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$159+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$317
(American Airlines)

One-way from

$159
(Delta)

Popular in

December

Cheapest in

April

Average price

$477
From Tallahassee to Chicago (CHI)
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One-way flight from Tallahassee to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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 10/15:40 amTLH - ORD
1 stop4h 00mDelta
Tue 10/76:45 amORD - TLH
1 stop6h 39mDelta
Deal found 9/10$317
This Delta deal was found by Cheapflights users on 9/10. 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 9/265:12 pmTLH - ORD
1 stop5h 13mDelta
Wed 10/15:30 amORD - TLH
1 stop5h 30mDelta
Deal found 9/10$392
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 10/236:00 amTLH - MDW
1 stop4h 40mDelta
Mon 10/276:00 amMDW - TLH
1 stop4h 30mDelta
Deal found 9/10$407
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sun 11/168:04 pmTLH - ORD
1 stop4h 36mAmerican Airlines
Sat 11/222:03 pmORD - TLH
1 stop7h 41mAmerican Airlines
Deal found 9/11$432
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 10/177:33 pmTLH - ORD
1 stop5h 20mAmerican Airlines
Sun 10/195:22 amORD - TLH
1 stop5h 23mAmerican Airlines
Deal found 9/10$437
This Delta deal was found by Cheapflights users on 9/11. 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 9/265:12 pmTLH - ORD
1 stop5h 13mDelta
Tue 9/309:50 amORD - TLH
1 stop5h 37mDelta
Deal found 9/11$467
This American Airlines deal was found by Cheapflights users on 9/11. 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 11/268:04 pmTLH - ORD
1 stop4h 52mAmerican Airlines
Mon 12/15:00 amORD - TLH
1 stop5h 38mAmerican Airlines
Deal found 9/11$472
This Delta deal was found by Cheapflights users on 9/10. 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 9/265:12 pmTLH - MDW
1 stop5h 24mDelta
Wed 10/16:00 amMDW - TLH
1 stop5h 00mDelta
Deal found 9/10$473
This Delta deal was found by Cheapflights users on 9/11. 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 12/27:00 amTLH - ORD
1 stop6h 05mDelta
Mon 1/57:10 amORD - TLH
1 stop5h 14mDelta
Deal found 9/11$483
This Delta deal was found by Cheapflights users on 9/9. 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 12/37:00 amTLH - MDW
1 stop5h 55mDelta
Mon 1/55:25 pmMDW - TLH
1 stop3h 57mDelta
Deal found 9/9$493
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sun 10/126:05 amTLH - ORD
1 stop5h 58mAmerican Airlines
Wed 10/151:51 pmORD - TLH
1 stop5h 19mAmerican Airlines
Deal found 9/10$502
This American Airlines deal was found by Cheapflights users on 9/11. 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 12/138:02 pmTLH - ORD
1 stop4h 59mAmerican Airlines
Mon 1/55:21 amORD - TLH
1 stop6h 50mAmerican Airlines
Deal found 9/11$513

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 September 11, 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 - ORD

TLHORD

Tallahassee

Sat 10/4

2:15 pm-7:15 pm

1 stop6h 00m

Chicago O'Hare Intl

Sat 10/11

1:51 pm-8:10 pm

1 stop5h 19m

$317

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 10/1

5:40 am-8:40 am

1 stop4h 00m

Chicago O'Hare Intl

Tue 10/7

6:45 am-2:24 pm

1 stop6h 39m

$317

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 9/26

5:12 pm-9:25 pm

1 stop5h 13m

Chicago O'Hare Intl

Wed 10/1

5:30 am-12:00 pm

1 stop5h 30m

$392

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 2/13

6:43 am-12:24 pm

1 stop6h 41m

Chicago O'Hare Intl

Sun 2/15

5:00 am-1:15 pm

1 stop7h 15m

$407

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Thu 10/23

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Mon 10/27

6:00 am-11:30 am

1 stop4h 30m

$407

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 10/17

7:33 pm-11:53 pm

1 stop5h 20m

Chicago O'Hare Intl

Sun 10/19

5:22 am-1:24 pm

1 stop7h 02m

$437

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 9/26

6:15 am-11:32 am

1 stop6h 17m

Chicago O'Hare Intl

Mon 9/29

5:00 am-12:44 pm

1 stop6h 44m

$467

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 9/26

5:12 pm-9:25 pm

1 stop5h 13m

Chicago O'Hare Intl

Tue 9/30

9:50 am-4:27 pm

1 stop5h 37m

$467

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 11/26

8:04 pm-11:56 pm

1 stop4h 52m

Chicago O'Hare Intl

Mon 12/1

5:00 am-11:38 am

1 stop5h 38m

$472

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 9/26

5:12 pm-9:36 pm

1 stop5h 24m

Chicago Midway

Wed 10/1

6:00 am-12:00 pm

1 stop5h 00m

$473

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 39 results
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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, August is the cheapest month in which you can book a flight from Tallahassee to Chicago (average of $245). Flying from Tallahassee 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 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 September 11, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 25% on flights from Tallahassee to Chicago by exploring options for tickets in the morning.

How much does it cost to fly round-trip from Tallahassee to Chicago?

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 11, 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
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

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
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

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
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

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 4h. 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, August is the cheapest month in which you can book a flight from Tallahassee to Chicago (average of $245). Flying from Tallahassee 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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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$578FlexibilityNo cancel feeOn-time71%
DeltaCheapest$356Average$586FlexibilityNo cancel feeOn-timeN/A

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