
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $157 (Kiwi.com) |
One-way from | $79 (Trip.com) |
Popular in | March |
Cheapest in | October |
Average price | $243 |
Good round-trip deal | $117 or less |
Good one-way deal | $90 or less |
Fly from
Fly to
Route
Depart
Return
TampaChicago
TPA - MDW
TPAMDW
Tampa
Wed 6/24
9:55 pm-11:35 pm
Nonstop2h 40m
Chicago Midway
Wed 7/1
8:15 pm-11:50 pm
Nonstop2h 35m
TampaChicago
TPA - MDW
TPAMDW
Tampa
Tue 7/7
4:40 pm-7:55 pm
1 stop4h 15m
Chicago Midway
Tue 7/14
7:25 am-1:20 pm
1 stop4h 55m
TampaChicago
TPA - ORD
TPAORD
Tampa
Sat 10/3
7:27 pm-9:38 pm
Nonstop3h 11m
Chicago O'Hare Intl
Tue 10/6
8:55 am-3:24 pm
1 stop5h 29m
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 10/3
3:10 pm-6:10 pm
1 stop4h 00m
Chicago Midway
Tue 10/6
1:25 pm-5:00 pm
Nonstop2h 35m
TampaChicago
TPA - ORD
TPAORD
Tampa
Tue 6/23
6:20 am-12:36 pm
1 stop7h 16m
Chicago O'Hare Intl
Wed 6/24
5:30 am-12:45 pm
1 stop6h 15m
TampaChicago
TPA - ORD
TPAORD
Tampa
Tue 8/4
8:15 am-1:13 pm
1 stop5h 58m
Chicago O'Hare Intl
Thu 8/13
9:52 am-4:48 pm
1 stop5h 56m
TampaChicago
TPA - MDW
TPAMDW
Tampa
Wed 6/17
7:00 pm-10:35 pm
1 stop4h 35m
Chicago Midway
Wed 6/24
8:15 pm-11:50 pm
Nonstop2h 35m
TampaChicago
TPA - MDW
TPAMDW
Tampa
Tue 7/7
9:55 pm-11:35 pm
Nonstop2h 40m
Chicago Midway
Sat 7/11
9:15 am-4:20 pm
1 stop6h 05m
TampaChicago
TPA - ORD
TPAORD
Tampa
Thu 5/28
10:55 am-9:55 pm
2 stops12h 00m
Chicago O'Hare Intl
Mon 6/1
2:40 pm-9:10 pm
1 stop5h 30m
TampaChicago
TPA - RFD
TPARFD
Tampa
Wed 8/12
8:28 pm-10:47 am
1 stop15h 19m
Chicago Greater Rockford
Sun 8/16
11:37 am-7:23 am
1 stop18h 46m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
Booking 65 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, January is the cheapest month in which you can book a flight from Tampa to Chicago (average of $47). Flying from Tampa to Chicago in February is currently the most expensive (average of $696). 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 24% 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 Friday (57 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (32 on average).
Overall
Boarding
Crew
Food
Entertainment
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Boarding
Crew
Food
Entertainment
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Boarding
Crew
Food
Entertainment
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Boarding
Crew
Food
Entertainment
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Boarding
Crew
Food
Entertainment
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Boarding
Crew
Food
Entertainment
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$162 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$68 | Average$159 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$98 | Average$557 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$324 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$296 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$158 | Average$322 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$158 | Average$277 | FlexibilityNo cancel fee | On-time71% |