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$309+ Cheap flights from Tallahassee (TLH) 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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Find flight deals from Tallahassee to Chicago

Cheapest flights from Tallahassee to Chicago
Explore the most affordable flight options available from Tallahassee to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 16, 2025.

This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:30 amTLH - MDW
1 stop5h 24mDelta
Tue 12/1610:49 amMDW - TLH
1 stop4h 33mDelta
Deal found 10/15$317
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:30 amTLH - ORD
1 stop5h 44mDelta
Tue 12/166:45 amORD - TLH
1 stop6h 19mDelta
Deal found 10/15$317
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:00 amTLH - ORD
1 stop6h 03mDelta
Sun 12/146:45 amORD - TLH
1 stop6h 19mDelta
Deal found 10/14$362
This American Airlines deal was found by Cheapflights users on 10/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:43 pmTLH - ORD
1 stop5h 11mAmerican Airlines
Tue 11/48:10 amORD - TLH
1 stop6h 21mAmerican Airlines
Deal found 10/14$392
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:00 amTLH - MDW
1 stop5h 55mDelta
Sun 12/76:00 amMDW - TLH
1 stop4h 42mDelta
Deal found 10/15$407
This American Airlines deal was found by Cheapflights users on 10/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:49 amTLH - ORD
1 stop5h 09mAmerican Airlines
Thu 11/208:20 amORD - TLH
1 stop5h 40mAmerican Airlines
Deal found 10/14$407
This American Airlines deal was found by Cheapflights users on 10/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/223:30 pmTLH - ORD
1 stop4h 48mAmerican Airlines
Mon 11/244:02 pmORD - TLH
1 stop5h 27mAmerican Airlines
Deal found 10/15$437
This American Airlines deal was found by Cheapflights users on 10/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/294:50 pmTLH - ORD
1 stop7h 04mAmerican Airlines
Sun 11/25:18 amORD - TLH
1 stop6h 57mAmerican Airlines
Deal found 10/14$467
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:00 amTLH - MDW
1 stop4h 40mDelta
Tue 11/45:09 pmMDW - TLH
1 stop4h 27mDelta
Deal found 10/14$483
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/245:35 amTLH - ORD
1 stop4h 06mDelta
Mon 12/111:19 amORD - TLH
1 stop4h 00mDelta
Deal found 10/15$518
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/97:00 amTLH - MDW
1 stop5h 52mDelta
Tue 11/116:00 amMDW - TLH
1 stop4h 34mDelta
Deal found 10/15$532
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/97:00 amTLH - ORD
1 stop6h 19mDelta
Tue 11/116:45 amORD - TLH
1 stop3h 49mDelta
Deal found 10/15$532

Cheap flight deals from Tallahassee to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Tallahassee (TLH) 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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$317
(Delta)

One-way from

$309
(Delta)

Popular in

December

Cheapest in

September

Average price

$668
Provider with most accurate pricing for Tallahassee-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tallahassee-Chicago (CHI) flights.
Search Deals
From Tallahassee to Chicago (CHI)
Search Deals
One-way flight from Tallahassee to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tallahassee 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 October 16, 2025.
Use the filters below to find and compare flights from Tallahassee to Chicago that are best for you.

Fly from

Tallahassee

Fly to

Chicago

Route

Depart

Return

Price

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 12/10

5:30 am-9:54 am

1 stop5h 24m

Chicago Midway

Tue 12/16

10:49 am-4:22 pm

1 stop4h 33m

$317

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 12/10

7:00 am-12:03 pm

1 stop6h 03m

Chicago O'Hare Intl

Sun 12/14

6:45 am-2:04 pm

1 stop6h 19m

$362

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Tue 10/28

6:43 pm-10:54 pm

1 stop5h 11m

Chicago O'Hare Intl

Tue 11/4

8:10 am-3:31 pm

1 stop6h 21m

$392

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 12/5

7:00 am-11:55 am

1 stop5h 55m

Chicago Midway

Sun 12/7

6:00 am-11:42 am

1 stop4h 42m

$407

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 12/5

5:07 pm-9:56 pm

1 stop5h 49m

Chicago O'Hare Intl

Sun 12/7

6:45 am-2:04 pm

1 stop6h 19m

$407

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 10/29

4:50 pm-10:54 pm

1 stop7h 04m

Chicago O'Hare Intl

Sun 11/2

5:18 am-1:15 pm

1 stop6h 57m

$467

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 11/1

5:06 pm-10:14 pm

1 stop6h 08m

Chicago Midway

Tue 11/4

5:09 pm-10:36 pm

1 stop4h 27m

$483

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Mon 11/24

5:35 am-8:41 am

1 stop4h 06m

Chicago O'Hare Intl

Mon 12/1

11:19 am-4:19 pm

1 stop4h 00m

$518

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sun 11/9

7:00 am-11:52 am

1 stop5h 52m

Chicago Midway

Tue 11/11

6:00 am-11:34 am

1 stop4h 34m

$532

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sun 11/9

7:00 am-12:19 pm

1 stop6h 19m

Chicago O'Hare Intl

Tue 11/11

6:45 am-11:34 am

1 stop3h 49m

$532

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 25 results
1
2
3

Compare providers for flights from Tallahassee to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Tallahassee to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Tallahassee-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tallahassee-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Tallahassee-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Tallahassee-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Tallahassee-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Tallahassee to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Tallahassee 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 Tallahassee to Chicago

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

Currently, June is the cheapest month in which you can book a flight from Tallahassee to Chicago (average of $99). Flying from Tallahassee to Chicago in November is currently the most expensive (average of $272). 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 TLH to CHI?

Find hourly flight availability from Tallahassee 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 October 16, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 19% on flights from Tallahassee to Chicago by exploring options for tickets at noon.

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 October 16, 2025.
See what other customers who have flown with Delta and American Airlines from Tallahassee to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,977 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
8.0
Very good
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,045 reviews
Delta
8.0
Very good
7,977 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Tallahassee 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 Tallahassee to Chicago?

    Located just 5.0 mi from the city center, Tallahassee is the airport most travelers will use when flying to Chicago from Tallahassee. Booking flights from Tallahassee (TLH) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 2 different airlines.

  • How long is the flight from Tallahassee to Chicago?

    Departing from Tallahassee to Chicago will take you 5h 11m. Tallahassee and Chicago are separated by a distance of 824 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 Tallahassee to Chicago round-trip?

    Delta, at $356, was found to be the cheapest airline from Tallahassee to Chicago. An alternate airline flying to your destination would be American Airlines. Users have found that Delta is 32% cheaper than the other options available to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Tallahassee 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 Tallahassee to Chicago?

    Currently, June is the cheapest month in which you can book a flight from Tallahassee to Chicago (average of $99). Flying from Tallahassee to Chicago in November is currently the most expensive (average of $272). 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
Porter
Benton Harbor
Chesterton

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Top 2 airlines flying from Tallahassee to Chicago

Discover the top 2 airlines that operate flights from Tallahassee 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$568FlexibilityNo cancel feeOn-time71%
DeltaCheapest$356Average$587FlexibilityNo cancel feeOn-timeN/A

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