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Cheap Flights from Chicago to Toledo

Compare Chicago to Toledo flight deals

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

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Flight deals from Chicago to Toledo

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Toledo? Find the lowest prices on one-way and round-trip tickets right here.
Madrid.$589 per passenger.Departing Wed, Mar 10, returning Tue, Mar 16.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Wed, Mar 10, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Tue, Mar 16, arriving in Chicago O'Hare International.Price includes taxes and charges.From $589, select.
Madrid.$590 per passenger.Departing Sun, Nov 1, returning Thu, Nov 12.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Sun, Nov 1, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Thu, Nov 12, arriving in Chicago O'Hare International.Price includes taxes and charges.From $590, select.
Madrid.$590 per passenger.Departing Wed, Dec 9, returning Tue, Mar 9.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Wed, Dec 9, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Tue, Mar 9, arriving in Chicago O'Hare International.Price includes taxes and charges.From $590, select.
Madrid.$591 per passenger.Departing Sun, Mar 7, returning Fri, Apr 9.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Sun, Mar 7, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Fri, Apr 9, arriving in Chicago O'Hare International.Price includes taxes and charges.From $591, select.
Madrid.$593 per passenger.Departing Wed, Feb 17, returning Wed, Mar 3.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Wed, Feb 17, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Wed, Mar 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From $593, select.
Madrid.$604 per passenger.Departing Wed, Oct 21, returning Wed, Oct 28.Round-trip flight with Allegiant Air and Ryanair.Outbound indirect flight with Allegiant Air, departing from Chicago Rockford on Wed, Oct 21, arriving in Madrid.Inbound indirect flight with Ryanair, departing from Madrid on Wed, Oct 28, arriving in Chicago Rockford.Price includes taxes and charges.From $604, select.
Madrid.$609 per passenger.Departing Fri, Dec 11, returning Wed, Feb 3.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Fri, Dec 11, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Wed, Feb 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From $609, select.
Madrid.$609 per passenger.Departing Sun, Jan 3, returning Sun, Jan 10.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Sun, Jan 3, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Sun, Jan 10, arriving in Chicago O'Hare International.Price includes taxes and charges.From $609, select.
Madrid.$611 per passenger.Departing Fri, Oct 23, returning Wed, Nov 4.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Fri, Oct 23, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Wed, Nov 4, arriving in Chicago O'Hare International.Price includes taxes and charges.From $611, select.
Madrid.$611 per passenger.Departing Sun, Dec 13, returning Sun, Jan 10.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Sun, Dec 13, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Sun, Jan 10, arriving in Chicago O'Hare International.Price includes taxes and charges.From $611, select.
Madrid.$614 per passenger.Departing Tue, Oct 13, returning Wed, Dec 2.Round-trip flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departing from Chicago O'Hare International on Tue, Oct 13, arriving in Madrid.Inbound indirect flight with Scandinavian Airlines, departing from Madrid on Wed, Dec 2, arriving in Chicago O'Hare International.Price includes taxes and charges.From $614, select.
Madrid.$614 per passenger.Departing Fri, Apr 9, returning Wed, Apr 28.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Fri, Apr 9, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Wed, Apr 28, arriving in Chicago O'Hare International.Price includes taxes and charges.From $614, select.
Madrid.$615 per passenger.Departing Sun, Aug 16, returning Tue, Aug 25.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Sun, Aug 16, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Tue, Aug 25, arriving in Chicago O'Hare International.Price includes taxes and charges.From $615, select.
Madrid.$615 per passenger.Departing Fri, Aug 14, returning Fri, Sep 18.Round-trip flight with Allegiant Air and Ryanair.Outbound indirect flight with Allegiant Air, departing from Chicago Rockford on Fri, Aug 14, arriving in Madrid.Inbound indirect flight with Ryanair, departing from Madrid on Fri, Sep 18, arriving in Chicago O'Hare International.Price includes taxes and charges.From $615, select.
Madrid.$619 per passenger.Departing Wed, Apr 21, returning Thu, May 6.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Wed, Apr 21, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Thu, May 6, arriving in Chicago O'Hare International.Price includes taxes and charges.From $619, select.
Madrid.$621 per passenger.Departing Wed, Feb 10, returning Wed, Feb 17.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Wed, Feb 10, arriving in Madrid.Inbound indirect flight with TAP Air Portugal, departing from Madrid on Wed, Feb 17, arriving in Chicago O'Hare International.Price includes taxes and charges.From $621, select.
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Chicago to Toledo: Flight information

The things to know before you go.
Fly intoMadrid Airport
Distance to Toledo79.4 km
Cheapest flight$589
Cheapest month to flyMarch
Most popular airlineAmerican Airlines
Average flight time8 hrs, 13 mins

Find the cheapest month to fly from Chicago to Toledo

We’re always keeping an eye on fares, so you can find the best flight deal in seconds. It looks like Chicago to Toledo flights are currently cheapest in August. We’ve based this on flights into Madrid Airport.
Jun
from $535
Jul
from $275
Aug
from $262
Sep
from $284
Oct
from $275
Nov
from $313
Dec
from $313
Jan
from $323
Feb
from $323
Mar
from $323
Apr
from $324
May
from $304

Finding cheap flights from Chicago to Toledo: Frequently asked questions

The best price we found for a round-trip flight from Chicago to Toledo is $589. 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.
American Airlines, Finnair, and Iberia all offer direct flights to Madrid Airport.
We've checked every Chicago to Toledo fare we could find, and the cheapest upcoming date to fly seems to be on Wednesday, March 10, 2027. Overall, the cheapest month to fly from Chicago to Toledo is usually March.
If you're flying from Chicago, the cheapest airport near Toledo is Madrid – which is 79.4 km away from the center of Toledo. We've found flights to this airport from $589.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Toledo on Wednesday, March 10, 2027.
No airlines currently offer direct flights between Chicago and Toledo. 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 Toledo 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 Toledo is around 40 days in advance, so don’t leave your flight to the last minute.

Madrid Airport is the best option, and is around 79.4km from Toledo.
Madrid Airport is closest to Toledo, at around 79.4 km away.