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$170+ 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$357
(Delta)

One-way from

$170
(Trip.com)

Popular in

December

Cheapest in

April

Average price

$494
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. 6% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/12. 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.
Sat 9/205:40 amTLH - MDW
1 stop5h 11mDelta
Sat 9/276:00 amMDW - TLH
1 stop6h 34mDelta
Deal found 6/12$357
This Delta deal was found by Cheapflights users on 6/10. 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.
Mon 6/301:01 pmTLH - ORD
1 stop4h 48mDelta
Sat 7/57:10 amORD - TLH
1 stop5h 45mDelta
Deal found 6/10$357
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Sat 9/205:36 pmTLH - ORD
1 stop5h 50mAmerican Airlines
Fri 9/268:05 amORD - TLH
1 stop7h 58mAmerican Airlines
Deal found 6/12$402
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/97:45 pmTLH - ORD
1 stop20h 10mUnited Airlines
Mon 7/147:00 amORD - TLH
1 stop24h 20mUnited Airlines
Deal found 6/10$423

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 June 12, 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 9/20

5:40 am-9:51 am

1 stop5h 11m

Chicago Midway

Sat 9/27

6:00 am-1:34 pm

1 stop6h 34m

$357

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Mon 6/30

1:01 pm-4:49 pm

1 stop4h 48m

Chicago O'Hare Intl

Sat 7/5

7:10 am-1:55 pm

1 stop5h 45m

$357

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sat 9/20

5:36 pm-10:26 pm

1 stop5h 50m

Chicago O'Hare Intl

Fri 9/26

8:05 am-5:03 pm

1 stop7h 58m

$402

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 7/9

7:45 pm-2:55 pm

1 stop20h 10m

Chicago O'Hare Intl

Mon 7/14

7:00 am-8:20 am

1 stop24h 20m

$423

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 7/31

9:05 am-11:53 pm

1 stop15h 48m

$170

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Mon 6/30

5:37 am-9:41 am

1 stop5h 04m

$179

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Mon 6/30

5:45 am-12:25 pm

1 stop7h 40m

$179

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 7/11

7:45 pm-2:55 pm

1 stop20h 10m

$232

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 7/11

7:00 am-12:16 pm

1 stop6h 16m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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 June 12, 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
7,950 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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.
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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
7,950 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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 $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 33% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Tallahassee to Chicago one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $179. Users have also found prices from $179 and $232 on American Airlines and United Airlines, respectively.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$380Average$544FlexibilityNo cancel feeOn-time71%
DeltaCheapest$417Average$631FlexibilityNo cancel feeOn-timeN/A

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