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$222+ 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 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$357
(Delta)

One-way from

$222
(United Airlines)

Popular in

April

Cheapest in

January

Average price

$1,217
Provider with most accurate pricing for Tallahassee-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Tallahassee-Chicago (CHI) flights.
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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. 18% potential increase in price ($140 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($53 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 15, 2025.

This Delta deal was found by Cheapflights users on 4/14. 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.
Sat 5/103:25 pmTLH - MDW
1 stop6h 49mDelta
Sat 5/176:00 amMDW - TLH
1 stop4h 32mDelta
Deal found 4/14$357
This Delta deal was found by Cheapflights users on 4/14. 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 5/275:40 amTLH - ORD
1 stop3h 49mDelta
Thu 5/2911:07 amORD - TLH
1 stop6h 14mDelta
Deal found 4/14$357
This American Airlines deal was found by Cheapflights users on 4/14. 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 7/26:25 amTLH - ORD
1 stop5h 20mAmerican Airlines
Sun 7/65:15 amORD - TLH
1 stop5h 29mAmerican Airlines
Deal found 4/14$412
This United Airlines deal was found by Cheapflights users on 4/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/307:45 pmTLH - ORD
2 stops28h 52mUnited Airlines
Fri 7/47:00 amORD - TLH
1 stop24h 20mUnited Airlines
Deal found 4/14$451

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 April 15, 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

Sat 5/10

3:25 pm-9:14 pm

1 stop6h 49m

Chicago Midway

Sat 5/17

6:00 am-11:32 am

1 stop4h 32m

$357

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Tue 5/27

5:40 am-8:29 am

1 stop3h 49m

Chicago O'Hare Intl

Thu 5/29

11:07 am-6:21 pm

1 stop6h 14m

$357

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 7/2

6:25 am-10:45 am

1 stop5h 20m

Chicago O'Hare Intl

Sun 7/6

5:15 am-11:44 am

1 stop5h 29m

$412

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Mon 6/30

7:45 pm-11:37 pm

2 stops28h 52m

Chicago O'Hare Intl

Fri 7/4

7:00 am-8:20 am

1 stop24h 20m

$451

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Mon 6/16

7:45 pm-2:55 pm

1 stop20h 10m

$222

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Tue 4/22

9:05 am-12:20 am

1 stop16h 15m

$235

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 5/3

5:38 am-9:07 am

1 stop4h 29m

$264

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sat 5/3

5:38 am-8:41 am

1 stop4h 03m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 eDreams the most. eDreams 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, 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 April 15, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 15, 2025.
See what other customers who have flown with Delta, United Airlines 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
7,918 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Delta
8.0
Very good
7,918 reviews
Delta
8.0
Very good
7,918 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
United Airlines
7.4
Good
8,658 reviews
Delta
8.0
Very good
7,918 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,918 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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 $357, was found to be the cheapest airline from Tallahassee to Chicago.Alternate airlines to your destination round-trip include American Airlines and United Airlines. Users have found that Delta is 43% 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 Tallahassee?

Book flights to Tallahassee if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$399Average$567FlexibilityNo cancel feeOn-time71%
DeltaCheapest$438Average$648FlexibilityNo cancel feeOn-timeN/A

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