What percentage of Tampa to Chicago flights are direct?

Based on data from the trailing 90 days, approximately 14.2% of flights from Tampa to Chicago are direct. For flights that include stopovers, travelers typically experience a median of 2 stopovers. This indicates that a significant portion of routes involve at least one connection.

How many hours is the flight from Tampa to Chicago?

A direct flight from Tampa to Chicago typically takes around 3 hours and 3 minutes, covering a distance of 1607 kilometers. Flights with one stop, however, have a significantly longer median duration, averaging about 9 hours and 20 minutes. This difference highlights the time savings associated with direct routes.

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

Based on historical trends over the trailing 30 days, cheap flights from Tampa to Chicago are classified as frequent. This suggests that travelers typically have regular opportunities to find deals on this route. The consistent availability makes it a favorable route for finding lower fares.

Flights From Tampa

To Chicago

Cheap Flights from Tampa to Chicago

Browse current best options from Tampa. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Tampa

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

Prices updated today

485 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Nov 2, 2026.)

Today’s best flight deals from Tampa to Chicago

Explore current cheapest deals departing from Tampa to Chicago

2026-11-20 – 2026-11-23
TPA - Chicago
67% AI deal score
$218
$167
Round trip
2026-11-18 – 2026-11-27
TPA - Chicago
50% AI deal score
$193
$168
Round trip
2026-11-20 – 2026-11-25
TPA - Chicago
67% AI deal score
$213
$170
Round trip
2026-11-26 – 2026-11-29
TPA - Chicago
43% AI deal score
$126
$181
Round trip
2026-11-20 – 2026-11-22
TPA - Chicago
66% AI deal score
$218
$182
Round trip
2026-11-09 – 2026-11-13
TPA - Chicago
75% AI deal score
$289
$191
Round trip
2026-11-22 – 2026-11-25
TPA - Chicago
49% AI deal score
$218
$193
Round trip
2026-11-06 – 2026-11-12
TPA - Chicago
67% AI deal score
$234
$199
Round trip
2026-11-20 – 2026-11-29
TPA - Chicago
42% AI deal score
$112
$200
Round trip
2026-11-24 – 2026-11-28
TPA - Chicago
42% AI deal score
$126
$202
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: $88 - $229

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

Regular prices for flights from Tampa to Chicago typically range from $88 to $229. The current lowest deal is $94 with Frontier Airlines, for travel from February 6 to February 27.

now $94

Low $88

High $229

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

Thu, Oct 29

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (ORD)

Frontier Airlines

$400

$327

One-way

Thu, Oct 29

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (ORD)

Frontier Airlines

$402

$346

One-way

Mon, Nov 2

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$256

$255

One-way

Mon, Nov 2

⌛ Last-Minute

PIE - Chicago

Tampa (PIE) - Chicago (RFD)

Allegiant Air

$372

$274

One-way

Tue, Nov 3

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$337

$284

One-way

Wed, Nov 4

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (RFD)

Breeze Airways

$316

$222

One-way

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

2 nights

Dec 11 - Dec 13

$241 → $93

61%

4 nights

Dec 4 - Dec 8

$274 → $133

51%

2 nights

Dec 4 - Dec 6

$276 → $140

49%

5 nights

Dec 4 - Dec 9

$268 → $133

50%

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, with 5% considered good deals.

📅 Best time to fly

January offers the lowest median price at $295

Historically, January, February, and November offer lower median prices for flights to Chicago.

⏱️ Flight duration

Direct flights average 3h 3m

Direct flights typically take 3h 3m, while connecting flights average 18h 19m.

✈️ Airlines & availability

Connecting flights are dominant on this route

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

🏆 Airline highlight

Frontier Airlines offers a deal at $94

Frontier Airlines has a recent deal for $94 from Tampa to Chicago, found via kiwi.

🎯 Booking tip

Deals appear frequently, consider booking soon

Deals on flights from Tampa to Chicago appear frequently, with 5% considered good deals.

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

65% AI deal score

$2,762

$2,676

Save $86

Air Canada, +1

Business Class

From TPA

Elite

Oct 26

Chicago, United States

50% AI deal score

$1,129

$1,002

Save $127

From TPA

Elite

Dec 10

Chicago, United States

48% AI deal score

$1,600

Porter Airlines, +1

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the lowest average prices for flights from Tampa to Chicago are found when booking 28-59 days in advance. During this period, the average price is typically around $453. Booking within 0-6 days of departure generally sees average prices rise significantly, reaching approximately $785. Prices tend to be higher for very last-minute bookings across the trailing 90 days.

Across the trailing 90 days, a good price for a flight from Tampa to Chicago is considered to be $322 or less. The median price for this route during the same period was $514. Prices can range significantly, with 75% of fares typically falling below $787.

Historically, January and February are typically the cheapest months to fly from Tampa to Chicago, with median prices around $295 and $301, respectively. November also offers relatively lower prices, with a median of $362. The annual median price for this route, based on data from the trailing 270 days, is $514.

Tampa to Chicago: Overview

Insights for flights from Tampa to Chicago

How much is a round trip from Tampa to Chicago

Regular price: $88 - $229

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

Regular prices for flights from Tampa to Chicago typically range from $88 to $229. The current lowest deal is $94 with Frontier Airlines, for travel from February 6 to February 27.

now $94

Low $88

High $229

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