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Cheap flights from Tallahassee to Chicago from $297

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Tallahassee to Chicago departing on 8/23. 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 - 9:36 amTLH-MDW
4h 56m1 stop
Delta Logo
6:00 am - 1:59 pmMDW-TLH
6h 59m1 stop
$297Delta
Find Deal
Sat, Aug 23 - Sat, Aug 30
Delta Logo
5:05 pm - 10:14 pmTLH-MDW
6h 09m1 stop
Delta Logo
10:35 am - 4:25 pmMDW-TLH
4h 50m1 stop
$338Delta
Find Deal
Tue, Oct 21 - Sat, Nov 1
Delta Logo
6:50 am - 9:40 amTLH-MDW
3h 50m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-TLH
5h 00m1 stop
$342Delta
Find Deal
Wed, Oct 1 - Sun, Oct 5
Delta Logo
7:11 pm - 9:12 pmTLH-MDW
27h 01m1 stop
Delta Logo
6:00 am - 1:56 pmMDW-TLH
6h 56m1 stop
$371Delta
Find Deal
Fri, Aug 29 - Sun, Aug 31
Delta Logo
5:10 pm - 9:26 pmTLH-MDW
5h 16m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-TLH
5h 00m1 stop
$383Delta
Find Deal
Wed, Sep 10 - Sun, Sep 14
Delta Logo
5:12 pm - 9:36 pmTLH-MDW
5h 24m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-TLH
5h 00m1 stop
$387Delta
Find Deal
Fri, Sep 12 - Sun, Sep 14
Delta Logo
7:11 pm - 12:28 pmTLH-MDW
18h 17m2 stops
Delta Logo
6:00 am - 1:56 pmMDW-TLH
6h 56m1 stop
$394Delta
Find Deal
Fri, Aug 29 - Sun, Aug 31
Delta Logo
5:12 pm - 9:36 pmTLH-MDW
5h 24m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-TLH
5h 00m1 stop
$398Delta
Find Deal
Wed, Sep 24 - Mon, Sep 29
Delta Logo
5:10 pm - 6:37 pmTLH-MDW
26h 27m2 stops
Delta Logo
6:00 am - 12:01 pmMDW-TLH
5h 01m1 stop
$399Delta
Find Deal
Fri, Aug 29 - Sun, Aug 31
Delta Logo
5:40 am - 9:40 amTLH-MDW
5h 00m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-TLH
5h 00m1 stop
$443Delta
Find Deal
Fri, Sep 26 - Mon, Sep 29

Delta flights from Tallahassee to Chicago Midway Airport

Our best Delta deals on Tallahassee to Chicago Midway Airport flight tickets
Delta
Aug 23
TLH5:40 amTallahassee
4h 56m
1 stop
MDW9:36 amChicago Midway
Aug 30
MDW6:00 amChicago Midway
6h 59m
1 stop
TLH1:59 pmTallahassee
$297
Find similar
Delta
Oct 21
TLH5:05 pmTallahassee
6h 09m
1 stop
MDW10:14 pmChicago Midway
Nov 1
MDW10:35 amChicago Midway
4h 50m
1 stop
TLH4:25 pmTallahassee
$338
Find similar
Delta
Oct 1
TLH6:50 amTallahassee
3h 50m
1 stop
MDW9:40 amChicago Midway
Oct 5
MDW6:00 amChicago Midway
5h 00m
1 stop
TLH12:00 pmTallahassee
$342
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Tallahassee to Chicago Midway Airport 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 July 31, 2025.
Use the filters below to find and compare flights from Tallahassee to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 8/23

5:40 am-9:36 am

1 stop4h 56m

Chicago Midway

Sat 8/30

6:00 am-1:59 pm

1 stop6h 59m

$297

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Tue 10/21

5:05 pm-10:14 pm

1 stop6h 09m

Chicago Midway

Sat 11/1

10:35 am-4:25 pm

1 stop4h 50m

$338

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 10/1

6:50 am-9:40 am

1 stop3h 50m

Chicago Midway

Sun 10/5

6:00 am-12:00 pm

1 stop5h 00m

$342

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 8/29

7:11 pm-9:12 pm

1 stop27h 01m

Chicago Midway

Sun 8/31

6:00 am-1:56 pm

1 stop6h 56m

$371

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 9/10

5:10 pm-9:26 pm

1 stop5h 16m

Chicago Midway

Sun 9/14

6:00 am-12:00 pm

1 stop5h 00m

$383

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 9/12

5:12 pm-9:36 pm

1 stop5h 24m

Chicago Midway

Sun 9/14

6:00 am-12:00 pm

1 stop5h 00m

$387

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 8/29

7:11 pm-12:28 pm

2 stops18h 17m

Chicago Midway

Sun 8/31

6:00 am-1:56 pm

1 stop6h 56m

$394

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 9/24

5:12 pm-9:36 pm

1 stop5h 24m

Chicago Midway

Mon 9/29

6:00 am-12:00 pm

1 stop5h 00m

$398

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 8/29

5:10 pm-6:37 pm

2 stops26h 27m

Chicago Midway

Sun 8/31

6:00 am-12:01 pm

1 stop5h 01m

$399

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 9/26

5:40 am-9:40 am

1 stop5h 00m

Chicago Midway

Mon 9/29

6:00 am-12:00 pm

1 stop5h 00m

$443

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 Midway Airport

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 day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Tallahassee. The lowest ticket price found for a Friday departure recently was $713. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Tallahassee because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $720.

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

Flying to Chicago Midway Airport from Tallahassee in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $585 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $720. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Tallahassee to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Tallahassee to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Tallahassee to Chicago Midway Airport (TLH to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Tallahassee to Chicago Midway Airport

Best Price Found

$299

Fastest flight time

3h 45m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Tallahassee in the past 72 hours is $299. The best round-trip flight deal from Tallahassee to Chicago Midway Airport found on momondo in the last 72 hours is $297.
The fastest flight from Tallahassee to Chicago Midway Airport takes 3h 45m
There are no direct flights from Tallahassee to Chicago Midway Airport. Popular non-direct route for this connection is Tallahassee Airport - Chicago Midway Airport.
Search flight deals

  • How far is Tallahassee to Chicago Midway by plane?

    The distance between Tallahassee and Chicago Midway is about 806.8 mi. Flights usually cover this in 3h 45m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Tallahassee Airport to Chicago Midway Airport?

    Prices for flights from Tallahassee Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Tallahassee Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Tallahassee Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Tallahassee Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Tallahassee to Chicago Midway Airport?

Best airlines flying from Tallahassee to Chicago Midway Airport

Compare and see reviews for airlines that fly from Tallahassee to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $426Free CancellationRating
8.0
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
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?

It is quick and easy to find Tallahassee to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Tallahassee to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Tallahassee with this policy.

How can momondo help me find flights from Tallahassee to Chicago?

Once you have performed a search for Tallahassee to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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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