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Find cheap flights from Chicago to Toledo from $259

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Toledo departing on 9/16. 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 6/15
Sat 6/22

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Good to know

Low season

January

High season

March

Cheapest flight

$259
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 Midway 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 15m.

  • 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 Fridays 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 Tuesdays.

  • 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 TAP AIR PORTUGAL for $423. Delta offered a round-trip connection from $476 and Air France from $550.

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 1376 reviews
7.8Boarding
8.2Crew
7.0Entertainment
6.9Food
7.5Comfort
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.

Seats comfortable on economy plus and attendants very helpful. Food was ok. Bathrooms needed servicing.

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.

Delayed takeoff was inconvenient. We should have boardrd later. Coffee/ beverage service on a 7:30 flight would have been good.

Flight from Lisbon to Barcelona was ok. Business flight Boston to Lisbon was awful. Attendants should pay more attention to Business Passengers and not be so stingy with water. Worse Business Flight I have ever taken. Food was awful. Cramped for space.

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.

- OK plane. Basic accommodations. OK food. The digital window shade wasn't working.

- OK plane. Basic accommodations. OK food. The digital window shade wasn't working. - Expect to be woken up more than an hour before landing when they start dinging the bell and making announcements and turning on all cabin lights to serve a snack. I would prefer they remain quiet and only serve people who want to wake up.

Better food and more space in the seats. Also when doing the web check in both times I was going in to your site the minute you open it and there is not really many seats to choose only to buy!!!

It was ok, not as good as it used to be. The Heathrow connection was a disaster - complete anarchy, unknowledgable and skimpy assistance and signage. Gate crew at next flight was great, held the flight while my wife struggled through security.

It was great! The seats were comfortable, and they fed me during the transatlantic flight, something which I have been missing out on for the past 3 years as I travel to and from school.

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

Book cheap flights from Chicago to Toledo

Recent round-trip flight deals

11/10Sun
1 stopDelta
15h 34mMDW-MAD
11/21Thu
2 stopsDelta
19h 05mMAD-MDW
$476
11/10Sun
2 stopsDelta
19h 00mMDW-MAD
11/21Thu
2 stopsDelta
19h 05mMAD-MDW
$480
8/7Wed
nonstopFinnair
8h 15mORD-MAD
9/22Sun
nonstopFinnair
9h 45mMAD-ORD
$714
8/14Wed
nonstopFinnair
8h 15mORD-MAD
10/11Fri
1 stopFinnair
14h 00mMAD-ORD
$717
5/21Tue
1 stopAmerican Airlines
10h 55mORD-MAD
11/13Wed
nonstopAmerican Airlines
9h 55mMAD-ORD
$722
8/10Sat
1 stopTAP AIR PORTUGAL
11h 40mORD-MAD
10/13Sun
1 stopTAP AIR PORTUGAL
25h 00mMAD-ORD
$729
8/10Sat
1 stopIberia
13h 52mORD-MAD
9/28Sat
nonstopIberia
9h 45mMAD-ORD
$744
8/9Fri
1 stopIberia
13h 52mORD-MAD
9/22Sun
nonstopIberia
9h 45mMAD-ORD
$769
8/10Sat
1 stopTAP AIR PORTUGAL
11h 40mORD-MAD
8/20Tue
1 stopTAP AIR PORTUGAL
24h 55mMAD-ORD
$772
5/21Tue
1 stopAmerican Airlines
10h 55mORD-MAD
11/9Sat
nonstopAmerican Airlines
9h 55mMAD-ORD
$773

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Recent one-way flight deals

9/16Mon
2 stops
34h 17mMDW-MAD
$259
9/9Mon
2 stops
54h 27mMDW-MAD
$261
9/23Mon
2 stops
34h 17mMDW-MAD
$263
8/4Sun
1 stopTAP AIR PORTUGAL
11h 40mORD-MAD
$423
7/31Wed
1 stopTAP AIR PORTUGAL
11h 40mORD-MAD
$424
7/6Sat
nonstopIberia
8h 15mORD-MAD
$645
7/4Thu
nonstopIberia
8h 15mORD-MAD
$656
7/28Sun
nonstopFinnair
8h 15mORD-MAD
$719
8/6Tue
nonstopBritish Airways
8h 15mORD-MAD
$738
7/24Wed
nonstopFinnair
8h 15mORD-MAD
$868

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Last minute flights from Chicago to Toledo

Last minute flight, train and bus deals

5/21Tue
multi-stopAmerican Airlines
10h 55mORD-MAD
11/13Wed
nonstopAmerican Airlines
9h 55mMAD-ORD
$722
5/20Mon
nonstopBritish Airways
8h 15mORD-MAD
11/12Tue
nonstopBritish Airways
9h 55mMAD-ORD
$724
5/19Sun
multi-stopAir Canada
12h 15mORD-MAD
11/12Tue
multi-stopAir Canada
20h 32mMAD-ORD
$730
5/18Sat
multi-stopUnited Airlines
16h 17mORD-MAD
11/15Fri
multi-stopUnited Airlines
20h 55mMAD-ORD
$787
5/20Mon
multi-stopFinnair
20h 45mORD-MAD
11/10Sun
nonstopFinnair
9h 55mMAD-ORD
$788
5/18Sat
nonstopIberia
8h 15mORD-MAD
11/14Thu
nonstopIberia
9h 55mMAD-ORD
$824
5/18Sat
multi-stopUnited Airlines
16h 17mORD-MAD
11/10Sun
multi-stopUnited Airlines
13h 55mMAD-ORD
$838
5/18Sat
nonstopIberia
8h 15mORD-MAD
11/11Mon
nonstopIberia
9h 55mMAD-ORD
$874
5/19Sun
multi-stopFinnair
15h 35mORD-MAD
11/11Mon
nonstopFinnair
9h 55mMAD-ORD
$889
5/20Mon
multi-stopTAP AIR PORTUGAL
11h 40mORD-MAD
5/24Fri
multi-stopTAP AIR PORTUGAL
11h 55mMAD-ORD
$1,191

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