$294 Find Cheap Flights from Chicago to Toledo - Compare and Save

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 8/3. 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
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$563
Typical prices: $473-$794
Scandinavian Airlines
Wed 11/18Tue 11/24
ORD - MAD • 1 stop
Cheapest non-stop
$696
Typical prices: $511-$799
Finnair
Sun 9/20Wed 11/25
ORD - MAD • Non-stop
Arrival airport
You can't fly directly to Toledo. It is served by Madrid (MAD), located 49.4 miles from Toledo.
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Flight Deals
Useful Info
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, Nov 18 - Tue, Nov 24
Scandinavian Airlines Logo
7:15 pm - 4:10 pm
ORD
-
MAD
13h 55m
1 stop
Scandinavian Airlines Logo
5:00 pm - 4:45 pm
MAD
-
ORD
30h 45m
1 stop
$563Scandinavian Airlines
Sun, Nov 15 - Tue, Nov 24
Scandinavian Airlines Logo
7:15 pm - 4:10 pm
ORD
-
MAD
13h 55m
1 stop
Scandinavian Airlines Logo
5:00 pm - 4:45 pm
MAD
-
ORD
30h 45m
1 stop
$564Scandinavian Airlines
Wed, Nov 11 - Tue, Nov 24
Scandinavian Airlines Logo
7:15 pm - 4:10 pm
ORD
-
MAD
13h 55m
1 stop
Scandinavian Airlines Logo
5:00 pm - 4:45 pm
MAD
-
ORD
30h 45m
1 stop
$565Scandinavian Airlines
Sun, Nov 1 - Thu, Nov 12
TAP AIR PORTUGAL Logo
8:10 pm - 5:10 pm
ORD
-
MAD
14h 00m
1 stop
TAP AIR PORTUGAL Logo
9:10 pm - 3:30 pm
MAD
-
ORD
25h 20m
1 stop
$571TAP AIR PORTUGAL
Wed, Nov 4 - Wed, Nov 11
TAP AIR PORTUGAL Logo
7:00 pm - 2:05 pm
ORD
-
MAD
12h 05m
1 stop
TAP AIR PORTUGAL Logo
7:40 am - 3:30 pm
MAD
-
ORD
14h 50m
1 stop
$572TAP AIR PORTUGAL
Wed, Nov 18 - Tue, Nov 24
Delta Logo
10:35 am - 9:55 am
MDW
-
MAD
16h 20m
1 stop
Delta Logo
11:55 am - 10:10 pm
MAD
-
MDW
17h 15m
1 stop
$721Delta
Wed, Nov 18 - Thu, Nov 26
Delta Logo
1:05 pm - 9:55 am
MDW
-
MAD
13h 50m
1 stop
Delta Logo
6:05 am - 6:37 pm
MAD
-
MDW
19h 32m
2 stops
$722Delta
Sun, Nov 1 - Thu, Nov 12
Virgin Atlantic Logo
9:29 am - 9:55 am
MDW
-
MAD
17h 26m
2 stops
Virgin Atlantic Logo
10:00 am - 10:10 pm
MAD
-
MDW
19h 10m
2 stops
$727Virgin Atlantic
Mon, Nov 16 - Wed, Nov 25
Virgin Atlantic Logo
1:00 pm - 9:55 am
MDW
-
MAD
13h 55m
2 stops
Virgin Atlantic Logo
10:00 am - 10:10 pm
MAD
-
MDW
19h 10m
2 stops
$728Virgin Atlantic
Thu, Oct 15 - Fri, Oct 30
Air France Logo
10:58 am - 12:15 pm
MDW
-
MAD
18h 17m
1 stop
Air France Logo
11:55 am - 10:25 pm
MAD
-
MDW
16h 30m
1 stop
$771Air France
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$294
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 6% 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 00m.

  • How many flights are there between Chicago and Toledo?

    10 direct flights run between Chicago and Toledo on a daily basis. On average, there are about 70 departures each week.

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

    Consider leaving on a Tuesday and avoid Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays 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 5 days, the cheapest one-way ticket between Chicago and Toledo found on KAYAK was with TAP AIR PORTUGAL for $167. JetBlue offered a round-trip connection from $120 and Virgin Atlantic from $215.

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 51 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 October.

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 1419 reviews
6.7Food
7.7Boarding
7.4Comfort
6.9Entertainment
8.2Crew
Airline reviews

Awful. Delayed for unknown reason. Boarded late, part of a Tight connection ands had to go through customs and immigration. And they lost my bags.

2.0 MediocreAnonymous, Jul 2026
DFW - DEN
Read more Finnair reviews

Awful. Delayed for unknown reason. Boarded late, part of a Tight connection ands had to go through customs and immigration. And they lost my bags.

The seats are very uncomfortable. They never have tomato juice. Usually late

Finnair was not able to get our luggage on a connecting flight and there was a substantial delay of two days to obtain our lugguage. They did not communicate well, and we had to travel a significant distance to finally get our luggage. It has been a very negative experience.

Comfort. Not good very little space after the person in front of you lay back.

Business seating is soooo uncomfortable. You can sit straight up or lay down. You need pillows behind you because the back doesn’t lay down. Those are need to “prop” you up. The chair has no padding whatsoever. Food was gross. I’ve eaten on Finnair before and the food was exceptional. This time it gave 2 people in our party diarrhea. It was the chicken dish. I took 2 bites and didn’t eat anything more. The flight attendants were nice. You needed an additional lounge in Terminal D at DFW Airport. After waiting 40 minutes to enter, we finally gave up and went to a bar across from the club doors. I’m unsure if I’ll ever book a Finnair flight again.

It was a good flight, very comfortable seats for sleeping in business class. Probably the most comfortable business class seat I've ever had (20+ times in business class on various airlines). Service was good, but the only downside is my screen didn't work and it had to be reset multiple times to get it to shut off. I had to block my eyes because the screen was white almost the entire flight and I wore an eye mask when I slept. But when eating and reading in my seat, my eyes hurt because the only way to turn the screen off was reset it and the screen would only be off for a few minutes at a time.

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.

Not great. Flight attendants were aloof, food was mediocre, seats that I paid $150 were given to someone else without any concession. I will probably never use kayak again. Terrible experience from start to finish.

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.

Flight was missed and now we have to catch one the next day

Negative. Food was awful, seat broken, flight was late, baggage lost and damaged

Plane was delayed, reading the gates on their screens was horrible. They posted it a half an hour before the plane boarded. By the time I got there with my premier boarding they have filled the plane because it was over booked. Gate closed at 12:03 I was there at 11:54 plane took over around 12:20. I was told they would put me on the next flight. I had to go to TAP information desk. They didn’t give me a voucher they just said they would put me on the next flight. At the desk I was told I had to punches a ticket. The woman said buy it online because it’s cheaper. It in fact was not cheaper. But I had gotten out of the long line that formed so I paid 200$ for a new ticket. At a later flight, not the next flight. I had checked my bag and was told it would be on my new flight. I was then bumped to an earlier flight and was told my bag would also be on my flight. After landing in Madrid loosing a day in my hotel i landed without my bag. They didn’t load it on any flight that day. It arrived in madrid the next day. Essentially ruining the first two days of my vacation. I’m now seeking compensation.

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

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

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

Our flight was delayed an hour and take-off was also delayed. Then our luggage was misplaced upon arrival causing a lot of stress snd more delays. We arrived at the hotel almost 5 hours later than anticipated and had to cancel our plans for the day. Overall a very bad experience. We will not travel with Portugalia in the future.

We Boarded the plane in the middle of the airport field . We were shuttled and climbed up the stairs, to board the plane,

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.

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.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The staff was very nice and helpful. Some of the best crew I have met.

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.

It was extremely cold in the back of the plane. The seats are uncomfortable and space very small. Crew was excellent as usual.

It was a wonderful experience with great food, great staff, and no difficulties boarding!

I was in business class for the 8 hour flight where: 1. The WiFi did not work 2. The entertainment system did not work 3. We were told there were no hot drinks for the entire flight

Paid for “extra room” selected seat. Wasn’t a benefit. Also was in aisle and was bumped almost every time attendants walked down aisle. Should have saved the assigned seat money and let them select.

Alaska located my mother, aware that she had mobility issues and they seated her closer to the door. She and I were seated together so I felt more secure to be able to assist her. The desk attendant reviewed what steps to take when boarding. Allowed us to board first, we loved that. I was allowed time to help her board slowly, seat her, put all her things in their place before the crowds came through. These small details made me want to travel Alaska more when possible.

I bought the ticket through Iberian, but I was unable to check in using my code. American wouldn’t let me check in and Iberian counter was closed.

The comfort level was low, but the staff was nice

Bad. Requested a diabetic meal. Was served everything i couldnt eat. So i did not estbthe whole flight dinner / breakfast. Sad and uncomfortable.

It's hard to tell where to plug in electronics, and the port on my seat didn't work. Their entertainment system was down. Vegetarian food options were tasty. Friendly, helpful flight attendants.

Lady next to me was coughing profusely the entire flight, other lady moved seats because of it, 8 hours of that during an overnight flight is a bit much.

The seats are extra cramped if you are taller than 5’8! Spring for the extra legroom seats for sure if you have a long flight!

Very disappointed with British Airways. It has been over 24 hours and I still have not received my checked baggage or any proper update. Customer support has been unresponsive, making the situation even more frustrating. Poor baggage handling and lack of communication seriously impacted my travel experience.

Cancelled flight and re booked seats were a downgrade. British Airways said the upgrade was t available but when I checked it was but then they wouldn’t make it right

Overall ok. Best part has always been the sundae dessert.

Very good staff members with sincere passion and responsibility in their job.

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

Everything you need to know for your flight from Chicago to Toledo

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