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$212+ Cheap flights from Toledo, OH (TOL) to Chicago (CHI)

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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
TOL — CHI
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Toledo to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Toledo (TOL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$395
(Kiwi.com)

One-way from

$212
(Kiwi.com)

Popular in

June

Cheapest in

October

Average price

$144
Provider with most accurate pricing for Toledo Express-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toledo Express-Chicago (CHI) flights.
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From Toledo Express to Chicago (CHI)
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One-way flight from Toledo Express to Chicago (CHI)
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Highest demand for flights based on searches. 22% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Toledo to Chicago

Cheapest flights from Toledo to Chicago
Explore the most affordable flight options available from Toledo to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Tue 11/259:04 pmTOL - ORD
2 stops28h 04mMultiple Airlines
Mon 12/16:48 amORD - TOL
1 stop12h 23mMultiple Airlines
Deal found 10/27$395
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Mon 11/310:15 amTOL - ORD
1 stop13h 51mMultiple Airlines
Wed 11/512:37 pmORD - TOL
2 stops28h 23mMultiple Airlines
Deal found 10/27$589

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toledo to Chicago 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 October 29, 2025.
Use the filters below to find and compare flights from Toledo to Chicago that are best for you.

Fly from

Toledo

Fly to

Chicago

Route

Depart

Return

Price

ToledoChicago

TOL - ORD

TOLORD

Toledo Express

Tue 11/25

9:04 pm-12:08 am

2 stops28h 04m

Chicago O'Hare Intl

Mon 12/1

6:48 am-8:11 pm

1 stop12h 23m

$395

ToledoChicago

TOL - ORD

TOLORD

Toledo Express

Fri 12/12

12:16 pm-8:01 pm

3 stops32h 45m

$212

ToledoChicago

TOL - ORD

TOLORD

Toledo Express

Fri 11/7

10:45 am-11:29 pm

3 stops37h 44m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Compare providers for flights from Toledo to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Toledo to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Toledo, Ohio-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Toledo, Ohio-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Toledo, Ohio-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toledo, Ohio-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toledo, Ohio-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Toledo to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Toledo 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 Toledo to Chicago

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

Currently, November is the cheapest month in which you can book a flight from Toledo, Ohio to Chicago (average of $69). Flying from Toledo, Ohio to Chicago in January is currently the most expensive (average of $137). 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.

Related info for your journey

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

  • What airport do you fly from for flights from Toledo to Chicago?

    Located just 13.9 mi from the city center, Toledo Express is the airport most travelers will use when flying to Chicago from Toledo. Booking flights from Express (TOL) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 0 different airlines.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Toledo to Chicago 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 Toledo, Ohio to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Toledo, Ohio to Chicago (average of $69). Flying from Toledo, Ohio to Chicago in January is currently the most expensive (average of $137). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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