Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

TLH - CHI

$184 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 9/17. 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
0 bags
Fri 6/21
Fri 6/28

Search 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
In the last 7 days travelers have searched 43,423,329 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Tallahassee to Chicago (TLH-CHI)

 
These are the cheapest deals for flights from Tallahassee to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Tallahassee to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Tallahassee to Chicago.

Recent one-way flight deals from Tallahassee to Chicago

Only flying one-way? Below are some of the best one-way flight deals from Tallahassee to Chicago found on KAYAK recently.

Recent last minute flight deals from Tallahassee to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Tallahassee to Chicago.

Recent direct flight deals from Tallahassee to Chicago

The latest deals for direct flights from Tallahassee to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Tallahassee to Chicago

Find recent round-trip train or bus tickets from Tallahassee to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:55 pm - 9:45 amTLH-ORD
14h 50m1 stop
7:40 am - 7:10 pmORD-TLH
10h 30m1 stop
$385United Airlines
Find Deal
Fri, Jul 12 - Tue, Jul 16
7:55 pm - 11:15 pmTLH-ORD
28h 20m2 stops
6:20 pm - 7:10 pmORD-TLH
23h 50m1 stop
$390United Airlines
Find Deal
Fri, Jul 12 - Tue, Jul 16
4:05 pm - 9:34 pmTLH-ORD
6h 29m1 stop
1:20 pm - 11:56 pmORD-TLH
9h 36m1 stop
$399American Airlines
Find Deal
Mon, Sep 23 - Wed, Sep 25
7:00 pm - 2:39 pmTLH-ORD
20h 39m1 stop
6:20 pm - 7:55 pmORD-TLH
24h 35m1 stop
$404United Airlines
Find Deal
Mon, Aug 19 - Sun, Aug 25
5:46 am - 4:39 pmTLH-ORD
11h 53m1 stop
5:30 am - 11:22 amORD-TLH
4h 52m1 stop
$418American Airlines
Find Deal
Wed, Jun 19 - Wed, Jun 26
8:20 am - 11:44 amTLH-MDW
4h 24m1 stop
6:50 pm - 11:56 pmMDW-TLH
4h 06m1 stop
$553Delta
Find Deal
Fri, Aug 2 - Mon, Aug 5
6:00 am - 11:55 amTLH-MDW
6h 55m1 stop
6:49 pm - 11:59 pmMDW-TLH
4h 10m1 stop
$558Delta
Find Deal
Wed, Jun 19 - Wed, Jun 26
10:00 am - 5:45 pmTLH-ORD
8h 45m1 stop
1:20 pm - 11:56 pmORD-TLH
9h 36m1 stop
$559American Airlines
Find Deal
Fri, Oct 4 - Sun, Oct 6
5:50 pm - 9:46 pmTLH-MDW
4h 56m1 stop
6:55 pm - 11:58 pmMDW-TLH
4h 03m1 stop
$568Delta
Find Deal
Fri, Jul 12 - Sun, Jul 14
6:39 am - 4:02 pmTLH-ORD
10h 23m2 stops
7:25 am - 3:04 pmORD-TLH
6h 39m1 stop
$570American Airlines
Find Deal
Mon, Aug 19 - Sun, Aug 25
4:45 pm - 9:39 amTLH-ORD
17h 54m1 stop
$184United Airlines
Find Deal
Tue, Sep 17
10:33 am - 9:28 pmTLH-ORD
11h 55m1 stop
$201American Airlines
Find Deal
Tue, Jun 11
9:25 am - 11:15 pmTLH-ORD
14h 50m2 stops
$203United Airlines
Find Deal
Wed, Jul 10
9:25 am - 11:20 pmTLH-ORD
14h 55m2 stops
$213United Airlines
Find Deal
Tue, Jun 11
6:40 pm - 9:44 pmTLH-MDW
4h 04m1 stop
$214Delta
Find Deal
Tue, Sep 17
8:35 pm - 9:13 pmTLH-ORD
25h 38m2 stops
$222United Airlines
Find Deal
Tue, Sep 17
8:10 pm - 11:59 pmTLH-ORD
4h 49m1 stop
$223American Airlines
Find Deal
Wed, Jul 10
5:37 pm - 9:46 pmTLH-MDW
5h 09m1 stop
$224Delta
Find Deal
Tue, Jun 11
5:37 pm - 9:38 pmTLH-ORD
5h 01m1 stop
$224Delta
Find Deal
Tue, Jun 11
9:25 am - 6:27 pmTLH-ORD
34h 02m2 stops
$296United Airlines
Find Deal
Thu, Jun 13
10:40 am - 7:39 pmTLH-ORD
9h 59m1 stop
10:10 am - 7:53 pmORD-TLH
8h 43m1 stop
$787American Airlines
Find Deal
Sat, May 25 - Wed, May 29
6:00 am - 10:11 amTLH-MDW
5h 11m1 stop
12:42 pm - 8:44 pmMDW-TLH
7h 02m1 stop
$828Delta
Find Deal
Sat, May 25 - Wed, May 29
1:30 pm - 8:19 pmTLH-ORD
7h 49m2 stops
5:15 am - 1:01 pmORD-TLH
6h 46m1 stop
$830American Airlines
Find Deal
Sat, May 25 - Wed, May 29
11:06 am - 6:40 pmTLH-ORD
8h 34m2 stops
1:35 pm - 11:52 pmORD-TLH
9h 17m2 stops
$835American Airlines
Find Deal
Sat, May 25 - Wed, May 29
5:35 pm - 9:29 pmTLH-ORD
4h 54m1 stop
6:30 am - 1:01 pmORD-TLH
5h 31m1 stop
$865American Airlines
Find Deal
Fri, May 24 - Sun, May 26
7:00 pm - 9:31 amTLH-ORD
15h 31m1 stop
10:35 am - 4:40 pmORD-TLH
29h 05m2 stops
$903United Airlines
Find Deal
Fri, May 24 - Sun, May 26
7:00 pm - 12:13 amTLH-ORD
30h 13m2 stops
1:10 pm - 4:40 pmORD-TLH
26h 30m2 stops
$908United Airlines
Find Deal
Fri, May 24 - Sun, May 26
11:00 am - 2:55 pmTLH-MDW
4h 55m1 stop
9:32 am - 6:12 pmMDW-TLH
7h 40m2 stops
$1,016Delta
Find Deal
Sat, May 25 - Wed, May 29

Flights from Tallahassee to Chicago - Travel Insights & Trends

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 flights from Tallahassee to Chicago clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago on a Wednesday and more expensive on a Sunday. On your return trip to Tallahassee, you should consider flying back on a Saturday, and avoid Sundays for better 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 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 February, where tickets cost $435 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $757 and $677 respectively.

How far in advance should I book a flight from Tallahassee to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Tallahassee to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Tallahassee to Chicago, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 82 days before departure.

Which airlines provide the cheapest flights from Tallahassee to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Tallahassee to Chicago found on KAYAK was with United Airlines for $184. United Airlines proposed a round-trip connection from $385 and American Airlines from $399.

Good to know

Low season

January

High season

July

Cheapest flight

$184
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 16% 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 $184 for a one-way ticket and $385 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?

    Star Alliance, 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 $598 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 $557 and an overall rating of 7.3.

  • 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.

See more FAQs

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 10585 reviews
7.4Food
8.2Boarding
8.6Crew
7.9Comfort
8.0Entertainment
Airline reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

8.0 Excellentrghinftl, May 2024FLL - BOS
Read more about Delta reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from Tallahassee to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Tallahassee to Chicago found on KAYAK in the last 72 hours.
9/17Tue
1 stopUnited Airlines
17h 54mTLH-ORD
$184
6/11Tue
1 stopAmerican Airlines
11h 55mTLH-ORD
$201
7/10Wed
2 stopsUnited Airlines
14h 50mTLH-ORD
$203
6/11Tue
2 stopsUnited Airlines
14h 55mTLH-ORD
$213
9/17Tue
1 stopDelta
4h 04mTLH-MDW
$214
9/17Tue
2 stopsUnited Airlines
25h 38mTLH-ORD
$222
7/10Wed
1 stopAmerican Airlines
4h 49mTLH-ORD
$223
6/11Tue
1 stopDelta
5h 09mTLH-MDW
$224
6/11Tue
1 stopDelta
5h 01mTLH-ORD
$224
6/13Thu
2 stopsUnited Airlines
34h 02mTLH-ORD
$296

Search by stops

Search by airline

Search by price

Last minute flights from Tallahassee to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Tallahassee to Chicago that are departing in the next 10 days.
5/25Sat
multi-stopAmerican Airlines
9h 59mTLH-ORD
5/29Wed
multi-stopAmerican Airlines
8h 43mORD-TLH
$787
5/25Sat
multi-stopDelta
5h 11mTLH-MDW
5/29Wed
multi-stopDelta
7h 02mMDW-TLH
$828
5/25Sat
multi-stopAmerican Airlines
7h 49mTLH-ORD
5/29Wed
multi-stopAmerican Airlines
6h 46mORD-TLH
$830
5/25Sat
multi-stopAmerican Airlines
8h 34mTLH-ORD
5/29Wed
multi-stopAmerican Airlines
9h 17mORD-TLH
$835
5/24Fri
multi-stopAmerican Airlines
4h 54mTLH-ORD
5/26Sun
multi-stopAmerican Airlines
5h 31mORD-TLH
$865
5/24Fri
multi-stopUnited Airlines
15h 31mTLH-ORD
5/26Sun
multi-stopUnited Airlines
29h 05mORD-TLH
$903
5/24Fri
multi-stopUnited Airlines
30h 13mTLH-ORD
5/26Sun
multi-stopUnited Airlines
26h 30mORD-TLH
$908
5/25Sat
multi-stopDelta
4h 55mTLH-MDW
5/29Wed
multi-stopDelta
7h 40mMDW-TLH
$1,016

Search by stops

Search by airline

Search by price

Tallahassee - Chicago Flights

Departure:

Tallahassee (undefined)United States

Return flight deals:

Chicago - Tallahassee

Cabin classes: