Chicago's accommodation section runs 3 curated guides, each built around a different planning question. The luxury guide carries 12 verified entries, the deepest roster in the section. Both the boutique guide and the where-to-stay guide hold 10 entries each. The 3-guide composition separates high-end stays, independently operated properties, and a broader orientation into distinct planning lenses.
If you're still deciding how to approach the city, the where-to-stay guide and its 10 entries is likely the better first read. It covers wider ground than the boutique and luxury guides. The boutique guide, also at 10 entries, narrows the field to properties where the concept or the building is part of the draw. The luxury guide's 12 entries sit at the top of the section and tend to reward travelers who already know what tier of stay they're after.
August's 27°C highs and 10 rain days make your room's climate control a real planning factor in Chicago, while September's drop to 24°C and 7 rain days brings more comfortable conditions for moving between properties on foot.
- 12 picks
Best luxury hotels
Five-star hotels with the service to match Club Quarters Hotel, Central Loop · JW Marriott Chicago · Bluegreen Vacations Hotel Blake, Ascend Resort Collection - 10 picks
Best boutique hotels
Boutique hotels with character and a story River North · Magnificent Mile · O'Hare, Chicago - 10 picks
Where to stay
Neighborhood-by-neighborhood orientation with hotel picks across budget, mid-range, and luxury tiers River North · Oak Street Beach · Chicago Loop