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
The bargain shopper with flexibility can find price tags as low as $499 for Mediterranean cruises often for last-minute sailings.
Zach Custer Travel Deal Expert
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