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$55+ Cheap flights from Tampa (TPA) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
TPA — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Tampa to Chicago are usually found in January or February, booked 86 days in advance, depart on a Friday or Thursday and return on a Wednesday

Cheap flight deals from Tampa to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Tampa (TPA) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2025.

Round-trip from

$100
(Frontier)

One-way from

$55
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$198

Good round-trip deal

$95 or less

Good one-way deal

$78 or less
From Tampa to Chicago (CHI)
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One-way flight from Tampa to Chicago (CHI)
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Highest demand for flights based on searches. 8% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Tampa to Chicago (CHI).
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Price to beat on a one-way flight from Tampa to Chicago (CHI).
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Find flight deals from Tampa to Chicago

Cheapest flights from Tampa to Chicago
Explore the most affordable flight options available from Tampa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Priceline deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/172:22 pmTPA - MDW
Nonstop2h 47mFrontier
Sun 10/195:20 amMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/17$100
This Expedia deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:13 amTPA - ORD
Nonstop2h 55mSpirit Airlines
Fri 10/246:18 pmORD - TPA
Nonstop2h 39mSpirit Airlines
Deal found 9/17$100
This Priceline deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/199:57 amTPA - MDW
Nonstop2h 47mFrontier
Sun 10/265:20 amMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/17$101
This CheapOair deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:45 amTPA - ORD
Nonstop3h 00mFrontier
Sun 10/125:50 amORD - TPA
Nonstop2h 55mFrontier
Deal found 9/17$101
This Cheapflightsfares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/129:57 amTPA - MDW
Nonstop2h 47mFrontier
Fri 10/179:45 amMDW - TPA
Nonstop2h 37mFrontier
Deal found 9/14$102
This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:11 pmTPA - MDW
Nonstop2h 46mFrontier
Sun 11/166:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/15$103
This Booking.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:13 amTPA - ORD
Nonstop2h 55mSpirit Airlines
Mon 10/272:25 pmORD - TPA
Nonstop2h 37mSpirit Airlines
Deal found 9/15$103
This Frontier deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/242:22 pmTPA - MDW
Nonstop2h 47mFrontier
Mon 10/279:45 amMDW - TPA
Nonstop2h 37mFrontier
Deal found 9/15$104
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/308:15 amTPA - ORD
Nonstop3h 03mSpirit Airlines
Thu 10/166:18 pmORD - TPA
Nonstop2h 39mSpirit Airlines
Deal found 9/16$105
This CheapOair deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/129:57 amTPA - MDW
Nonstop2h 47mFrontier
Sun 10/195:20 amMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/17$107
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/78:13 amTPA - ORD
Nonstop2h 55mSpirit Airlines
Sat 10/116:00 pmORD - TPA
Nonstop2h 39mSpirit Airlines
Deal found 9/17$107
This Booking.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/199:57 amTPA - MDW
Nonstop2h 47mFrontier
Mon 10/209:45 amMDW - TPA
Nonstop2h 37mFrontier
Deal found 9/16$108

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tampa to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Tampa to Chicago that are best for you.

Fly from

Tampa

Fly to

Chicago

Route

Depart

Return

Price

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 10/20

7:16 pm-11:46 pm

1 stop5h 30m

Chicago Midway

Sun 10/26

5:20 am-8:55 am

Nonstop2h 35m

$123

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 11/11

7:15 pm-9:00 pm

Nonstop2h 45m

Chicago Midway

Wed 11/12

6:00 pm-9:35 pm

Nonstop2h 35m

$137

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 11/4

7:15 pm-9:00 pm

Nonstop2h 45m

Chicago Midway

Tue 11/11

6:20 am-11:35 am

1 stop4h 15m

$147

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 11/7

9:30 pm-11:10 pm

Nonstop2h 40m

Chicago Midway

Tue 11/11

7:10 am-10:45 am

Nonstop2h 35m

$148

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 12/10

7:15 pm-9:00 pm

Nonstop2h 45m

Chicago Midway

Sun 12/14

5:20 am-8:55 am

Nonstop2h 35m

$148

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 12/10

12:45 pm-2:45 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 12/14

11:55 am-3:35 pm

Nonstop2h 40m

$148

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 10/14

6:35 pm-10:05 pm

1 stop4h 30m

Chicago Midway

Tue 10/21

10:10 am-3:50 pm

1 stop4h 40m

$157

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 12/13

1:55 pm-8:35 pm

1 stop7h 40m

Chicago Midway

Wed 12/17

7:10 am-10:45 am

Nonstop2h 35m

$157

TampaChicago

TPA - ORD

TPAORD

Tampa

Fri 12/5

12:45 pm-2:45 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 12/8

11:55 am-3:35 pm

Nonstop2h 40m

$158

TampaChicago

TPA - ORD

TPAORD

Tampa

Mon 11/24

7:30 am-9:29 am

Nonstop2h 59m

Chicago O'Hare Intl

Fri 11/28

11:15 am-3:08 pm

Nonstop2h 53m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 47 results
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The best insider tips for Tampa to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Tampa to Chicago trip
Airlines
Frontier

Consider extra comfort seats for more legroom, ideal for taller passengers.


Early check-in can secure your place onboard due to frequent overbooking.

Read more about Frontierby Marisa Garcia
Spirit Airlines

Purchase Big Front Seats for wider seats and more legroom.


Use Spirit Bag-O-Tron to compare baggage costs and save money.

Read more about Spirit Airlinesby Daniel Scheffler
United Airlines

Economy Plus offers extra legroom and priority boarding for a comfortable journey.


Prepay for checked bags to save on fees and streamline your travel.

Read more about United Airlinesby Harriet Baskas
Airports
TPA

TPA's Blue Express Curbside lets travelers without checked bags quickly reach their gate, avoiding crowds and saving time.

Read more about TPAby Ramsey Qubein
ORD

ORD's Hilton hotel is directly connected to the terminal, providing easy access for travelers needing accommodation.

Read more about ORDby Ramsey Qubein
MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a convenient and affordable transit option.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD, MDW and TPA

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Best time to book a flight from Tampa to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Tampa with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Tampa to Chicago

How far ahead should I book a flight from Tampa to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Tampa to Chicago. Price data was last updated on September 12, 2025.

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.

What is the cheapest month to book a flight from Tampa to Chicago?

Currently, August is the cheapest month in which you can book a flight from Tampa to Chicago (average of $245). Flying from Tampa to Chicago in March is currently the most expensive (average of $321). 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.

What is the cheapest time of day to fly from TPA to CHI?

Find hourly flight availability from Tampa to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

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 66% on airfare.

What is the cheapest day to fly from Tampa to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Tampa to Chicago. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Tampa to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Tampa to Chicago

Explore weekly flight availability from Tampa to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 17, 2025.

The most flights from TPA to CHI are scheduled on a Monday (42 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 17, 2025.
Read through reviews of airlines operating flights from Tampa to Chicago, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Tampa to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Tampa to Chicago?

    Located just 4.9 mi from the city center, Tampa is the airport most travelers will use when flying to Chicago from Tampa. Booking flights from Tampa (TPA) to Chicago should be relatively easy as there are 36 daily outbound flights to Chicago from 6 different airlines.

  • How long is the flight from Tampa to Chicago?

    Departing from Tampa to Chicago will take you 2h 45m. The distance between Tampa and Chicago is about 998 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Tampa to Chicago round-trip?

    Cheapflights users have booked flights from Tampa to Chicago round-trip from $53. Other airlines that can offer you cheap pricing are Spirit Airlines, from $75, and Delta, from $138. These flights start at 74% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Tampa to Chicago one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $69. Users have also found prices from $69 and $69 on United Airlines and American Airlines, respectively.

  • What are the most popular routes from Tampa to Chicago?

    When deciding which route to take from Tampa to Chicago consider Tampa - Chicago O'Hare Intl, Tampa - Chicago Midway or Tampa - Chicago Greater Rockford as they are the most popular.

  • What are the most reliable airlines from Tampa to Chicago?

    Consider ANA (90%), Spirit Airlines (90%) or SWISS (87%) when booking your flight. These represent the most reliable airlines when flying from Tampa to Chicago.

  • What are the cheapest flights from Tampa to Chicago?

    Looking at all options, your cheapest flight can be booked for $56. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $86 on average, our data indicates $844 when flying from Tampa to Chicago.

  • Can I find deals for flights from Tampa to Chicago that include hotel bookings?

    Yes. In addition to deals on Tampa to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Tampa to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Tampa to Chicago.

  • Can I find deals for business class flights from Tampa to Chicago?

    Yes. Cheapflights offers flight deals from Tampa to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Tampa to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Tampa to Chicago (average of $245). Flying from Tampa to Chicago in March is currently the most expensive (average of $321). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Tampa to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Tampa to Chicago

Discover the top 6 airlines that operate flights from Tampa to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$53Average$164FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$75Average$153FlexibilityNo cancel feeOn-time65%
DeltaCheapest$138Average$487FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$143Average$265FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$317FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$282FlexibilityNo cancel feeOn-time71%

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