iStock International
It’s all about timing. To avoid crowds and inflated prices, we recommend the period between high and low seasons when the weather is fine, places are still open and happy to welcome travelers, and you can explore a destination at your own pace. ShermansTravel experts call this magical time and space continuum the Sweet Spot.

When to go to Chicago

Peak Season: June to September

Summers in the city are akin to urban nirvana as long as you don’t mind jacked-up room prices, long lines, and high humidity in July and August.

Off Season: January to March

Now is your chance to grab a cheap room at a luxury hotel, as only thrill seekers and the extremely budget conscious seek out brutal Chicago winters.

Sweet Spot: April to May; October to December

Moderate springtime temps and the romance of autumn and the holiday season serve as the perfect backdrop for itinerant exploring and chilling out.

Compare Rates to Chicago

Sign up for the Top 25 Newsletter
to get exclusive weekly deals

Tell Us Your Preferences

To help us understand your travel preferences, please select from the following categories

Check all that apply
Oops, something went wrong.
No Thanks