Airfare Expert: How to find the best fares to Chicago

That said, Chicago is a great place to visit because it really does have something for everyone: Wrigley Field for the sports fan, the Magnificent Mile for the shopper, the Art Institute for the beauty lover, the Willis (formerly Sears) Tower for the daredevil, and Chicago-style deep-dish pizza for everyone.

What's the best time to fly to Chicago? 

Recently Chicago has been caught up in the new airline mantra (since the oil crisis and recession, anyway): "Never be a dollar more or less than your competitor." This means both airline price hikes and airfare sales figures are matched very quickly, with the exception of some non-stop routes where certain airlines feel fliers will pay a premium.

Recent targeted sales have reinforced our historical studies that Tuesday, Wednesday and Saturday are the cheapest days to fly . They are also the least crowded days to fly, but don't expect an empty middle seat on your flight to Chicago even on these slower days.

The magic day to depart right now is Tuesday, August 23, as airlines deal with the end of the busy summer season by dropping prices by $50 to $100 round-trip. This is mainly due to typical softness in demand and the dropping of summer peak travel surcharges.

Both American and United tend to toss in weekend rates to Chicago that can be up to half off from many cities in the country. The catch? You'll have to leave on a Friday or Saturday and return the following Monday or Tuesday; unfortunately, Sunday isn't usually included in most of these weekender deals.

What's the best time to buy my tickets? 

Domestic flights to Chicago tend to follow the predominant pattern across the nation where airlines begin to discount about three-and-a-half months before departure. Buying before that date can be much more expensive.

The window of time to buy extends up to about 14 days before departure; after that date, you'll be treated as a deep-pocketed business traveler who can afford much higher prices. Luckily, with Southwest in the mix at Midway, the really bruising price increase won't occur until 7 days before departure.

Shop as early in this window as you can; procrastination is the number one cause of paying too much for your ticket.

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