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Cheap flights from Tallahassee to Chicago from $169

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 4/25. 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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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.
American Airlines Logo
6:30 am - 12:36 pm
TLH
-
ORD
7h 06m
1 stop
American Airlines Logo
12:20 pm - 7:45 pm
ORD
-
TLH
6h 25m
1 stop
$357American Airlines
Sat, May 2 - Tue, May 5
Delta Logo
5:12 pm - 9:10 pm
TLH
-
ORD
4h 58m
1 stop
Delta Logo
5:15 am - 12:11 pm
ORD
-
TLH
5h 56m
1 stop
$372Delta
Wed, Apr 8 - Tue, Apr 14
Delta Logo
7:04 am - 10:14 am
TLH
-
MDW
4h 10m
1 stop
Delta Logo
6:00 am - 12:11 pm
MDW
-
TLH
5h 11m
1 stop
$408Delta
Sat, May 2 - Tue, May 5
Delta Logo
3:50 pm - 9:10 pm
TLH
-
ORD
6h 20m
1 stop
Delta Logo
5:15 am - 3:00 pm
ORD
-
TLH
8h 45m
1 stop
$409Delta
Wed, Apr 8 - Mon, Apr 13
American Airlines Logo
7:54 pm - 11:54 pm
TLH
-
ORD
5h 00m
1 stop
American Airlines Logo
3:07 pm - 11:15 pm
ORD
-
TLH
7h 08m
1 stop
$417American Airlines
Wed, Apr 8 - Sat, Apr 11
Delta Logo
1:00 pm - 4:27 pm
TLH
-
MDW
4h 27m
1 stop
Delta Logo
10:35 am - 4:35 pm
MDW
-
TLH
5h 00m
1 stop
$417Delta
Wed, Aug 26 - Sat, Aug 29
American Airlines Logo
7:54 pm - 11:54 pm
TLH
-
ORD
5h 00m
1 stop
American Airlines Logo
5:00 am - 11:42 am
ORD
-
TLH
5h 42m
1 stop
$427American Airlines
Thu, Apr 9 - Sun, Apr 12
Delta Logo
3:50 pm - 9:10 pm
TLH
-
ORD
6h 20m
1 stop
Delta Logo
7:10 am - 10:33 pm
ORD
-
TLH
14h 23m
2 stops
$441Delta
Wed, Apr 8 - Sat, Apr 11
Delta Logo
7:05 pm - 10:28 pm
TLH
-
MDW
4h 23m
1 stop
Delta Logo
6:00 am - 12:11 pm
MDW
-
TLH
5h 11m
1 stop
$447Delta
Thu, Apr 23 - Mon, Apr 27
Delta Logo
5:15 pm - 8:16 pm
TLH
-
ORD
4h 01m
1 stop
Delta Logo
5:15 am - 12:11 pm
ORD
-
TLH
5h 56m
1 stop
$447Delta
Fri, Apr 24 - Mon, Apr 27

Delta flights from Tallahassee to Chicago

Our best Delta deals on Tallahassee to Chicago flight tickets
Delta
Apr 8
TLH5:12 pmTallahassee
4h 58m
1 stop
ORD9:10 pmChicago O'Hare Intl
Apr 14
ORD5:15 amChicago O'Hare Intl
5h 56m
1 stop
TLH12:11 pmTallahassee
$372
Delta
May 2
TLH7:04 amTallahassee
4h 10m
1 stop
MDW10:14 amChicago Midway
May 5
MDW6:00 amChicago Midway
5h 11m
1 stop
TLH12:11 pmTallahassee
$408
Delta
Apr 8
TLH3:50 pmTallahassee
6h 20m
1 stop
ORD9:10 pmChicago O'Hare Intl
Apr 13
ORD5:15 amChicago O'Hare Intl
8h 45m
1 stop
TLH3:00 pmTallahassee
$409

American Airlines flights from Tallahassee to Chicago

Our best American Airlines deals on Tallahassee to Chicago flight tickets
American Airlines
May 2
TLH6:30 amTallahassee
7h 06m
1 stop
ORD12:36 pmChicago O'Hare Intl
May 5
ORD12:20 pmChicago O'Hare Intl
6h 25m
1 stop
TLH7:45 pmTallahassee
$357
American Airlines
Apr 8
TLH7:54 pmTallahassee
5h 00m
1 stop
ORD11:54 pmChicago O'Hare Intl
Apr 11
ORD3:07 pmChicago O'Hare Intl
7h 08m
1 stop
TLH11:15 pmTallahassee
$417
American Airlines
Apr 9
TLH7:54 pmTallahassee
5h 00m
1 stop
ORD11:54 pmChicago O'Hare Intl
Apr 12
ORD5:00 amChicago O'Hare Intl
5h 42m
1 stop
TLH11:42 amTallahassee
$427

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 March 11, 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

Sat 5/2

6:30 am-12:36 pm

1 stop7h 06m

Chicago O'Hare Intl

Tue 5/5

12:20 pm-7:45 pm

1 stop6h 25m

$357

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 4/8

5:12 pm-9:10 pm

1 stop4h 58m

Chicago O'Hare Intl

Tue 4/14

5:15 am-12:11 pm

1 stop5h 56m

$372
Quickest round-trip

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 5/2

7:04 am-10:14 am

1 stop4h 10m

Chicago Midway

Tue 5/5

6:00 am-12:11 pm

1 stop5h 11m

$408

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 4/8

3:50 pm-9:10 pm

1 stop6h 20m

Chicago O'Hare Intl

Mon 4/13

5:15 am-3:00 pm

1 stop8h 45m

$409

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 4/8

7:54 pm-11:54 pm

1 stop5h 00m

Chicago O'Hare Intl

Sat 4/11

3:07 pm-11:15 pm

1 stop7h 08m

$417

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 8/26

1:00 pm-4:27 pm

1 stop4h 27m

Chicago Midway

Sat 8/29

10:35 am-4:35 pm

1 stop5h 00m

$417

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 4/9

7:54 pm-11:54 pm

1 stop5h 00m

Chicago O'Hare Intl

Sun 4/12

5:00 am-11:42 am

1 stop5h 42m

$427

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Wed 4/8

3:50 pm-9:10 pm

1 stop6h 20m

Chicago O'Hare Intl

Sat 4/11

7:10 am-10:33 pm

2 stops14h 23m

$441

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Thu 4/23

7:05 pm-10:28 pm

1 stop4h 23m

Chicago Midway

Mon 4/27

6:00 am-12:11 pm

1 stop5h 11m

$447

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 4/24

5:15 pm-8:16 pm

1 stop4h 01m

Chicago O'Hare Intl

Mon 4/27

5:15 am-12:11 pm

1 stop5h 56m

$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 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
8,278 reviews
Search Delta flights
American AirlinesPriceFrom $341Free CancellationRating
7.1
11,419 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
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