TLH - CHI

$328 Find Cheap Flights from Tallahassee to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Tallahassee to Chicago departing on 4/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tallahassee to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tallahassee to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$357
Delta
Sat 4/18Sat 4/25
TLH - MDW • 1 stop
Cheapest one-way
$328
Delta
Sat 4/11
TLH - ORD • 1 stop
Top airlines
Cheapest • from $357 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Tallahassee and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $461 (round-trip)
Shortest trip • 4h 33m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 30% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Tallahassee to Chicago (TLH-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Tallahassee to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Tallahassee to Chicago

Sat, Apr 18 - Sat, Apr 25
Delta Logo
6:44 pm - 10:28 pm
TLH
-
MDW
4h 44m
1 stop
Delta Logo
6:00 am - 12:11 pm
MDW
-
TLH
5h 11m
1 stop
$357Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
6:44 pm - 11:59 pm
TLH
-
ORD
6h 15m
1 stop
Delta Logo
2:25 pm - 7:34 pm
ORD
-
TLH
4h 09m
1 stop
$357Delta
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
6:42 pm - 11:48 pm
TLH
-
ORD
6h 06m
1 stop
American Airlines Logo
3:07 pm - 11:15 pm
ORD
-
TLH
7h 08m
1 stop
$402American Airlines
Wed, Apr 8 - Wed, Apr 15
Delta Logo
7:09 pm - 10:31 pm
TLH
-
MDW
4h 22m
1 stop
Delta Logo
6:00 am - 12:11 pm
MDW
-
TLH
5h 11m
1 stop
$402Delta
Wed, Apr 29 - Wed, Apr 29
American Airlines Logo
6:09 am - 12:11 pm
TLH
-
ORD
7h 02m
1 stop
American Airlines Logo
5:20 pm - 11:56 pm
ORD
-
TLH
5h 36m
1 stop
$408American Airlines
Fri, Apr 10 - Wed, Apr 15
Delta Logo
5:12 pm - 10:31 pm
TLH
-
MDW
6h 19m
1 stop
Delta Logo
10:41 am - 4:24 pm
MDW
-
TLH
4h 43m
1 stop
$422Delta
Fri, Apr 10 - Wed, Apr 15
Delta Logo
1:16 pm - 6:49 pm
TLH
-
ORD
6h 33m
1 stop
Delta Logo
8:15 am - 3:00 pm
ORD
-
TLH
5h 45m
1 stop
$422Delta
Thu, Jun 11 - Tue, Jun 16
Delta Logo
5:10 pm - 9:45 pm
TLH
-
MDW
5h 35m
1 stop
Delta Logo
6:00 am - 12:04 pm
MDW
-
TLH
5h 04m
1 stop
$437Delta
Thu, May 21 - Tue, May 26
American Airlines Logo
7:48 pm - 11:59 pm
TLH
-
ORD
5h 11m
1 stop
American Airlines Logo
2:24 pm - 11:59 pm
ORD
-
TLH
8h 35m
1 stop
$437American Airlines
Fri, Apr 24 - Mon, Apr 27
Delta Logo
7:05 pm - 10:28 pm
TLH
-
MDW
4h 23m
1 stop
Delta Logo
6:00 am - 12:11 pm
MDW
-
TLH
5h 11m
1 stop
$447Delta
Booking Insights

KAYAK's insights & trends for Tallahassee to Chicago flights

Get data-powered insights and trends into flights from Tallahassee to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Tallahassee to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Tallahassee to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Tallahassee to Chicago is September, where tickets cost $349 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is $720 and $636 respectively.

Good to know

Low seasonFebruary
Cheapest flight$328
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 19% lower on average.
Flight from Tallahassee to Chicago O'Hare Airport

When to book flights from Tallahassee to Chicago

Are your dates flexible? Find out the best times to travel from Tallahassee to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Tallahassee to Chicago

  • What is the cheapest flight from Tallahassee to Chicago?

    In the last 3 days, the lowest price for a flight from Tallahassee to Chicago was $328 for a one-way ticket and $357 for a round-trip.

  • Do I need a passport to fly between Tallahassee and Chicago?

    A passport is not required to fly from Tallahassee to Chicago.

  • Which airports will I be using when flying from Tallahassee to Chicago?

    Tallahassee is served by only 1 airport and there are 2 airports in Chicago. You will leave Tallahassee from Tallahassee and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Tallahassee to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Tallahassee to Chicago?

    SkyTeam, and oneworld are the airline alliances operating flights between Tallahassee and Chicago, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Tallahassee to Chicago, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Tallahassee to Chicago are Delta and American Airlines. With an average price for the route of $516 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $456 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Tallahassee to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Tallahassee to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Tallahassee to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Tallahassee is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Tallahassee to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Tallahassee with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Tallahassee to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Tallahassee up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Tallahassee to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Tallahassee to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Tallahassee to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8296 reviews
8.5Crew
7.9Comfort
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

10.0 ExcellentAnonymous, Mar 2026
TPA - ATL
Read more Delta reviews

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The flight was great as well as the airline staff

Got on the plane and sat there for an hour before departure.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Everything you need to know for your flight from Tallahassee to Chicago

Information on your arrival and departure airports