
Most accurate provider | Justfly.com 3 stars |
|---|---|
Most trusted provider | Justfly.com 3 stars |
Round-trip from | $71 (Priceline) |
One-way from | $45 (CheapOair) |
Popular in | March |
Cheapest in | September |
Average price | $198 |
Good round-trip deal | $78 or less |
Good one-way deal | $52 or less |
Fly from
Fly to
Route
Depart
Return
Price
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 1/15
12:39 pm-10:19 pm
1 stop10h 40m
Chicago Midway
Sun 1/18
6:01 pm-9:49 pm
Nonstop2h 48m
TampaChicago
TPA - ORD
TPAORD
Tampa
Thu 1/15
2:57 pm-4:58 pm
Nonstop3h 01m
Chicago O'Hare Intl
Sun 1/18
7:58 pm-11:59 pm
Nonstop3h 01m
Fort LauderdaleChicago
FLL - ORD
FLLORD
Fort Lauderdale
Thu 1/15
9:25 pm-11:46 pm
Nonstop3h 21m
Chicago O'Hare Intl
Sun 1/18
12:44 pm-8:10 pm
1 stop6h 26m
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Thu 1/29
4:02 pm-9:42 pm
1 stop6h 40m
Chicago O'Hare Intl
Thu 2/5
4:19 pm-11:57 pm
1 stop6h 38m
Fort LauderdaleChicago
FLL - ORD
FLLORD
Fort Lauderdale
Thu 1/8
12:54 pm-7:41 pm
1 stop7h 47m
Chicago O'Hare Intl
Fri 1/9
5:32 pm-9:40 pm
Nonstop3h 08m
Fort LauderdaleChicago
FLL - ORD
FLLORD
Fort Lauderdale
Thu 1/15
9:25 pm-11:46 pm
Nonstop3h 21m
Chicago O'Hare Intl
Mon 1/19
12:44 pm-8:10 pm
1 stop6h 26m
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Wed 1/7
12:17 pm-2:21 pm
Nonstop3h 04m
Chicago O'Hare Intl
Fri 1/9
8:43 pm-7:43 am
1 stop10h 00m
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 1/15
8:30 am-10:32 am
Nonstop3h 02m
Chicago Midway
Thu 1/22
5:01 pm-12:31 am
1 stop6h 30m
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 2/5
5:49 pm-7:52 pm
Nonstop3h 03m
Chicago Midway
Mon 2/9
5:01 pm-12:31 am
1 stop6h 30m
MiamiChicago
MIA - ORD
MIAORD
Miami
Wed 1/7
2:35 pm-5:00 pm
Nonstop3h 25m
Chicago O'Hare Intl
Sat 1/17
9:23 am-1:41 pm
Nonstop3h 18m
Currently, January is the cheapest month in which you can book a flight from Florida to Chicago (average of $30). Flying from Florida to Chicago in June is currently the most expensive (average of $107). 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.
A simple way to save on the total cost of your ticket is to fly from Florida to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 31% on your trip compared to booking a flight at noon.
Travelers seeking maximum savings on their Florida to Chicago flight should consider departing on Sunday evenings when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 |
|---|---|---|---|---|
| Cheapest$44 | Average$177 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$61 | Average$171 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$72 | Average$150 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$98 | Average$358 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$131 | Average$334 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$148 | Average$328 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$301 | FlexibilityNo cancel fee | On-time71% |