Toledo

$331+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAD
Jul 9 — Jul 161
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Cheapflights Tip: The best prices from Chicago to Toledo are usually found in October or February, booked 73 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 June 9, 2026.

This Delta deal was found by Cheapflights users on 6/8. 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 9/15:45 pm
MDW
-
MAD
2 stops15h 40m
Delta
Tue 9/86:00 am
MAD
-
MDW
2 stops19h 05m
Delta
Deal found 6/8$824
This Justfly.com deal was found by Cheapflights users on 6/6. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/225:10 pm
ORD
-
MAD
1 stop11h 45m
British Airways
Wed 11/251:00 pm
MAD
-
ORD
Nonstop9h 10m
British Airways
Deal found 6/6$824
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Fri 8/287:25 pm
ORD
-
MAD
2 stops22h 50m
Multiple Airlines
Tue 9/88:10 am
MAD
-
ORD
1 stop20h 10m
Multiple Airlines
Deal found 6/7$825
This Delta deal was found by Cheapflights users on 6/7. 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.
Fri 11/136:00 am
MDW
-
MAD
2 stops19h 00m
Delta
Sat 11/2111:55 am
MAD
-
MDW
1 stop17h 15m
Delta
Deal found 6/7$826
This Delta deal was found by Cheapflights users on 6/5. 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.
Fri 9/255:42 pm
ORD
-
MAD
2 stops16h 03m
Delta
Sun 10/42:35 pm
MAD
-
ORD
1 stop14h 47m
Delta
Deal found 6/5$826
This Delta deal was found by Cheapflights users on 6/5. 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 8/51:27 pm
MDW
-
MAD
2 stops15h 43m
Delta
Thu 8/209:50 am
MAD
-
MDW
2 stops15h 43m
Delta
Deal found 6/5$827
This FlightHub deal was found by Cheapflights users on 6/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/225:40 pm
ORD
-
MAD
Nonstop8h 10m
British Airways
Fri 11/271:00 pm
MAD
-
ORD
Nonstop9h 10m
British Airways
Deal found 6/6$827
This Delta deal was found by Cheapflights users on 6/8. 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 10/171:00 pm
MDW
-
MAD
2 stops13h 55m
Delta
Sat 10/246:00 am
MAD
-
MDW
2 stops17h 50m
Delta
Deal found 6/8$828
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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.
Thu 9/36:00 pm
ORD
-
MAD
1 stop14h 20m
TAP AIR PORTUGAL
Fri 9/187:40 am
MAD
-
ORD
1 stop15h 20m
TAP AIR PORTUGAL
Deal found 6/8$828
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:40 pm
ORD
-
MAD
Nonstop8h 10m
Multiple Airlines
Sun 11/297:40 am
MAD
-
ORD
1 stop14h 50m
Multiple Airlines
Deal found 6/6$829
This KAYAK deal was found by Cheapflights users on 6/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:20 pm
ORD
-
MAD
1 stop32h 10m
JetBlue
Mon 8/312:05 pm
MAD
-
ORD
1 stop27h 01m
JetBlue
Deal found 6/9$830
This Delta deal was found by Cheapflights users on 6/8. 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.
Thu 10/17:13 pm
MDW
-
MAD
2 stops14h 12m
Delta
Mon 10/129:50 am
MAD
-
MDW
1 stop13h 35m
Delta
Deal found 6/8$831

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 June 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$824
(Delta)

One-way from

$331
(KLM)

Popular in

June

Cheapest in

October

Average price

$1,113
Provider with most accurate pricing for Chicago (CHI)-Madrid Barajas flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Madrid Barajas flights.
From Chicago (CHI) to Toledo
One-way flight from Chicago (CHI) to Toledo
Highest demand for flights based on searches. 21% potential increase in price ($200 potential increase over avg. RT price).
Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
Average for round-trip flights in June 2026

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 June 9, 2026.
Use the filters below to find and compare flights from Chicago to Toledo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 9/27

10:48 am-12:15 pm

1 stop18h 27m

Madrid Barajas

Tue 10/6

9:50 am-4:25 pm

1 stop13h 35m

$842

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Thu 11/5

1:00 pm-5:10 pm

2 stops21h 10m

Madrid Barajas

Wed 11/11

7:40 am-3:30 pm

1 stop14h 50m

$857

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 9/2

6:00 pm-4:45 pm

2 stops15h 45m

Madrid Barajas

Mon 9/7

6:00 am-2:30 pm

1 stop15h 30m

$860
Quickest round-trip

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Thu 9/10

4:55 pm-8:20 am

Nonstop8h 25m

Madrid Barajas

Thu 9/17

10:15 am-5:50 pm

1 stop14h 35m

$862

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sat 11/7

9:00 am-8:00 am

2 stops16h 00m

Madrid Barajas

Sat 11/14

1:35 pm-12:41 pm

2 stops30h 06m

$867

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 8/17

10:54 am-12:15 pm

1 stop18h 21m

Madrid Barajas

Sat 8/22

9:50 am-10:36 pm

1 stop19h 46m

$874

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sun 8/16

6:00 am-12:15 pm

2 stops23h 15m

Madrid Barajas

Sun 8/23

9:50 am-6:28 pm

2 stops15h 38m

$878

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sun 8/2

7:17 pm-4:25 pm

2 stops14h 08m

Madrid Barajas

Sun 8/23

6:00 am-4:24 pm

2 stops17h 24m

$884

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Thu 11/5

8:55 am-9:15 am

2 stops17h 20m

Madrid Barajas

Mon 11/9

11:15 am-8:11 pm

2 stops15h 56m

$888

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Mon 8/24

7:55 am-6:20 am

1 stop15h 25m

Madrid Barajas

Wed 8/26

9:50 am-4:51 pm

1 stop14h 01m

$906

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/6

Showing 1-10 of 41 resultsSorted by cheapest first
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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

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 June 9, 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.

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 June 9, 2026.

The most flights from CHI to TO9 are scheduled on a Monday (10 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (5 on average).

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 June 9, 2026.
Peruse reviews from past customers who have flown with Finnair,TAP AIR PORTUGAL, andAmerican Airlines 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.

Food

6.7

Overall

7.7

Comfort

7.4

Entertainment

6.9

Crew

8.2

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

LAX - HEL

All crew members are really nice behavior. Devdutt also nice person.

Food

6.7

Overall

7.7

Comfort

7.4

Entertainment

6.9

Crew

8.2

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

LAX - HEL

All crew members are really nice behavior. Devdutt also nice person.

Food

6.7

Overall

7.7

Comfort

7.4

Entertainment

6.9

Crew

8.2

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

LAX - HEL

All crew members are really nice behavior. Devdutt also nice person.

Food

6.7

Overall

7.7

Comfort

7.4

Entertainment

6.9

Crew

8.2

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

LAX - HEL

All crew members are really nice behavior. Devdutt also nice person.

Food

6.7

Overall

7.7

Comfort

7.4

Entertainment

6.9

Crew

8.2

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

LAX - HEL

All crew members are really nice behavior. Devdutt also nice person.

Food

6.7

Overall

7.7

Comfort

7.4

Entertainment

6.9

Crew

8.2

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

LAX - HEL

All crew members are really nice behavior. Devdutt also nice person.

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 15h 45m. 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 $167. Users have also found prices from $289 and $325 on JetBlue and British Airways, 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 (56%), Finnair (56%) and Iberia (56%).

  • What are the cheapest flights from Chicago to Toledo?

    On average you can expect to pay $1,786 for a flight from Chicago to Toledo. The cheapest flight overall is $330 while the most popular route, (Chicago O'Hare Intl - Madrid Barajas) is currently priced at $562.

  • 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.

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.

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 June 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$203FlexibilityNo cancel feeOn-time62%
TAP AIR PORTUGALCheapest$288Average$542FlexibilityNo cancel feeOn-timeN/A
FinnairCheapest$353Average$647FlexibilityNo cancel feeOn-time76%
Air CanadaCheapest$366Average$560FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$376Average$654FlexibilityNo cancel feeOn-time69%
DeltaCheapest$393Average$602FlexibilityNo cancel feeOn-timeN/A
IberiaCheapest$416Average$741FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$423Average$667FlexibilityNo cancel feeOn-time70%
Scandinavian AirlinesCheapest$439Average$542FlexibilityNo cancel feeOn-time77%
American AirlinesCheapest$473Average$777FlexibilityNo cancel feeOn-time71%

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