HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Toledo

$355+ 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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAD
May 10 — May 171
Sat 5/10
Sat 5/17
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Toledo with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Toledo are usually found in February or January, booked 86 days in advance, depart on a Wednesday or Sunday and return on a Thursday

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 May 5, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$626
(Gurufare)

One-way from

$355
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$957
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. 25% potential increase in price ($247 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
Search Deals

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 May 5, 2025.

This Delta deal was found by Cheapflights users on 5/4. 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.
Sat 9/135:59 pmMDW - MAD
2 stops14h 36mDelta
Wed 9/2410:05 amMAD - MDW
1 stop18h 39mDelta
Deal found 5/4$635
This SWISS deal was found by Cheapflights users on 5/4. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/292:20 pmORD - MAD
1 stop21h 25mSWISS
Mon 9/87:35 pmMAD - ORD
1 stop27h 20mSWISS
Deal found 5/4$635
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/294:30 pmORD - MAD
Nonstop8h 25mIberia
Sun 9/74:40 pmMAD - ORD
Nonstop8h 35mIberia
Deal found 5/4$636
This Delta deal was found by Cheapflights users on 5/4. 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.
Mon 6/26:18 pmORD - MAD
1 stop30h 32mDelta
Thu 6/1212:40 pmMAD - ORD
2 stops14h 47mDelta
Deal found 5/4$637
This United Airlines deal was found by Cheapflights users on 5/3. 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 5/106:15 pmORD - MAD
1 stop15h 00mUnited Airlines
Sat 5/1712:45 pmMAD - ORD
2 stops17h 33mUnited Airlines
Deal found 5/3$638
This FlightHub deal was found by Cheapflights users on 5/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/218:25 pmORD - MAD
2 stops52h 40mMultiple Airlines
Sun 11/307:35 pmMAD - ORD
1 stop27h 40mMultiple Airlines
Deal found 5/4$639
This Gurufare deal was found by Cheapflights users on 5/4. 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.
Tue 5/138:30 pmORD - MAD
1 stop13h 05mBritish Airways
Sat 6/74:40 pmMAD - ORD
Nonstop9h 10mBritish Airways
Deal found 5/4$644
This Air Canada deal was found by Cheapflights users on 5/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/278:40 amORD - MAD
2 stops16h 40mAir Canada
Sun 9/712:45 pmMAD - ORD
2 stops17h 40mAir Canada
Deal found 5/5$647
This TAP AIR PORTUGAL deal was found by Cheapflights users on 5/4. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/86:00 pmORD - MAD
1 stop11h 40mTAP AIR PORTUGAL
Sat 10/1111:05 amMAD - ORD
1 stop12h 25mTAP AIR PORTUGAL
Deal found 5/4$654
This KLM deal was found by Cheapflights users on 5/5. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2410:35 amMDW - MAD
1 stop16h 00mKLM
Mon 9/810:05 amMAD - MDW
1 stop13h 18mKLM
Deal found 5/5$667
This Virgin Atlantic deal was found by Cheapflights users on 5/4. 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 Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/159:30 amMDW - MAD
2 stops17h 05mVirgin Atlantic
Fri 8/2210:05 amMAD - MDW
1 stop18h 42mVirgin Atlantic
Deal found 5/4$687
This StudentUniverse deal was found by Cheapflights users on 5/4. 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 StudentUniverse is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/54:30 pmORD - MAD
Nonstop8h 25mFinnair
Mon 5/124:40 pmMAD - ORD
Nonstop9h 10mFinnair
Deal found 5/4$688

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 May 5, 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

MDW - MAD

MDWMAD

Chicago Midway

Thu 7/31

6:20 pm-4:45 pm

2 stops15h 25m

Madrid Barajas

Sat 8/30

10:05 am-9:47 pm

1 stop18h 42m

$635

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sat 7/12

8:25 pm-8:20 am

1 stop28h 55m

Madrid Barajas

Mon 7/21

11:45 am-6:15 pm

1 stop13h 30m

$635

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sat 6/21

4:59 pm-6:00 am

1 stop30h 01m

Madrid Barajas

Sun 9/7

11:35 am-2:15 pm

Nonstop9h 40m

$636

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Mon 6/2

6:18 pm-7:50 am

1 stop30h 32m

Madrid Barajas

Thu 6/12

12:40 pm-8:27 pm

2 stops14h 47m

$637

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sat 5/10

6:15 pm-4:15 pm

1 stop15h 00m

Madrid Barajas

Sun 5/18

12:45 pm-7:34 am

2 stops25h 49m

$638

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sun 5/11

4:20 pm-11:00 am

2 stops35h 40m

Madrid Barajas

Sat 5/17

11:45 am-1:20 pm

2 stops32h 35m

$639

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Mon 7/21

10:35 pm-1:25 pm

Nonstop7h 50m

Madrid Barajas

Sat 8/2

9:50 pm-2:30 pm

1 stop23h 40m

$642

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Mon 6/9

6:15 pm-6:40 am

2 stops29h 25m

Madrid Barajas

Fri 7/18

12:45 pm-7:55 am

2 stops26h 10m

$651

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sun 8/3

4:30 pm-7:55 am

Nonstop8h 25m

Madrid Barajas

Mon 8/11

11:35 am-2:15 pm

Nonstop9h 40m

$654

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Thu 5/8

6:35 pm-6:45 pm

1 stop17h 10m

Madrid Barajas

Sun 6/8

7:35 pm-3:55 pm

1 stop27h 20m

$664

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Showing 1-10 of 36 results
1
2
3
4

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 May 2, 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 86 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 $1,086). 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 May 5, 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. Thursday 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 May 5, 2025.

The most flights from CHI to TO9 are scheduled on a Friday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Toledo by month

Plan your trip to Toledo by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Toledo ranges from 0.4 - 2.4 inches per month. November is typically the wettest month, when rainfall can reach 2.4 in. July is typically the driest time to visit Toledo when rainfall is around 0.4 in.

Temperature in Toledo by month

Plan your trip to Toledo by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Toledo, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

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 May 5, 2025.
To help decide which airline to fly from Chicago to Toledo, see what other customers have to say about Delta, KLM and Finnair. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,941 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,941 reviews
Delta
8.0
Very good
7,941 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,337 reviews
Delta
8.0
Very good
7,941 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Finnair
7.6
Good
1,276 reviews
Delta
8.0
Very good
7,941 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
SWISS
7.5
Good
1,589 reviews
Delta
8.0
Very good
7,941 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air France
7.4
Good
1,448 reviews
Delta
8.0
Very good
7,941 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

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

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $379. Users have also found prices from $382 and $387 on TAP AIR PORTUGAL and SWISS, 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 (72%), Finnair (72%) and Iberia (72%).

  • What are the cheapest flights from Chicago to Toledo?

    On average you can expect to pay $1,717 for a flight from Chicago to Toledo. The cheapest flight overall is $463 while the most popular route, (Chicago O'Hare Intl - Madrid Barajas) is currently priced at $391.

  • 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 $1,086). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
O'Hare Intl to Alicante flights
St. Louis to Madrid 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 May 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$355Average$549FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$384Average$495FlexibilityNo cancel feeOn-time77%
FinnairCheapest$456Average$648FlexibilityNo cancel feeOn-time76%
IberiaCheapest$461Average$794FlexibilityNo cancel feeOn-time77%
DeltaCheapest$465Average$790FlexibilityNo cancel feeOn-timeN/A
KLMCheapest$477Average$687FlexibilityNo cancel feeOn-time75%
British AirwaysCheapest$479Average$669FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$480Average$700FlexibilityNo cancel feeOn-time67%
Aer LingusCheapest$484Average$642FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$490Average$798FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.