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Cheap flights from Tallahassee to Chicago from $309

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 12/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
Delta Logo
1:43 pm - 4:34 pmTLH-MDW
3h 51m1 stop
Delta Logo
6:00 am - 11:42 amMDW-TLH
4h 42m1 stop
$362Delta
Find Deal
Wed, Dec 3 - Sun, Dec 7
Delta Logo
1:43 pm - 4:42 pmTLH-ORD
3h 59m1 stop
Delta Logo
6:45 am - 2:04 pmORD-TLH
6h 19m1 stop
$362Delta
Find Deal
Wed, Dec 3 - Sun, Dec 7
American Airlines Logo
6:00 am - 1:01 pmTLH-ORD
8h 01m1 stop
American Airlines Logo
5:26 pm - 11:55 pmORD-TLH
5h 29m1 stop
$382American Airlines
Find Deal
Wed, Feb 18 - Sun, Feb 22
Delta Logo
3:40 pm - 7:01 pmTLH-ORD
4h 21m1 stop
Delta Logo
7:10 am - 2:42 pmORD-TLH
6h 32m1 stop
$397Delta
Find Deal
Sat, May 2 - Wed, May 6
American Airlines Logo
6:05 am - 12:28 pmTLH-ORD
7h 23m1 stop
American Airlines Logo
2:03 pm - 7:37 pmORD-TLH
4h 34m1 stop
$402American Airlines
Find Deal
Wed, Nov 19 - Sat, Dec 13
Delta Logo
1:39 pm - 4:39 pmTLH-MDW
4h 00m1 stop
Delta Logo
11:05 am - 4:22 pmMDW-TLH
4h 17m1 stop
$402Delta
Find Deal
Wed, Nov 19 - Sat, Dec 13
Delta Logo
5:30 am - 9:54 amTLH-MDW
5h 24m1 stop
Delta Logo
10:49 am - 4:22 pmMDW-TLH
4h 33m1 stop
$407Delta
Find Deal
Thu, Dec 4 - Sun, Dec 7
Delta Logo
5:30 am - 8:39 amTLH-ORD
4h 09m1 stop
Delta Logo
6:45 am - 2:04 pmORD-TLH
6h 19m1 stop
$407Delta
Find Deal
Thu, Dec 4 - Sun, Dec 7
Delta Logo
5:35 am - 10:19 amTLH-ORD
5h 44m1 stop
Delta Logo
5:23 am - 11:34 amORD-TLH
5h 11m1 stop
$437Delta
Find Deal
Thu, Nov 20 - Mon, Nov 24
Delta Logo
3:40 pm - 7:01 pmTLH-ORD
4h 21m1 stop
Delta Logo
7:00 am - 8:46 pmORD-TLH
12h 46m2 stops
$477Delta
Find Deal
Sat, May 2 - Wed, May 6

American Airlines flights from Tallahassee to Chicago

Our best American Airlines deals on Tallahassee to Chicago flight tickets
American Airlines
Feb 18
TLH6:00 amTallahassee
8h 01m
1 stop
ORD1:01 pmChicago O'Hare Intl
Feb 22
ORD5:26 pmChicago O'Hare Intl
5h 29m
1 stop
TLH11:55 pmTallahassee
$382
Find similar
American Airlines
Nov 19
TLH6:05 amTallahassee
7h 23m
1 stop
ORD12:28 pmChicago O'Hare Intl
Dec 13
ORD2:03 pmChicago O'Hare Intl
4h 34m
1 stop
TLH7:37 pmTallahassee
$402
Find similar
American Airlines
Dec 24
TLH3:30 pmTallahassee
4h 52m
1 stop
ORD7:22 pmChicago O'Hare Intl
Dec 30
ORD11:35 amChicago O'Hare Intl
9h 48m
1 stop
TLH10:23 pmTallahassee
$490
Find similar

Delta flights from Tallahassee to Chicago

Our best Delta deals on Tallahassee to Chicago flight tickets
Delta
Dec 3
TLH1:43 pmTallahassee
3h 59m
1 stop
ORD4:42 pmChicago O'Hare Intl
Dec 7
ORD6:45 amChicago O'Hare Intl
6h 19m
1 stop
TLH2:04 pmTallahassee
$362
Find similar
Delta
May 2
TLH3:40 pmTallahassee
4h 21m
1 stop
ORD7:01 pmChicago O'Hare Intl
May 6
ORD7:10 amChicago O'Hare Intl
6h 32m
1 stop
TLH2:42 pmTallahassee
$397
Find similar
Delta
Nov 19
TLH1:39 pmTallahassee
4h 07m
1 stop
ORD4:46 pmChicago O'Hare Intl
Dec 13
ORD11:22 amChicago O'Hare Intl
4h 00m
1 stop
TLH4:22 pmTallahassee
$402
Find similar

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 November 6, 2025.
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

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 12/3

1:43 pm-4:34 pm

1 stop3h 51m

Chicago Midway

Sun 12/7

6:00 am-11:42 am

1 stop4h 42m

$362

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 12/3

1:43 pm-4:42 pm

1 stop3h 59m

Chicago O'Hare Intl

Sun 12/7

6:45 am-2:04 pm

1 stop6h 19m

$362

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 2/18

6:00 am-1:01 pm

1 stop8h 01m

Chicago O'Hare Intl

Sun 2/22

5:26 pm-11:55 pm

1 stop5h 29m

$382

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sat 5/2

3:40 pm-7:01 pm

1 stop4h 21m

Chicago O'Hare Intl

Wed 5/6

7:10 am-2:42 pm

1 stop6h 32m

$397

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 11/19

6:05 am-12:28 pm

1 stop7h 23m

Chicago O'Hare Intl

Sat 12/13

2:03 pm-7:37 pm

1 stop4h 34m

$402

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 11/19

1:39 pm-4:39 pm

1 stop4h 00m

Chicago Midway

Sat 12/13

11:05 am-4:22 pm

1 stop4h 17m

$402

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Thu 12/4

5:30 am-9:54 am

1 stop5h 24m

Chicago Midway

Sun 12/7

10:49 am-4:22 pm

1 stop4h 33m

$407

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 12/4

5:30 am-8:39 am

1 stop4h 09m

Chicago O'Hare Intl

Sun 12/7

6:45 am-2:04 pm

1 stop6h 19m

$407

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 11/20

5:35 am-10:19 am

1 stop5h 44m

Chicago O'Hare Intl

Mon 11/24

5:23 am-11:34 am

1 stop5h 11m

$437

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sat 5/2

3:40 pm-7:01 pm

1 stop4h 21m

Chicago O'Hare Intl

Wed 5/6

7:00 am-8:46 pm

2 stops12h 46m

$477

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?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Tallahassee, with most prices found around $349. If you’re not able to fly to Chicago in September, then April is your next best option. Flight prices from Tallahassee to Chicago during April average around $388.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $520. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Tallahassee to Chicago for around $738.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Tallahassee to Chicago during this time can be as low as $554. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $738.

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

Direct flights

None
There are no direct flights from Tallahassee to Chicago. There are no popular flight routes from Tallahassee to Chicago.
Search flight deals

  • 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 3h 51m.

  • 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
American AirlinesPriceFrom $356Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
DeltaPriceFrom $356Free CancellationRating
7.9
8,001 reviews
Search Delta flights

Traveling to a place near Chicago?

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