Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Tallahassee to Chicago from $159

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 2/28. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Tallahassee to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:21 am - 11:59 am
TLH
-
MDW
5h 38m1 stop
Delta Logo
10:46 am - 6:40 pm
MDW
-
TLH
6h 54m1 stop
$317Delta
Wed, Jan 28 - Wed, Feb 4
American Airlines Logo
6:15 am - 11:06 am
TLH
-
ORD
5h 51m1 stop
American Airlines Logo
3:23 pm - 10:16 pm
ORD
-
TLH
5h 53m1 stop
$317American Airlines
Wed, Jan 28 - Sat, Jan 31
Delta Logo
5:30 am - 9:53 am
TLH
-
MDW
5h 23m1 stop
Delta Logo
10:48 am - 6:40 pm
MDW
-
TLH
6h 52m1 stop
$362Delta
Sat, Jan 31 - Fri, Feb 6
Delta Logo
1:47 pm - 4:59 pm
TLH
-
ORD
4h 12m1 stop
Delta Logo
11:15 am - 6:40 pm
ORD
-
TLH
6h 25m1 stop
$362Delta
Sat, Jan 31 - Fri, Feb 6
Delta Logo
10:11 am - 3:38 pm
TLH
-
MDW
6h 27m1 stop
Delta Logo
6:25 am - 1:01 pm
MDW
-
TLH
5h 36m1 stop
$378Delta
Sat, Jan 31 - Sat, Feb 7
American Airlines Logo
7:54 pm - 11:57 pm
TLH
-
ORD
5h 03m1 stop
American Airlines Logo
5:00 am - 11:42 am
ORD
-
TLH
5h 42m1 stop
$397American Airlines
Wed, May 13 - Sat, May 16
Delta Logo
5:30 am - 9:53 am
TLH
-
MDW
5h 23m1 stop
Delta Logo
12:46 pm - 8:45 pm
MDW
-
TLH
6h 59m1 stop
$407Delta
Fri, Jan 30 - Mon, Feb 2
Delta Logo
3:41 pm - 6:49 pm
TLH
-
ORD
4h 08m1 stop
Delta Logo
11:18 am - 6:40 pm
ORD
-
TLH
6h 22m1 stop
$407Delta
Fri, Feb 13 - Mon, Feb 16
American Airlines Logo
7:55 pm - 12:16 am
TLH
-
ORD
5h 21m1 stop
American Airlines Logo
5:00 am - 11:36 am
ORD
-
TLH
5h 36m1 stop
$433American Airlines
Thu, Mar 19 - Mon, Mar 23
Delta Logo
7:09 pm - 10:31 pm
TLH
-
MDW
4h 22m1 stop
Delta Logo
6:25 am - 12:28 pm
MDW
-
TLH
5h 03m1 stop
$453Delta
Fri, Mar 20 - Mon, Mar 23

American Airlines flights from Tallahassee to Chicago

Our best American Airlines deals on Tallahassee to Chicago flight tickets
American Airlines
Jan 28
TLH6:15 amTallahassee
5h 51m
1 stop
ORD11:06 amChicago O'Hare Intl
Jan 31
ORD3:23 pmChicago O'Hare Intl
5h 53m
1 stop
TLH10:16 pmTallahassee
$317
American Airlines
May 13
TLH7:54 pmTallahassee
5h 03m
1 stop
ORD11:57 pmChicago O'Hare Intl
May 16
ORD5:00 amChicago O'Hare Intl
5h 42m
1 stop
TLH11:42 amTallahassee
$397
American Airlines
Mar 19
TLH7:55 pmTallahassee
5h 21m
1 stop
ORD12:16 amChicago O'Hare Intl
Mar 23
ORD5:00 amChicago O'Hare Intl
5h 36m
1 stop
TLH11:36 amTallahassee
$433

Delta flights from Tallahassee to Chicago

Our best Delta deals on Tallahassee to Chicago flight tickets
Delta
Jan 28
TLH7:21 amTallahassee
5h 38m
1 stop
MDW11:59 amChicago Midway
Jan 31
MDW10:46 amChicago Midway
4h 05m
1 stop
TLH3:51 pmTallahassee
$317
Delta
Jan 31
TLH1:47 pmTallahassee
4h 12m
1 stop
ORD4:59 pmChicago O'Hare Intl
Feb 6
ORD11:15 amChicago O'Hare Intl
6h 25m
1 stop
TLH6:40 pmTallahassee
$362
Delta
Jan 31
TLH10:11 amTallahassee
6h 27m
1 stop
MDW3:38 pmChicago Midway
Feb 7
MDW6:25 amChicago Midway
5h 36m
1 stop
TLH1:01 pmTallahassee
$378

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 January 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

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 1/28

7:21 am-11:59 am

1 stop5h 38m

Chicago Midway

Wed 2/4

10:46 am-6:40 pm

1 stop6h 54m

$317

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 1/28

6:15 am-11:06 am

1 stop5h 51m

Chicago O'Hare Intl

Sat 1/31

3:23 pm-10:16 pm

1 stop5h 53m

$317

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 1/31

5:30 am-9:53 am

1 stop5h 23m

Chicago Midway

Fri 2/6

10:48 am-6:40 pm

1 stop6h 52m

$362

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sat 1/31

1:47 pm-4:59 pm

1 stop4h 12m

Chicago O'Hare Intl

Fri 2/6

11:15 am-6:40 pm

1 stop6h 25m

$362

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 1/31

10:11 am-3:38 pm

1 stop6h 27m

Chicago Midway

Sat 2/7

6:25 am-1:01 pm

1 stop5h 36m

$378

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 5/13

7:54 pm-11:57 pm

1 stop5h 03m

Chicago O'Hare Intl

Sat 5/16

5:00 am-11:42 am

1 stop5h 42m

$397

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 1/30

5:30 am-9:53 am

1 stop5h 23m

Chicago Midway

Mon 2/2

12:46 pm-8:45 pm

1 stop6h 59m

$407

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 2/13

3:41 pm-6:49 pm

1 stop4h 08m

Chicago O'Hare Intl

Mon 2/16

11:18 am-6:40 pm

1 stop6h 22m

$407

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 3/19

7:55 pm-12:16 am

1 stop5h 21m

Chicago O'Hare Intl

Mon 3/23

5:00 am-11:36 am

1 stop5h 36m

$433

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 3/20

7:09 pm-10:31 pm

1 stop4h 22m

Chicago Midway

Mon 3/23

6:25 am-12:28 pm

1 stop5h 03m

$453

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 October is your next best option. Flight prices from Tallahassee to Chicago during October average around $386.

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 54m

Direct flights

None
The fastest flight from Tallahassee to Chicago takes 3h 54m
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 54m.

  • 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
8,025 reviews
Search Delta flights
American AirlinesPriceFrom $356Free CancellationRating
7.2
11,095 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
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 2/7
Sat 2/14
By creating a price alert you accept our terms of use and privacy policy.

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