Where you stay shapes how you experience Chicago. Your hotel is more than a place to sleep — it’s your home base, your launching-off point for the city’s restaurants, museums, architecture, and neighborhoods.
The right hotel can elevate an entire trip; the wrong one can quietly diminish it. With more than 500 hotels to choose from, finding one that’s genuinely special — and that fits your own interests, priorities, and budget — isn’t easy. After years of informally steering friends and family toward the right places, we decided to pool our collective expertise in Chicago’s historic hotels into one website, so a wider audience can find a great place to stay with far less guesswork.
A Virtual Concierge
ChicagoHistoricHotels.org offers heritage travelers high-quality, well-researched guidance written by local architectural historians and preservation advocates. Think of us as your virtual concierge: our goal is to give you the information and recommendations you need for a marvelous stay. We love this city and its buildings, and we’d love for you to fall for them too.
This is a lovingly curated selection of Chicago’s most delightful and authentic historic hotels. From the 500-plus hotels in the city, we’ve chosen only those that meet our criteria — every one personally reviewed and documented so that each is a place we’d genuinely recommend. Many we know intimately, having helped save them from demolition and working alongside developers and city officials to reimagine them as hotels.
The list spans the full range: purpose-built grand hotels and recent adaptive-reuse conversions, decadent luxury and hip energy, top-dollar suites and affordable hostels, and everything in between. They sit across a variety of prices and neighborhoods, though most cluster in and around the Loop. These are hotels we treasure and have long recommended to the people closest to us — and now we’re sharing those recommendations with you.
How Hotels Are Selected
Hotels cannot buy their way onto this site. To qualify, a hotel must occupy a historic building at least 50 years old, must be unique and authentic, and must be charming enough to enhance a visit to Chicago. The test we apply is simple: would we send an old friend here on their first trip to the city? If the answer is an enthusiastic yes, the hotel makes the list.
In fact, many are so special that we encourage you to visit even if you’re staying elsewhere — step into their glorious lobbies, have a drink in their beautiful bars, linger over a meal in their restaurants. As we like to say, everything is just a little bit better in a historic building.
Who We Are
Preservation Chicago is a Candid Platinum-rated 501(c)(3) nonprofit advocacy organization that harnesses the power of historic preservation to build healthy, dynamic, and vibrant communities. Our work is made possible by the generosity of our donors.
Every hotel featured here is independently selected by our staff — no exceptions. If you book through a link on our site, we may earn an affiliate commission from Booking.com, and every dollar of it goes directly toward supporting our mission. It costs you nothing extra and helps keep this work going.
Find your historic hotel
Explore Chicago’s most authentic places to stay — by neighborhood, era, or on the map.
Thank you, from your friends at Preservation Chicago.
Love Your City Fiercely!