What percentage of Tampa to Chicago flights are direct?

In the trailing 90 days, approximately 29.5% of flights from Tampa to Chicago have been direct. For flights that include stopovers, the median number of stopovers observed is 1. This means that while direct options are available, a significant portion of flights will involve at least one connection.

How many hours is the flight from Tampa to Chicago?

The typical direct flight from Tampa to Chicago has a duration of 3 hours and 3 minutes. For flights with one stop, the median travel time is considerably longer, averaging 8 hours and 46 minutes. The distance covered on this route is approximately 1607 kilometers.

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

Based on historical data from the trailing 30 days, cheap flights from Tampa to Chicago are classified as frequent. This suggests that travelers have regular opportunities to find good deals on this route. The consistent availability makes it easier to plan a trip without waiting for rare price drops.

Flights From Tampa

To Chicago

Cheap Flights from Tampa to Chicago

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Prices updated 1 day ago

461 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Tampa to Chicago

Explore current cheapest deals departing from Tampa to Chicago

2026-10-23 – 2026-10-30
TPA - Chicago
47% AI deal score
$103
$103
Round trip
2026-10-21 – 2026-10-30
TPA - Chicago
46% AI deal score
$98
$110
Round trip
2026-11-03 – 2026-11-09
TPA - Chicago
79% AI deal score
$205
$117
Round trip
2027-01-15 – 2027-01-18
TPA - Chicago
46% AI deal score
$117
$125
Round trip
2026-12-04 – 2026-12-06
TPA - Chicago
48% AI deal score
$143
$127
Round trip
2026-11-03 – 2026-11-10
TPA - Chicago
76% AI deal score
$205
$130
Round trip
2026-11-04 – 2026-11-09
TPA - Chicago
77% AI deal score
$212
$130
Round trip
2026-12-04 – 2026-12-07
TPA - Chicago
47% AI deal score
$142
$132
Round trip
2026-12-07 – 2026-12-14
TPA - Chicago
46% AI deal score
$119
$133
Round trip
2027-01-15 – 2027-01-22
TPA - Chicago
46% AI deal score
$115
$133
Round trip

Tampa to Chicago: Overview

Insights for flights from Tampa to Chicago

Right now, 8% of recent fares for flights from Tampa to Chicago are considered a good price. Fares typically range from $130–$389, with a median of $215. Current fares are significantly below the typical level, suggesting a favorable time to find cheap flights from Tampa to Chicago. New deals for this route appear almost daily, indicating frequent opportunities for savings.

When is the cheapest time to fly from Tampa to Chicago? The data shows that September is typically the most affordable month, with a median fare of just $125. Following closely, August offers a median fare of $140, and October presents another economical option with a median of $142. These months offer the best value for travelers planning their trips.

A typical journey from Tampa to Chicago takes about 3h 3m for direct flights. However, since most itineraries connect at least once, the median journey time including connections is considerably longer. For connecting flights, the typical duration is 13h 10m, reflecting the time spent on layovers.

The distance between Tampa and Chicago is 1607 kilometers, classifying this as a medium-haul route. This distance means that while direct flights are available, most itineraries connect at least once. Specifically, only 29.5% of recent fares are for direct flights from Tampa to Chicago; for the remaining itineraries, the typical number of connections is 1.

How much is a round trip from Tampa to Chicago

Regular price: $88 - $231

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

The regular price range for this route is $88-$231. The current lowest deal is $104 with Allegiant Air for travel from Oct 23-Oct 30.

now $104

Low $88

High $231

The cheapest time to fly from Tampa to Chicago

The cheapest month to fly from Tampa to Chicago is September, with a median price of $118. The most expensive month is December, with a median price of $692. Prices are generally lower from January to November.

September

Cheapest

Flights from $118

December

Most Expensive

Flights from $692

Jan

Feb

Apr

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

Tue, Sep 15

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$489

$314

One-way

Tue, Sep 15

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$480

$348

One-way

Wed, Sep 16

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$392

$272

One-way

Wed, Sep 16

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$480

$312

One-way

Thu, Sep 17

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (ORD)

Frontier Airlines

$499

$334

One-way

Fri, Sep 18

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$459

$332

One-way

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

1 night

Sep 15 - Sep 16

$489 → $268

45%

2 nights

Sep 19 - Sep 21

$499 → $322

35%

3 nights

Sep 16 - Sep 19

$480 → $312

35%

2 nights

Sep 17 - Sep 19

$499 → $334

33%

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 at $104.

📅 Best time to fly

Fly in September for the best prices

Historically, September offers the lowest median prices at $125 for this route.

⏱️ Flight duration

Direct flights average 3h 3m

Direct flights to Chicago typically take 3 hours 3 minutes, while connecting flights average 13 hours 10 minutes.

✈️ Airlines & availability

29.5% of recent flights are direct

Connecting flights are more common, with 29.5% of recent flights being direct.

🏆 Airline highlight

Allegiant Air offers direct flights

Allegiant Air and Frontier Airlines both offer direct flights on this route.

🎯 Booking tip

Deals are frequent for this route

Deals for flights from Tampa to Chicago are frequently available, appearing often within 30 days.

Tampa main airports to depart from

St. Pete–Clearwater International (PIE)

Cheapest

St. Pete–Clearwater International Airport offers flights to Chicago, potentially at a lower price.

📍 ~23 km from Tampa (reachable by car)

💸 Flights from ~$100

Tampa International (TPA)

Tampa International Airport is a convenient option for flights to Chicago.

📍 ~8 km from Tampa (reachable by car)

💸 Flights from ~$129

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International is a good option for travelers seeking flights to the wider Chicago area.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$100

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 ~$217

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Tampa to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From TPA

Elite

Dec 08

Chicago, United States

80% AI deal score

$1,126

$732

Save $394

United Airlines

Business Class

From TPA

Elite

Nov 14

Chicago, United States

76% AI deal score

$925

$709

Save $216

United Airlines

Business Class

From TPA

Elite

Oct 27

Chicago, United States

76% AI deal score

$935

$709

Save $226

United Airlines

Business Class

From TPA

Elite

Oct 28

Chicago, United States

72% AI deal score

$923

$709

Save $214

United Airlines

Business Class

From TPA

Elite

Nov 07

Chicago, United States

71% AI deal score

$841

$706

Save $135

United Airlines

Business Class

From TPA

Elite

Oct 21

Chicago, United States

71% AI deal score

$900

$709

Save $191

United Airlines

Business Class

From TPA

Elite

Oct 07

Chicago, United States

71% AI deal score

$882

$722

Save $160

United Airlines

Business Class

From TPA

Elite

Dec 16

Chicago, United States

71% AI deal score

$900

$722

Save $178

United Airlines

Business Class

From TPA

Elite

Oct 15

Chicago, United States

71% AI deal score

$899

$722

Save $177

United Airlines

Business Class

From TPA

Elite

Dec 17

Chicago, United States

71% AI deal score

$900

$722

Save $178

United Airlines

Business Class

From TPA

Elite

Oct 31

Chicago, United States

70% AI deal score

$853

$706

Save $147

United Airlines

Business Class

From TPA

Elite

Oct 24

Chicago, United States

70% AI deal score

$828

$706

Save $122

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the best 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 $196. Booking within 0-6 days of departure usually results in a significantly higher average price of $479. Even booking 60+ days out tends to be slightly more expensive, with an average price of $218.

Across the trailing quarter, a good price for a flight from Tampa to Chicago is considered to be $130 or less. The median price for this route has been $215. Fares can go up to $389 or more, which represents the 75th percentile of prices observed in the trailing 90 days.

Historically, September has been the cheapest month to fly from Tampa to Chicago, with a median price of $125. August and October also offer competitive prices, with median fares of $140 and $142 respectively. The annual median price for this route is $215, indicating that these months offer notable savings.

Tampa to Chicago: Overview

Insights for flights from Tampa to Chicago

How much is a round trip from Tampa to Chicago

Regular price: $88 - $231

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

The regular price range for this route is $88-$231. The current lowest deal is $104 with Allegiant Air for travel from Oct 23-Oct 30.

now $104

Low $88

High $231

The cheapest time to fly from Tampa to Chicago

September

Cheapest

Flights from $118

December

Most Expensive

Flights from $692

Jan

Feb

Apr

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

Tue, Sep 15

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$489

$314

One-way

Tue, Sep 15

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$480

$348

One-way

Wed, Sep 16

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$392

$272

One-way

Wed, Sep 16

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$480

$312

One-way

Thu, Sep 17

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (ORD)

Frontier Airlines

$499

$334

One-way

Fri, Sep 18

⌛ Last-Minute

TPA - Chicago

Tampa (TPA) - Chicago (MDW)

Frontier Airlines

$459

$332

One-way

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

1 night

Sep 15 - Sep 16

$489 → $268

45%

2 nights

Sep 19 - Sep 21

$499 → $322

35%

3 nights

Sep 16 - Sep 19

$480 → $312

35%

2 nights

Sep 17 - Sep 19

$499 → $334

33%

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 at $104.

📅 Best time to fly

Fly in September for the best prices

Historically, September offers the lowest median prices at $125 for this route.

⏱️ Flight duration

Direct flights average 3h 3m

Direct flights to Chicago typically take 3 hours 3 minutes, while connecting flights average 13 hours 10 minutes.

✈️ Airlines & availability

29.5% of recent flights are direct

Connecting flights are more common, with 29.5% of recent flights being direct.

🏆 Airline highlight

Allegiant Air offers direct flights

Allegiant Air and Frontier Airlines both offer direct flights on this route.

🎯 Booking tip

Deals are frequent for this route

Deals for flights from Tampa to Chicago are frequently available, appearing often within 30 days.

Tampa main airports to depart from

St. Pete–Clearwater International (PIE)

Cheapest

St. Pete–Clearwater International Airport offers flights to Chicago, potentially at a lower price.

📍 ~23 km from Tampa (reachable by car)

💸 Flights from ~$100

Tampa International (TPA)

Tampa International Airport is a convenient option for flights to Chicago.

📍 ~8 km from Tampa (reachable by car)

💸 Flights from ~$129

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International is a good option for travelers seeking flights to the wider Chicago area.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$100

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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

Chicago, United States

70% AI deal score

$828

$706

Save $122

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Tampa to Chicago

Today’s best flight deals from Tampa to Chicago

Tampa to Chicago: Overview

Insights for flights from Tampa to Chicago

How much is a round trip from Tampa to Chicago

The cheapest time to fly from Tampa to Chicago

Direct flights from Tampa to Chicago

Last-minute flights going from Tampa to Chicago

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

Popular Airports to fly from Tampa to Chicago

Tampa - Chicago route insights

Recent fares are below the typical level

Fly in September for the best prices

Direct flights average 3h 3m

29.5% of recent flights are direct

Allegiant Air offers direct flights

Deals are frequent for this route

Tampa main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Dec 08

Nov 14

Oct 27

Oct 28

Nov 07

Oct 21

Oct 07

Dec 16

Oct 15

Dec 17

Oct 31

Oct 24

Frequently Asked Questions About Flights to Chicago

How early should I book Tampa to Chicago flights to get the cheapest price?

What's a cheap fare from Tampa to Chicago?

What's the best month to fly from Tampa to Chicago?

What percentage of Tampa to Chicago flights are direct?

How many hours is the flight from Tampa to Chicago?

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

Related routes

More routes from Tampa

Flights to Chicago from other cities

Tampa to Chicago: Overview

Insights for flights from Tampa to Chicago

How much is a round trip from Tampa to Chicago

The cheapest time to fly from Tampa to Chicago

Direct flights from Tampa to Chicago

Last-minute flights going from Tampa to Chicago

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

Popular Airports to fly from Tampa to Chicago

Tampa - Chicago route insights

Recent fares are below the typical level

Fly in September for the best prices

Direct flights average 3h 3m

29.5% of recent flights are direct

Allegiant Air offers direct flights

Deals are frequent for this route

Tampa main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Dec 08

Nov 14

Oct 27

Oct 28

Nov 07

Oct 21

Oct 07

Dec 16

Oct 15

Dec 17

Oct 31

Oct 24

Frequently Asked Questions About Flights to Chicago

How early should I book Tampa to Chicago flights to get the cheapest price?

What's a cheap fare from Tampa to Chicago?

What's the best month to fly from Tampa to Chicago?