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Find cheap flights from Chicago to Toledo from $334

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Toledo departing on 10/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/8
Sat 6/15

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Good to know

Low season

January

High season

March

Cheapest flight

$334
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago O'Hare Airport to Madrid

When to book flights from Chicago to Toledo

Are your dates flexible? Find out the best times to travel from Chicago to Toledo based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Toledo

  • Which airports will I be using when flying from Chicago to Toledo?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Toledo does not have its own airport so you’ll be flying into nearby Madrid Barajas airport, which is 49.4 mi away.

  • How long does a flight from Chicago to Toledo take?

    Direct flights cover the 4,179 miles separating Chicago and Toledo in about 8h 10m.

  • How many flights are there between Chicago and Toledo?

    6 direct flights run between Chicago and Toledo on a daily basis. On average, there are about 42 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Toledo?

    Consider leaving on a Sunday and avoid Tuesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Mondays.

  • How does KAYAK find such low prices on flights from Chicago to Toledo?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Toledo.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Toledo?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Toledo from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Toledo?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Toledo with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Toledo?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Toledo from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Toledo?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Toledo found on KAYAK was with Icelandair for $427. TAP AIR PORTUGAL offered a round-trip connection from $334 and Iberia from $425.

See more FAQs

Top tips for finding cheap flights from Chicago to Toledo

  • There is no airport in Toledo. Instead, you’ll be flying into Madrid Barajas Airport when flying between Chicago and Toledo.
  • The cheapest flight from Chicago to Toledo was found 11 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is February.
See more tips

Top 5 airlines serving Chicago to Toledo

 
Need help choosing which airline to fly with from Chicago to Toledo? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.7
FinnairOverall score based on 1378 reviews
7.8Boarding
7.0Entertainment
6.9Food
7.6Comfort
8.2Crew
Airline reviews

All good- I love BA and the professionalism of the crew and pilots.

8.0 ExcellentAnonymous, Apr 2024JFK - LHR
Read more about Finnair reviews

All good- I love BA and the professionalism of the crew and pilots.

Great flight- smooth, nice crew, nice clean aircraft, departed a little late but arrived 10 early.

It was listed on my ticket as Finnair but there was no indication that the flight was Finnair. In fact the number was even different. There were no employees there until exactly 2 hours before so we had to wait in line at Iberia and hope

Sorting on line would have been appreciated Onward information on flights missed No ability to get seating arranged before we got to gate Very unfriendly at gate

The flight was Finnair but there was no indications anywhere that the checkin was for Finnair also. There was no one to ask. I think at a minimum they should list the code shares so people don’t stand in the wrong line for an hour.

I booked the flight with Finnair, which made the arrangements for downloading a boarding pass unnecessarily complicated. I wouldn't do that again. Instead I'd book direct with AA.

Had a nice flight to London on BA will fly with them again in the future

Finnair cancelled my flight 12 hours prior to leaving for Helsinki. They stated there were mechanical problems. I had to scurry around to find a new flight that would meet my needs for arrival in Helsinki. Luckily I was able to find alternate transportation through Lufthansa/United.

I’m very disappointed, to fly into an airplane for 10 straight hours, and not having a TV even though when I put the ticket I was told that I will have entertainment for the TV. Very disappointed.

Helpful steward. Allowed me to move to some empty seats and I was able to get some sleep. He also had milk for my tea. Americans don’t realise that cream or half and half ruin tea.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Good food, prompt and timely flight, good on-board personnel

Thankful for 2-4-2 economy seating. Food was ok. Free beer & wine in economy was nice. Served hot dinner, mud- flight snack and pre-arrival ham sandwich. Seat with pillow & blanket. Reasonable movie options. Overall, a good experience. IBERIA APP is terrible terrible terrible.... needs to get upgraded to equivalent of TAP Airlines App. No option to bid or request an upgrade. Very disappointing.

My luggage did not get to my Miami destination/home. I am waiting for it 24 hours later.

The only comment I have is why do you sell snacks on board? They should be free. When we take domestic flights here in US, our snacks are free. Also, please communicate with me in English. I received so many emails way before my flight that were in Spanish that I had to ask my son to interpret for me. You should be WELL AWARE if the customers you are communicating speak the language, it does mean that we speak and understand Spanish because we are traveling to Spain, NOT NECESSARILY! Thank you!

Flight was delayed by well over an hour. Communication was terrible.

I like the team but I don't like the food you provided with money. I want free food and free water.

An average flight experience. For our transatlantic portion, they provided a main meal and two snacks. However, the food was not very tasty and the drinks far too small and infrequent for such a long flight. The regrettable part of the flight was that the toilets were extremely filthy. I feel this is unacceptable.

Both flights were delayed. I lost my connection on the way back. No voucher or anything was givenx I had business ticket and no support to make it on time. I got to the door running 5 min after they close. Food really bad. Breakfast in business was worst that I what I remember in economy. Even though I have accumulated many miles, I don’t think Inwill keep buying Iberia. I am a frequent business traveler.

The food is really eco only level. Breakfast was shameful. I am considering to stop flying with Iberia. Business prices are as expensive as other companies with much better service.

Why no entertainment? Also water should be free, it is basic human right.

I thought Miami's airport was very disorganized during the Boarding.

Very efficient boarding - other airlines could learn from them. Friendly, efficient crew. Red eye flight, so dinner meal was irrelevant. Breakfast could have been more substantial. Seats reasonably comfy.

Disastrous boarding. Entered air bridge only to descend stairs and enter a bus. Plane had insufficient storage, was old and chair recline was damaged. Air stewardess was sullen.

Perfect although it took an hour to board the plane but other than that it was great

The flight crew was good, the flight itself was quick and comfortable

Boarding was late by 30 min due to a bus missing to take us to the plane... And then the flight was delayed by about 90 minutes, in a 60 min flight

The quality of the aircraft and the professionalism of TAP's staff were perfect. The quality of vegan meals can be hit or miss depending on the airline and the city of departure; on this flight, our vegan meals were quite good. The boarding process for the connecting flight in Lisbon could have been organized a bit better, but it did not spoil our overall experience with TAP, which was excellent. I'd definitely recommend TAP to others.

We liked the crew. They were competent, professional and friendly. The only big negative was our departure was delayed several times and the airport staff did not communicate what the problems were and what we should expect.

O comissário não nos serviu bebida no jantar. Quando voltou somente serviu água.

Airline attendant never walks along the isle to check if everyone is ok. The food is worst I’ve experienced. Chicken pasta is very salty while the fish is bland and over-cooked. Only two toilets for the entire economy section.

This flight was cancelled at the last minute. We were rebooked on another flight but a day later. We lost a day of our vacation and paid for a night in a hotel we couldn’t use. The flights we were rebooked on (both American) messed up our seating on both flights-we didn’t get the seats we had paid for. All in all, a terrible experience.

Lost our luggage in Heathrow. Showed up 3 days into a 7 day vacation. Very inconvenient and disappointing!!

Lost our bags in Heathrow, We didn’t receive bags in Mallorca for 3 days, out of a 7 day cycling vacation. Really inconvenient and disappointing!

Our luggage is missing. We are at the Hotel Gran Via in Barcelona

We missed the flight to Barcelona because the flight from Baltimore was delayed. We flew on Vueling VW6653. Our luggage didn’t arrive. Please help us get our luggage. We are staying at Hotel Gran Via in Barcelona

The seats were tiny, being of a fairly petite build, I don’t usually expect to feel crammed and cramped in a seat, but I definitely was on this flight. I couldn’t even bend over to get anything out from under the seat in front and getting up to go to the bathroom at night with the seat backs reclined was nearly impossible. I had to do gymnastics to get over and out. For an airline that does long flights overnight, it’s kind of ridiculous.

Not connecting flights. Missed my flight from Dublin to Liverpool because I arrived at Dublin one hour too late. For this mistake, they offered me a flight from Dublin to Manchester. Thats great and all, but I waste time and money to commute to Liverpool. Be sure to check the time of your connecting flights, because they sure don’t when they sell it to you

Excellent! Great flight attendants, good food (in business class, at least), very comfortable. Touchscreen and remote wasn’t great.

In economy and food was ok, but with limited leg space (and I was in a 2 seat configuration) it was difficult to eat with a tiny seat tray. I spilt wine on my trousers. First time on British Air (I usually fly Turkish Air) and in a 777. Heathrow was pleasant but changing terminals awkward.

We paid to have overhead carry-on baggage. When we got to the gate we were told that our carry on bags would need to be checked and go below because the flight was full. Notably we were nowhere near the last people to board and about 30 other passengers also had to check their carry-on bags. Other than that the flight was fine.

Book cheap flights from Chicago to Toledo

Recent round-trip flight deals

10/6Sun
1 stopTAP AIR PORTUGAL
11h 40mORD-MAD
10/21Mon
1 stopTAP AIR PORTUGAL
16h 40mMAD-ORD
$334
10/6Sun
1 stopTAP AIR PORTUGAL
20h 25mORD-MAD
10/21Mon
1 stopTAP AIR PORTUGAL
12h 10mMAD-ORD
$350
10/30Wed
1 stopIberia
13h 35mORD-MAD
11/13Wed
nonstopIberia
9h 55mMAD-ORD
$425
10/30Wed
1 stopIberia
13h 35mORD-MAD
11/13Wed
nonstopIberia
9h 55mMAD-ORD
$432
11/4Mon
nonstopFinnair
8h 10mORD-MAD
11/13Wed
nonstopFinnair
9h 55mMAD-ORD
$440
11/4Mon
1 stopAmerican Airlines
15h 20mORD-MAD
11/14Thu
1 stopAmerican Airlines
13h 40mMAD-ORD
$449
11/4Mon
1 stopBritish Airways
11h 45mORD-MAD
11/12Tue
1 stopBritish Airways
13h 00mMAD-ORD
$451
11/4Mon
nonstopAmerican Airlines
8h 10mORD-MAD
12/2Mon
1 stopAmerican Airlines
24h 30mMAD-ORD
$453
11/3Sun
2 stopsBritish Airways
15h 42mORD-MAD
11/13Wed
1 stopBritish Airways
15h 15mMAD-ORD
$455
11/2Sat
nonstopFinnair
8h 10mORD-MAD
11/12Tue
nonstopFinnair
9h 55mMAD-ORD
$490

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Recent one-way flight deals

7/9Tue
2 stops
34h 17mMDW-MAD
$415
6/27Thu
2 stops
27h 28mORD-MAD
$415
6/19Wed
3 stops
54h 10mORD-MAD
$417
7/21Sun
1 stopTAP AIR PORTUGAL
20h 25mORD-MAD
$431
7/21Sun
1 stopTAP AIR PORTUGAL
20h 25mORD-MAD
$433
6/7Fri
1 stopBritish Airways
31h 25mORD-MAD
$680
6/5Wed
nonstopIberia
8h 15mORD-MAD
$686
6/5Wed
nonstopIberia
8h 15mORD-MAD
$695
6/12Wed
2 stopsDelta
16h 11mMDW-MAD
$1,167
6/8Sat
2 stopsDelta
16h 17mMDW-MAD
$1,217

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Last minute flights from Chicago to Toledo

Last minute flight, train and bus deals

5/13Mon
multi-stopITA Airways
19h 10mORD-MAD
5/20Mon
multi-stopITA Airways
32h 35mMAD-ORD
$699
5/10Fri
multi-stopITA Airways
12h 45mORD-MAD
5/16Thu
multi-stopITA Airways
26h 05mMAD-ORD
$755
5/10Fri
nonstopIberia
8h 15mORD-MAD
5/23Thu
nonstopIberia
9h 45mMAD-ORD
$801
5/10Fri
multi-stopIberia
11h 38mORD-MAD
5/23Thu
nonstopIberia
9h 45mMAD-ORD
$802
5/10Fri
nonstopFinnair
8h 15mORD-MAD
5/23Thu
nonstopFinnair
9h 45mMAD-ORD
$819
5/12Sun
nonstopAmerican Airlines
8h 15mORD-MAD
5/18Sat
multi-stopAmerican Airlines
20h 55mMAD-ORD
$837
5/11Sat
nonstopAmerican Airlines
8h 15mORD-MAD
5/19Sun
nonstopAmerican Airlines
9h 45mMAD-ORD
$874
5/10Fri
nonstopFinnair
8h 15mORD-MAD
5/23Thu
nonstopFinnair
9h 45mMAD-ORD
$1,001
5/13Mon
multi-stopTAP AIR PORTUGAL
27h 40mORD-MAD
5/17Fri
multi-stopTAP AIR PORTUGAL
16h 25mMAD-ORD
$1,314
5/13Mon
multi-stopTAP AIR PORTUGAL
27h 40mORD-MAD
5/17Fri
multi-stopTAP AIR PORTUGAL
29h 51mMAD-ORD
$1,441

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