Cheap Flights from Toledo (TOL) to Chicago (CHI)

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Flights from Toledo (TOL) to Chicago (CHI)
Origin airport
Toledo Express
Destination airport
CHI-All Airports
Distance
251 mi

Toledo to Chicago Flights

The cheapest times to fly from Toledo to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Toledo to Chicago are during the month of . You can find some of the cheapest flights from Toledo to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Toledo to Chicago

Sunday is one of the best days to book for cheap flights from Toledo to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Toledo to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Toledo to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Toledo to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Toledo to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much is a flight from TOL to Chicago, IL (CHI-All Airports)?
Pack your bags, because round-trip journeys from Eugene F Kranz Toledo Express Airport to Chicago, IL (CHI-All Airports) start from . That’s based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can increase quickly, so book now to get the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Eugene F Kranz Toledo Express Airport to Chicago, IL (CHI-All Airports)?
Every air carrier has its own set of terms and conditions. If you do decide to cancel, follow the instructions on our Customer Service Portal.
How do I find cheap flights from Toledo Express Airport (TOL) to Chicago, IL (CHI-All Airports) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for TOL to Chicago, IL (CHI-All Airports) flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from Toledo Express Airport (TOL) to Chicago, IL (CHI-All Airports)?
A flight distance of just 255 mi separates Swanton and Illinois. Once you’re in the air, you won’t get a chance to do much more than read the in-flight magazine.
Which airlines fly direct from Toledo Express Airport (TOL) to Chicago, IL (CHI-All Airports)?
Unfortunately, there are no airlines that directly fly between Toledo Express Airport (TOL) and Chicago, IL (CHI-All Airports). You’ll need to book a flight with one or more stops.
Are Eugene F Kranz Toledo Express Airport to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
It is possible to get amazing last-minute deals from Eugene F Kranz Toledo Express Airport to Chicago, IL (CHI-All Airports), but there’s no guarantee. As many airlines release prices up to a year in advance, it’s worthwhile keeping an eye on fares early and being ready to book when you see a good bargain. Expedia compares air carrier prices and updates flight deals often, so you can rest easy knowing you’re always getting the latest offers.

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*Available to One Key members.