
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $121 (Kiwi.com) |
One-way from | $77 (WAYA) |
Popular in | March |
Cheapest in | October |
Average price | $273 |
Good round-trip deal | $179 or less |
Good one-way deal | $56 or less |
Fly from
Fly to
Route
Depart
Return
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 5/9
9:00 am-10:45 am
Nonstop2h 45m
Chicago Midway
Tue 5/12
7:40 am-12:30 pm
1 stop3h 50m
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 5/2
6:55 am-8:40 am
Nonstop2h 45m
Chicago Midway
Mon 5/4
8:30 pm-12:05 am
Nonstop2h 35m
TampaChicago
TPA - MDW
TPAMDW
Tampa
Tue 5/12
1:45 pm-7:35 pm
2 stops6h 50m
Chicago Midway
Tue 5/19
7:50 am-3:15 pm
2 stops6h 25m
TampaChicago
TPA - ORD
TPAORD
Tampa
Tue 4/21
9:35 am-6:25 pm
2 stops9h 50m
Chicago O'Hare Intl
Sat 5/2
6:00 am-8:05 pm
2 stops13h 05m
TampaChicago
TPA - ORD
TPAORD
Tampa
Wed 5/6
10:10 am-6:25 pm
2 stops9h 15m
Chicago O'Hare Intl
Fri 5/8
6:00 am-7:10 pm
2 stops12h 10m
TampaChicago
TPA - MDW
TPAMDW
Tampa
Fri 4/17
6:30 pm-8:20 pm
Nonstop2h 50m
Chicago Midway
Mon 4/20
1:00 pm-4:35 pm
Nonstop2h 35m
TampaChicago
TPA - RFD
TPARFD
Tampa
Wed 4/1
10:54 pm-9:47 am
1 stop11h 53m
Chicago Greater Rockford
Sun 4/5
10:37 am-7:19 am
1 stop19h 42m
TampaChicago
TPA - ORD
TPAORD
Tampa
Thu 5/7
9:35 am-6:50 pm
2 stops10h 15m
Chicago O'Hare Intl
Sun 5/10
3:45 pm-1:00 am
1 stop8h 15m
TampaChicago
TPA - ORD
TPAORD
Tampa
Thu 5/7
9:35 am-6:50 pm
2 stops10h 15m
Chicago O'Hare Intl
Mon 5/11
2:40 pm-9:00 am
2 stops17h 20m
TampaChicago
TPA - MDW
TPAMDW
Tampa
Fri 4/17
5:59 pm-10:28 pm
1 stop5h 29m
Chicago Midway
Mon 4/20
9:27 am-2:54 pm
1 stop4h 27m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Tampa to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, September is the cheapest month in which you can book a flight from Tampa to Chicago (average of $46). Flying from Tampa 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.
One of the essential ways to save on airfare from Tampa to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 27% on airfare.
Travelers seeking maximum savings on their Tampa to Chicago flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from TPA to CHI are scheduled on a Saturday (58 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (32 on average).
Comfort
Crew
Entertainment
Food
Overall
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Crew
Entertainment
Food
Overall
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Crew
Entertainment
Food
Overall
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Crew
Entertainment
Food
Overall
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Crew
Entertainment
Food
Overall
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Crew
Entertainment
Food
Overall
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$168 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$68 | Average$156 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$98 | Average$461 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$328 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$155 | Average$310 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$291 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$158 | Average$273 | FlexibilityNo cancel fee | On-time71% |