In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

How far in advance should I book a flight from Toledo, Ohio to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 33 days in advance, which can save you up to 187% on flights from Toledo, Ohio to Chicago compared to booking the week you need them. Waiting 33 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $118. For sooner than that we have options available in the next 3 days from $200.

What is the cheapest month to fly from Toledo, Ohio to Chicago?

The best pricing can be found in the month of October. Prices to Chicago from Toledo, Ohio average $218. You can even find prices in October for less than $218, as users have found deals to Chicago from as low as $48. The month of December appears to be one of the more expensive times to travel to Chicago from Toledo, Ohio. Flying in the targeted month can save you up to 42%.

What is the cheapest time of day to fly from TOL to CHI?

When flying from Toledo, Ohio to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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.

$201+ Flights from Toledo, OH to Chicago

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Cheap flight deals from Toledo to Chicago

Round-trip from	$424 (Kiwi.com)
One-way from	$201 (Kiwi.com)
Popular in	December
Cheapest in	October
Average price	$112

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. 15% potential increase in price ($39 potential increase over avg. RT price).

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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).

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Average for round-trip flights in September 2025

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One-way flights from Toledo to Chicago
Search for one-way flight options from Toledo to Chicago. Find affordable one-way fares based on user searches. Data last updated September 11, 2025.

Mon 10/1310:40 amTOL - ORD

2 stops51h 05mMultiple Airlines

Deal found 9/9

$201

Fly from

Fly to

Route

Depart

Return

Price

ToledoChicago

TOL - ORD

TOLORD

Toledo Express

Mon 10/13

10:40 am-12:45 pm

2 stops51h 05m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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, August is the cheapest month in which you can book a flight from Toledo, Ohio to Chicago (average of $245). Flying from Toledo, Ohio to Chicago in March is currently the most expensive (average of $321). 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

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, August is the cheapest month in which you can book a flight from Toledo, Ohio to Chicago (average of $245). Flying from Toledo, Ohio to Chicago in March is currently the most expensive (average of $321). 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.

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$201+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Toledo to Chicago with Cheapflights

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Cheap flight deals from Toledo to Chicago

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One-way flights from Toledo to ChicagoSearch for one-way flight options from Toledo to Chicago. Find affordable one-way fares based on user searches. Data last updated September 11, 2025.

Search for one-way flight options from Toledo to Chicago. Find affordable one-way fares based on user searches. Data last updated September 11, 2025.

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

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.

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?

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?

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

How can I find direct flights from Toledo to Chicago?

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

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

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One-way flights from Toledo to Chicago
Search for one-way flight options from Toledo to Chicago. Find affordable one-way fares based on user searches. Data last updated September 11, 2025.