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$184+ Cheap flights from Chicago (CHI) to Toledo, Spain

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Toledo are usually found in February or January, booked 67 days in advance, depart on a Wednesday or Monday and return on a Monday

Cheap flight deals from Chicago to Toledo

Keep the following information in mind while searching for Chicago to Toledo flight deals. Data was last updated September 15, 2025.

Round-trip from

$365
(eDestinos)

One-way from

$184
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$577
From Chicago (CHI) to Toledo
Search Deals
One-way flight from Chicago (CHI) to Toledo
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Highest demand for flights based on searches. 20% potential increase in price ($182 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Toledo

Cheapest flights from Chicago to Toledo
Explore the most affordable flight options available from Chicago to Toledo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This eDestinos deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/34:45 pmORD - MAD
Nonstop8h 10mIberia
Wed 12/1011:35 amMAD - ORD
Nonstop9h 55mIberia
Deal found 9/14$365
This oojo deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:10 pmORD - MAD
1 stop15h 00mTAP AIR PORTUGAL
Thu 11/209:10 pmMAD - ORD
1 stop25h 05mTAP AIR PORTUGAL
Deal found 9/13$375
This oojo deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:10 pmORD - MAD
1 stop21h 20mTAP AIR PORTUGAL
Fri 11/217:40 amMAD - ORD
1 stop14h 35mTAP AIR PORTUGAL
Deal found 9/14$376
This Flightnetwork deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/28:25 pmORD - MAD
1 stop20h 05mTAP AIR PORTUGAL
Tue 11/116:00 pmMAD - ORD
1 stop28h 00mTAP AIR PORTUGAL
Deal found 9/14$380
This FlightHub deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:15 pmORD - MAD
1 stop10h 50mTAP AIR PORTUGAL
Sat 11/229:10 pmMAD - ORD
1 stop24h 35mTAP AIR PORTUGAL
Deal found 9/13$381
This oojo deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/57:10 pmORD - MAD
1 stop18h 10mTAP AIR PORTUGAL
Wed 11/127:40 amMAD - ORD
1 stop14h 20mTAP AIR PORTUGAL
Deal found 9/14$382
This FlightHub deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:10 pmORD - MAD
1 stop18h 10mTAP AIR PORTUGAL
Wed 11/197:40 amMAD - ORD
1 stop14h 20mTAP AIR PORTUGAL
Deal found 9/15$387
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amMDW - MAD
2 stops19h 00mDelta
Wed 12/1011:15 amMAD - MDW
1 stop19h 17mDelta
Deal found 9/15$443
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/196:00 amMDW - MAD
1 stop20h 35mKLM
Tue 10/287:05 amMAD - MDW
2 stops32h 40mKLM
Deal found 9/15$445
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2012:48 pmMDW - MAD
1 stop13h 47mDelta
Wed 10/2911:00 amMAD - MDW
2 stops28h 45mDelta
Deal found 9/15$464
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amMDW - MAD
2 stops19h 00mDelta
Tue 12/96:00 amMAD - MDW
2 stops19h 00mDelta
Deal found 9/15$467
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/261:14 pmMDW - MAD
2 stops15h 56mDelta
Fri 12/1211:15 amMAD - MDW
1 stop19h 17mDelta
Deal found 9/15$470

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Toledo that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Chicago to Toledo that are best for you.

Fly from

Chicago

Fly to

Toledo

Route

Depart

Return

Price

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 11/12

7:10 pm-8:20 pm

1 stop18h 10m

Madrid Barajas

Thu 11/20

6:00 pm-3:15 pm

1 stop28h 15m

$376

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sat 10/25

5:55 pm-9:05 am

1 stop32h 10m

Madrid Barajas

Fri 11/7

1:35 pm-11:18 am

1 stop28h 43m

$416

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Mon 11/3

2:50 pm-8:55 am

1 stop11h 05m

Madrid Barajas

Tue 11/11

11:35 am-2:30 pm

Nonstop9h 55m

$428

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 12/3

7:15 am-8:00 am

1 stop17h 45m

Madrid Barajas

Tue 12/9

11:15 am-7:24 pm

2 stops15h 09m

$438

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sun 11/9

8:15 pm-8:00 am

2 stops52h 45m

Madrid Barajas

Mon 11/24

7:35 pm-4:20 pm

1 stop27h 45m

$444

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 11/12

10:35 pm-8:15 pm

1 stop14h 40m

Madrid Barajas

Wed 11/26

1:35 pm-2:39 pm

2 stops32h 04m

$456

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 11/12

10:30 am-11:30 am

2 stops18h 00m

Madrid Barajas

Thu 11/20

10:00 am-9:27 pm

1 stop18h 27m

$457

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 11/12

10:30 am-11:30 am

2 stops18h 00m

Madrid Barajas

Fri 11/21

10:00 am-9:27 pm

1 stop18h 27m

$457

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sun 11/9

12:50 pm-8:00 am

1 stop12h 10m

Madrid Barajas

Mon 11/24

1:35 pm-2:40 pm

2 stops32h 05m

$461

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Mon 10/20

9:42 am-9:35 am

1 stop16h 53m

Madrid Barajas

Wed 10/29

10:00 am-9:19 pm

2 stops17h 19m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 40 results
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Best time to book a flight from Chicago to Toledo

Have a flexible travel schedule? Discover the best time to fly to Toledo from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Toledo?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Toledo. Price data was last updated on September 12, 2025.

The price you pay for your flight from Chicago to Toledo may vary depending on when you book. For the best chance of a lower fare, look to book 67 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Toledo?

Currently, November is the cheapest month in which you can book a flight from Chicago to Toledo (average of $543). Flying from Chicago to Toledo in June is currently the most expensive (average of $1,054). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to TO9?

Find hourly flight availability from Chicago to Toledo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Toledo as you normally would.

What is the cheapest day to fly from Chicago to Toledo?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Toledo. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Toledo flight should consider departing on Wednesday mornings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Toledo

Explore weekly flight availability from Chicago to Toledo. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2025.

The most flights from CHI to TO9 are scheduled on a Monday (11 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (11 on average).

Reviews of airlines servicing Toledo

Get insights into the airlines that provide service to Toledo. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Toledo. Reviews last updated September 15, 2025.
Peruse reviews from past customers who have flown with Finnair, American Airlines, and TAP AIR PORTUGAL from Chicago to Toledo to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Finnair
7.6
Good
1,323 reviews

Entertainment

6.9

Boarding

7.6

Crew

8.1

Food

6.7

Overall

7.6

Comfort

7.5

Reviews

1 / 20
6.0
Good

Matt,May 2025

LHR - MIA

Difficult to say what I liked, cabin crew very miserable, looked like they were sick of the job and it was their 50th flight if the day, long wait between drinks and food was somewhat very budget. We did travel in economy but with such a long flight you'd expect this type of service with Ryanair for a two/three hour flight to benidorm, not 8 hours over the Altantic.. entertainment was limited with films and difficult to hear even with headphones on. I think the pilot spoke once and I couldn't hear him over the noise in the cabin. I'd say to say you get what you pay for but my opinion I've flown with a much better airlines. Sorry...you dud ask :(
Finnair
7.6
Good
1,323 reviews
Finnair
7.6
Good
1,323 reviews

Entertainment

6.9

Boarding

7.6

Crew

8.1

Food

6.7

Overall

7.6

Comfort

7.5

Reviews

1 / 20
6.0
Good

Matt,May 2025

LHR - MIA

Difficult to say what I liked, cabin crew very miserable, looked like they were sick of the job and it was their 50th flight if the day, long wait between drinks and food was somewhat very budget. We did travel in economy but with such a long flight you'd expect this type of service with Ryanair for a two/three hour flight to benidorm, not 8 hours over the Altantic.. entertainment was limited with films and difficult to hear even with headphones on. I think the pilot spoke once and I couldn't hear him over the noise in the cabin. I'd say to say you get what you pay for but my opinion I've flown with a much better airlines. Sorry...you dud ask :(
American Airlines
7.2
Good
10,000 reviews
Finnair
7.6
Good
1,323 reviews

Entertainment

6.9

Boarding

7.6

Crew

8.1

Food

6.7

Overall

7.6

Comfort

7.5

Reviews

1 / 20
6.0
Good

Matt,May 2025

LHR - MIA

Difficult to say what I liked, cabin crew very miserable, looked like they were sick of the job and it was their 50th flight if the day, long wait between drinks and food was somewhat very budget. We did travel in economy but with such a long flight you'd expect this type of service with Ryanair for a two/three hour flight to benidorm, not 8 hours over the Altantic.. entertainment was limited with films and difficult to hear even with headphones on. I think the pilot spoke once and I couldn't hear him over the noise in the cabin. I'd say to say you get what you pay for but my opinion I've flown with a much better airlines. Sorry...you dud ask :(
TAP AIR PORTUGAL
7.1
Good
1,975 reviews
Finnair
7.6
Good
1,323 reviews

Entertainment

6.9

Boarding

7.6

Crew

8.1

Food

6.7

Overall

7.6

Comfort

7.5

Reviews

1 / 20
6.0
Good

Matt,May 2025

LHR - MIA

Difficult to say what I liked, cabin crew very miserable, looked like they were sick of the job and it was their 50th flight if the day, long wait between drinks and food was somewhat very budget. We did travel in economy but with such a long flight you'd expect this type of service with Ryanair for a two/three hour flight to benidorm, not 8 hours over the Altantic.. entertainment was limited with films and difficult to hear even with headphones on. I think the pilot spoke once and I couldn't hear him over the noise in the cabin. I'd say to say you get what you pay for but my opinion I've flown with a much better airlines. Sorry...you dud ask :(
Iberia
7.0
Good
2,924 reviews
Finnair
7.6
Good
1,323 reviews

Entertainment

6.9

Boarding

7.6

Crew

8.1

Food

6.7

Overall

7.6

Comfort

7.5

Reviews

1 / 20
6.0
Good

Matt,May 2025

LHR - MIA

Difficult to say what I liked, cabin crew very miserable, looked like they were sick of the job and it was their 50th flight if the day, long wait between drinks and food was somewhat very budget. We did travel in economy but with such a long flight you'd expect this type of service with Ryanair for a two/three hour flight to benidorm, not 8 hours over the Altantic.. entertainment was limited with films and difficult to hear even with headphones on. I think the pilot spoke once and I couldn't hear him over the noise in the cabin. I'd say to say you get what you pay for but my opinion I've flown with a much better airlines. Sorry...you dud ask :(
British Airways
6.7
Okay
7,361 reviews
Finnair
7.6
Good
1,323 reviews

Entertainment

6.9

Boarding

7.6

Crew

8.1

Food

6.7

Overall

7.6

Comfort

7.5

Reviews

1 / 20
6.0
Good

Matt,May 2025

LHR - MIA

Difficult to say what I liked, cabin crew very miserable, looked like they were sick of the job and it was their 50th flight if the day, long wait between drinks and food was somewhat very budget. We did travel in economy but with such a long flight you'd expect this type of service with Ryanair for a two/three hour flight to benidorm, not 8 hours over the Altantic.. entertainment was limited with films and difficult to hear even with headphones on. I think the pilot spoke once and I couldn't hear him over the noise in the cabin. I'd say to say you get what you pay for but my opinion I've flown with a much better airlines. Sorry...you dud ask :(

Related info for your journey

Find useful and relevant information for your journey from Chicago to Toledo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Toledo?

    Departing from Chicago to Toledo will take you 18h 10m. There are 4188 mi between Chicago and Toledo. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Toledo one-way?

    For one-way options, check prices for TAP AIR PORTUGAL. According to our data, you can fly for as low as $220. Users have also found prices from $374 and $374 on Delta and KLM, respectively.

  • What are the most reliable airlines from Chicago to Toledo?

    The top 3 most reliable airlines when flying from Chicago to Toledo are American Airlines (48%), Finnair (48%) and Iberia (48%).

  • What are the cheapest flights from Chicago to Toledo?

    On average you can expect to pay $1,310 for a flight from Chicago to Toledo. The cheapest flight overall is $395 while the most popular route, (Chicago O'Hare Intl - Madrid Barajas) is currently priced at $373.

  • Can I find deals for flights from Chicago to Toledo that include hotel bookings?

    Yes. In addition to deals on Chicago to Toledo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Toledo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Toledo.

  • Can I find deals for business class flights from Chicago to Toledo?

    Yes. Cheapflights offers flight deals from Chicago to Toledo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Toledo?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Toledo (average of $543). Flying from Chicago to Toledo in June is currently the most expensive (average of $1,054). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Toledo

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Madrid flights
Midway to Madrid flights
St. Louis to Madrid flights
O'Hare Intl to Alicante flights

Top 10 airlines flying from Chicago to Toledo

Discover the top 10 airlines that operate flights from Chicago to Toledo. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$203FlexibilityNo cancel feeOn-time62%
TAP AIR PORTUGALCheapest$288Average$537FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$366Average$635FlexibilityNo cancel feeOn-time67%
FinnairCheapest$373Average$615FlexibilityNo cancel feeOn-time76%
Scandinavian AirlinesCheapest$387Average$465FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$427Average$727FlexibilityNo cancel feeOn-time69%
British AirwaysCheapest$438Average$633FlexibilityNo cancel feeOn-time70%
IberiaCheapest$455Average$732FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$474Average$742FlexibilityNo cancel feeOn-timeN/A
KLMCheapest$482Average$740FlexibilityNo cancel feeOn-time75%

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