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Cheap flights from Tallahassee to Chicago from $129

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Tallahassee to Chicago departing on 10/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Tallahassee to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:25 am - 7:35 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
12h 10m2 stops Raleigh-Durham Dallas/Fort Worth
Multiple Airlines Logo
7:11 am - 10:30 amORD  Chicago O'Hare Intl-TLH Tallahassee
26h 19m1 stop Fort Lauderdale
$248Multiple Airlines
Thu, Sep 17 - Mon, Sep 21
Multiple Airlines Logo
8:25 am - 10:20 amTLH  Tallahassee-ORD Chicago O'Hare Intl
26h 55m2 stops Raleigh-Durham Orlando
Multiple Airlines Logo
7:11 am - 7:45 amORD  Chicago O'Hare Intl-TLH Tallahassee
23h 34m1 stop Fort Lauderdale
$266Multiple Airlines
Sun, Sep 13 - Wed, Sep 16
Multiple Airlines Logo
1:07 pm - 2:45 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
26h 38m1 stop Fort Lauderdale
Multiple Airlines Logo
7:11 am - 10:30 amORD  Chicago O'Hare Intl-TLH Tallahassee
26h 19m1 stop Fort Lauderdale
$275Multiple Airlines
Thu, Sep 17 - Mon, Sep 21
Multiple Airlines Logo
8:25 am - 7:35 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
12h 10m2 stops Raleigh-Durham Dallas/Fort Worth
Multiple Airlines Logo
7:11 am - 10:30 amORD  Chicago O'Hare Intl-TLH Tallahassee
26h 19m1 stop Fort Lauderdale
$284Multiple Airlines
Thu, Sep 17 - Mon, Sep 21
American Airlines Logo
10:50 am - 4:05 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
6h 15m1 stop Charlotte Douglas
American Airlines Logo
6:29 am - 2:21 pmORD  Chicago O'Hare Intl-TLH Tallahassee
6h 52m1 stop Charlotte Douglas
$437American Airlines
Tue, Oct 20 - Tue, Oct 27
Delta Logo
8:07 am - 2:20 pmTLH  Tallahassee-ORD Chicago O'Hare Intl
7h 13m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:40 pm - 10:48 pmORD  Chicago O'Hare Intl-TLH Tallahassee
6h 08m1 stop Atlanta Hartsfield-Jackson
$447Delta
Sun, Sep 6 - Tue, Sep 15
Delta Logo
5:53 pm - 10:44 pmTLH  Tallahassee-MDW Chicago Midway
5h 51m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 11:15 amMDW  Chicago Midway-TLH Tallahassee
4h 10m1 stop Atlanta Hartsfield-Jackson
$447Delta
Wed, Sep 30 - Sun, Oct 4
American Airlines Logo
6:32 am - 11:05 amTLH  Tallahassee-ORD Chicago O'Hare Intl
5h 33m1 stop Charlotte Douglas
American Airlines Logo
8:00 am - 4:14 pmORD  Chicago O'Hare Intl-TLH Tallahassee
7h 14m1 stop Charlotte Douglas
$447American Airlines
Fri, Dec 25 - Wed, Dec 30
Delta Logo
5:45 pm - 10:36 pmTLH  Tallahassee-MDW Chicago Midway
5h 51m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:00 pm - 7:34 pmMDW  Chicago Midway-TLH Tallahassee
5h 34m1 stop Atlanta Hartsfield-Jackson
$447Delta
Sun, Sep 6 - Tue, Sep 15
American Airlines Logo
6:00 am - 11:05 amTLH  Tallahassee-ORD Chicago O'Hare Intl
6h 05m1 stop Miami
American Airlines Logo
5:18 am - 11:06 amORD  Chicago O'Hare Intl-TLH Tallahassee
4h 48m1 stop Charlotte Douglas
$447American Airlines
Wed, Jan 13 - Mon, Jan 18

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American Airlines flights from Tallahassee to Chicago

Our best American Airlines deals on Tallahassee to Chicago flight tickets
American Airlines
Oct 20
TLH10:50 amTallahassee
6h 15m
1 stop
ORD4:05 pmChicago O'Hare Intl
Oct 27
ORD6:29 amChicago O'Hare Intl
6h 52m
1 stop
TLH2:21 pmTallahassee
$437
American Airlines
Dec 25
TLH6:32 amTallahassee
5h 33m
1 stop
ORD11:05 amChicago O'Hare Intl
Dec 30
ORD8:00 amChicago O'Hare Intl
7h 14m
1 stop
TLH4:14 pmTallahassee
$447
American Airlines
Sep 3
TLH6:52 pmTallahassee
6h 00m
1 stop
ORD11:52 pmChicago O'Hare Intl
Sep 7
ORD6:49 amChicago O'Hare Intl
7h 44m
1 stop
TLH3:33 pmTallahassee
$457

Delta flights from Tallahassee to Chicago

Our best Delta deals on Tallahassee to Chicago flight tickets
Delta
Sep 2
TLH12:05 pmTallahassee
4h 39m
1 stop
MDW3:44 pmChicago Midway
Sep 8
MDW4:30 pmChicago Midway
5h 18m
1 stop
TLH10:48 pmTallahassee
$437
Delta
Sep 6
TLH5:45 pmTallahassee
5h 51m
1 stop
MDW10:36 pmChicago Midway
Sep 15
MDW1:00 pmChicago Midway
5h 34m
1 stop
TLH7:34 pmTallahassee
$447
Delta
Nov 5
TLH10:18 amTallahassee
5h 59m
1 stop
MDW3:17 pmChicago Midway
Nov 8
MDW6:04 amChicago Midway
4h 05m
1 stop
TLH11:09 amTallahassee
$457

momondo Fare Finder

 
Customize your flight search to find flights from Tallahassee to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 8, 2026.
Use the filters below to find and compare flights from Tallahassee to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TallahasseeChicago

TLH Tallahassee - ORD Chicago O'Hare Intl

TLHORD

Tallahassee

Thu 9/17

8:25 am-7:35 pm

2 stops12h 10m

Chicago O'Hare Intl

Mon 9/21

7:11 am-10:30 am

1 stop26h 19m

$248

TallahasseeChicago

TLH Tallahassee - ORD Chicago O'Hare Intl

TLHORD

Tallahassee

Sun 9/13

8:25 am-10:20 am

2 stops26h 55m

Chicago O'Hare Intl

Wed 9/16

7:11 am-7:45 am

1 stop23h 34m

$266

TallahasseeChicago

TLH Tallahassee - ORD Chicago O'Hare Intl

TLHORD

Tallahassee

Thu 9/17

1:07 pm-2:45 pm

1 stop26h 38m

Chicago O'Hare Intl

Mon 9/21

7:11 am-10:30 am

1 stop26h 19m

$275

TallahasseeChicago

TLH Tallahassee - ORD Chicago O'Hare Intl

TLHORD

Tallahassee

Thu 9/17

8:25 am-7:35 pm

2 stops12h 10m

Chicago O'Hare Intl

Mon 9/21

7:11 am-10:30 am

1 stop26h 19m

$284

TallahasseeChicago

TLH Tallahassee - ORD Chicago O'Hare Intl

TLHORD

Tallahassee

Tue 10/20

10:50 am-4:05 pm

1 stop6h 15m

Chicago O'Hare Intl

Tue 10/27

6:29 am-2:21 pm

1 stop6h 52m

$437

TallahasseeChicago

TLH Tallahassee - ORD Chicago O'Hare Intl

TLHORD

Tallahassee

Sun 9/6

8:07 am-2:20 pm

1 stop7h 13m

Chicago O'Hare Intl

Tue 9/15

3:40 pm-10:48 pm

1 stop6h 08m

$447
Quickest round-trip

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Wed 9/30

5:53 pm-10:44 pm

1 stop5h 51m

Chicago Midway

Sun 10/4

6:05 am-11:15 am

1 stop4h 10m

$447

TallahasseeChicago

TLH Tallahassee - ORD Chicago O'Hare Intl

TLHORD

Tallahassee

Fri 12/25

6:32 am-11:05 am

1 stop5h 33m

Chicago O'Hare Intl

Wed 12/30

8:00 am-4:14 pm

1 stop7h 14m

$447

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Sun 9/6

5:45 pm-10:36 pm

1 stop5h 51m

Chicago Midway

Tue 9/15

1:00 pm-7:34 pm

1 stop5h 34m

$447

TallahasseeChicago

TLH Tallahassee - ORD Chicago O'Hare Intl

TLHORD

Tallahassee

Wed 1/13

6:00 am-11:05 am

1 stop6h 05m

Chicago O'Hare Intl

Mon 1/18

5:18 am-11:06 am

1 stop4h 48m

$447

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Tallahassee to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Tallahassee and Chicago?

Prices are currently low for flights on this route.

Typical prices usually range from $446 to $838.
The lowest price recently found on this route was $248.

What is the cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Tallahassee, with most prices found around $406. If you’re not able to fly to Chicago in May, then December is your next best option. Flight prices from Tallahassee to Chicago during December average around $453.

How have Tallahassee to Chicago flight prices changed over time?

When to book flights from Tallahassee to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Tallahassee to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Tallahassee to Chicago (TLH to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Tallahassee to Chicago

Fastest flight time

4h 59m

Direct flights

None
The fastest flight from Tallahassee to Chicago takes 4h 59m
There are no direct flights from Tallahassee to Chicago. There are no popular flight routes from Tallahassee to Chicago.
Search flight deals

Frequently asked questions about flying from Tallahassee to Chicago

  • How far is Tallahassee to Chicago by plane?

    The straight-line distance from Tallahassee to Chicago is 811.3 mi. By plane, this route typically takes 4h 59m.

  • When did momondo last update prices for flights from Tallahassee Airport to Chicago?

    Prices for flights from Tallahassee Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Tallahassee Airport to Chicago?

  • How old do you have to be to fly from Tallahassee Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Tallahassee Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Tallahassee to Chicago?

Best airlines flying from Tallahassee to Chicago

Compare and see reviews for airlines that fly from Tallahassee to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $158Free CancellationRating
7.8
8,504 reviews
Search Delta flights
American AirlinesPriceFrom $316Free CancellationRating
7.1
11,885 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Tallahassee to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Tallahassee.

Can I find flights from Tallahassee to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Tallahassee on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Tallahassee to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Tallahassee.

I’m not ready to book a flight from Tallahassee to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Tallahassee are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport