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Toledo

$333+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAD
Feb 21 — Feb 281
Sat 2/21
Sat 2/28
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Toledo are usually found in February or October, booked 89 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap 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 January 22, 2026.

This United Airlines deal was found by Cheapflights users on 1/22. 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.
Tue 3/1012:50 pm
ORD
-
MAD
1 stop12h 10m
United Airlines
Mon 3/238:25 am
MAD
-
ORD
1 stop33h 45m
United Airlines
Deal found 1/22$474
This British Airways deal was found by Cheapflights users on 1/21. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:15 pm
ORD
-
MAD
Nonstop8h 15m
British Airways
Sun 10/1111:35 am
MAD
-
ORD
Nonstop9h 40m
British Airways
Deal found 1/21$475
This oojo deal was found by Cheapflights users on 1/19. 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.
Fri 2/274:10 pm
ORD
-
MAD
2 stops19h 25m
British Airways
Fri 3/612:40 pm
MAD
-
ORD
1 stop19h 15m
British Airways
Deal found 1/19$476
This Air Canada deal was found by Cheapflights users on 1/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/187:15 am
ORD
-
MAD
1 stop17h 45m
Air Canada
Wed 3/256:25 am
MAD
-
ORD
2 stops19h 45m
Air Canada
Deal found 1/21$477
This oojo deal was found by Cheapflights users on 1/20. 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.
Fri 2/205:10 pm
ORD
-
MAD
1 stop18h 25m
British Airways
Tue 2/241:00 pm
MAD
-
ORD
1 stop18h 06m
British Airways
Deal found 1/20$478
This Finnair deal was found by Cheapflights users on 1/21. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/289:00 pm
ORD
-
MAD
1 stop11h 50m
Multiple Airlines
Sat 10/1012:00 pm
MAD
-
ORD
1 stop14h 35m
Multiple Airlines
Deal found 1/21$479
This oojo deal was found by Cheapflights users on 1/21. 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.
Thu 2/195:10 pm
ORD
-
MAD
1 stop11h 45m
British Airways
Mon 3/28:50 pm
MAD
-
ORD
1 stop24h 00m
British Airways
Deal found 1/21$480
This Air France deal was found by Cheapflights users on 1/22. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/210:49 am
MDW
-
MAD
1 stop15h 26m
Multiple Airlines
Wed 3/1110:05 am
MAD
-
MDW
1 stop18h 26m
Multiple Airlines
Deal found 1/22$481
This Air Canada deal was found by Cheapflights users on 1/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:25 am
ORD
-
MAD
2 stops16h 15m
Air Canada
Fri 10/912:45 pm
MAD
-
ORD
2 stops14h 31m
Air Canada
Deal found 1/21$481
This Air France deal was found by Cheapflights users on 1/20. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/112:45 pm
MDW
-
MAD
1 stop13h 30m
Multiple Airlines
Tue 3/1010:05 am
MAD
-
MDW
1 stop18h 26m
Multiple Airlines
Deal found 1/20$482
This oojo deal was found by Cheapflights users on 1/22. 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.
Sat 4/116:40 pm
ORD
-
MAD
1 stop27h 50m
British Airways
Sun 4/191:35 pm
MAD
-
ORD
Nonstop9h 25m
British Airways
Deal found 1/22$482
This United Airlines deal was found by Cheapflights users on 1/21. 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.
Sun 3/227:00 am
ORD
-
MAD
2 stops18h 00m
United Airlines
Tue 4/215:55 am
MAD
-
ORD
1 stop14h 00m
United Airlines
Deal found 1/21$483

Find flight deals from Chicago to Toledo

Keep the following information in mind while searching for Chicago to Toledo flight deals. Data was last updated January 22, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$474
(United Airlines)

One-way from

$333
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$600
Provider with most accurate pricing for Chicago (CHI)-Madrid Barajas flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Madrid Barajas flights.
Search Deals
From Chicago (CHI) to Toledo
Search Deals
One-way flight from Chicago (CHI) to Toledo
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 22, 2026.
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

Tue 2/24

5:40 pm-8:50 am

Nonstop8h 10m

Madrid Barajas

Sat 3/7

12:00 pm-2:55 pm

Nonstop9h 55m

$475

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 2/25

9:45 pm-8:05 pm

1 stop15h 20m

Madrid Barajas

Sun 3/1

1:00 pm-12:16 am

1 stop18h 16m

$481

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Mon 3/16

7:00 am-9:15 am

2 stops20h 15m

Madrid Barajas

Mon 3/23

8:25 am-12:10 pm

1 stop33h 45m

$485

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Tue 4/28

10:15 pm-1:30 pm

Nonstop8h 15m

Madrid Barajas

Tue 5/12

11:35 am-2:15 pm

Nonstop9h 40m

$487

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 3/1

10:49 am-9:15 am

1 stop15h 26m

Madrid Barajas

Tue 3/10

10:05 am-10:31 pm

1 stop18h 26m

$489

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 3/9

1:10 pm-11:30 am

2 stops16h 20m

Madrid Barajas

Wed 3/18

10:05 am-10:31 pm

1 stop18h 26m

$493

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 2/25

1:49 pm-11:30 am

2 stops14h 41m

Madrid Barajas

Wed 3/4

11:15 am-5:45 pm

1 stop13h 30m

$493

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 4/13

6:34 pm-4:45 pm

2 stops15h 11m

Madrid Barajas

Wed 4/29

12:40 pm-10:29 pm

1 stop16h 49m

$493

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 4/13

1:10 pm-12:15 pm

2 stops16h 05m

Madrid Barajas

Wed 4/29

12:40 pm-10:29 pm

2 stops16h 49m

$494

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Fri 4/17

2:25 pm-8:05 am

1 stop10h 40m

Madrid Barajas

Thu 4/23

10:50 am-7:22 pm

2 stops15h 32m

$494

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 45 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 January 16, 2026.

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 89 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 January 22, 2026.

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.

How much does it cost to fly round-trip from Chicago to Toledo?

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 January 22, 2026.
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
1,353 reviews

Comfort

7.5

Entertainment

6.9

Food

6.7

Overall

7.6

Crew

8.2

Boarding

7.7

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
1,353 reviews
Finnair
7.6
Good
1,353 reviews

Comfort

7.5

Entertainment

6.9

Food

6.7

Overall

7.6

Crew

8.2

Boarding

7.7

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
11,177 reviews
Finnair
7.6
Good
1,353 reviews

Comfort

7.5

Entertainment

6.9

Food

6.7

Overall

7.6

Crew

8.2

Boarding

7.7

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
2,126 reviews
Finnair
7.6
Good
1,353 reviews

Comfort

7.5

Entertainment

6.9

Food

6.7

Overall

7.6

Crew

8.2

Boarding

7.7

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
3,097 reviews
Finnair
7.6
Good
1,353 reviews

Comfort

7.5

Entertainment

6.9

Food

6.7

Overall

7.6

Crew

8.2

Boarding

7.7

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
7,690 reviews
Finnair
7.6
Good
1,353 reviews

Comfort

7.5

Entertainment

6.9

Food

6.7

Overall

7.6

Crew

8.2

Boarding

7.7

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 8h 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 $170. Users have also found prices from $265 and $357 on Scandinavian Airlines and Finnair, 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 (64%), Qatar Airways (64%) and Alaska Airlines (64%).

  • What are the cheapest flights from Chicago to Toledo?

    On average you can expect to pay $1,063 for a flight from Chicago to Toledo. The cheapest flight overall is $248 while the most popular route, (Chicago O'Hare Intl - Madrid Barajas) is currently priced at $392.

  • 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 January 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$203FlexibilityNo cancel feeOn-time62%
TAP AIR PORTUGALCheapest$288Average$547FlexibilityNo cancel feeOn-timeN/A
FinnairCheapest$355Average$635FlexibilityNo cancel feeOn-time76%
Air CanadaCheapest$366Average$709FlexibilityNo cancel feeOn-time67%
Scandinavian AirlinesCheapest$387Average$515FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$427Average$635FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$440Average$688FlexibilityNo cancel feeOn-time69%
IberiaCheapest$458Average$762FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$474Average$743FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$479Average$837FlexibilityNo cancel feeOn-time76%

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