1. The Robey
💎 Best for: a ‘live like a local’ vibe
Occupying two connected historic structures—the 1929 Art Deco Northwest Tower and a 1905 industrial warehouse—The Robey offers immense character within its unique architecture. Its 89 Tower rooms combine mid-century boutique aesthetics with romantic base for a city getaway.
Time Out tip: Hotel guests get Starting around $195, with many dates in the $250-$550 range depending on the season
Closest transport: 0.5-block walk to CTA Blue Line with service to O’Hare Airport (30 minutes) and Chicago’s downtown district (20 minutes).
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