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 SeptemberSummers 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 MarchNow 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 DecemberModerate springtime temps and the romance of autumn and the holiday season serve as the perfect backdrop for itinerant exploring and chilling out.
Our Experts save you money with travel deals and advice
It’s nearly always the more economical option to check two bags than to go overboard on one.
Laura Motta Director, Deals Publishing
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