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$297+ Cheap flights from Tallahassee (TLH) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
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 agosto 14, 2025.

Round-trip from

$297
(Delta)

Popular in

December

Cheapest in

April

Average price

$509
From Tallahassee to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 14, 2025.

This Delta deal was found by Cheapflights users on 8/13. 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.
sáb. 9/1311:50 amTLH - ORD
1 stop5h 41mDelta
mié. 9/177:20 amORD - TLH
1 stop6h 04mDelta
Deal found 8/13$297
This Delta deal was found by Cheapflights users on 8/13. 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.
mié. 9/105:10 pmTLH - MDW
1 stop5h 16mDelta
mié. 9/176:00 amMDW - TLH
1 stop5h 00mDelta
Deal found 8/13$338
This American Airlines deal was found by Cheapflights users on 8/11. 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.
sáb. 12/138:12 pmTLH - ORD
1 stop5h 02mAmerican Airlines
lun. 1/51:15 pmORD - TLH
1 stop7h 22mAmerican Airlines
Deal found 8/11$342
This American Airlines deal was found by Cheapflights users on 8/12. 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.
mié. 10/87:01 amTLH - ORD
1 stop6h 02mAmerican Airlines
sáb. 10/119:10 amORD - TLH
1 stop4h 59mAmerican Airlines
Deal found 8/12$367
This Delta deal was found by Cheapflights users on 8/12. 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.
mié. 8/275:10 pmTLH - MDW
1 stop5h 34mDelta
dom. 8/316:00 amMDW - TLH
1 stop5h 01mDelta
Deal found 8/12$372
This Delta deal was found by Cheapflights users on 8/12. 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.
mié. 8/275:10 pmTLH - ORD
1 stop6h 27mDelta
dom. 8/317:05 amORD - TLH
1 stop3h 56mDelta
Deal found 8/12$372
This American Airlines deal was found by Cheapflights users on 8/11. 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.
vie. 12/126:22 amTLH - ORD
1 stop5h 35mAmerican Airlines
mar. 1/61:54 pmORD - TLH
1 stop7h 08mAmerican Airlines
Deal found 8/11$377
This Delta deal was found by Cheapflights users on 8/13. 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.
sáb. 10/45:09 pmTLH - MDW
1 stop5h 01mDelta
dom. 10/56:00 amMDW - TLH
1 stop5h 00mDelta
Deal found 8/13$378
This American Airlines deal was found by Cheapflights users on 8/12. 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.
sáb. 12/136:02 pmTLH - ORD
1 stop4h 40mAmerican Airlines
sáb. 1/34:21 pmORD - TLH
1 stop6h 55mAmerican Airlines
Deal found 8/12$378
This Delta deal was found by Cheapflights users on 8/13. 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.
jue. 9/45:40 amTLH - MDW
1 stop4h 56mDelta
lun. 9/86:00 amMDW - TLH
1 stop3h 37mDelta
Deal found 8/13$387
This Delta deal was found by Cheapflights users on 8/14. 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.
vie. 9/267:09 pmTLH - ORD
1 stop5h 45mDelta
dom. 9/285:30 amORD - TLH
1 stop5h 30mDelta
Deal found 8/14$387
This Delta deal was found by Cheapflights users on 8/12. 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.
mié. 10/86:00 amTLH - MDW
2 stops13h 25mDelta
dom. 10/126:00 amMDW - TLH
1 stop4h 30mDelta
Deal found 8/12$410

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 agosto 14, 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

mar. 10/28

4:31 pm-10:35 pm

1 stop7h 04m

Chicago O'Hare Intl

vie. 10/31

3:32 pm-10:35 pm

1 stop6h 03m

$297

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

sáb. 9/13

5:09 pm-10:14 pm

1 stop6h 05m

Chicago O'Hare Intl

mié. 9/17

7:20 am-12:00 pm

1 stop3h 40m

$297

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

mié. 9/10

4:55 pm-8:27 pm

1 stop4h 32m

Chicago O'Hare Intl

mié. 9/17

1:37 pm-10:38 pm

1 stop8h 01m

$297

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

mié. 9/10

5:10 pm-9:26 pm

1 stop5h 16m

Chicago Midway

mié. 9/17

6:00 am-12:00 pm

1 stop5h 00m

$338

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

sáb. 10/4

7:07 am-1:42 pm

1 stop7h 35m

Chicago O'Hare Intl

dom. 10/5

4:40 pm-11:50 pm

1 stop6h 10m

$342

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

sáb. 10/4

5:40 am-10:10 am

1 stop5h 30m

Chicago O'Hare Intl

lun. 10/6

5:51 pm-10:36 pm

1 stop3h 45m

$342

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

sáb. 10/18

6:00 am-11:03 am

1 stop6h 03m

Chicago O'Hare Intl

dom. 10/26

7:00 am-3:51 pm

1 stop7h 51m

$342

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

sáb. 9/6

2:15 pm-7:15 pm

1 stop6h 00m

Chicago O'Hare Intl

dom. 9/7

5:00 am-1:26 pm

1 stop7h 26m

$342

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

mié. 10/8

7:01 am-12:03 pm

1 stop6h 02m

Chicago O'Hare Intl

sáb. 10/11

9:10 am-3:09 pm

1 stop4h 59m

$367

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

mié. 8/27

5:40 am-9:36 am

1 stop4h 56m

Chicago Midway

sáb. 8/30

6:00 am-1:59 pm

1 stop6h 59m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 33 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 agosto 14, 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.

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 agosto 14, 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
7,980 reviews

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

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
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

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
7,980 reviews

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

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.

  • 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 34% 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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See prices for flight routes from nearby airports that may be better suited for you.
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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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$577FlexibilityNo cancel feeOn-time71%
DeltaCheapest$356Average$598FlexibilityNo cancel feeOn-timeN/A

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