Cheap Flights from Tallahassee to Chicago

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Compare Tallahassee to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals Cheapest month Find the best route Route info FAQs Tips and advice

Flight deals from Tallahassee to Chicago

Looking for a cheap last-minute deal or the best return flight from Tallahassee Airport to Chicago? If you want to travel next month, return fares start from $783. Find the lowest prices on one-way and return tickets right here.

Chicago.$763 per passenger.Departing Wed, 10 Feb, returning Sat, 13 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Tallahassee on Wed, 10 Feb, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 13 Feb, arriving in Tallahassee.Price includes taxes and charges.From $763, select.

Chicago.$763 per passenger.Departing Thu, 14 Jan, returning Tue, 19 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Tallahassee on Thu, 14 Jan, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 19 Jan, arriving in Tallahassee.Price includes taxes and charges.From $763, select.

Chicago.$765 per passenger.Departing Wed, 18 Nov, returning Mon, 23 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Tallahassee on Wed, 18 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 23 Nov, arriving in Tallahassee.Price includes taxes and charges.From $765, select.

Chicago.$766 per passenger.Departing Wed, 14 Oct, returning Sat, 14 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Tallahassee on Wed, 14 Oct, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 14 Nov, arriving in Tallahassee.Price includes taxes and charges.From $766, select.

Chicago.$781 per passenger.Departing Fri, 4 Dec, returning Mon, 7 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Tallahassee on Fri, 4 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 7 Dec, arriving in Tallahassee.Price includes taxes and charges.From $781, select.

Chicago.$783 per passenger.Departing Mon, 3 May, returning Mon, 10 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Tallahassee on Mon, 3 May, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 10 May, arriving in Tallahassee.Price includes taxes and charges.From $783, select.

Chicago.$783 per passenger.Departing Thu, 15 Oct, returning Mon, 19 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Tallahassee on Thu, 15 Oct, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 19 Oct, arriving in Tallahassee.Price includes taxes and charges.From $783, select.

Chicago.$929 per passenger.Departing Sat, 19 Sep, returning Wed, 23 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Tallahassee on Sat, 19 Sep, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Wed, 23 Sep, arriving in Tallahassee.Price includes taxes and charges.From $929, select.

Chicago.$1,171 per passenger.Departing Tue, 27 Apr, returning Fri, 30 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Tallahassee on Tue, 27 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Fri, 30 Apr, arriving in Tallahassee.Price includes taxes and charges.From $1,171, select.

Find the cheapest month to fly from Tallahassee to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Tallahassee to Chicago flights are currently cheapest in January.

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Alternative Tallahassee to Chicago routes

Looking for the cheapest, fastest or easiest route from Tallahassee to Chicago? You could fly into the following airports instead.

Tallahassee to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$763
Cheapest month to fly	January

Finding cheap flights from Tallahassee to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are return flights from Tallahassee to Chicago?

The best price we found for a return flight from Tallahassee to Chicago is $763. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

Which airlines fly direct from Tallahassee to Chicago?

Currently, there are no airlines that fly direct from Tallahassee to Chicago. But we found flights with one or more stops from $763.

How many flights are there a week from Tallahassee to Chicago?

As of September 2026, there are no flights flying from Tallahassee to Chicago.

When is the cheapest time to fly from Tallahassee to Chicago?

The cheapest month to fly from Tallahassee to Chicago is usually January.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Tallahassee Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from $763.

Which upcoming date is cheapest to fly from Tallahassee Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Tallahassee Airport to Chicago on Thursday, 14 January 2027.

Can I get a direct flight from Tallahassee Airport to Chicago?

No airlines currently offer direct flights between Tallahassee Airport and Chicago. Most routes have one or more stops.

How can I get the best flight deal from Tallahassee Airport to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In September, the average temperature is usually around 20°C. July is typically the warmest month in Chicago, when it usually averages around 27°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -5°C. The rainiest month is June.

Which is the cheapest airline to fly from Tallahassee Airport to Chicago with?

Currently, Delta offers the cheapest flight tickets to Chicago.

Flying from Tallahassee International Airport (TLH) to Chicago: what you need to know

Tallahassee International Airport is located in Tallahassee. Following the UTC-6 timezone, Chicago is one hour behind Tallahassee.
Leave enough time to make your TLH to Chicago flight. As a general rule, turn up at least two hours before international departures and an hour ahead for domestic flights.
During popular months like November, it's a good idea to get to the airport earlier than usual. Plan to arrive two hours before a domestic departure and four hours ahead of an international flight whenever you're travelling during high season in general.
Travelling from central Tallahassee to TLH takes about 30 minutes on public transport. If you ride-share, drive or take a taxi, you'll cover the 8 kilometres in 15 minutes or so, depending on traffic conditions.
Searching for a hotel close to TLH? If you're catching an early flight from Tallahassee International Airport to Chicago, these stays will put you moments from your departure lounge:
Tallahassee International Airport scores top marks for its on-time performance. 81% of flights that depart TLH land on time.
TLH is located at 3300 Capitol Circle Southwest.

How to find the cheapest flights from Tallahassee International Airport (TLH) to Chicago

The best price we've found for a one-way Tallahassee International Airport to Chicago flight is $568. The cheapest price for a return flight is $763. Keep in mind fares may change due to demand at the time of booking.
To pick up cheap flights from TLH to Chicago, book as early as possible. Airlines typically offer lower prices when flights first go on sale.
The 'Whole month' tool will show you the cheapest tickets from Tallahassee International Airport to Chicago throughout the entire month. It's a good way to find a bargain if your trip dates aren't set in stone.
Never miss a deal on cheap flights from TLH to Chicago by setting up a Price Alert. You'll get an email or notification through the app when fares go down.
Snag an affordable flight from Tallahassee International Airport to Chicago with the help of our filters. Choose your ideal departure time, duration and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometres. It takes about 30 minutes to reach the centre driving.
It takes around 45 minutes if you're travelling by public transport.
Look into staying at a hotel close to ORD if you're coming in on a late flight from Tallahassee International Airport to Chicago. Settle into one of these accommodation options and avoid the hassle of a long transfer:
To lock in the lowest price, reserve your vehicle from Chicago O'Hare International Airport around four weeks ahead of your flight from TLH to Chicago.
ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Chicago Midway International Airport (MDW) is around 16 kilometres from central Chicago. Once you've disembarked your flight from Tallahassee International Airport to Chicago, it'll take you around 25 minutes to get to the heart of the city in a ride-share or taxi.
If you travel by public transport, the ride to the centre will take you 30 minutes or so.
Following your TLH to Chicago flight, rest your head at a hotel close to MDW. These are some great options that'll help you slip into relaxation mode:
Get the pick of the lot. Reserving your ride from MDW four weeks in advance often means lower prices and a wider choice of vehicles.
The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Step off your flight from Tallahassee International Airport to Chicago and head straight for your hotel or jump right into sightseeing. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 40 minutes to reach by car.
Public transport will get you there in roughly 2 hours.
Enjoy a quiet, low-key start to your trip by checking in to a hotel near RFD after your TLH to Chicago flight. Rest up after a long day of travel or simply give yourself time to get your bearings in a new city at:
Rental agencies sometimes offer promotions for early bookings, so book your vehicle from RFD in advance of your flight from Tallahassee International Airport to Chicago. A little prep work can make a big difference in cost.
Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

July is the busiest month for flights from Tallahassee International Airport to Chicago. To steer clear of the crowds, plan your trip to Chicago in January.
Book a Tallahassee International Airport to Chicago plane ticket with a departure in July to experience the city during its warmest month. Expect temperatures to range from 16ºC to 28ºC.
If you want to travel in cooler conditions, search for a cheap ticket from TLH to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

When it comes to searching for somewhere to lay your head, you'll find the best stays in Chicago right here. Browse these hotels after locking in your flight from Tallahassee International Airport to Chicago:
There are so many things to discover in this city it can be difficult to know where to begin. Art Institute of Chicago, Millennium Park and Willis Tower are major attractions which should be on any good Chicago itinerary.

Explore more of the United States

You've done Chicago, now it's time to discover other corners of the United States. Journey around 451 kilometres southeast to Columbus to tick off its top sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, you'll have a packed itinerary ahead.
If you want to check out another corner of the United States, consider Indianapolis, about 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are among its highlights.