo cancel fee | On-time65% |
United Airlines | Cheapest$89 | Average$322 | FlexibilityNo cancel fee | On-time69% |
Allegiant Air | Cheapest$119 | Average$202 | FlexibilityNo cancel fee | On-time88% |
American Airlines | Cheapest$158 | Average$295 | FlexibilityNo cancel fee | On-time71% |
Delta | Cheapest$186 | Average$362 | FlexibilityNo cancel fee | On-timeN/A |
7%of flight departures | Early morningMidnight to 6 am |
---|---|
36%of flight departures | Morning6 am to noon |
53%of flight departures | AfternoonNoon to 6 pm |
4%of flight departures | Evening6 pm to midnight |