$458 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 7/4. 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
$775
Typical prices: $677-$421
TAP AIR PORTUGAL
Thu 9/24Sun 10/4
ORD - MAD • 1 stop
Cheapest non-stop
$829
Typical prices: $864-$551
Iberia
Tue 8/11Wed 8/19
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

Thu, Sep 24 - Sun, Oct 4
TAP AIR PORTUGAL Logo
6:00 pm - 3:20 pm
ORD
-
MAD
14h 20m
1 stop
TAP AIR PORTUGAL Logo
6:35 am - 4:00 pm
MAD
-
ORD
16h 25m
1 stop
$775TAP AIR PORTUGAL
Sun, Sep 20 - Sun, Sep 27
Delta Logo
5:45 pm - 4:45 pm
ORD
-
MAD
16h 00m
2 stops
Delta Logo
6:00 am - 3:10 pm
MAD
-
ORD
16h 10m
1 stop
$776Delta
Sun, Sep 20 - Sat, Oct 3
Delta Logo
5:45 pm - 3:35 pm
ORD
-
MAD
14h 50m
2 stops
Delta Logo
10:25 am - 10:06 pm
MAD
-
ORD
18h 41m
2 stops
$778Delta
Sun, Nov 15 - Wed, Nov 25
Air Canada Logo
1:55 pm - 11:45 am
ORD
-
MAD
14h 50m
2 stops
Air Canada Logo
6:00 am - 2:55 pm
MAD
-
ORD
15h 55m
2 stops
$783Air Canada
Fri, Sep 18 - Mon, Oct 5
SWISS Logo
7:05 pm - 6:40 pm
ORD
-
MAD
16h 35m
1 stop
SWISS Logo
7:30 pm - 12:35 pm
MAD
-
ORD
24h 05m
1 stop
$786SWISS
Thu, Sep 3 - Mon, Sep 21
Scandinavian Airlines Logo
7:15 pm - 5:40 pm
ORD
-
MAD
15h 25m
1 stop
Scandinavian Airlines Logo
6:30 pm - 4:10 pm
MAD
-
ORD
28h 40m
1 stop
$792Scandinavian Airlines
Wed, Sep 9 - Wed, Sep 23
Finnair Logo
4:55 pm - 8:20 am
ORD
-
MAD
8h 25mnonstop
Finnair Logo
1:00 pm - 7:17 pm
MAD
-
ORD
13h 17m
1 stop
$794Finnair
Sat, Jul 11 - Sun, Sep 6
British Airways Logo
8:37 pm - 6:50 am
ORD
-
MAD
27h 13m
1 stop
British Airways Logo
1:35 pm - 4:00 pm
MAD
-
ORD
9h 25mnonstop
$795British Airways
Thu, Oct 1 - Mon, Oct 19
Finnair Logo
4:55 pm - 8:20 am
ORD
-
MAD
8h 25mnonstop
Finnair Logo
11:45 am - 2:25 pm
MAD
-
ORD
9h 40mnonstop
$796Finnair
Wed, Sep 9 - Thu, Sep 24
British Airways Logo
10:15 pm - 1:30 pm
ORD
-
MAD
8h 15mnonstop
British Airways Logo
1:35 pm - 4:00 pm
MAD
-
ORD
9h 25mnonstop
$797British Airways
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$458
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 1% 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 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 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 73 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 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.
7.7
FinnairOverall score based on 1399 reviews
7.7Boarding
8.2Crew
6.9Entertainment
6.7Food
7.5Comfort
Airline reviews

The crew was friendly, and the flight landed on time

10.0 ExcellentDarwin, May 2026
HEL - JFK
Read more Finnair reviews

The crew was friendly, and the flight landed on time

Rude Iberia security crew at the Madrid terminal. No Iberia officials to be found to redress complaints at the gate. No supervisors. Nothing for processing upgrades at the gate Iberia app did not work to let me upgrade my options to higher classes. No water was offered on a hot day in Madrid. Madrid airport air conditioning was so weak that people were sweating. Never book on any airlines that codeshare with Iberia.

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

On a more than 8 hours flight was only one meal included, which I have never experienced before. Always two meals on the overseas flight. It was very weird.

Great if not for the boarding by bus at Heathrow terminal 3. Medieval disappointing time-consuming and very hard on handicapped flyers. It was awful

Positive: It was refreshingly easy and polite check-in and boarding staff. Flight was on time and Helsinki is a very well-signposted airport. Shopping was nice as well. Flight was not full and I had lots of space in economy. Flight was perfectly on time. Negative: Food and drink not very good, but that it is normal on any airline. Didn't expect anything else.

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.

Everything was wonderful! AirBus seats are more comfortable to sleep in as compared to the Boeing planes.

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.

Flight attendants in business class were rather indifferent While in second leg operated by Portugalia TAP subsidiary were outstanfy

The chicken was so dry it was impossible to eat. No substitute was offered. The port to charge my phone was broken and all I got was a shrug from the crew. The entertainment system was glitchy and subtitles didn’t load. Crew seemed fully uninterested and unfriendly.

The flight crew were absolute rock stars. When they came to the gate they looked like royalty, so chic. They also were extremely kind. Food was good and I loved the lack of plastic waste. The flight was lovely and smooth.

We were unable to check in due to technical problems on TAP’s end. The flight was delayed forty minutes with no reason given. We received timely notice of the flight delay. We were also notified of a gate change. The new gate was at a different terminal. When we got to the new terminal, we learned that we had to go back to the old terminal first to check in. This information should have been included along with the gate change notification. Also unexplained, the steward skipped us when offering breakfast.

Horrible experience at tbe check in ladie she was very racist ,she doesn't speak portuguese too and forced me to check in my carrion bag and I saw everyone with carrion bag inside anda lot of space ,she was rude unprofessional

No difference between business class and normal same seat everything same, waste of money

Absolutely unacceptable level of service for a Business class: lousy drink and food options, disgusting food (inedible meat, watery rice, etc...), pathetic level of attentiveness from staff, Business class restrooms were not accessible for long periods because blocked of by staff...overall extremely disappointing, will NEVER fly Business on TAP again.

First time flying Business with Tap, I think it was a very good experience. It beats many domestic US carriers, the food options were really great, authentic Portuguese food, wines & deserts. Next time will do the free 24-48 hour stopover in Lisbon or Porto for sure.

Late. Lack of updates. Rude hostesses. Terrible food. Lack of headphones.

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

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

Couldn’t get boarding passes online, delayed an hour, and smallest amount of space on board I’ve ever encountered for such a long flight.

I’m an Iberia fan but this time They dropped the ball. I went from ALC to MAD to LHR. Boarding in ALC was by group… to get you in a bus. Then we sat for almost an hour when most people had connections. When we landed in Madrid we did so and they put us in another bus almost like if they wanted to make people lose their connection. We made ours by the skin of our teeth but our luggage did not. And on top of this we had to listen to the pilot bragging about Iberia being punctual. To be true we made it on time to LHR but we are Still waiting for our luggage

I have to compare it to the AA flight back home. AA was a little better. Perhaps it was that American English is my native tongue. My seat on AA was newer and more comfortable. The food was a little better. The entertainment was much better, more movies worth watching. The sound was lousy on both.

Excellent liked business class except wife’s luggage was lost on 10 Hours connecting flight to Miami and we were priority! 1:20 layover! Expect better From American Airlines partner

Service was good , communication and emails were in Spanish though I booked in English , end up figuring it out but also flight was partnered with air maroc and I had to call them to check on not Iberea doesn’t make sense

In general, I've had excellent experiences with Iberia flights and will continue to use them. In this last flight there were two things that didn't go right. I didn't get the kosher meal I had pre-requested when I had checked in on-line. Things worked out OK as we ended up eating the fish and vegetarian choices, which were really good. The other issue was that some movies for me and my wife started fine but after 8-12 minutes the content just switched to something else. The flight attendant reset our entertainment systems, but the problem persisted. We ended up choosing other movies/TV shows that did work fine.

Awful. They didn't even show concern that her connecting flight( Dallas to Mardrid) was gone/missing. I don't understand how that is even possible. Rudest answer from one of the crew was that American Airlines sold the tickets to somebody else. My daughter was not in the list.

The flight was canceled on a Thursday last minute. I lost thousands of dollars in hotels and car rental

Excellent lie flat seat for premium economy! Great staff. Bad food . Not so great entertainment. My bag didn’t make it either.

Really like the idea experience on this airline I will use again

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

Wonderful business class flight in a lovely new plane with an excellent crew

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

BA code for a Vueling flight. All god but the temperature in the plane (too hot when engine not running but otherwise ok)

Food options limited and quality wasn’t very good. I was I was in premium economy and the people in front of me pushed their seats back to fully reclined position which made it difficult for me. My seat wouldn’t recline at all. I suggest that BA restrict the recliner more. Also, the audio in my headset didn’t work unless I held it in all the time. Entertainment choices were good. Customer services is excellent. Thank you to BA team.

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

The luggage problem I previously mentioned was actually this flight

Late. And service was very slow - passengers sat for well over an hour with dirty trays etc surrounding them

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

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