HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$118+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
Aug 21 — Aug 281
Fri 8/21
Fri 8/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Tallahassee to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 July 22, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:17 pm
TLH
-
ORD
1 stop23h 33m
Multiple Airlines
Sat 8/298:05 am
ORD
-
TLH
1 stop22h 23m
Multiple Airlines
Deal found 7/17$203
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 9/12:17 pm
TLH
-
ORD
1 stop23h 33m
Multiple Airlines
Mon 9/217:45 am
ORD
-
TLH
1 stop25h 45m
Multiple Airlines
Deal found 7/19$230
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:47 pm
TLH
-
ORD
1 stop25h 03m
Multiple Airlines
Mon 8/318:05 am
ORD
-
TLH
1 stop23h 53m
Multiple Airlines
Deal found 7/17$248
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Thu 8/208:08 am
TLH
-
ORD
2 stops16h 00m
Multiple Airlines
Mon 8/248:05 am
ORD
-
TLH
1 stop23h 53m
Multiple Airlines
Deal found 7/19$277
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:47 pm
TLH
-
ORD
1 stop25h 03m
Multiple Airlines
Mon 9/79:10 pm
ORD
-
TLH
2 stops15h 27m
Multiple Airlines
Deal found 7/17$307
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 8/112:17 pm
TLH
-
ORD
1 stop22h 58m
Multiple Airlines
Fri 8/148:58 pm
ORD
-
TLH
2 stops33h 30m
Multiple Airlines
Deal found 7/16$364
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Thu 8/2012:47 pm
TLH
-
ORD
1 stop25h 03m
Multiple Airlines
Wed 8/268:05 am
ORD
-
TLH
1 stop22h 23m
Multiple Airlines
Deal found 7/21$368
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
TLH
-
MDW
1 stop6h 51m
Delta
Tue 8/2512:46 pm
MDW
-
TLH
1 stop6h 23m
Delta
Deal found 7/17$437
This Delta deal was found by Cheapflights users on 7/19. 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 12/2110:20 am
TLH
-
MDW
1 stop24h 32m
Delta
Fri 12/256:00 am
MDW
-
TLH
1 stop5h 05m
Delta
Deal found 7/19$438
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 pm
TLH
-
MDW
1 stop5h 36m
Delta
Mon 8/316:05 am
MDW
-
TLH
1 stop4h 05m
Delta
Deal found 7/17$447
This Delta deal was found by Cheapflights users on 7/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:07 am
TLH
-
MDW
1 stop4h 44m
Delta
Wed 8/1210:54 am
MDW
-
TLH
1 stop5h 17m
Delta
Deal found 7/16$467
This Delta deal was found by Cheapflights users on 7/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:18 am
TLH
-
MDW
1 stop6h 05m
Delta
Sun 11/85:15 pm
MDW
-
TLH
1 stop4h 49m
Delta
Deal found 7/16$483

Find 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 July 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$203
(Kiwi.com)

One-way from

$118
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$522
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. 13% potential increase in price ($91 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 22, 2026.
Use the filters below to find and compare flights from Tallahassee to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 8/27

8:08 am-11:08 pm

2 stops16h 00m

Chicago O'Hare Intl

Mon 8/31

8:05 am-8:58 am

1 stop23h 53m

$267

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 8/20

12:47 pm-12:50 pm

1 stop25h 03m

Chicago O'Hare Intl

Wed 8/26

8:05 am-7:28 am

1 stop22h 23m

$368

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 8/20

12:47 pm-12:50 pm

1 stop25h 03m

Chicago O'Hare Intl

Mon 8/24

8:05 am-8:58 am

1 stop23h 53m

$375

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sun 8/16

6:00 am-11:51 am

1 stop6h 51m

Chicago Midway

Tue 8/25

12:46 pm-8:09 pm

1 stop6h 23m

$437

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Tue 8/25

6:00 am-9:59 am

1 stop4h 59m

Chicago Midway

Sat 8/29

6:11 am-1:20 pm

1 stop6h 09m

$437

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sun 8/16

8:07 am-12:40 pm

1 stop5h 33m

Chicago O'Hare Intl

Tue 8/25

10:33 am-5:11 pm

1 stop5h 38m

$437

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 8/28

5:31 pm-12:35 am

1 stop8h 04m

Chicago O'Hare Intl

Sun 8/30

2:30 pm-11:59 pm

1 stop8h 29m

$447

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 9/5

5:45 pm-10:36 pm

1 stop5h 51m

Chicago Midway

Sat 9/12

4:30 pm-10:48 pm

1 stop5h 18m

$447

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Thu 8/20

6:00 pm-10:36 pm

1 stop5h 36m

Chicago Midway

Wed 8/26

5:10 pm-11:03 pm

1 stop4h 53m

$447

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Thu 8/27

6:00 pm-10:36 pm

1 stop5h 36m

Chicago Midway

Mon 8/31

6:05 am-11:10 am

1 stop4h 05m

$447

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/19

Showing 1-10 of 29 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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, May is the cheapest month in which you can book a flight from Tallahassee to Chicago (average of $406). Flying from Tallahassee to Chicago in January is currently the most expensive (average of $808). 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.

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 July 22, 2026.
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
7.8
Good
8,473 reviews

Entertainment

7.8

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

7.8

Food

7.2

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
7.8
Good
8,473 reviews
Delta
7.8
Good
8,473 reviews

Entertainment

7.8

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

7.8

Food

7.2

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
7.1
Good
11,832 reviews
Delta
7.8
Good
8,473 reviews

Entertainment

7.8

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

7.8

Food

7.2

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 6h 51m. Tallahassee and Chicago are separated by a distance of 809 mi.

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

    Delta, at $158, 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 72% 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, May is the cheapest month in which you can book a flight from Tallahassee to Chicago (average of $406). Flying from Tallahassee to Chicago in January is currently the most expensive (average of $808). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Tallahassee to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to O'Hare Intl flights
Tampa to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Orlando to Midway flights
Jacksonville to O'Hare Intl flights
Tampa to Midway flights
Fort Myers to O'Hare Intl flights
Miami to Midway flights
Fort Lauderdale to Midway flights
West Palm Beach to O'Hare Intl flights
Sarasota to O'Hare Intl flights
Orlando to St. Louis flights
West Palm Beach to Midway flights
Jacksonville to Midway flights
Pensacola to O'Hare Intl flights
Tampa to St. Louis flights
Fort Myers to Midway flights
Miami to St. Louis flights
Fort Lauderdale to St. Louis flights
Panama City to O'Hare Intl flights
Jacksonville to St. Louis flights
Tallahassee to O'Hare Intl flights
Sarasota to Midway flights
Pensacola to Midway flights
Orlando Sanford Intl to Rockford flights
St Petersburg to Rockford flights
Sarasota to St. Louis flights
Fort Myers to Peoria flights
Tampa to Moline flights
Fort Myers to St. Louis flights
Daytona Beach to O'Hare Intl flights
West Palm Beach to St. Louis flights
Fort Myers to Moline flights
Gainesville to O'Hare Intl flights
Fort Lauderdale to Rockford flights
Panama City to Midway flights
Pensacola to St. Louis flights
Daytona Beach to St. Louis flights
Orlando to Bloomington flights
Tampa to Peoria flights
Valparaiso to O'Hare Intl flights
Gainesville to Midway flights
Daytona Beach to Midway flights
Pensacola to Peoria flights
Tampa to Rockford flights
Tampa to Bloomington flights
Miami to Bloomington flights

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 July 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$158Average$472FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$316Average$501FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.