Consider extra comfort seats for more legroom, ideal for taller passengers.
Early check-in can secure your place onboard due to frequent overbooking.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $101 (Frontier) |
One-way from | $66 (Cheapflightsfares) |
Popular in | June |
Cheapest in | January |
Average price | $183 |
Good round-trip deal | $104 or less |
Good one-way deal | $91 or less |
Fly from
Fly to
Route
Depart
Return
Price
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 12/13
7:00 am-11:08 am
1 stop29h 08m
Chicago Midway
Mon 12/15
6:15 am-6:46 pm
1 stop11h 31m
TampaChicago
TPA - ORD
TPAORD
Tampa
Thu 12/4
7:00 am-12:12 am
1 stop18h 12m
Chicago O'Hare Intl
Sat 12/6
1:24 pm-9:31 pm
1 stop7h 07m
TampaChicago
TPA - ORD
TPAORD
Tampa
Sat 12/13
6:12 pm-12:09 am
1 stop6h 57m
Chicago O'Hare Intl
Mon 12/15
11:44 am-6:46 pm
1 stop6h 02m
TampaChicago
TPA - ORD
TPAORD
Tampa
Fri 12/5
8:07 pm-12:09 am
1 stop5h 02m
Chicago O'Hare Intl
Sun 12/7
5:11 am-12:22 pm
1 stop6h 11m
TampaChicago
TPA - ORD
TPAORD
Tampa
Thu 1/8
12:25 pm-2:28 pm
Nonstop3h 03m
Chicago O'Hare Intl
Sun 1/11
7:15 am-11:08 am
Nonstop2h 53m
TampaChicago
TPA - ORD
TPAORD
Tampa
Thu 11/27
6:00 am-11:34 am
1 stop6h 34m
Chicago O'Hare Intl
Tue 12/2
4:22 pm-11:29 pm
1 stop6h 07m
TampaChicago
TPA - MDW
TPAMDW
Tampa
Thu 11/27
5:20 am-10:17 pm
1 stop17h 57m
Chicago Midway
Tue 12/2
2:49 pm-11:29 pm
1 stop7h 40m
TampaChicago
TPA - ORD
TPAORD
Tampa
Mon 11/24
8:58 pm-7:21 pm
1 stop23h 23m
Chicago O'Hare Intl
Thu 11/27
3:37 pm-7:25 pm
Nonstop2h 48m
TampaChicago
TPA - ORD
TPAORD
Tampa
Sat 12/6
8:07 pm-12:09 am
1 stop5h 02m
Chicago O'Hare Intl
Mon 12/22
1:34 pm-5:17 pm
Nonstop2h 43m
TampaChicago
TPA - MDW
TPAMDW
Tampa
Wed 12/10
7:35 am-11:25 am
1 stop4h 50m
Chicago Midway
Wed 12/10
1:30 pm-7:55 pm
1 stop5h 25m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
Booking 86 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 $31). 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 at noon tend to be the most expensive. A flight in the evening could potentially save you up to 61% on airfare.
Travelers seeking maximum savings on their Tampa to Chicago flight should consider departing on Friday evenings 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 Monday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).
Crew
Boarding
Comfort
Entertainment
Food
Overall
Reviews
Anonymous,Feb 2025
MCO - STL
Crew
Boarding
Comfort
Entertainment
Food
Overall
Reviews
Anonymous,Feb 2025
MCO - STL
Crew
Boarding
Comfort
Entertainment
Food
Overall
Reviews
Anonymous,Feb 2025
MCO - STL
Crew
Boarding
Comfort
Entertainment
Food
Overall
Reviews
Anonymous,Feb 2025
MCO - STL
Crew
Boarding
Comfort
Entertainment
Food
Overall
Reviews
Anonymous,Feb 2025
MCO - STL
Crew
Boarding
Comfort
Entertainment
Food
Overall
Reviews
Anonymous,Feb 2025
MCO - STL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$156 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$82 | Average$157 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$98 | Average$414 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$143 | Average$263 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$158 | Average$304 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$160 | Average$278 | FlexibilityNo cancel fee | On-time71% |