TLH - CHI

$153 Find Cheap Flights from Tallahassee to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$278
Typical prices: $437-$637
Multiple Airlines
Mon 11/12Fri 11/16
TLH - ORD • 2 stops
Cheapest one-way
$153
Typical prices: $337-$559
Multiple Airlines
Mon 12/10
TLH - MDW • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Tallahassee and Chicago. You'll need to take a connecting flight to reach the destination.
Insights
Insights
Top routes
TLH - ORD
Cheapest • 1% average savings
TLH - MDW
Most popular
Insights
Insights
When to travel
May
Cheapest • 21% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Miami (MIA)
Cheapest • Avg $456 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 4h 44m (one-way)
Insights
Insights
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Flight Deals

Cheap Flights from Tallahassee to Chicago (TLH-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Tallahassee to Chicago

Thu, Nov 12 - Mon, Nov 16
Multiple Airlines Logo
8:20 am - 6:45 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
11h 25m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson
Multiple Airlines Logo
7:55 am - 10:35 amORD  Chicago O'Hare Intl-TLH Tallahassee
25h 40m1 stop Fort Lauderdale
$278Multiple Airlines
Thu, Nov 12 - Mon, Nov 16
Multiple Airlines Logo
1:02 pm - 3:37 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
27h 35m1 stop Fort Lauderdale
Multiple Airlines Logo
7:55 am - 10:35 amORD  Chicago O'Hare Intl-TLH Tallahassee
25h 40m1 stop Fort Lauderdale
$291Multiple Airlines
Tue, Nov 10 - Sat, Nov 14
Multiple Airlines Logo
11:15 am - 6:30 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
32h 15m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
Multiple Airlines Logo
7:55 am - 7:40 amORD  Chicago O'Hare Intl-TLH Tallahassee
22h 45m1 stop Fort Lauderdale
$351Multiple Airlines
Thu, Nov 26 - Wed, Dec 2
Multiple Airlines Logo
9:15 am - 11:34 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
15h 19m1 stop Fort Lauderdale
Multiple Airlines Logo
3:55 pm - 12:32 pmORD  Chicago O'Hare Intl-TLH Tallahassee
19h 37m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham
$385Multiple Airlines
Thu, Nov 26 - Wed, Dec 2
American Airlines Logo
6:10 am - 11:06 amTLH  Tallahassee-ORD Chicago O'Hare Intl
5h 56m1 stop Miami
American Airlines Logo
4:44 pm - 11:37 pmORD  Chicago O'Hare Intl-TLH Tallahassee
5h 53m1 stop Miami
$487American Airlines
Wed, Jan 13 - Sun, Jan 17
American Airlines Logo
6:52 pm - 10:46 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
4h 54m1 stop Charlotte Douglas
American Airlines Logo
5:00 am - 1:23 pmORD  Chicago O'Hare Intl-TLH Tallahassee
7h 23m1 stop Miami
$487American Airlines
Thu, Dec 10 - Thu, Dec 24
Delta Logo
12:04 pm - 5:06 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
6h 02m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:00 am - 4:50 pmORD  Chicago O'Hare Intl-TLH Tallahassee
6h 50m1 stop Atlanta Hartsfield-Jackson
$497Delta
Thu, Dec 24 - Thu, Dec 31
American Airlines Logo
10:14 am - 2:30 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
5h 16m1 stop Charlotte Douglas
American Airlines Logo
12:05 pm - 7:19 pmORD  Chicago O'Hare Intl-TLH Tallahassee
6h 14m1 stop Charlotte Douglas
$497American Airlines
Sat, Nov 21 - Sat, Nov 28
Delta Logo
5:09 pm - 8:49 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
4h 40m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 11:25 amORD  Chicago O'Hare Intl-TLH Tallahassee
4h 55m1 stop Atlanta Hartsfield-Jackson
$507Delta
Sat, Nov 21 - Sat, Nov 28
Delta Logo
2:59 pm - 8:49 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
6h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 11:25 amORD  Chicago O'Hare Intl-TLH Tallahassee
4h 55m1 stop Atlanta Hartsfield-Jackson
$507Delta
Booking Insights

Price, demand and travel trends for Tallahassee to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What is the cheapest Tallahassee to Chicago flight route?

There's little price difference between Tallahassee to Chicago routes. They average around $517 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Tallahassee to Chicago?

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Tallahassee to Chicago. It’s 15% cheaper than the average day, while Monday is the most expensive, with prices 27% higher.

What’s the cheapest month to fly from Tallahassee to Chicago?

•May is the cheapest month to fly from Tallahassee to Chicago at $406 round-trip.
•October ($654) and January ($633) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 61% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Tallahassee to Chicago flights

Low season

January

Cheapest flight

$153
Beat the crowds with an average 32% drop in travelers.
The most popular month to fly with an average 35% increase in travelers.
One-way 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

Your Tallahassee to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Tallahassee to Chicago?

    Two cabin classes are available on flights from Tallahassee to Chicago:

    • Economy Class
    • First Class

  • How long is a flight from Tallahassee to Chicago?

    A nonstop flight from Tallahassee to Chicago takes 00m, covering 813 miles.

  • Do I need a passport to fly from Tallahassee to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Tallahassee to Chicago flight?

    Round-trip flights from Tallahassee to Chicago range from $437 to $637, with an average of $512 over the past 12 months. Anything below $437 counts as a good deal.

  • Have flight prices from Tallahassee to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $278 to $2,545. That means the highest observed fare was about 9x higher than the lowest one.

  • How are flight prices from Tallahassee to Chicago looking right now?

    One-way fares from Tallahassee to Chicago are currently lower than usual. Average one-way flight prices are about $282, which is 42% below the typical average for this route.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $28:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from Tallahassee to Chicago?

    Flights from Tallahassee to Chicago usually depart from Tallahassee (TLH) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from Tallahassee to Chicago pass through?

    One-stop flights from Tallahassee to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 73% of one-stop connections
    • Charlotte Douglas (CLT) - 24% of one-stop connections
    • Dallas/Fort Worth (DFW) - 1% of one-stop connections
    • Miami (MIA) - 1% of one-stop connections

  • Can I save money by using flexible dates for flights from Tallahassee to Chicago?

    Yes. Flexible dates can save you up to 34% on flights from Tallahassee to Chicago. Saturday is the cheapest departure day at $438 round-trip on average, while Monday is the most expensive at $654, a difference of $216.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • How much time can I save by choosing a different layover airport from Tallahassee to Chicago?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 4h 44m, compared with 5h 17m via Charlotte Douglas (CLT) and 5h 41m via Miami (MIA).

  • What is the time difference between Tallahassee and Chicago?

    Chicago is 1 hour behind Tallahassee (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

Your guide to booking Tallahassee to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Saturday departure and avoid flying on Monday. On this route, Saturday flights average $438, about $216 less than Monday fares (33% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Tallahassee to Chicago trip for May. Fares historically average $406 round-trip in that month - typically $248 less than the most expensive month, which is October (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

More options for your flight from Tallahassee to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago