$312 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 8/17. 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
$519
Typical prices: $921-$598
TAP AIR PORTUGAL
Sun 4/12Thu 5/7
ORD - MAD • 1 stop
Cheapest non-stop
$777
Typical prices: $934-$649
Finnair
Mon 4/27Mon 5/4
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

Sun, Apr 12 - Thu, May 7
TAP AIR PORTUGAL Logo
6:00 pm - 9:25 pm
ORD
-
MAD
20h 25m
1 stop
TAP AIR PORTUGAL Logo
10:25 pm - 4:00 pm
MAD
-
ORD
24h 35m
1 stop
$519TAP AIR PORTUGAL
Sun, Apr 19 - Sun, Apr 26
TAP AIR PORTUGAL Logo
6:00 pm - 5:20 pm
ORD
-
MAD
16h 20m
1 stop
TAP AIR PORTUGAL Logo
6:35 am - 4:00 pm
MAD
-
ORD
16h 25m
1 stop
$530TAP AIR PORTUGAL
Sun, Apr 12 - Sun, Apr 19
TAP AIR PORTUGAL Logo
6:00 pm - 9:25 pm
ORD
-
MAD
20h 25m
1 stop
TAP AIR PORTUGAL Logo
6:35 am - 4:00 pm
MAD
-
ORD
16h 25m
1 stop
$532TAP AIR PORTUGAL
Wed, Sep 23 - Wed, Sep 30
Multiple Airlines Logo
1:05 pm - 12:15 pm
MDW
-
MAD
16h 10m
1 stop
Multiple Airlines Logo
9:50 am - 4:27 pm
MAD
-
MDW
13h 37m
1 stop
$771Multiple Airlines
Tue, Sep 22 - Tue, Sep 29
Delta Logo
10:35 am - 9:55 am
MDW
-
MAD
16h 20m
2 stops
Delta Logo
6:00 am - 6:31 pm
MAD
-
MDW
19h 31m
2 stops
$797Delta
Mon, Sep 28 - Tue, Oct 27
Delta Logo
5:59 pm - 3:35 pm
MDW
-
MAD
14h 36m
2 stops
Delta Logo
10:15 am - 9:45 pm
MAD
-
MDW
17h 30m
1 stop
$798Delta
Mon, Sep 28 - Tue, Oct 27
Virgin Atlantic Logo
10:35 am - 9:55 am
MDW
-
MAD
16h 20m
2 stops
Virgin Atlantic Logo
9:00 am - 9:45 pm
MAD
-
MDW
18h 45m
2 stops
$799Virgin Atlantic
Mon, Apr 27 - Mon, May 4
KLM Logo
5:21 pm - 12:15 pm
MDW
-
MAD
11h 54m
1 stop
KLM Logo
12:45 pm - 10:28 pm
MAD
-
MDW
16h 43m
1 stop
$821KLM
Wed, Sep 23 - Mon, Sep 28
Multiple Airlines Logo
1:05 pm - 12:15 pm
MDW
-
MAD
16h 10m
1 stop
Multiple Airlines Logo
9:50 am - 9:46 pm
MAD
-
MDW
18h 56m
1 stop
$822Multiple Airlines
Mon, Apr 27 - Mon, May 4
Virgin Atlantic Logo
12:52 pm - 12:15 pm
MDW
-
MAD
16h 23m
1 stop
Virgin Atlantic Logo
12:45 pm - 10:28 pm
MAD
-
MDW
16h 43m
1 stop
$832Virgin Atlantic
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$312
Best time to beat the crowds with an average 11% 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 7h 50m.

  • 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 Mondays.

  • 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 $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 37 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 1376 reviews
6.9Entertainment
7.7Boarding
6.7Food
7.5Comfort
8.2Crew
Airline reviews

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

10.0 ExcellentFrancesca, Mar 2026
LHR - BOS
Read more Finnair reviews

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.

Very good seat, very comfortable, good food, and good service.

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.

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.

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.

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.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

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

Flight was delayed but crew gave little to no communication, then “began boarding” but really just had everyone stand up and wait for an hour without any news or updates, as if we were going to start boarding at any second. Total chaos. Seemed like this was their first time boarding a plane. When we arrived at our destination, we waited for over an hour for the baggage claim belt to even turn on. Probably waited at baggage claim for our luggage for close to two hours. Everyone was very confused and of course we all worried that the luggage was lost. Again, zero communication and everyone we asked just said “I don’t know.” So we were left wondering whether to wait, or file a missing baggage claim, or check the other baggage claim belts (which we did every fifteen-twenty minutes because we were just confused). Lack of communication throughout the experience was a huge issue.

Booked business with TAP from LAX to Cabo Verde - overall ok, but just doesn’t feel like business class. More of a budget airline

Poor. Our flight was delayed and they told me I would be fine to make my connection in Lisbon, I missed it. Then they told me my bag would be automatically loaded onto my new flight to rome. It wasn’t. It’s been 4 days and I still don’t have it.

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.

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 pilot was professional and very good. The flight crew, very young and often looked flustered and overwhelmed. The seats were among the most uncomfortable in the air. The boarding somewhat chaotic. The price reasonable. Overall it was an average budget airline experience...although Iberia is not a budget airline. I fear if Iberia doesn't up it's game customers like us will go elsewhere.

Bad weather Excelent pilot Spoke British 😆on time seats small ad expected in a discount airline

It wasn’t great because the third-party from Kayak there was just no information about how to check in with Vueling. And the purchase of the ticket from under pricer just made everything really difficult. I’m unlikely to use Kayak again for these reasons.

It was fine, older plane with limited entertainment, otherwise fine.

the seats were bad and uncomfortable and the food was not tasty.

the seats were so cramped you could barely move. it was difficult to eat when passengers would recline their seats. the seats were so flimsy and unstable that whenever someone got in and out of their seat, it bounced like a spring back in your face. the movies were nice. the food was terrible. even though the conditions were terrible, they tried to pressure passengers to relocate their seats to accommodate adults who were related and wanted to sit next to each other, even after the passengers expressed that they did not want to move for that purpose. on the connecting flight, the “service” consisted of items for purchase. even though the flight was only 45 minutes, once again passengers (including me) were pressured to relocate for people to sit next to each other. they couldn’t be apart for 45 minutes? this was much less compelling than being apart for an 8 hour flight.

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

Getting the boarding passes between the BA and AA apps was very clunky.

The plane was dirty the food was awful and the boarding process took too long

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.

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

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