Cheap flights from Tallahassee (TLH) to Chicago (CHI) from $150

This is the cheapest one-way flight price, found on 9/19. Prices may vary by date and flight preferences.
TLH — CHI
Sep 26 — Oct 31

The best prices from Tallahassee to Chicago are usually found in April or December, booked 60 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

How to find the cheapest flight from Tallahassee (TLH) to Chicago (CHI)

All the information you need to plan the best TLH to CHI flight in 2023: compare Tallahassee to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

Popular in

November

Cheapest in

April

Average price

$617

Round-trip from

$207
High demand for flights, 20% potential price rise
Best time to find cheap flights, 29% potential price drop
Average for round-trip flights in September 2023
From Tallahassee to Chicago (CHI)

TLH - CHI

Price

$207 - $364

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

What is the cheapest day to fly round-trip from Tallahassee to Chicago?

It’s generally more expensive to depart on a Tuesday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 59 days in advance, which can save you up to 44% on flights from Tallahassee to Chicago compared to booking the week you need them. Waiting 59 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $605. For sooner than that we have options available in the next 3 days from $710.

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

April can be a great time to fly to Chicago from Tallahassee with a flight ticket averaging about $560. Cheapflights users have found deals in the month of April for as cheap as $366. The most expensive prices can be found in the month of November.

When is the cheapest time to fly from Tallahassee to Chicago (TLH - CHI)?

Unlike in the afternoon, when flights are generally more expensive, you can save up to 36% on flights from Tallahassee to Chicago by exploring options for tickets in the morning.

Cheap United Airlines flights from Tallahassee to Chicago

Take a look at some of the lowest-priced United Airlines flights heading from Tallahassee to Chicago. Come back soon if you're not finding the exact deal you're looking for.

Cheap Delta flights from Tallahassee to Chicago

To aid your search, here are some of the cheapest Delta flights we've found from Tallahassee to Chicago. Deals frequently update to provide users with more options.

Cheap Tallahassee to Chicago flights in September & October 2023

The best prices found for TLH to CHI flights for September, October
Scroll through some of the best deals on flights from Tallahassee to Chicago in 2023. Check back in a little while for more flight options.

Tallahassee to Chicago 2023 flight deals

Cheap flights to Chicago from Tallahassee found for this year
Scroll through some of the best deals on flights from Tallahassee to Chicago in 2023. Check back in a little while for more flight options.

Tallahassee to Chicago flights leaving soon

Late deals on return flights to Chicago from Tallahassee, departing today and this week
Have a look at some of the flights available from Tallahassee to Chicago departing last-minute. Tip: verify your flight details before completing your reservation.

One-way flights to Chicago from Tallahassee

The cheapest one-way flights from Tallahassee to Chicago
Users traveling one-way from Tallahassee to Chicago can select one of these great deals. Users can also find round-trip Tallahassee to Chicago flights by using the search form above.

Find flights from Tallahassee to Chicago within your budget

Use the slider to find flights from Tallahassee to Chicago that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$249 - $599

Route

Depart

Return

Price

TallahasseeChicago Midway

TLH - MDW

TLHMDW

Tallahassee

Thu 10/19

2 stops12h 51m

Chicago Midway

Mon 10/23

1 stop9h 21m

TallahasseeChicago O'Hare Intl

TLH - ORD

TLHORD

Tallahassee

Thu 10/5

1 stop13h 44m

Chicago O'Hare Intl

Mon 10/9

2 stops22h 05m

TallahasseeChicago O'Hare Intl

TLH - ORD

TLHORD

Tallahassee

Wed 10/11

1 stop15h 39m

Chicago O'Hare Intl

Sat 10/14

2 stops23h 57m

TallahasseeChicago Midway

TLH - MDW

TLHMDW

Tallahassee

Fri 10/27

1 stop22h 57m

Chicago Midway

Sun 10/29

2 stops37h 40m

TallahasseeChicago Midway

TLH - MDW

TLHMDW

Tallahassee

Fri 10/27

1 stop22h 57m

Chicago Midway

Sun 10/29

1 stop23h 54m

TallahasseeChicago O'Hare Intl

TLH - ORD

TLHORD

Tallahassee

Thu 10/26

1 stop23h 52m

Chicago O'Hare Intl

Mon 10/30

1 stop10h 40m

TallahasseeChicago O'Hare Intl

TLH - ORD

TLHORD

Tallahassee

Thu 11/16

1 stop5h 20m

Chicago O'Hare Intl

Sun 11/19

1 stop6h 54m

TallahasseeChicago O'Hare Intl

TLH - ORD

TLHORD

Tallahassee

Thu 10/26

2 stops7h 53m

Chicago O'Hare Intl

Mon 10/30

1 stop5h 29m

TallahasseeChicago Midway

TLH - MDW

TLHMDW

Tallahassee

Fri 10/27

1 stop4h 01m

Chicago Midway

Sun 10/29

1 stop4h 05m

Flights are sorted by cheapest first

Deals found on 9/21

Reviews of airlines servicing Chicago

See what other customers who have flown with United Airlines, Delta and American Airlines from Tallahassee to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
3,019 reviews

Boarding

8.0

Food

7.2

Overall

7.9

Entertainment

7.8

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Landing in Syracuse was ruff no bad weather just bad piloting. A/C barely. Working from LGA to Syracuse.

Delta
7.9
Good
3,019 reviews
Delta
7.9
Good
3,019 reviews

Boarding

8.0

Food

7.2

Overall

7.9

Entertainment

7.8

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Landing in Syracuse was ruff no bad weather just bad piloting. A/C barely. Working from LGA to Syracuse.

United Airlines
7.4
Good
1,890 reviews
Delta
7.9
Good
3,019 reviews

Boarding

8.0

Food

7.2

Overall

7.9

Entertainment

7.8

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Landing in Syracuse was ruff no bad weather just bad piloting. A/C barely. Working from LGA to Syracuse.

American Airlines
7.2
Good
2,635 reviews
Delta
7.9
Good
3,019 reviews

Boarding

8.0

Food

7.2

Overall

7.9

Entertainment

7.8

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Landing in Syracuse was ruff no bad weather just bad piloting. A/C barely. Working from LGA to Syracuse.

Spirit Airlines
6.3
Okay
1,481 reviews
Delta
7.9
Good
3,019 reviews

Boarding

8.0

Food

7.2

Overall

7.9

Entertainment

7.8

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Landing in Syracuse was ruff no bad weather just bad piloting. A/C barely. Working from LGA to Syracuse.

Related info for your journey

Useful info, stats and facts about Tallahassee to Chicago flights.

What airport do you fly from for flights from Tallahassee to Chicago?

Located just 5.0 mi from the city center, Tallahassee is the airport most travelers will use when flying to Chicago from Tallahassee. Booking flights from Tallahassee (TLH) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 2 different airlines.

Can I find flights from Tallahassee to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from Tallahassee to Chicago for under $300. The cheapest flight booked recently is on Multiple Airlines for just $249, but on average you can expect to pay $296.

Are there last-minute flights available from Tallahassee to Chicago for under $500?

There are currently 5+ open flights from Tallahassee to Chicago within the next 7 days for less than $500.

What are the cheapest airlines flying from Tallahassee to Chicago round-trip?

United Airlines, at $385, was found to be the cheapest airline from Tallahassee to Chicago.Alternate airlines to your destination round-trip include Delta and American Airlines. Users have found that United Airlines is 31% cheaper than the other options available to this destination.

What are the cheapest airlines to fly from Tallahassee to Chicago one-way?

For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $198. Users have also found prices from $220 and $303 on Delta and American Airlines, respectively.

What does TLH to ORD mean?

These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Tallahassee Airport to Chicago O'Hare Intl Airport flight would often be abbreviated as a TLH to ORD flight. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

Top 2 airlines flying from Tallahassee to Chicago

The chart below displays the airlines Cheapflights users traveling from Tallahassee to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$385Average$575FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapest$417Average$635FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
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