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

Popular airlines from Toledo Express Airport (TOL) to Chicago Midway Airport (MDW)

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Frequently asked questions

How much does a flight from Toledo Express Airport (TOL) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight or cheap return flight from Toledo Express Airport (TOL) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Toledo Express Airport (TOL) to Midway Intl. Airport (MDW)?
Planning your getaway for is a great way to save, as it's the cheapest month for flights between TOL and MDW. You'll often find the lowest prices during the off-season.
Which airlines fly direct from Toledo Express Airport (TOL) to Midway Intl. Airport (MDW)?
Direct flights aren't available from Toledo, OH (TOL-Toledo Express) to Midway Intl. Airport (MDW). However, there are other airports that have nonstop flights. Hop on your plane at Detroit Metropolitan Wayne County Airport (DTW) and travel straight to Chicago without a layover.
What is the cheapest airline that flies from Toledo Express Airport (TOL) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll fly you from TOL to MDW. Then, sort your results by "Price (lowest to highest)" to snap up the best deal available.
How many flights per day from Toledo Express Airport (TOL) to Midway Intl. Airport (MDW)?
You'll have to book a flight with a layover when traveling from Toledo Express Airport (TOL) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, just filter your search to include one or more stops to discover the best option for your trip.
What day of the week has the most flights from TOL to MDW?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Toledo Express Airport (TOL) to Midway Intl. Airport (MDW)?
Choose a flight from Toledo Express Airport (TOL) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Toledo Express Airport (TOL) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from TOL to MDW are usually more expensive. To secure the cheapest rates, start searching for flights early. That being said, if you're flexible with your travel dates, you may score a cheap ticket right before your journey.
Is it cheaper to book a TOL to MDW flight and hotel package?
You'll typically save money by securing a TOL to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. Once you've selected your ideal accommodations and flights, consider adding extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Toledo Express Airport (TOL) to Midway Intl. Airport (MDW)?
Typically, it's possible to cancel or reschedule your TOL to MDW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Toledo Express
Destination airport
Midway Intl.
Distance
203 mi

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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.

 

Toledo to Chicago Flights

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*Available to One Key members.