Ah…fall. Some people dread the end of summer, while others look forward to the cooler temps and changing seasons. While people generally associate fall and leaf-peeping with New England, many will be surprised that the Midwest has just as many spots that are ideal for viewing the fall foliage. For example, Brockway Mountain Drive in Copper Harbor at the Keweenaw Peninsula in Michigan has over nine miles of colorful views and Lake Superior. If you want some Cape Cod-like experience, you can head over in Door County, Wisconsin, nicknamed the Cape Cod of the Midwest; with white clapboard homes and quaint fishing villages such as Sturgeon Bay and Fish Creek. Or take a drive along the Illinois River Road National Scenic Byway where you can take in water views, bluffs and fall foliage, and be treated to locally produced wines, art and history.

So why not take advantage of today’s hot deals to Chicago found by the deal experts at Fly.com, and take in a new fall experience in the Midwest? And did I mention that fall is the perfect time to be in Chicago, since the weather is pleasant and the summer crowds have thinned out?

If the Midwest isn’t striking your fancy, we have more great deals to Denver, Las Vegas & more!

Cheap Flights to Chicago

The prices below represent a savings of up to $150 on typical roundtrip prices. These fares are not part of an airline sale and may disappear at any time, so book ASAP.

Availability varies by route. Click on the Fare Calendar links below to find the best dates to travel September to December, unless otherwise noted (blackouts may apply). All prices roundtrip, including taxes.

More Cheap Flights

Is the Windy City and the Midwest isn’t thrilling enough for you, we have more deals to other popular destinations including Denver, Las Vegas & more!

The prices below represent a savings of up to $150 on typical roundtrip prices. These fares are not part of an airline sale and may disappear at any time, so book ASAP.

Availability varies by route. Click on the Fare Calendar links below to find the best dates to travel through December, unless otherwise noted (blackouts may apply). All prices roundtrip, including taxes.

Don’t see fares from your hometown? Browse Today’s Best Fares from your city. And for hotel suggestions, check out Fly.com/hotels for deals and offers.

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Featured Image: Chicago Skyline in Fall (Shutterstock.com)

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Kim has been hunting flight deals and writing travel articles for over 13 years. His articles have appeared in the Boston Herald, Chicago Daily Herald, and Frommer’s Budget Travel, among other publications. Amsterdam, Bangkok, Rome, and Sydney are some of his favorite destinations and he aspires to one day live in Italy. La dolce vita!

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