$284 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 1/9. 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

KAYAK searches hundreds of travel sites at once for deals on flights from Chicago to Toledo

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$471
Overall average: $537
Scandinavian Airlines
Sat 1/31Sat 2/7
ORD - MAD • 1 stop
Cheapest non-stop
$472
Typical prices: $496-$663
Finnair
Tue 1/20Tue 1/27
ORD - MAD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Toledo!
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

Sat, Jan 31 - Sat, Feb 7
Scandinavian Airlines Logo
7:20 pm - 5:45 pm
ORD
-
MAD
15h 25m1 stop
Scandinavian Airlines Logo
6:35 pm - 4:55 pm
MAD
-
ORD
29h 20m1 stop
$471Scandinavian Airlines
Tue, Mar 24 - Tue, Mar 31
British Airways Logo
11:40 am - 11:05 am
ORD
-
MAD
17h 25m2 stops
British Airways Logo
4:40 pm - 6:50 pm
MAD
-
ORD
9h 10mnonstop
$472British Airways
Sun, Jan 11 - Tue, Jan 20
American Airlines Logo
10:10 am - 5:45 am
ORD
-
MAD
12h 35m1 stop
American Airlines Logo
12:00 pm - 2:55 pm
MAD
-
ORD
9h 55mnonstop
$473American Airlines
Sun, Jan 11 - Tue, Jan 20
Multiple Airlines Logo
10:10 am - 5:45 am
ORD
-
MAD
12h 35m1 stop
Multiple Airlines Logo
12:00 pm - 2:55 pm
MAD
-
ORD
9h 55mnonstop
$474Multiple Airlines
Thu, Jan 29 - Sun, Feb 8
Scandinavian Airlines Logo
7:10 pm - 4:10 pm
ORD
-
MAD
14h 00m1 stop
Scandinavian Airlines Logo
6:35 pm - 4:45 pm
MAD
-
ORD
29h 10m1 stop
$475Scandinavian Airlines
Tue, Feb 10 - Thu, Feb 19
United Airlines Logo
5:52 pm - 8:00 am
ORD
-
MAD
31h 08m1 stop
United Airlines Logo
6:00 am - 1:25 pm
MAD
-
ORD
14h 25m1 stop
$477United Airlines
Wed, Mar 11 - Wed, Mar 18
American Airlines Logo
4:19 pm - 10:00 am
ORD
-
MAD
11h 41m1 stop
American Airlines Logo
1:45 pm - 5:00 pm
MAD
-
ORD
9h 15mnonstop
$478American Airlines
Wed, Dec 31 - Fri, Jan 16
Air Canada Logo
12:50 pm - 8:00 am
ORD
-
MAD
12h 10m1 stop
Air Canada Logo
1:35 pm - 8:10 pm
MAD
-
ORD
13h 35m1 stop
$480Air Canada
Sun, Jan 25 - Tue, Feb 3
Delta Logo
6:14 pm - 9:15 am
MDW
-
MAD
32h 01m1 stop
Delta Logo
11:15 am - 10:22 pm
MAD
-
MDW
18h 07m1 stop
$480Delta
Mon, Feb 2 - Tue, Feb 10
Delta Logo
12:48 pm - 9:15 am
MDW
-
MAD
13h 27m1 stop
Delta Logo
6:00 am - 5:55 pm
MAD
-
MDW
18h 55m2 stops
$491Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$283
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 15% increase in price.
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?

    7 direct flights run between Chicago and Toledo on a daily basis. On average, there are about 49 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 Saturdays and the most expensive ones on Wednesdays.

  • 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 $170. JetBlue offered a round-trip connection from $120 and TAP AIR PORTUGAL from $288.

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 89 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 November, December and January. 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 1334 reviews
7.4Comfort
6.9Entertainment
7.6Boarding
8.1Crew
6.7Food
Airline reviews

All reviews good because...flight from BWI to London ,economy seats was miserable. I usually book 1,step up from economy but this would have added 1500 bucks 1 way. Bit the bullet and upgraded for retun flight, otherwise all ratings would have been rock bottom.

8.0 ExcellentDavid, Oct 2025
LHR - BWI
Read more Finnair reviews

All reviews good because...flight from BWI to London ,economy seats was miserable. I usually book 1,step up from economy but this would have added 1500 bucks 1 way. Bit the bullet and upgraded for retun flight, otherwise all ratings would have been rock bottom.

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.

We loved the steward on the plane. He made the night enjoyable

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

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 business class seats were smaller and closer together than other airlines.

Didn't like much. Wheelchair assistance was almost nonexistent. No one at TAP check in process helpful. On the plane, stewards were not friendly and disorganized. Food was terrible for 8 hr flight. We were skipped at snack time and even though we tried to get attention using overhead call system no one even looked up at us to acknowledge. Being at the back of first section and by the lavatory we only were able to request when they came to pick up everyone else's garbage and they were nonchalant...no apology or even choice. The 1/2 half bread with slice of cheese was a waste. Deplaning was horrible but I'll blame lisbon airport for that. Plane left late at made good time still arrived about 15 behind schedule and for using remote deplaning and bus to terminal took another 20 min to gate. Those with connections were highly stressed. Took us 2 hrs from landing to get to ground transportation and exit airport. And that was with wheelchair assistance.

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

Everything went smoothly, and we even arrived 40min earlier than scheduled, on an Orland-Madrid route.

It was budget airline Veuling, even though we booked Iberia.

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

Bad experience. The seat room are very tight. The food is not good and the breakfast has no hot drink.

Suddenly, I don't find my flight back on the app Help Ticket 0757345716866 Hoeflich Flight back Sunday ib5333 Ib2629 Ib4268

Great : The crew was awesome ♥️ To improve : - The rice in the "Rice with chicken" was rather s kind of rice pudding, not good at all - No power outlet to charge your phone. 😒

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.

I don't know about the others but the flight attendant that took care of us had the absolute wrong approach "how do we dare asking for water or anything else for that matter"

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

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

Complete your trip to Toledo with a hotel stay or car rental