$166 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 10/23. 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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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 12 - Thu, Nov 20
TAP AIR PORTUGAL Logo
7:10 pm - 11:30 pmORD-MAD
21h 20m1 stop
TAP AIR PORTUGAL Logo
9:10 pm - 3:15 pmMAD-ORD
25h 05m1 stop
$322TAP AIR PORTUGAL
Find Deal
Wed, Nov 12 - Wed, Nov 19
TAP AIR PORTUGAL Logo
7:10 pm - 8:20 pmORD-MAD
18h 10m1 stop
TAP AIR PORTUGAL Logo
7:40 am - 3:00 pmMAD-ORD
14h 20m1 stop
$324TAP AIR PORTUGAL
Find Deal
Fri, Jan 16 - Tue, Jan 27
TAP AIR PORTUGAL Logo
8:15 pm - 8:20 pmORD-MAD
17h 05m1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 3:00 pmMAD-ORD
28h 00m1 stop
$328TAP AIR PORTUGAL
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Wed, Oct 15 - Wed, Oct 22
Iberia Logo
1:43 pm - 8:15 amORD-MAD
11h 32m1 stop
Iberia Logo
1:45 pm - 8:11 pmMAD-ORD
13h 26m1 stop
$364Iberia
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Sun, Nov 2 - 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
$372Finnair
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Mon, Oct 6 - Mon, Oct 13
Iberia Logo
2:41 pm - 9:35 amORD-MAD
11h 54m1 stop
Iberia Logo
11:35 am - 2:15 pmMAD-ORD
9h 40mnonstop
$404Iberia
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Wed, Nov 26 - Fri, Dec 12
Lufthansa Logo
9:50 pm - 5:50 pmORD-MAD
13h 00m1 stop
Lufthansa Logo
7:25 am - 6:25 pmMAD-ORD
18h 00m1 stop
$407Lufthansa
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Fri, Nov 7 - Fri, Nov 14
Finnair Logo
4:45 pm - 7:55 amORD-MAD
8h 10mnonstop
Finnair Logo
11:35 am - 2:30 pmMAD-ORD
9h 55mnonstop
$426Finnair
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Mon, Feb 2 - Thu, Feb 12
KLM Logo
1:05 pm - 9:00 amMDW-MAD
12h 55m1 stop
KLM Logo
11:00 am - 9:46 pmMAD-MDW
17h 46m1 stop
$587KLM
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Tue, Nov 4 - Thu, Nov 20
KLM Logo
10:35 am - 9:30 amMDW-MAD
15h 55m1 stop
KLM Logo
11:00 am - 9:44 pmMAD-MDW
17h 44m1 stop
$592KLM
Find Deal
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Good to know

Low seasonJanuary
Cheapest flight$166
Best time to beat the crowds with an average 22% 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 Thursdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Thursdays.

  • 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 $166. TAP AIR PORTUGAL offered a round-trip connection from $322 and SWISS from $363.

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 1321 reviews
7.5Comfort
6.9Entertainment
7.6Boarding
8.1Crew
6.7Food
Airline reviews

Great. It was awesome to have boarding from the front and back of the plane as it made the process go very quickly

10.0 ExcellentSarah, Aug 2025CPH - HEL
Read more Finnair reviews

Great. It was awesome to have boarding from the front and back of the plane as it made the process go very quickly

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.

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!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

Boarding experience was awful. TAP claims I did not have check in luggage with tickets. I went 3-4 check in agents until I finally found a helpful kind agent who checked in my luggage with no fees. On top of that our flight was over 2 hours delayed with barely an apology or explanation.

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.

The long wait at JFK made the trip horrible. Also not having enough buses when we deplaned was annoying

Flight was delayed on 6/20 to miss international connection. Next flight out was 24 hours later. Not acceptable.

Food was edible, not great, and served by attendants who looked like they really were not happy working the flight. The section I was in was too warm making the 11 hour flight uncomfortable. Other areas on the plane were fine.

Checked bG chstgr was extremely high. Over $120. It was s bsit and switch knowing an international passenger would have t9 check a bag.

On time, politeness, food okay but entertneiment mediocre with only old movie and the so called new we’re 2 or 3…

Flight was packed. This was a very uncomfortable experience. Boarding process could be explained better. Despite recommending a window seat when travelling with a pet in the cabin, the seat in front of me had less space than the center and aisle seats. For Premium Economy, the seats were crammed with minimal legroom. I hate to think what Regular Economy was like. The cabin crew missed me at first when handing out meals. When my meal eventually came, there were no utensils. I'd originally booked to fly Business Class; those seats didn't look that great either.

Delayed first flight Geneva Madrid.. We didn’t miss our 2nd flight only because the 2nd flight Madrid Dallas was 1h delayed. However we did end up missing the 3rd leg Dallas Austin. Luggage didn’t show up in Dallas. So we re missing 2 suit cases. Customer service sent us to a hotel in Dallas. Only one room booked for 5!! Pretty bad experience overall. I won’t book a flight on Iberia in the future

Crew was excellent, great customer service, checked luggage took 1 hour and a half to come out at the baggage claim, the only negative thing about the flight.

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

Horrible experience airline crew was unprofessional. Flight was delayed. Suit cases did not arrive. Never flying iberia again

People point to America as the model of late stage capitalism. My friends, airlines in america at least give you WiFi, and they haven’t quite smashed people into cardboard tv dinner trays yet. Iberia has mastered the tv dinner seat and WiFi is 20 euros. Be serious yall.

Iberia lost my bag, said they found it in another country, said they sent it to me, but never did. Went my whole trip without my stuff, but expecting it to show up because that’s what they said would happen. Their communication sucks, their website sucks, and to top it all off, their seats are small and uncomfortable. They’re bad at their jobs and they should feel bad about themselves. Do not even get me started on the flight home. AVOID!

The flight was delayed over 4 hours. Business class is just slightly upgraded economy.

Delayed and missed connections on leaving the states and returning Planes were old and small- very uncomfortable. Meals were good but very infrequent service for even water/drinks. No explanations for 3+ hour delay

Boarding on the buses isn’t efficient. Overall, it was great.

BEWARE!!! Iberia changes your seats at random. I paid for a window seat and they changed it to one in the middle aisle resting against the bathroom- can’t lean back + hear every flush. This on a 11 hour flight.. There were families that were broken up with separate seats all over the plane. Lots of upset passengers showing their seat confirmation to the besieged and helpless airline steward. Also, the gluten free meal was tasteless.

There was a slight delay. Otherwise, everything else was satisfactory.

Although the crew were great and the good nice, I might as well have been on Ryanair for the amount of space I had. Not good enough BA. I’d rather pay more and not feel like a human sardine.

The company that I bought my tickets through, Cheapflightsfares, failed to provide my confirmation information in a timely manner, so I was unable to check on at the country and therefore unable to make my flight. As a matter of fact, I STILL have not received the confirmation. After having read more and more reviews about the company, Cheapflightsfares appears to have scammed hundreds of hopeful travelers out of thousands of dollars. Please look into this company and, for the sake of anyone planning their next trip, stop allowing them to do business through you.

Love the A380 - loads of room. Headphone socket on my seat didn’t work. Sounds like a trivial issue? Well when flying long-haul the in-flight entertainment is what keeps you going so when it doesn’t work it’s a disaster. Pay attention to the details please BA. Spoiled what was otherwise an excellent flight with the usual brilliant 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!

A little better than outward journey but mild chaos at the boarding gate because some people with boarding cards from connecting flights had cards which weren't recognised

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

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