$181 Find Cheap Flights from Chicago to Toledo

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 11/12. 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.
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1 adult, Economy

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Flight Deals

Cheap Flights from Chicago to Toledo (CHI-MAD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Toledo that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Toledo

Wed, Mar 4 - Tue, Mar 17
TAP AIR PORTUGAL Logo
7:10 pm - 2:05 pmORD-MAD
11h 55m1 stop
TAP AIR PORTUGAL Logo
9:10 pm - 4:00 pmMAD-ORD
24h 50m1 stop
$456TAP AIR PORTUGAL
Find Deal
Wed, Nov 26 - Wed, Dec 10
Delta Logo
4:26 pm - 3:20 pmORD-MAD
15h 54m2 stops
Delta Logo
10:00 am - 5:46 pmMAD-ORD
14h 46m1 stop
$457Delta
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Tue, Mar 3 - Wed, Mar 18
British Airways Logo
5:10 pm - 4:55 pmORD-MAD
16h 45m1 stop
British Airways Logo
12:50 pm - 7:45 pmMAD-ORD
12h 55m1 stop
$458British Airways
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Fri, Nov 28 - Fri, Dec 5
British Airways Logo
4:45 pm - 7:55 amORD-MAD
8h 10mnonstop
British Airways Logo
11:35 am - 2:30 pmMAD-ORD
9h 55mnonstop
$459British Airways
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Wed, Dec 10 - Thu, Dec 18
United Airlines Logo
6:00 am - 8:00 amORD-MAD
19h 00m2 stops
United Airlines Logo
1:35 pm - 3:28 pmMAD-ORD
32h 53m2 stops
$465United Airlines
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Fri, Nov 28 - Fri, Dec 5
Iberia Logo
11:48 am - 8:50 amORD-MAD
14h 02m1 stop
Iberia Logo
11:35 am - 2:30 pmMAD-ORD
9h 55mnonstop
$468Iberia
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Tue, Oct 28 - Sat, Jan 31
Iberia Logo
5:45 pm - 7:55 amORD-MAD
8h 10mnonstop
Iberia Logo
11:35 am - 2:30 pmMAD-ORD
9h 55mnonstop
$469Iberia
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Wed, Mar 18 - Wed, Mar 25
United Airlines Logo
7:15 am - 7:00 amORD-MAD
17h 45m1 stop
United Airlines Logo
5:55 am - 4:20 pmMAD-ORD
16h 25m1 stop
$472United Airlines
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Wed, Nov 12 - Thu, Nov 20
Finnair Logo
4:45 pm - 7:55 amORD-MAD
8h 10mnonstop
Finnair Logo
11:35 am - 2:30 pmMAD-ORD
9h 55mnonstop
$474Finnair
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Tue, Nov 4 - Thu, Nov 13
Finnair Logo
4:45 pm - 7:55 amORD-MAD
8h 10mnonstop
Finnair Logo
11:35 am - 2:30 pmMAD-ORD
9h 55mnonstop
$476Finnair
Find Deal

Everything you should know

Cheapest round-trip
$456
Overall average: $639
TAP AIR PORTUGAL
Wed 3/4Tue 3/17
ORD - MAD • 1 stop
Cheapest non-stop
$459
Typical prices: $504-$1,119
British Airways
Fri 11/28Fri 12/5
ORD - MAD • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Toledo!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$181
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 14% 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?

    11 direct flights run between Chicago and Toledo on a daily basis. On average, there are about 77 departures each week.

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

    Consider leaving on a Wednesday 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 Sundays.

  • 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 $181. TAP AIR PORTUGAL offered a round-trip connection from $456 and Delta from $457.

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 67 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.

Reviews of the 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.
7.6
FinnairOverall score based on 1332 reviews
7.4Comfort
6.9Entertainment
7.6Boarding
6.7Food
8.1Crew
Airline reviews

It was okay. The airplane was a little smaller than a flight from Thailand to Helsinki.

6.0 GoodAnonymous, Jul 2025HEL - DFW
Read more Finnair reviews

It was okay. The airplane was a little smaller than a flight from Thailand to Helsinki.

Wish that everyone would board the back of the plane first. Also let kids on first. The gate wasn’t open at arrival and we waited 45 minutes to takeoff. They made up for time in the air.

This was an absolutely exceptional flight. The flight attendants were extremely attentive and very friendly. They seemed to go out of their way to make us comfortable and to make sure that we had everything we needed., We were in business and were very happy with the size and the details for our pods. We would definitely recommend Finnair and will definitely be flying with them again.

Crew very lovely. Arrived an hour late due to bad weather. We were given new tickets to an other flight but it could have been organised better, so we did not have to run through the whole airport to.

Flight delayed over an hour. They said they would hold our connection but then did not.

Major problems checking in at Alaska counter. They could not find our booking code because it came from Finnair.

Do not use KAYAK or Finair for future travel. Unless you purchase the tickets directly from the airline, you were going to have a difficult time checking in. Kayak canceled my flights twice and ended up causing great difficulty in me getting back from Europe because they double sold my tickets between American Airlines and Finair. The event caused significant delays and led to me having to rebook my flights.

The staff were all particularly great. The plane was clean and fresh. The bassinet worked great. It was all very nice.

Boarding uncomfortable. Stewardess said I would have to check my carry on as there was no room in the overhead bins. Another passenger helped me find a spot.

Any flight that lands safely is a good flight. However our leg from Helsinki was delayed 1 hour with no explanation. The delay would not allow us to make our connection to Cincinnati. I was informed by American Airlines that our Cincinnati flight was rescheduled for the following day. I immediately made a non refundable hotel reservation in Dallas. Upon exiting the plane at Dallas I was given a hotel voucher. Nice, but I can't get a refund on the hotel I booked. A little communication would have been helpful. Food on Finnair is below quality of Korean Air.

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

The person at the checkin was very helpful. We couldn’t check in through the keyosk, but the agent was very helpful.

Great price for really nice seats and the plane and staff were great, only 5-10 minute delays!

Everything went as expected. Luggage arrived at my same destination and nothing disturbed my vacation.

This flight arrived late. We joined well over a thousand of other people waiting to go through customs. Air Portugal has lost my bag. We had to chase down a representative even though we had waited at the baggage claim for well over 1 hour and 35 minutes for baggage to come. No representative was there to explain the delay or to give any direction. After 1 hour and 35 minutes at least four passengers had no baggage to pick up or had a fraction of their baggage. The representative was a young woman who clearly did not have the experience to deal with what was happening. Very disappointing as of course we were dealing with great amount of jet lag and having been up for 24 hours at that point and not being able to have any of the things necessary at home that were contained in the bag was quite upsetting. That instant occurred last night at approximately 11:15 p.m. and as of 12:30 p.m. the next day I have not heard anything from Air Portugal.

An old airplane with very uncomfortable seats in the Comfort “class! Small, narrow, and hard seat. Entertainment options are inferior, old movies. Boarding started at the back of the airplane, as we entered the aircraft last instead of after business class, risking the possibility that the comfort section would not have room for carry-on in the overhead bin. The food was ok. White wine was terrible. Overall, the flight felt worse than cheap airliners, and the price was as high as premium carriers.

I had a business class ticket from EWR to Madrid with a layover at LIS for 11 hours. It was obvious that I needed to pick up my luggage in Lisbon for 11 hours and check it in again when boarding the second flight to Madrid. Before buying the ticket, I called TAP customer service. Customer service assured me that I could get my luggage in Lisbon. When I arrived at Newark airport, I immediately asked to check my luggage to Lisbon. However, the TAP employee refused me, saying that I should resolve this issue upon arrival in Lisbon. She checked my luggage to Madrid. I asked the TAP employee at the gate to help me when boarding the plane, I asked the flight attendants manager on board the plane to help me. All the employees refused to help me and said that I should resolve this issue in Lisbon. It took me 4 hours to resolve this issue in Lisbon. I arrived at 11am and they didn't give me my luggage until 3pm. As a result, I was so tired after a sleepless night on the plane and 4 hours on my feet at the airport and all my plans were ruined that I couldn't fly to Madrid. It was a terrible experiance,

The seats were not designed to comfortably see people in coach for more than 10 minutes

We flew TAP last October from Newark to Lisbon. The meal was bad. This flight had good food. Also, this flight was delayed. There were TAP employees waiting at Lisbon to make sure we made our connecting flight. I find the TAP website and app frustrating, but the service once we reached the airport was very good

Flight being delayed for 35 minutes had me lose the connection to my transport

Tap air Portugal was the best I will traveling again with u guys. Thank u.

It was a good flight overall. Nothing to add. Keep it up!

Excellent. Thanks to United Star Alliance, since economy was overbooked, I’m grateful to have been upgraded to Business Class.

Good plane, excellent food, crew and entertainment. Seats in business could use an upgrade

Delayed. Mismanagement of gate lines. Passengers arguing with eachother as a result of lack of organization by airline. Avoid this airline.

Disaster. Downgraded. Zero apology. No effort or coordination between gate and crew. Awful seat blocked by door emergency slide box. Iberia is a mess. App never works. Avoid this airline.

We departed late but made up most of the time in flight. Our ticket was pure economy, so it wasn’t anything fancy; however, I heard that we arrived in Madrid at the exact same time that First Class passengers arrived! Overall, our experience was similar to what we had on other American Airlines transatlantic flights - good value at a reasonable price. We were even able to get our carry-on baggage onto the plane without needing to gate check it.

Flight was OK. Waiting for luggage in Madrid for 55 minutes, unacceptable

Transportation from gate to airplane was poor we stayed in hot bus for 20 minute no vantilation

Because the plane was delayed from Madrid to LAX, we missed our connecting flight to Malaga. Iberia offered to book us a hotel room but I needed to be in Malaga that evening. I ended up buying train tickets to Malaga from Madrid. I also feel Iberia should compensate me for the cost of the train tickets because they didn't meet their travel obligation.

The crew were friendly and helpful. Iberia lost our luggage on arrival, Friday and we didn't get it until Sunday at 10:00 p.m. local Malaga time. I also paid $382.80 for seat assignments but two out out of the four were not together. Iberia mentioned that it was because the plane was delayed in Madrid before our flight began in LAX. They should compensate us half of my payment.

No WiFi in either flight. No leg room, the seat in front of me left dents on my knees and the tray was so low my knees propped it up if I tried to use it.

It was a good experience, especially travelling with a baby and their accessories

Three major things that led to my low rating, 1. Internet wasn't available for the whole time, and 2. TV became available way into flight, after numerous system reboots, and 3. Food is not good at all.

Boarding was efficient and quick, crew was very attentive, seats were comfortable.

Had a nice little suite although I couldn’t close the door (but I didn’t ask anyone to help). 5K is a nice seat and very private (you look in on first class). Enjoyable flight and nice crew.

The plane was known to be late in advance of takeoff. My guess is that it was known to be late at 11am or 5 hours before scheduled takeoff time. We were late to leave and with a wheelchair and the a cart, we only made it to gate. We raced! Inside plane, all was great

Was delayed on first leg and missed connection. They would not let me board although I arrived at the gate 5 min before take off. I was delayed 24hrs

We were never able to take this flight because our first flight from Austin to Dallas was cancelled.

More Indian vegetarian food options would have been better Availability of seat selection free of charge 72 hours before departure would be great

As I said Al & AJ were absolutely the best and wow they should be recognized for their amazing service!

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