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Cheap flights from Tallahassee to Chicago

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Compare Tallahassee to Chicago flight deals

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Flight deals from Tallahassee to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Tallahassee to Chicago? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.C$500 per passenger.Departing Sat, May 24, returning Fri, May 30.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Tallahassee on Sat, May 24, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Fri, May 30, arriving in Tallahassee.Price includes taxes and charges.From C$500, select.
Chicago.C$500 per passenger.Departing Tue, Jul 8, returning Sat, Jul 12.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Tallahassee on Tue, Jul 8, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Sat, Jul 12, arriving in Tallahassee.Price includes taxes and charges.From C$500, select.
Chicago.C$500 per passenger.Departing Wed, May 28, returning Wed, Jun 4.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Tallahassee on Wed, May 28, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departing from Chicago O'Hare International on Wed, Jun 4, arriving in Tallahassee.Price includes taxes and charges.From C$500, select.
Chicago.C$566 per passenger.Departing Sun, Jun 15, returning Sat, Jun 21.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Tallahassee on Sun, Jun 15, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Sat, Jun 21, arriving in Tallahassee.Price includes taxes and charges.From C$566, select.
Chicago.C$566 per passenger.Departing Sat, Jun 28, returning Sun, Jul 6.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Tallahassee on Sat, Jun 28, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Sun, Jul 6, arriving in Tallahassee.Price includes taxes and charges.From C$566, select.
Chicago.C$615 per passenger.Departing Wed, Nov 19, returning Sun, Nov 23.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Tallahassee on Wed, Nov 19, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departing from Chicago O'Hare International on Sun, Nov 23, arriving in Tallahassee.Price includes taxes and charges.From C$615, select.
Chicago.C$629 per passenger.Departing Fri, Aug 15, returning Sun, Aug 17.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Tallahassee on Fri, Aug 15, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departing from Chicago O'Hare International on Sun, Aug 17, arriving in Tallahassee.Price includes taxes and charges.From C$629, select.
Chicago.C$677 per passenger.Departing Mon, Dec 15, returning Tue, Dec 23.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Tallahassee on Mon, Dec 15, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago O'Hare International on Tue, Dec 23, arriving in Tallahassee.Price includes taxes and charges.From C$677, 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 May.
May
from C$500
Jun
from C$566
Jul
from C$500
Aug
from C$629
Sep
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Oct
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Nov
from C$615
Dec
from C$677
Jan
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Feb
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Mar
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Apr
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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 foundC$500
Cheapest month to flyMay

Finding cheap flights from Tallahassee to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Tallahassee to Chicago is C$500. 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.
Currently, there are no airlines that fly direct from Tallahassee to Chicago. But we found flights with one or more stops from C$500.
There are no flights flying from Tallahassee to Chicago, as of May 2025.
The cheapest month to fly from Tallahassee to Chicago is usually May.
If you're flying from Tallahassee Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the center of Chicago. We've found flights to this airport from C$500.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Tallahassee Airport to Chicago on Saturday, May 24, 2025.
No airlines currently offer direct flights between Tallahassee Airport and Chicago. Most routes have one or more stops.
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.
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.
In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Delta offers the cheapest flight tickets to Chicago.

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

  • Chicago is one hour behind Tallahassee, where Tallahassee International Airport is located. Chicago runs on the UTC-5 timezone.

  • For hassle-free travel, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to catch your TLH to Chicago flight.

  • Planning to travel during a peak period like school or public holidays? Expect longer queues at check-in and security. For peace of mind, arrive up to four hours before international flights and two hours ahead of domestic departures.

  • Central Tallahassee to TLH is around 8 kilometres. Depending on traffic conditions, it'll take you about 15 minutes to reach there if you're ride-sharing, catching a cab or driving.

  • Want a hassle-free start to your vacation? Stay near TLH. Whether you're boarding an early flight from Tallahassee International Airport to Chicago or want to avoid feeling rushed, these hotels are worth a look:

  • When it comes to the on-time performance of Tallahassee International Airport, data shows 75.17% of flights stick to their scheduled arrival time.

  • TLH's address is 3300 Capitol Circle Southwest.

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

  • C$249 is the lowest price we've seen for a one-way Tallahassee International Airport to Chicago flight. A return ticket right now is C$500. Depending on how early you book and the availability, these fares can change.

  • To find cheap flights from TLH to Chicago, book early. Airlines usually offer the most competitive fares when tickets first go on sale.

  • Finding cheap tickets from Tallahassee International Airport to Chicago is more likely if you're flexible with your travel plans. Use the 'Whole month' search tool to get the lowest prices across every month and bag an incredible deal.

  • You don't need to keep checking in to see if fares have dropped when you set up a Price Alert. We'll update you when there's an even better deal on cheap flights from TLH to Chicago.

  • Tailor your trip with filters. Pick your ideal arrival and departure times, airlines and total journey duration. You can also sort your results by 'Fastest,' 'Best' or 'Cheapest' flights from Tallahassee International Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It takes around 35 minutes to get to the centre driving.

  • It'll take around 55 minutes if you're using public transport.

  • If you have a late flight from Tallahassee International Airport to Chicago, nothing beats the convenience of staying close to the terminal. Pick up your bags from the carousel and then be showered and sleeping soon after at one of these hotels near ORD:

  • Grab an O'Hare International Airport rental car and explore Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are popular outlets you can book with here.

  • For the lowest price, book your ride from O'Hare International Airport around four weeks ahead of your flight from TLH to Chicago.

  • The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from Tallahassee International Airport to Chicago has landed, you can reach the city centre in about 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • If you travel by public transport, the journey will take you 45 minutes or so.

  • Place the 'Do not disturb' sign on your door and relax at a hotel close to MDW. Here are a few options where you can check in after your TLH to Chicago flight:

  • Dollar, Hertz and Budget make collecting a Chicago Midway International Airport rental car easy and quick. These reliable suppliers are located in or around the terminal and will have you behind the wheel before you know it.

  • Avoid last-minute price surges. Securing your ride four weeks before your arrival at MDW will help you save.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Find your way to the city centre after your flight from Tallahassee International Airport to Chicago has touched down. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach by cab or ride-share.

  • The journey will take about 4 hours 15 minutes if you use public transport.

  • Enjoy a more relaxed start to your trip by checking in to a hotel near RFD after your TLH to Chicago flight. Take a load off after a long travel day or just take a moment to find your footing in a new place at:

  • Be in control of the next chapter of your journey with a Chicago Rockford International Airport rental car. Budget, Alamo and National make getting on the road smooth sailing.

  • If you're hoping for a certain type of vehicle, booking early gives you a better shot at getting exactly what you want. Secure your ride from RFD at least a few weeks ahead of your flight from Tallahassee International Airport to Chicago.

  • Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your trip dates before securing your flight from Tallahassee International Airport to Chicago. The city comes alive during high season, but rates are usually higher and attractions can get crowded. Visit Chicago in the low season if you prefer a more relaxed vibe.

  • When booking your Tallahassee International Airport to Chicago flight ticket, think about the kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • Search for cheap tickets from TLH to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of United States

  • Chicago has plenty going for it, but there are so many other corners of United States you'll want to see. About 451 kilometres south-east of Chicago, a trip to Columbus will fill your itinerary to the brim. Start with popular sights like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another sought-after destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Tallahassee to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.