TLH - CHI

$149 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 8/27. 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

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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Flights 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, Aug 23 - Sat, Aug 30
American Airlines Logo
6:35 am - 10:43 amTLH-ORD
5h 08m1 stop
American Airlines Logo
11:45 am - 7:11 pmORD-TLH
6h 26m1 stop
$296American Airlines
Find Deal
Sat, Aug 23 - Sat, Aug 30
Delta Logo
5:40 am - 9:36 amTLH-MDW
4h 56m1 stop
Delta Logo
6:00 am - 1:59 pmMDW-TLH
6h 59m1 stop
$297Delta
Find Deal
Wed, Oct 1 - Sun, Oct 5
Delta Logo
6:50 am - 9:40 amTLH-MDW
3h 50m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-TLH
5h 00m1 stop
$342Delta
Find Deal
Sat, Sep 20 - Fri, Sep 26
American Airlines Logo
10:45 am - 6:13 pmTLH-ORD
8h 28m1 stop
American Airlines Logo
12:32 pm - 6:16 pmORD-TLH
4h 44m1 stop
$342American Airlines
Find Deal
Fri, Aug 29 - Sun, Aug 31
Delta Logo
7:11 pm - 9:12 pmTLH-MDW
27h 01m1 stop
Delta Logo
6:00 am - 1:56 pmMDW-TLH
6h 56m1 stop
$371Delta
Find Deal
Sat, Aug 23 - Sat, Aug 30
American Airlines Logo
5:45 am - 12:22 pmTLH-ORD
7h 37m1 stop
American Airlines Logo
6:06 am - 4:16 pmORD-TLH
9h 10m2 stops
$371American Airlines
Find Deal
Wed, Sep 10 - Sun, Sep 14
Delta Logo
5:10 pm - 9:26 pmTLH-MDW
5h 16m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-TLH
5h 00m1 stop
$383Delta
Find Deal
Fri, Sep 12 - Sun, Sep 14
American Airlines Logo
10:45 am - 4:46 pmTLH-ORD
7h 01m1 stop
American Airlines Logo
8:05 am - 5:03 pmORD-TLH
7h 58m1 stop
$387American Airlines
Find Deal
Fri, Aug 29 - Sun, Aug 31
Delta Logo
7:11 pm - 12:28 pmTLH-MDW
18h 17m2 stops
Delta Logo
6:00 am - 1:56 pmMDW-TLH
6h 56m1 stop
$394Delta
Find Deal
Fri, Aug 29 - Fri, Sep 5
American Airlines Logo
3:05 pm - 9:25 pmTLH-ORD
7h 20m1 stop
American Airlines Logo
4:40 pm - 11:50 pmORD-TLH
6h 10m1 stop
$394American Airlines
Find Deal
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’s the cheapest day of the week to fly from Tallahassee to Chicago?

The average price of all round-trip flights from Tallahassee to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Tallahassee to Chicago. For your return ticket, we recommend flying on a Saturday and avoiding Mondays for the best deals.

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 April, where tickets cost $388 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is $745 and $655 respectively.

Good to know

Low seasonApril
Cheapest flight$149
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 15% increase in price.
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 $149 for a one-way ticket and $296 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?

    oneworld, and SkyTeam 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 $620 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $588 and an overall rating of 7.2.

  • 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.
8.0
DeltaOverall score based on 7980 reviews
8.2Boarding
7.3Food
7.9Entertainment
7.9Comfort
8.5Crew
Airline reviews

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

2.0 MediocreRosa, Jul 2025TPA - JFK
Read more Delta reviews

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

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

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