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Toledo

$218+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAD
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$447
(Delta)

One-way from

$218
(Air France)

Popular in

December

Cheapest in

February

Average price

$629
Provider with most accurate pricing for Chicago (CHI)-Madrid Barajas flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Madrid Barajas flights.
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From Chicago (CHI) to Toledo
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One-way flight from Chicago (CHI) to Toledo
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Highest demand for flights based on searches. 3% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 6, 2025.

This Delta deal was found by Cheapflights users on 11/6. 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 11/179:51 amORD - MAD
1 stop16h 24mDelta
Wed 12/36:00 amMAD - ORD
1 stop16h 10mDelta
Deal found 11/6$447
This Mytrip deal was found by Cheapflights users on 11/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:05 amORD - MAD
1 stop17h 55mAir Canada
Wed 12/106:25 amMAD - ORD
2 stops15h 30mAir Canada
Deal found 11/5$451
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/172:00 pmORD - MAD
2 stops14h 00mAir Canada
Wed 12/36:25 amMAD - ORD
2 stops15h 30mAir Canada
Deal found 11/6$452
This Delta deal was found by Cheapflights users on 11/6. 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.
Tue 11/185:23 amORD - MAD
1 stop20h 52mDelta
Tue 12/21:05 pmMAD - ORD
1 stop32h 15mDelta
Deal found 11/6$453
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/177:05 amORD - MAD
1 stop20h 55mMultiple Airlines
Wed 12/36:25 amMAD - ORD
2 stops15h 30mMultiple Airlines
Deal found 11/6$455
This Gotogate deal was found by Cheapflights users on 11/5. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/179:50 pmORD - MAD
1 stop18h 45mMultiple Airlines
Wed 11/265:55 amMAD - ORD
2 stops16h 00mMultiple Airlines
Deal found 11/5$456
This Delta deal was found by Cheapflights users on 11/6. 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.
Tue 11/1810:35 amORD - MAD
2 stops17h 55mDelta
Thu 12/411:15 amMAD - ORD
1 stop19h 46mDelta
Deal found 11/6$457
This Gurufare deal was found by Cheapflights users on 11/4. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1010:29 amORD - MAD
1 stop12h 16mBritish Airways
Thu 11/2011:35 amMAD - ORD
Nonstop9h 55mBritish Airways
Deal found 11/4$458
This Delta deal was found by Cheapflights users on 11/6. 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 11/176:45 amORD - MAD
2 stops18h 15mDelta
Tue 12/211:00 amMAD - ORD
1 stop34h 20mDelta
Deal found 11/6$460
This United Airlines deal was found by Cheapflights users on 11/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2911:59 pmORD - MAD
1 stop25h 06mUnited Airlines
Wed 12/101:35 pmMAD - ORD
1 stop25h 25mUnited Airlines
Deal found 11/4$461
This Delta deal was found by Cheapflights users on 11/4. 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.
Sun 12/710:49 amMDW - MAD
1 stop15h 26mDelta
Tue 12/166:00 amMAD - MDW
2 stops19h 00mDelta
Deal found 11/4$462
This Delta deal was found by Cheapflights users on 11/5. 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 11/267:00 amORD - MAD
1 stop18h 00mDelta
Fri 12/126:00 amMAD - ORD
2 stops19h 27mDelta
Deal found 11/5$462

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 November 6, 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

Sun 2/1

8:25 pm-8:20 pm

1 stop16h 55m

Madrid Barajas

Sun 2/8

7:40 am-2:45 pm

1 stop14h 05m

$460

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sun 2/1

5:10 pm-12:40 pm

1 stop12h 30m

Madrid Barajas

Sun 2/8

12:00 pm-2:55 pm

Nonstop9h 55m

$470

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 11/12

3:50 pm-4:05 pm

2 stops17h 15m

Madrid Barajas

Thu 11/20

11:15 am-9:56 pm

1 stop17h 41m

$470

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Fri 1/2

5:40 pm-8:50 am

Nonstop8h 10m

Madrid Barajas

Wed 1/14

12:00 pm-2:55 pm

Nonstop9h 55m

$473

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sun 11/23

2:50 pm-8:55 am

1 stop11h 05m

Madrid Barajas

Sun 12/7

12:00 pm-2:55 pm

Nonstop9h 55m

$478

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sun 2/1

2:50 pm-8:55 am

1 stop11h 05m

Madrid Barajas

Sun 2/8

12:40 pm-7:50 pm

1 stop14h 10m

$479

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Tue 11/18

8:55 am-8:00 am

2 stops16h 05m

Madrid Barajas

Thu 11/27

6:25 am-12:10 pm

1 stop12h 45m

$480

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 11/12

5:55 pm-4:40 pm

1 stop15h 45m

Madrid Barajas

Wed 11/19

5:55 am-8:05 pm

1 stop21h 10m

$480

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 11/12

5:55 pm-4:40 pm

1 stop15h 45m

Madrid Barajas

Thu 11/20

6:00 am-2:55 pm

2 stops15h 55m

$481

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Fri 12/5

1:05 pm-9:15 am

1 stop13h 10m

Madrid Barajas

Thu 12/11

11:15 am-11:47 pm

1 stop19h 32m

$488

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 42 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 October 31, 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, September is the cheapest month in which you can book a flight from Chicago to Toledo (average of $289). Flying from Chicago to Toledo in June is currently the most expensive (average of $641). 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 November 6, 2025.

One of the essential ways to save on airfare from Chicago to Toledo is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight at noon could potentially save you up to 18% on airfare.

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 Monday mornings when fares are most often at their lowest. Saturday mornings 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 November 6, 2025.

The most flights from CHI to TO9 are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 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 November 6, 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
1,335 reviews

Food

6.7

Entertainment

6.9

Comfort

7.4

Crew

8.1

Boarding

7.6

Overall

7.6

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
1,335 reviews
Finnair
7.6
Good
1,335 reviews

Food

6.7

Entertainment

6.9

Comfort

7.4

Crew

8.1

Boarding

7.6

Overall

7.6

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
11,040 reviews
Finnair
7.6
Good
1,335 reviews

Food

6.7

Entertainment

6.9

Comfort

7.4

Crew

8.1

Boarding

7.6

Overall

7.6

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
2,047 reviews
Finnair
7.6
Good
1,335 reviews

Food

6.7

Entertainment

6.9

Comfort

7.4

Crew

8.1

Boarding

7.6

Overall

7.6

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
3,007 reviews
Finnair
7.6
Good
1,335 reviews

Food

6.7

Entertainment

6.9

Comfort

7.4

Crew

8.1

Boarding

7.6

Overall

7.6

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
7,500 reviews
Finnair
7.6
Good
1,335 reviews

Food

6.7

Entertainment

6.9

Comfort

7.4

Crew

8.1

Boarding

7.6

Overall

7.6

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 12h 30m. 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 most reliable airlines from Chicago to Toledo?

    The top 3 most reliable airlines when flying from Chicago to Toledo are American Airlines (62%), Finnair (62%) and Iberia (62%).

  • What are the cheapest flights from Chicago to Toledo?

    On average you can expect to pay $1,237 for a flight from Chicago to Toledo. The cheapest flight overall is $414 while the most popular route, (Chicago O'Hare Intl - Madrid Barajas) is currently priced at $320.

  • 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, September is the cheapest month in which you can book a flight from Chicago to Toledo (average of $289). Flying from Chicago to Toledo in June is currently the most expensive (average of $641). 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$203FlexibilityNo cancel feeOn-time62%
TAP AIR PORTUGALCheapest$288Average$525FlexibilityNo cancel feeOn-timeN/A
FinnairCheapest$364Average$632FlexibilityNo cancel feeOn-time76%
Air CanadaCheapest$366Average$647FlexibilityNo cancel feeOn-time67%
Scandinavian AirlinesCheapest$387Average$491FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$433Average$666FlexibilityNo cancel feeOn-time69%
British AirwaysCheapest$438Average$627FlexibilityNo cancel feeOn-time70%
IberiaCheapest$461Average$737FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$474Average$694FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$479Average$855FlexibilityNo cancel feeOn-time76%

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