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Cheap flights from Tallahassee to Chicago from $167

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 8/16. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Tallahassee to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
1:07 pm - 3:26 pm
TLH
-
ORD
27h 19m
1 stop
Multiple Airlines Logo
2:03 pm - 12:27 pm
ORD
-
TLH
21h 24m
2 stops
$310Multiple Airlines
Sun, Sep 20 - Sat, Oct 3
Multiple Airlines Logo
12:47 pm - 12:15 pm
TLH
-
ORD
24h 28m
1 stop
Multiple Airlines Logo
8:05 am - 7:28 am
ORD
-
TLH
22h 23m
1 stop
$338Multiple Airlines
Thu, Jul 9 - Sat, Jul 11
Multiple Airlines Logo
12:47 pm - 12:15 pm
TLH
-
ORD
24h 28m
1 stop
Multiple Airlines Logo
1:50 pm - 1:37 pm
ORD
-
TLH
22h 47m
2 stops
$374Multiple Airlines
Thu, Jul 9 - Mon, Jul 13
Delta Logo
6:00 am - 11:51 am
TLH
-
MDW
6h 51m
1 stop
Delta Logo
12:46 pm - 8:09 pm
MDW
-
TLH
6h 23m
1 stop
$427Delta
Wed, Aug 5 - Wed, Aug 12
American Airlines Logo
10:42 am - 5:42 pm
TLH
-
ORD
8h 00m
1 stop
American Airlines Logo
8:54 am - 3:33 pm
ORD
-
TLH
5h 39m
1 stop
$427American Airlines
Wed, Aug 5 - Wed, Aug 12
Delta Logo
7:01 pm - 10:36 pm
TLH
-
MDW
4h 35m
1 stop
Delta Logo
4:30 pm - 10:21 pm
MDW
-
TLH
4h 51m
1 stop
$437Delta
Thu, Sep 3 - Wed, Sep 9
American Airlines Logo
10:42 am - 4:48 pm
TLH
-
ORD
7h 06m
1 stop
American Airlines Logo
1:19 pm - 9:54 pm
ORD
-
TLH
7h 35m
1 stop
$437American Airlines
Thu, Sep 3 - Wed, Sep 9
Delta Logo
7:16 pm - 10:25 pm
TLH
-
MDW
4h 09m
1 stop
Delta Logo
1:00 pm - 8:08 pm
MDW
-
TLH
6h 08m
1 stop
$447Delta
Fri, Sep 25 - Mon, Sep 28
Delta Logo
5:10 pm - 9:45 pm
TLH
-
ORD
5h 35m
1 stop
Delta Logo
7:10 am - 12:05 pm
ORD
-
TLH
3h 55m
1 stop
$447Delta
Fri, Nov 6 - Sun, Nov 8
American Airlines Logo
7:50 pm - 12:01 am
TLH
-
ORD
5h 11m
1 stop
American Airlines Logo
5:07 am - 11:34 am
ORD
-
TLH
5h 27m
1 stop
$457American Airlines
Fri, Jul 31 - Sun, Aug 2

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American Airlines flights from Tallahassee to Chicago

Our best American Airlines deals on Tallahassee to Chicago flight tickets
American Airlines
Aug 5
TLH10:42 amTallahassee
8h 00m
1 stop
ORD5:42 pmChicago O'Hare Intl
Aug 12
ORD8:54 amChicago O'Hare Intl
5h 39m
1 stop
TLH3:33 pmTallahassee
$427
American Airlines
Sep 3
TLH10:42 amTallahassee
7h 06m
1 stop
ORD4:48 pmChicago O'Hare Intl
Sep 9
ORD1:19 pmChicago O'Hare Intl
7h 35m
1 stop
TLH9:54 pmTallahassee
$437
American Airlines
Jul 31
TLH7:50 pmTallahassee
5h 11m
1 stop
ORD12:01 amChicago O'Hare Intl
Aug 2
ORD5:07 amChicago O'Hare Intl
5h 27m
1 stop
TLH11:34 amTallahassee
$457

Delta flights from Tallahassee to Chicago

Our best Delta deals on Tallahassee to Chicago flight tickets
Delta
Aug 5
TLH6:00 amTallahassee
6h 51m
1 stop
MDW11:51 amChicago Midway
Aug 12
MDW12:46 pmChicago Midway
6h 23m
1 stop
TLH8:09 pmTallahassee
$427
Delta
Sep 3
TLH7:01 pmTallahassee
4h 35m
1 stop
MDW10:36 pmChicago Midway
Sep 9
MDW4:30 pmChicago Midway
4h 51m
1 stop
TLH10:21 pmTallahassee
$437
Delta
Nov 6
TLH5:10 pmTallahassee
5h 35m
1 stop
ORD9:45 pmChicago O'Hare Intl
Nov 8
ORD7:10 amChicago O'Hare Intl
3h 55m
1 stop
TLH12:05 pmTallahassee
$447

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 June 15, 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 - ORD

TLHORD

Tallahassee

Sun 9/20

1:07 pm-3:26 pm

1 stop27h 19m

Chicago O'Hare Intl

Sat 10/3

2:03 pm-12:27 pm

2 stops21h 24m

$310

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 7/9

12:47 pm-12:15 pm

1 stop24h 28m

Chicago O'Hare Intl

Sat 7/11

8:05 am-7:28 am

1 stop22h 23m

$338

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 7/9

12:47 pm-12:15 pm

1 stop24h 28m

Chicago O'Hare Intl

Mon 7/13

1:50 pm-1:37 pm

2 stops22h 47m

$374

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 8/5

6:00 am-11:51 am

1 stop6h 51m

Chicago Midway

Wed 8/12

12:46 pm-8:09 pm

1 stop6h 23m

$427

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 8/5

10:42 am-5:42 pm

1 stop8h 00m

Chicago O'Hare Intl

Wed 8/12

8:54 am-3:33 pm

1 stop5h 39m

$427
Quickest round-trip

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Thu 9/3

7:01 pm-10:36 pm

1 stop4h 35m

Chicago Midway

Wed 9/9

4:30 pm-10:21 pm

1 stop4h 51m

$437

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 9/3

10:42 am-4:48 pm

1 stop7h 06m

Chicago O'Hare Intl

Wed 9/9

1:19 pm-9:54 pm

1 stop7h 35m

$437

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 9/25

7:16 pm-10:25 pm

1 stop4h 09m

Chicago Midway

Mon 9/28

1:00 pm-8:08 pm

1 stop6h 08m

$447

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 11/6

5:10 pm-9:45 pm

1 stop5h 35m

Chicago O'Hare Intl

Sun 11/8

7:10 am-12:05 pm

1 stop3h 55m

$447

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 7/31

7:50 pm-12:01 am

1 stop5h 11m

Chicago O'Hare Intl

Sun 8/2

5:07 am-11:34 am

1 stop5h 27m

$457

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 November is, on average, the cheapest month to fly to Chicago from Tallahassee, with most prices found around $66. If you’re not able to fly to Chicago in November, then December is your next best option. Flight prices from Tallahassee to Chicago during December average around $158.

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

3h 59m

Direct flights

None
The fastest flight from Tallahassee to Chicago takes 3h 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 3h 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
7.9
8,396 reviews
Search Delta flights
American AirlinesPriceFrom $316Free CancellationRating
7.1
11,660 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
Benton Harbor
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
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