TLH - CHI

$148 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 8/16. 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
$214
Typical prices: $622-$503
Multiple Airlines
Tue 9/1Sat 9/5
TLH - ORD • 1 stop
Cheapest one-way
$148
Multiple Airlines
Sun 8/16
TLH - ORD • 2 stops
Top airlines
Cheapest • from $437 (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 16m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 79% 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

Tue, Sep 1 - Sat, Sep 5
Multiple Airlines Logo
2:17 pm - 12:25 pm
TLH
-
ORD
23h 08m
1 stop
Multiple Airlines Logo
5:26 pm - 7:28 am
ORD
-
TLH
13h 02m
1 stop
$214Multiple Airlines
Tue, Sep 1 - Sat, Sep 5
Multiple Airlines Logo
9:38 am - 8:03 am
TLH
-
ORD
23h 25m
2 stops
Multiple Airlines Logo
5:26 pm - 7:28 am
ORD
-
TLH
13h 02m
1 stop
$248Multiple Airlines
Thu, Aug 20 - Sat, Aug 22
Multiple Airlines Logo
12:47 pm - 11:08 pm
TLH
-
ORD
11h 21m
1 stop
Multiple Airlines Logo
5:26 pm - 7:28 am
ORD
-
TLH
13h 02m
1 stop
$288Multiple Airlines
Thu, Aug 20 - Sat, Aug 22
Multiple Airlines Logo
8:08 am - 11:18 pm
TLH
-
ORD
16h 10m
2 stops
Multiple Airlines Logo
5:26 pm - 7:28 am
ORD
-
TLH
13h 02m
1 stop
$332Multiple Airlines
Thu, Jul 2 - Sat, Jul 11
Multiple Airlines Logo
12:47 pm - 11:59 pm
TLH
-
ORD
12h 12m
1 stop
Multiple Airlines Logo
8:05 am - 7:28 am
ORD
-
TLH
22h 23m
1 stop
$334Multiple Airlines
Thu, Jul 2 - Sat, Jul 11
Multiple Airlines Logo
8:08 am - 7:53 pm
TLH
-
ORD
12h 45m
2 stops
Multiple Airlines Logo
8:05 am - 7:28 am
ORD
-
TLH
22h 23m
1 stop
$356Multiple Airlines
Tue, Jul 14 - Fri, Jul 17
Multiple Airlines Logo
2:17 pm - 11:59 pm
TLH
-
ORD
10h 42m
1 stop
Multiple Airlines Logo
8:05 pm - 7:28 am
ORD
-
TLH
34h 23m
2 stops
$358Multiple Airlines
Sun, May 17 - Tue, May 26
Delta Logo
5:23 pm - 9:09 pm
TLH
-
MDW
4h 46m
1 stop
Delta Logo
6:23 am - 1:57 pm
MDW
-
TLH
6h 34m
1 stop
$437Delta
Thu, Sep 3 - Wed, Sep 9
Delta Logo
7:15 pm - 11:57 pm
TLH
-
ORD
5h 42m
1 stop
Delta Logo
7:10 am - 2:42 pm
ORD
-
TLH
6h 32m
1 stop
$437Delta
Thu, May 21 - Mon, Jun 1
Delta Logo
5:23 pm - 9:09 pm
TLH
-
MDW
4h 46m
1 stop
Delta Logo
6:23 am - 1:57 pm
MDW
-
TLH
6h 34m
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.

How much is a round-trip flight from Tallahassee to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Tallahassee to Chicago departing in September.

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 November, where tickets cost $66 (return) on average. On the other hand, the most expensive months are January and August, where the average cost of round-trip tickets is $487 and $442 respectively.

Good to know

Low seasonFebruary
Cheapest flight$148
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 29% 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 $148 for a one-way ticket and $214 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 $522 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 $461 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 8466 reviews
7.2Food
7.9Comfort
7.8Entertainment
8.5Crew
8.1Boarding
Airline reviews

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

4.0 OkayAnonymous, Apr 2026
MCO - ATL
Read more Delta reviews

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

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

Information on your arrival and departure airports