$159 Cheap Flights from Tallahassee (TLH) to Chicago (ORD)

View $159 flight on Sat, Jan 17, 2026Opens in a new window

Popular airlines from Tallahassee Intl. Airport (TLH) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Tallahassee to Chicago (TLH-ORD)

Prices were available within the past 7 days and start at $159 for one-way flights and $319 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Feb 18 - Sat, Feb 21
TLH
Tallahassee
ORD
Chicago
$319 Roundtrip, found 4 days ago
$319
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Feb 18 from Tallahassee to Chicago, returning Sat, Feb 21, priced at $319 found 4 days ago
Delta
Tue, Dec 9 - Sat, Dec 13
TLH
Tallahassee
ORD
Chicago
$322 Roundtrip, found 3 days ago
$322
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Dec 9 from Tallahassee to Chicago, returning Sat, Dec 13, priced at $322 found 3 days ago
Delta
Sat, Dec 13 - Tue, Dec 16
TLH
Tallahassee
ORD
Chicago
$348 Roundtrip, found 10 hours ago
$348
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Dec 13 from Tallahassee to Chicago, returning Tue, Dec 16, priced at $348 found 10 hours ago
American Airlines
Thu, Feb 19 - Sat, Feb 21
TLH
Tallahassee
ORD
Chicago
$350 Roundtrip, found 16 hours ago
$350
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Thu, Feb 19 from Tallahassee to Chicago, returning Sat, Feb 21, priced at $350 found 16 hours ago
Delta
Thu, Feb 19 - Sat, Feb 21
TLH
Tallahassee
ORD
Chicago
$352 Roundtrip, found 16 hours ago
$352
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Feb 19 from Tallahassee to Chicago, returning Sat, Feb 21, priced at $352 found 16 hours ago
Delta
Tue, Dec 9 - Sat, Dec 13
TLH
Tallahassee
ORD
Chicago
$353 Roundtrip, found 3 days ago
$353
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Dec 9 from Tallahassee to Chicago, returning Sat, Dec 13, priced at $353 found 3 days ago
American Airlines
Wed, Feb 18 - Sat, Feb 21
TLH
Tallahassee
ORD
Chicago
$355 Roundtrip, found 4 days ago
$355
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Feb 18 from Tallahassee to Chicago, returning Sat, Feb 21, priced at $355 found 4 days ago
American Airlines
Tue, Dec 9 - Sat, Dec 13
TLH
Tallahassee
ORD
Chicago
$357 Roundtrip, found 3 days ago
$357
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Dec 9 from Tallahassee to Chicago, returning Sat, Dec 13, priced at $357 found 3 days ago
Delta
Mon, Dec 1 - Sat, Dec 6
TLH
Tallahassee
ORD
Chicago
$362 Roundtrip, found 2 hours ago
$362
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, Dec 1 from Tallahassee to Chicago, returning Sat, Dec 6, priced at $362 found 2 hours ago
Delta
Sat, Dec 13 - Tue, Jan 6
TLH
Tallahassee
ORD
Chicago
$369 Roundtrip, just found
$369
Roundtrip
just found
Select Delta flight, departing Sat, Dec 13 from Tallahassee to Chicago, returning Tue, Jan 6, priced at $369 just found

Find the cheapest month to fly from Tallahassee (TLH) to Chicago (ORD)

September is typically the cheapest month to fly

From $296 - $696 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $437
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $437

Frequently asked questions

How much does a flight from Tallahassee Intl. Airport (TLH) to O'Hare Intl. Airport (ORD) cost?
Lock in a cheap one-way flight from $159 or cheap return flight from $319 from Tallahassee Intl. Airport (TLH) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Tallahassee Intl. Airport (TLH) to O'Hare Intl. Airport (ORD)?
Planning your getaway for February may help you find better deals, as it's the cheapest month for flights between TLH and ORD. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from Tallahassee Intl. Airport (TLH) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline that'll fly you from TLH to ORD, use Expedia's filter tool. Customize your search based on what matters most to you, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Tallahassee Intl. Airport (TLH) to O'Hare Intl. Airport (ORD)?
You'll need to hop on a flight with a layover when traveling from Tallahassee Intl. Airport (TLH) to O'Hare Intl. Airport (ORD). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from TLH to ORD?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Tallahassee Intl. Airport (TLH) to O'Hare Intl. Airport (ORD)?
Opt for a flight from Tallahassee Intl. Airport (TLH) to O'Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Tallahassee Intl. Airport (TLH) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute bookings from TLH to ORD are generally more expensive. To lock in the cheapest rates, start looking for flights well ahead of time. That being said, if your travel plans are flexible, you may land a cheap ticket right before your journey.
Is it cheaper to book a TLH to ORD flight and hotel package?
You'll generally save money by securing a TLH to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After selecting your ideal flights and accommodations, consider other add-ons like car rentals, tours and activities.
Can I cancel or change the date of my flight from Tallahassee Intl. Airport (TLH) to O'Hare Intl. Airport (ORD)?
Typically, you can modify or cancel your TLH to ORD flight. However, there may be additional charges, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you need more details, go to our Customer Service portal.

Travel information

Origin airport
Tallahassee Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta
Roundtrip price
$316
Distance
824 mi

Book with confidence

Tallahassee to Chicago Flights

The cheapest times to fly from Tallahassee to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Tallahassee to Chicago are during the month of February. You can find some of the cheapest flights from Tallahassee to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Tallahassee to Chicago

Sunday is one of the best days to book for cheap flights from Tallahassee to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Tallahassee to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Tallahassee to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $159 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Tallahassee to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Tallahassee to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Tallahassee to Chicago Flights

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*Available to One Key members.