HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$366+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
TOL — CHI
Jul 18 — Jul 251
Sat 7/18
Sat 7/25
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Toledo to Chicago 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.

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 June 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/14. 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 6/1811:16 am
TOL
-
ORD
2 stops29h 37m
Multiple Airlines
Sun 6/214:59 pm
ORD
-
TOL
1 stop21h 40m
Multiple Airlines
Deal found 6/14$1,037

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 June 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

June

Cheapest in

September

Average price

$439
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
Highest demand for flights based on searches. 22% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 June 18, 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
Quickest one-way

ToledoChicago

TOL - ORD

TOLORD

Toledo Express

Fri 8/7

8:03 pm-12:15 pm

3 stops41h 12m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

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 June.
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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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.

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.