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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 return flight from Chicago to Toledo? Find the lowest prices on one-way and return tickets right here.
Madrid.Rs71,247 per passenger.Departing Sun, 26 Apr.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Sun, 26 Apr, arriving in Madrid.Price includes taxes and charges.From Rs71,247, select.
Madrid.Rs78,761 per passenger.Departing Mon, 4 May.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Mon, 4 May, arriving in Madrid.Price includes taxes and charges.From Rs78,761, select.
Madrid.Rs85,884 per passenger.Departing Sun, 16 Aug.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Sun, 16 Aug, arriving in Madrid.Price includes taxes and charges.From Rs85,884, select.
Madrid.Rs86,863 per passenger.Departing Sun, 15 Mar.One-way flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Sun, 15 Mar, arriving in Madrid.Price includes taxes and charges.From Rs86,863, select.
Madrid.Rs87,625 per passenger.Departing Sun, 20 Sep.One-way flight with Aer Lingus.Outbound indirect flight with Aer Lingus, departs from Chicago O'Hare International on Sun, 20 Sep, arriving in Madrid.Price includes taxes and charges.From Rs87,625, select.
Madrid.Rs90,210 per passenger.Departing Sun, 17 Jan.One-way flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Sun, 17 Jan, arriving in Madrid.Price includes taxes and charges.From Rs90,210, select.
Madrid.Rs90,578 per passenger.Departing Sun, 26 Jul.One-way flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Sun, 26 Jul, arriving in Madrid.Price includes taxes and charges.From Rs90,578, select.
Madrid.Rs90,793 per passenger.Departing Wed, 28 Oct.One-way flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Wed, 28 Oct, arriving in Madrid.Price includes taxes and charges.From Rs90,793, select.
Madrid.Rs91,081 per passenger.Departing Wed, 2 Dec.One-way flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Wed, 2 Dec, arriving in Madrid.Price includes taxes and charges.From Rs91,081, select.
Madrid.Rs91,609 per passenger.Departing Wed, 25 Nov.One-way flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Wed, 25 Nov, arriving in Madrid.Price includes taxes and charges.From Rs91,609, select.
Madrid.Rs95,359 per passenger.Departing Sun, 7 Jun.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Sun, 7 Jun, arriving in Madrid.Price includes taxes and charges.From Rs95,359, select.
Madrid.Rs123,058 per passenger.Departing Sun, 20 Sep.One-way flight with Iberia.Outbound direct flight with Iberia departs from Chicago O'Hare International on Sun, 20 Sep, arriving in Madrid.Price includes taxes and charges.From Rs123,058, select.
Madrid.Rs123,199 per passenger.Departing Tue, 27 Oct.One-way flight with Iberia.Outbound direct flight with Iberia departs from Chicago O'Hare International on Tue, 27 Oct, arriving in Madrid.Price includes taxes and charges.From Rs123,199, select.
Madrid.Rs124,479 per passenger.Departing Mon, 16 Nov.One-way flight with Finnair.Outbound direct flight with Finnair departs from Chicago O'Hare International on Mon, 16 Nov, arriving in Madrid.Price includes taxes and charges.From Rs124,479, select.
Madrid.Rs125,100 per passenger.Departing Wed, 20 Jan.One-way flight with Finnair.Outbound direct flight with Finnair departs from Chicago O'Hare International on Wed, 20 Jan, arriving in Madrid.Price includes taxes and charges.From Rs125,100, select.
Madrid.Rs125,100 per passenger.Departing Sun, 26 Apr.One-way flight with Finnair.Outbound direct flight with Finnair departs from Chicago O'Hare International on Sun, 26 Apr, arriving in Madrid.Price includes taxes and charges.From Rs125,100, select.

Chicago to Toledo: Flight information

The things to know before you go.
Fly intoMadrid Airport
Distance to Toledo79.5 km
Cheapest flightRs71,247
Cheapest month to flyApril
Most popular airlineIberia
Average flight time8 hrs, 9 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 April. We’ve based this on flights into Madrid Airport.
Mar
from Rs86,863
Apr
from Rs71,247
May
from Rs78,761
Jun
from Rs95,359
Jul
from Rs90,578
Aug
from Rs85,884
Sep
from Rs87,625
Oct
from Rs90,793
Nov
from Rs91,609
Dec
from Rs91,081
Jan
from Rs90,210
Feb
Find prices

Finding cheap flights from Chicago to Toledo: Frequently asked questions

The best price we found for a return flight from Chicago to Toledo is Rs127,161. 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.
Iberia, Finnair, American Airlines 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, 4 November 2026. Overall, the cheapest month to fly from Chicago to Toledo is usually November.
If you're flying from Chicago, the cheapest airport near Toledo is Madrid – which is 79.5 km away from the centre of Toledo. We've found flights into this airport from Rs127,161.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Toledo on Wednesday, 4 November 2026.
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 79.5km from Toledo.
Madrid Airport is closest to Toledo, at around 79.5 km away.