$221 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 8/10. 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

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 20% 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.

Flights Deals
Useful Info
Flights 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, Aug 13 - Thu, Aug 21
 Logo
2:20 pm - 8:55 pmORD-MAD
23h 35m1 stop
 Logo
7:50 am - 12:10 pmMAD-ORD
35h 20m1 stop
Sun, Oct 5 - Wed, Oct 22
TAP AIR PORTUGAL Logo
6:00 pm - 5:20 pmORD-MAD
16h 20m1 stop
TAP AIR PORTUGAL Logo
4:20 pm - 12:35 pmMAD-ORD
27h 15m1 stop
$391TAP AIR PORTUGAL
Find Deal
Sun, Sep 28 - Wed, Nov 26
Iberia Logo
10:35 pm - 1:25 pmORD-MAD
7h 50mnonstop
Iberia Logo
11:35 am - 2:30 pmMAD-ORD
9h 55mnonstop
$468Iberia
Find Deal
Wed, Oct 8 - Wed, Oct 29
Finnair Logo
1:23 pm - 9:05 amORD-MAD
12h 42m1 stop
Finnair Logo
11:35 am - 3:30 pmMAD-ORD
9h 55mnonstop
$477Finnair
Find Deal
Wed, Sep 24 - Thu, Oct 2
Iberia Logo
1:59 pm - 8:15 amORD-MAD
11h 16m1 stop
Iberia Logo
1:45 pm - 6:50 pmMAD-ORD
12h 05m1 stop
$482Iberia
Find Deal
Mon, Oct 6 - Mon, Oct 13
Finnair Logo
10:35 pm - 1:25 pmORD-MAD
7h 50mnonstop
Finnair Logo
9:35 pm - 1:30 pmMAD-ORD
22h 55m1 stop
$483Finnair
Find Deal
Wed, Oct 1 - Wed, Oct 8
American Airlines Logo
1:59 pm - 8:15 amORD-MAD
11h 16m1 stop
American Airlines Logo
1:00 pm - 9:25 pmMAD-ORD
15h 25m1 stop
$487American Airlines
Find Deal
Sun, Sep 28 - Fri, Oct 10
British Airways Logo
10:35 pm - 1:25 pmORD-MAD
7h 50mnonstop
British Airways Logo
1:45 pm - 2:12 pmMAD-ORD
31h 27m1 stop
$511British Airways
Find Deal
Wed, Aug 6 - Tue, Aug 19
British Airways Logo
1:24 pm - 9:05 amORD-MAD
12h 41m1 stop
British Airways Logo
4:40 pm - 6:50 pmMAD-ORD
9h 10mnonstop
$530British Airways
Find Deal
Thu, Oct 16 - Mon, Oct 27
American Airlines Logo
10:35 pm - 1:25 pmORD-MAD
7h 50mnonstop
American Airlines Logo
12:30 pm - 9:25 pmMAD-ORD
14h 55m1 stop
$583American Airlines
Find Deal
Useful Info

Good to know

Low seasonJanuary
High seasonMarch
Cheapest flight$221
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 15% 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 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 Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Tuesdays.

  • 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 $221. TAP AIR PORTUGAL offered a round-trip connection from $391 and Scandinavian Airlines from $409.

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 May, June and July. The cheapest month to fly is February.

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 1290 reviews
7.6Boarding
7.4Comfort
6.9Entertainment
6.7Food
8.1Crew
Airline reviews

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.

2.0 MediocreAnonymous, May 2025ORD - IND
Read more Finnair reviews

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.

Any flight that lands safely is a good flight. However our leg from Helsinki was delayed 1 hour with no explanation. The delay would not allow us to make our connection to Cincinnati. I was informed by American Airlines that our Cincinnati flight was rescheduled for the following day. I immediately made a non refundable hotel reservation in Dallas. Upon exiting the plane at Dallas I was given a hotel voucher. Nice, but I can't get a refund on the hotel I booked. A little communication would have been helpful. Food on Finnair is below quality of Korean Air.

The cabin crew really looked like they wanted to be somewhere else. They weren't really interested in providing an attentive service to full fare paying passengers at all. However the Captiain's in flight announcements were relaxed and very entertaining.

Crew were professional and responsive. Food was mediocre and breakfast could do with revampinmg

Food was very ordinary for premium economy, very small portions.

i dont know WHY they call it business class. the seats are NOT significantly wider than economy seats, they just do not let the middle seats be beepked to give the illusion of more space between passengers. the seats do NOT recline any more than economy seats either. the only real difference is the full meal served to business (vs none for economy). I would rather have a wider, lie flat ACTUAL business class seat with no food for a 3 hr flight. this was pretty disappointing to say the least.

There wore nice leather like sits, in my opinion seats lay out bit tight . Crew was great they did averything possible to make averywone comfortable as possible, food was, think worst I ever head on flight, head chicken and yellow rice. Ice cream was a nic treat.

Our previous flight was delayed but they waited for us to board.

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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…

Awful. I told them to cancel my return flight and they didn’t then charged me +$800 days before the flight for a biz class upgrade bid. When I called to confirm cancellation and get refund on buz class upgrade they said I had to go thru orbitz and it was too late. Scammers. Beware.

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.

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.

First time and I enjoyed the trip…. Will fly again soon 🔜

Delayed flight because other plane was occupying the gate for longer than expected. Once we boarded the plane had to wait 1 hour before taking off. We. Almost lost our connection flight and the baggage didn’t make it. We had to wait two days to receive our luggage. Hope they improve the timing or work with the airport to get better service.

I’m still missing my bags. I’m soo frustrated

TAP boarding gate agents singled out Group A line to gate check all carry on bags …. Supposedly because of lack on bin space. BUT ALL OTHERS WERE PERMITTED WITH CARRY ON BAGS. Additionally so many passengers entering the plane after us were permitted carry on bags. And when the plane was fully loaded, there was a number of open spaces in the overhead bins. I WILL SEARCH OTHER OPTIONS BEFORE FLYING TAP AGAIN

Boarding went fast. Lisbon's gates are too small for the flights they serve.

Not having to check carry on bags when plane wasn’t full. (The told us it was)

Service and food were excellent, could have been more info in English.

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

I had an issue with the name on my ticket vs my passport name. I was very upset that the Iberia ticket clerk had no authorization to help me and I was left to fix it. It took 19 calls of persons promising to accomplish and not doing anything before I reached someone who helped me in 10 minutes. Two of them even hung up on me. I missed my original flight because of this. Terrible customer service.

Flight boarded three hours late for no reason other than someone made a huge error in crew scheduling. We missed our connecting flight in Madrid and got zero help from American or Iberian airlines on rebooking. We had to pay for a car to take us to the Madrid train station and pay for train tickets to Santiago. We never used our booked flight to Santiago. American claims I can submit the expenses but they are not obligated to cover them. Very frustrating.

Flight delayed Service could be better Iberia staff are not really friendly

They cancelled the flight)(they said bad weather but many other flights took off) and made us wait 5 hours in line to figure out what to do. We ended up making a new flight the next day on another airlines...I hope they honor giving us our money back

Flight from Costa Rica to Madrid was excellent. Good food and service. The flight from Madrid to Brussels was very poor . No food , no entertainment, no usb … Total package was quite expensive so you should give same service on the second flight

We travelled with Level, which is a subsidiary of Iberia. They mixed up all our seats, downgraded few from premium economy fo economy. The crew were not professional, they seem to be in a rush! Also some with an attitude

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.

The payment system was not working so was unable to connect wifi the entire flight

everything to do with KAYAK was terrible. Your customer facing departments are utterly useless, timewasting and unhelpful.

I ordered short ribs for main course. It tasted sweet, really sweet. Horrible.

Our luggage didn’t arrive with us, that puts a damper on the whole trip.

The screen didn’t work and I didn’t get the seat upgrade I paid $300 for. They were no help with that,

Paid $180 for seat selection, and selection essnt honored. Have to call for a refund.

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

Too much long line at the TSA and Security. Prepare for long walk for baggage claim.

The boarding process was quite loud and chaotic. The flight attendants kept barking over the PA system about people needing to only stow large items in the overhead bins. During the one and only service, I was hit by the service cart. At the same time, a passenger was returning from the bathroom and the crew definitely saw him but stopped a few seats short of allowing him to sit down before starting service and made him wait a good 10 minutes before passing his seat and allowing him to sit down, after which he had to ask for his snack and beverage or he would have been passed over. Neither flight attendant thanked passengers as they left; in fact, I did not see them again once the plane door was opened.

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

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

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.