TLH - CHI

$159 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 10/15. 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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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

Wed, Oct 1 - Tue, Oct 7
Delta Logo
5:40 am - 8:40 amTLH-ORD
4h 00m1 stop
Delta Logo
6:45 am - 2:24 pmORD-TLH
6h 39m1 stop
$317Delta
Find Deal
Sat, Oct 4 - Mon, Oct 6
American Airlines Logo
7:23 am - 11:30 amTLH-ORD
5h 07m1 stop
American Airlines Logo
1:51 pm - 8:10 pmORD-TLH
5h 19m1 stop
$362American Airlines
Find Deal
Fri, Sep 26 - Wed, Oct 1
Delta Logo
5:12 pm - 9:25 pmTLH-ORD
5h 13m1 stop
Delta Logo
5:30 am - 12:00 pmORD-TLH
5h 30m1 stop
$392Delta
Find Deal
Wed, Oct 8 - Sun, Oct 12
American Airlines Logo
4:25 pm - 10:31 pmTLH-ORD
7h 06m1 stop
American Airlines Logo
5:22 am - 11:45 amORD-TLH
5h 23m1 stop
$399American Airlines
Find Deal
Thu, Oct 23 - Mon, Oct 27
Delta Logo
6:00 am - 9:40 amTLH-MDW
4h 40m1 stop
Delta Logo
6:00 am - 11:30 amMDW-TLH
4h 30m1 stop
$407Delta
Find Deal
Fri, Oct 3 - Sun, Oct 5
American Airlines Logo
6:31 pm - 11:59 pmTLH-ORD
6h 28m1 stop
American Airlines Logo
8:05 am - 5:02 pmORD-TLH
7h 57m1 stop
$407American Airlines
Find Deal
Fri, Oct 17 - Sun, Oct 19
American Airlines Logo
7:33 pm - 11:53 pmTLH-ORD
5h 20m1 stop
American Airlines Logo
5:22 am - 1:24 pmORD-TLH
7h 02m1 stop
$437American Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
American Airlines Logo
6:15 am - 11:32 amTLH-ORD
6h 17m1 stop
American Airlines Logo
5:00 am - 12:44 pmORD-TLH
6h 44m1 stop
$467American Airlines
Find Deal
Wed, Nov 26 - Mon, Dec 1
American Airlines Logo
8:04 pm - 11:56 pmTLH-ORD
4h 52m1 stop
American Airlines Logo
5:00 am - 11:38 amORD-TLH
5h 38m1 stop
$472American Airlines
Find Deal
Fri, Sep 26 - Wed, Oct 1
Delta Logo
5:12 pm - 9:36 pmTLH-MDW
5h 24m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-TLH
5h 00m1 stop
$473Delta
Find Deal

Everything you should know

Top airlines
Delta
Cheapest • from $317 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
April
Cheapest • 27% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$317
Typical prices: $416-523
Delta
Wed 10/1Tue 10/7
TLH - ORD • 1 stop
Cheapest one-way
$159
Delta
Wed 10/15
TLH - MDW • 1 stop
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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?

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 $668 respectively.

Good to know

Low seasonApril
Cheapest flight$159
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Tallahassee to Chicago Midway 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 $159 for a one-way ticket and $317 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 $605 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 $518 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.
7.9
DeltaOverall score based on 7960 reviews
8.5Crew
7.9Entertainment
7.9Comfort
7.3Food
8.2Boarding
Airline reviews

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

8.0 ExcellentOlaf, Sep 2025FLL - ATL
Read more Delta reviews

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

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.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

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.

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

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