What percentage of Tampa to Chicago flights are direct?

In the trailing 90 days, approximately 14.2% of flights from Tampa to Chicago were direct. For travelers opting for connecting flights, the median number of stopovers was 2. This suggests that while direct options are available, a significant portion of routes involve at least one stop.

How many hours is the flight from Tampa to Chicago?

A direct flight from Tampa to Chicago typically takes about 3 hours and 3 minutes, covering a distance of 1607 kilometers. If your journey includes one stop, the median flight time increases significantly to approximately 9 hours and 20 minutes. Travelers should consider these durations when planning their trip.

How often do cheap flights from Tampa to Chicago come up?

Historically, cheap flights from Tampa to Chicago are classified as frequent. This indicates that opportunities for finding affordable fares on this route arise regularly across the trailing quarter. Travelers looking for deals can expect to see them appear often.

Flights From Tampa

To Chicago

Cheap Flights from Tampa to Chicago

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Deals from

Tampa

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated 2 days ago

476 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 12, 2026.)

Today’s best flight deals from Tampa to Chicago

Explore current cheapest deals departing from Tampa to Chicago

2027-01-27 – 2027-02-01
TPA - Chicago
73% AI deal score
$125
$89
Round trip
2027-01-20 – 2027-01-27
TPA - Chicago
67% AI deal score
$115
$90
Round trip
2027-01-27 – 2027-02-22
TPA - Chicago
65% AI deal score
$105
$90
Round trip
2027-01-27 – 2027-02-04
TPA - Chicago
72% AI deal score
$119
$90
Round trip
2027-02-04 – 2027-02-22
TPA - Chicago
65% AI deal score
$107
$92
Round trip
2027-02-04 – 2027-03-01
TPA - Chicago
65% AI deal score
$106
$92
Round trip
2027-01-09 – 2027-01-26
TPA - Chicago
45% AI deal score
$92
$94
Round trip
2027-01-06 – 2027-01-26
TPA - Chicago
45% AI deal score
$91
$94
Round trip
2027-01-20 – 2027-01-26
TPA - Chicago
66% AI deal score
$115
$94
Round trip
2027-01-12 – 2027-01-26
TPA - Chicago
46% AI deal score
$96
$94
Round trip

Tampa to Chicago: Overview

Insights for flights from Tampa to Chicago

Right now, 5% of recent fares from Tampa to Chicago are considered a good price. Over a 90-day period, fares for this route typically range from $322–$787, with a median of $514. Current fares are below the typical level, suggesting a potentially favorable time to find cheap flights from Tampa to Chicago.

When is the cheapest time to fly from Tampa to Chicago? The data indicates that January is typically the most affordable month, with a median fare of $295. This is closely followed by February, where the median fare is $301. November also presents a more budget-friendly option, with a median fare of $362.

A typical journey from Tampa to Chicago covers a distance of 1607 km, classifying it as a medium-haul route. This distance is often covered with connecting flights, as only 14.2% of recent fares were for direct flights from Tampa to Chicago. For itineraries that include connections, the median number of stopovers is 2.

The typical journey time from Tampa to Chicago, including connections, is 3h 3m. For connecting itineraries, the median duration extends to 18h 19m. New deals for this route appear almost daily, making it beneficial to monitor prices regularly.

How much is a round trip from Tampa to Chicago

Regular price: $96 - $259

Prices are currently below the regular range for flights from Tampa to Chicago.

The regular price range for this route is $96 to $259. The current lowest deal is $89 with Frontier Airlines, for travel from Jan 27-Feb 1.

now $89

Low $96

High $259

The cheapest time to fly from Tampa to Chicago

The cheapest month to fly from TPA to CHI is January, with a median price of $295. The most expensive month is July, with a median price of $758. Prices are generally lower from January to November.

January

Cheapest

Flights from $295

July

Most Expensive

Flights from $758

Jan

Feb

Mar

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Tampa to Chicago

Allegiant Air

Frontier Airlines

Last-minute flights going from Tampa to Chicago

Sat, Oct 10

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$475

$288

One-way

Sun, Oct 11

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$425

$341

One-way

Mon, Oct 12

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (ORD)

Frontier Airlines

$400

$323

One-way

Tue, Oct 13

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (ORD)

Frontier Airlines

$393

$379

One-way

Wed, Oct 14

⌛ Last-Minute

PIE - Chicago

Tampa (PIE) - Chicago (RFD)

Allegiant Air

$421

$290

One-way

Thu, Oct 15

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$408

$341

One-way

Biggest price drops on these dates for flights from Tampa to Chicago

3 nights

Oct 10 - Oct 13

$475 → $288

39%

2 nights

Oct 10 - Oct 12

$480 → $329

32%

2 nights

Dec 9 - Dec 11

$244 → $136

44%

5 nights

Nov 19 - Nov 24

$243 → $140

42%

Popular Airports to fly from Tampa to Chicago

Tampa - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Tampa to Chicago are below the typical level for the route.

📅 Best time to fly

January offers the lowest median prices

Historically, January, February, and November offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights average 3h 3m

The median flight duration for direct flights is 3h 3m, while connecting flights average 18h 19m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 85.8% of recent deals, with a median of 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers a recent deal for $89

A recent deal with Frontier Airlines from Tampa to Chicago was found for $89.

🎯 Booking tip

Deals appear frequently on this route

Deals for flights from Tampa to Chicago appear frequently, with many options in a 30-day window.

Tampa main airports to depart from

Tampa International (TPA)

Cheapest

Tampa International Airport (TPA) is a convenient option for flights from Tampa to Chicago.

📍 ~8 km from Tampa (reachable by car or bus).

💸 Flights from ~$93

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International offers the cheapest flights to Chicago from Tampa, providing a budget-friendly option.

📍 ~126 km from Chicago city center (reachable by car)

💸 Flights from ~$112

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$308

Business & First Class Flight Deals to Chicago

66% AI deal score

$879

$852

Save $27

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the best time to book flights from Tampa to Chicago for the cheapest prices is typically between 28 and 59 days before departure. During this window, the average price for a flight is around $453. Booking within 0-6 days of departure, for example, sees prices rise significantly to an average of $785. Planning ahead by at least a month can lead to considerable savings on your fare.

Across the trailing quarter, a good price for a flight from Tampa to Chicago is considered to be $322 or less. The median price for this route over the same period was $514. Prices can vary, with some fares historically reaching up to $787, so finding a deal at or below the $322 threshold represents a notable saving.

Historically, January and February have offered the cheapest flights from Tampa to Chicago, with median prices of $295 and $301 respectively. November also tends to be a more affordable month, with a median price of $362. The annual median price for this route is $514, indicating that these months provide opportunities for significant savings compared to other times of the year.

Tampa to Chicago: Overview

Insights for flights from Tampa to Chicago

How much is a round trip from Tampa to Chicago

Regular price: $96 - $259

Prices are currently below the regular range for flights from Tampa to Chicago.

The regular price range for this route is $96 to $259. The current lowest deal is $89 with Frontier Airlines, for travel from Jan 27-Feb 1.

now $89

Low $96

High $259

The cheapest time to fly from Tampa to Chicago

The cheapest month to fly from TPA to CHI is January, with a median price of $295. The most expensive month is July, with a median price of $758. Prices are generally lower from January to November.

January

Cheapest

Flights from $295

July

Most Expensive

Flights from $758

Jan

Feb

Mar

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec