TLH - CHI

$199 Find Cheap Flights from Tallahassee to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$289
Typical prices: $419-$633
Multiple Airlines
Sat 10/6Sat 10/13
TLH - ORD • 1 stop
Cheapest one-way
$199
Typical prices: $317-$534
Multiple Airlines
Thu 11/1
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 - MDW
Cheapest • 3% average savings
TLH - ORD
Most popular
Insights
Insights
When to travel
May
Cheapest • 16% price drop
October
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Miami (MIA)
Cheapest • Avg $387 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 4h 40m (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

Tue, Oct 6 - Tue, Oct 13
Multiple Airlines Logo
3:57 pm - 3:20 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
24h 23m1 stop Fort Lauderdale
Multiple Airlines Logo
7:44 pm - 12:32 pmORD  Chicago O'Hare Intl-TLH Tallahassee
39h 48m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham
$289Multiple Airlines
Thu, Oct 29 - Mon, Nov 2
Multiple Airlines Logo
1:12 pm - 3:37 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
27h 25m1 stop Fort Lauderdale
Multiple Airlines Logo
8:00 am - 10:35 amORD  Chicago O'Hare Intl-TLH Tallahassee
25h 35m1 stop Fort Lauderdale
$303Multiple Airlines
Thu, Oct 29 - Sat, Oct 31
Multiple Airlines Logo
8:30 am - 6:45 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
11h 15m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:00 am - 8:50 amORD  Chicago O'Hare Intl-TLH Tallahassee
23h 50m1 stop Fort Lauderdale
$320Multiple Airlines
Thu, Nov 26 - Mon, Dec 7
Multiple Airlines Logo
9:15 am - 12:53 amTLH  Tallahassee-ORD Chicago O'Hare Intl
16h 38m2 stops Fort Lauderdale Denver Intl
Multiple Airlines Logo
5:00 am - 10:35 amORD  Chicago O'Hare Intl-TLH Tallahassee
28h 35m1 stop Fort Lauderdale
$339Multiple Airlines
Tue, Oct 6 - Tue, Oct 13
American Airlines Logo
4:30 pm - 11:00 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
7h 30m1 stop Charlotte Douglas
American Airlines Logo
4:31 pm - 11:49 pmORD  Chicago O'Hare Intl-TLH Tallahassee
6h 18m1 stop Miami
$437American Airlines
Fri, Dec 25 - Wed, Dec 30
American Airlines Logo
6:00 am - 11:02 amTLH  Tallahassee-ORD Chicago O'Hare Intl
6h 02m1 stop Charlotte Douglas
American Airlines Logo
6:59 am - 1:49 pmORD  Chicago O'Hare Intl-TLH Tallahassee
5h 50m1 stop Miami
$447American Airlines
Fri, Nov 6 - Tue, Nov 10
American Airlines Logo
3:25 pm - 10:32 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
8h 07m1 stop Charlotte Douglas
American Airlines Logo
9:00 am - 2:25 pmORD  Chicago O'Hare Intl-TLH Tallahassee
4h 25m1 stop Charlotte Douglas
$447American Airlines
Tue, Oct 6 - Tue, Oct 13
Delta Logo
6:00 am - 10:03 amTLH  Tallahassee-MDW Chicago Midway
5h 03m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 11:14 amMDW  Chicago Midway-TLH Tallahassee
4h 10m1 stop Atlanta Hartsfield-Jackson
$457Delta
Fri, Nov 6 - Sun, Nov 8
Delta Logo
7:00 pm - 10:33 pmTLH  Tallahassee-MDW Chicago Midway
4h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 11:09 amMDW  Chicago Midway-TLH Tallahassee
4h 05m1 stop Atlanta Hartsfield-Jackson
$457Delta
Fri, Oct 30 - Tue, Nov 3
Delta Logo
3:24 pm - 8:38 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
6h 14m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:23 pm - 7:45 pmORD  Chicago O'Hare Intl-TLH Tallahassee
5h 22m1 stop Atlanta Hartsfield-Jackson
$467Delta
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 from Tallahassee to Chicago 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 $467 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?

Saturday is the cheapest day of the week to fly from Tallahassee to Chicago, it is 16% cheaper than the average day. Monday is the most expensive day with flight prices 35% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • May is the cheapest month to fly from Tallahassee to Chicago at $406 round-trip.
  • January ($633) and November ($615) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 55% 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

February

Cheapest flight

$199
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 7% 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

Your Tallahassee to Chicago flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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).

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

    Only Economy Class is available on flights from Tallahassee to Chicago.

  • 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) - 63% of one-stop connections
    • Charlotte Douglas (CLT) - 27% of one-stop connections
    • Miami (MIA) - 6% of one-stop connections
    • Washington, D.C. Reagan-National (DCA) - 2% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

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

    On the Tallahassee to Chicago route, being flexible with your departure day can save you up to 38%. Saturday is the cheapest day at $406 round-trip on average, while Monday is the most expensive at $654: a $248 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What popular places can I visit in Chicago?

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

  • How long is a flight from Tallahassee to Chicago?

    A nonstop flight from Tallahassee to Chicago takes 0h 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.

  • 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 $289 to $2,586. 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 $330, which is 20% below the typical average for this route.

  • 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 40m, compared with 5h 14m 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 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
    · Dollar
    · Ace

    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 $30:

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

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

    Round-trip flights from Tallahassee to Chicago range from $419 to $633, with an average of $481 over the past 12 months. Anything below $419 counts as a good deal.

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 can be flexible, aim for a Saturday departure instead of Monday. On this route, Saturday flights average $406 - about $248 less than Monday (38% 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 $227 less than the most expensive month, which is January (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