Best Time to Visit Chicago

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The best times to visit Chicago will depend on what you're looking for when choosing a date. If you're holding out on the cheapest time to visit Chicago, you'll find that a near %50 decrease on hotel occupancy rates during January and February make the winter months an ideal time to book lower Chicago hotel prices. The opposite can be said for the summer, when occupancy rates soar to near 90% making hotels, naturally, more expensive.

Weatherwise June, September, and October are gloriously mild and sunny. In turn, November through March will range from crisp cools to frigid chills. Meanwhile, April and May will see wilder extremes, ranging from cold and soggy to conspicuously bright and warm. Beyond that, The general consensus betweens locals in Chicago is that despite what the forecast might read, the weather will change in a heartbeat. Personally, we love the summertime in Chicago, jam-packed with awesome outdoor festivals and all-round cheery crowds. Although the holidays aren't bad either, especially once the city is flush with lights.