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$255+ 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 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
TOL — CHI
Jun 3 — Jun 101
Wed 6/3
Wed 6/10
1 adult, Economy
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Cheap 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 May 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/43:42 pm
TOL
-
ORD
2 stops29h 09m
Multiple Airlines
Thu 5/75:30 pm
ORD
-
TOL
1 stop20h 22m
Multiple Airlines
Deal found 5/1$831

Find 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 May 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars
Provider with most accurate pricing for Toledo Express-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toledo Express-Chicago (CHI) flights.
Search Deals

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 May 4, 2026.
Use the filters below to find and compare flights from Toledo to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest one-way

ToledoChicago

TOL - ORD

TOLORD

Toledo Express

Sat 6/13

10:16 am-11:30 am

3 stops50h 14m

$255

ToledoChicago

TOL - ORD

TOLORD

Toledo Express

Wed 6/10

5:40 pm-8:03 am

3 stops39h 23m

$305
Quickest one-way

ToledoChicago

TOL - ORD

TOLORD

Toledo Express

Thu 5/21

11:17 am-8:32 pm

2 stops34h 15m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Sorted by cheapest first

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toledo, Ohio-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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
No data available for this route at this time. Please check back soon.

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.

See more FAQs

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