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Cheap flights from Tallahassee to Chicago from $149

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 9/3. 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

Delta Logo
5:40 am - 9:48 amTLH-MDW
5h 08m1 stop
Delta Logo
6:00 am - 10:32 amMDW-TLH
3h 32m1 stop
$297Delta
Find Deal
Sat, Sep 27 - Sat, Oct 4
Delta Logo
5:09 pm - 10:14 pmTLH-ORD
6h 05m1 stop
Delta Logo
7:20 am - 12:00 pmORD-TLH
3h 40m1 stop
$297Delta
Find Deal
Sat, Sep 13 - Wed, Sep 17
Delta Logo
5:12 pm - 9:36 pmTLH-MDW
5h 24m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-TLH
5h 00m1 stop
$342Delta
Find Deal
Wed, Sep 17 - Wed, Sep 24
Delta Logo
7:08 pm - 12:01 amTLH-ORD
5h 53m1 stop
Delta Logo
9:46 am - 4:19 pmORD-TLH
5h 33m1 stop
$342Delta
Find Deal
Fri, Nov 14 - Tue, Nov 18
American Airlines Logo
10:45 am - 6:13 pmTLH-ORD
8h 28m1 stop
American Airlines Logo
5:00 am - 1:26 pmORD-TLH
7h 26m1 stop
$372American Airlines
Find Deal
Fri, Sep 5 - Sun, Sep 7
American Airlines Logo
2:15 pm - 9:45 pmTLH-ORD
8h 30m1 stop
American Airlines Logo
5:00 am - 12:44 pmORD-TLH
6h 44m1 stop
$387American Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
Delta Logo
5:09 pm - 9:10 pmTLH-MDW
5h 01m1 stop
Delta Logo
10:35 am - 4:20 pmMDW-TLH
4h 45m1 stop
$388Delta
Find Deal
Sat, Oct 4 - Sat, Oct 11
American Airlines Logo
6:02 pm - 9:42 pmTLH-ORD
4h 40m1 stop
American Airlines Logo
11:56 am - 9:37 pmORD-TLH
8h 41m1 stop
$398American Airlines
Find Deal
Sat, Dec 13 - Mon, Jan 5
American Airlines Logo
6:04 am - 11:06 amTLH-ORD
6h 02m1 stop
American Airlines Logo
1:37 pm - 10:38 pmORD-TLH
8h 01m1 stop
$417American Airlines
Find Deal
Sun, Sep 7 - Mon, Sep 15
Delta Logo
7:00 am - 9:53 amTLH-MDW
3h 53m1 stop
Delta Logo
5:34 pm - 10:18 pmMDW-TLH
3h 44m1 stop
$433Delta
Find Deal
Sat, Nov 15 - Mon, Nov 17

Delta flights from Tallahassee to Chicago

Our best Delta deals on Tallahassee to Chicago flight tickets
Delta
Sep 13
TLH5:09 pmTallahassee
6h 05m
1 stop
ORD10:14 pmChicago O'Hare Intl
Sep 17
ORD7:20 amChicago O'Hare Intl
3h 40m
1 stop
TLH12:00 pmTallahassee
$297
Find similar
Delta
Nov 14
TLH7:08 pmTallahassee
5h 53m
1 stop
ORD12:01 amChicago O'Hare Intl
Nov 18
ORD9:46 amChicago O'Hare Intl
5h 33m
1 stop
TLH4:19 pmTallahassee
$342
Find similar
Delta
Sep 6
TLH5:40 amTallahassee
4h 56m
1 stop
MDW9:36 amChicago Midway
Sep 8
MDW4:25 pmChicago Midway
5h 17m
1 stop
TLH10:42 pmTallahassee
$372
Find similar

American Airlines flights from Tallahassee to Chicago

Our best American Airlines deals on Tallahassee to Chicago flight tickets
American Airlines
Sep 5
TLH10:45 amTallahassee
8h 28m
1 stop
ORD6:13 pmChicago O'Hare Intl
Sep 7
ORD5:00 amChicago O'Hare Intl
7h 26m
1 stop
TLH1:26 pmTallahassee
$372
Find similar
American Airlines
Sep 26
TLH2:15 pmTallahassee
8h 30m
1 stop
ORD9:45 pmChicago O'Hare Intl
Sep 29
ORD5:00 amChicago O'Hare Intl
6h 44m
1 stop
TLH12:44 pmTallahassee
$387
Find similar
American Airlines
Dec 13
TLH6:02 pmTallahassee
4h 40m
1 stop
ORD9:42 pmChicago O'Hare Intl
Jan 5
ORD11:56 amChicago O'Hare Intl
8h 41m
1 stop
TLH9:37 pmTallahassee
$398
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 August 25, 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

Sat 9/27

5:40 am-9:48 am

1 stop5h 08m

Chicago Midway

Sat 10/4

6:00 am-10:32 am

1 stop3h 32m

$297

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sat 9/13

5:09 pm-10:14 pm

1 stop6h 05m

Chicago O'Hare Intl

Wed 9/17

7:20 am-12:00 pm

1 stop3h 40m

$297

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 9/17

5:12 pm-9:36 pm

1 stop5h 24m

Chicago Midway

Wed 9/24

6:00 am-12:00 pm

1 stop5h 00m

$342

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 11/14

7:08 pm-12:01 am

1 stop5h 53m

Chicago O'Hare Intl

Tue 11/18

9:46 am-4:19 pm

1 stop5h 33m

$342

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 9/5

10:45 am-6:13 pm

1 stop8h 28m

Chicago O'Hare Intl

Sun 9/7

5:00 am-1:26 pm

1 stop7h 26m

$372

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Fri 9/26

2:15 pm-9:45 pm

1 stop8h 30m

Chicago O'Hare Intl

Mon 9/29

5:00 am-12:44 pm

1 stop6h 44m

$387

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 10/4

5:09 pm-9:10 pm

1 stop5h 01m

Chicago Midway

Sat 10/11

10:35 am-4:20 pm

1 stop4h 45m

$388

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sat 12/13

6:02 pm-9:42 pm

1 stop4h 40m

Chicago O'Hare Intl

Mon 1/5

11:56 am-9:37 pm

1 stop8h 41m

$398

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sun 9/7

6:04 am-11:06 am

1 stop6h 02m

Chicago O'Hare Intl

Mon 9/15

1:37 pm-10:38 pm

1 stop8h 01m

$417

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 11/15

7:00 am-9:53 am

1 stop3h 53m

Chicago Midway

Mon 11/17

5:34 pm-10:18 pm

1 stop3h 44m

$433

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 April is, on average, the cheapest month to fly to Chicago from Tallahassee, with most prices found around $388. If you’re not able to fly to Chicago in April, then January is your next best option. Flight prices from Tallahassee to Chicago during January average around $389.

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 53m.

  • 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
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $356Free CancellationRating
7.9
7,981 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
Lansing
Portage
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