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Chicago · Hotel shortlist

The best hotels near Boystown

Stefan Bauer

Stefan Bauer The American west

Updated 1 September 2026 · 12 Chicago hotels assessed

These are my five favourites in Chicago, out of the 12 that qualified. I read what other travellers scored them before I picked, so the order follows the guests, 4.6 down to 4.2.

All five are within 2.4 km of Boystown.

Hotel Zachary, Chicago, a Tribute Portfolio Hotel

Highest rated of the five

Hotel Zachary, Chicago, a Tribute Portfolio Hotel

★★★★★4.6 from 908 reviews

Hotel Zachary, Chicago, a Tribute Portfolio Hotel comes out on top of this list, and not narrowly: 4.6 from 908 guest reviews is a score that holds up at that volume, which is the whole test here. A perfect ten from nine people does not beat it.

It is a 4 star property, found under poi and around $464 a night on the dates we checked.

12 hotels in Chicago qualified for this list and five made it. Villa D' Citta Bed & Breakfast is the one I would book if the first is full.

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All five, ranked

  1. Hotel Zachary, Chicago, a Tribute Portfolio Hotel1

    Hotel Zachary, Chicago, a Tribute Portfolio Hotel

    ★★★★★4.6 from 908 reviews

    900 m from Boystown, about a 11 minute walk

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    • Villa D' Citta Bed & Breakfast2

      Villa D' Citta Bed & Breakfast

      ★★★★★4.9 from 696 reviews

      2.4 km from Boystown

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      • Best Western Plus Hawthorne Terrace Hotel3

        Best Western Plus Hawthorne Terrace Hotel

        ★★★★★4.4 from 1,612 reviews

        under 200 m from Boystown, about a 1 minute walk

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        • Majestic Hotel4

          Majestic Hotel

          ★★★★★4.2 from 1,016 reviews

          500 m from Boystown, about a 6 minute walk

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          • The Villa Toscana Guest House5

            The Villa Toscana Guest House

            ★★★★★4.6 from 212 reviews

            200 m from Boystown, about a 2 minute walk

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            How this list was put together

            12 Chicago hotels qualify for this list. We ranked them on guest rating first and on how close they are to Boystown second, then took the top five.

            Two things decide these lists. The first is my own time in the city: every hotel on this page is one I have stayed in, walked into and looked at, or gone back to check. That is where the shortlist starts, and it is why some well reviewed places are not on it.

            The second is the numbers, and those are what set the order. The rating and review count come from the big travel sites, pooled through Google, so a score here reflects Expedia, Booking, Hotels.com and the rest together rather than any one of them. I also read the review breakdown by topic, which is where the figures on service, breakfast and location come from. Hotels with fewer than forty reviews are left out altogether, because a rating that thin is not a rating. No more than two come from one neighbourhood.

            What I do not do is move anyone up the order. The ranking is the guest score, highest first, and nobody pays to be on the list.

            Distances are straight lines from published coordinates, so the real walk is a little longer. Amenities are as recorded by Google Hotels and can change without notice. Rates are an indicative nightly figure for a midweek autumn stay, not a quote. Check the booking page before you commit.

            Stefan Bauer

            Stefan Bauer The American west

            Chases total solar eclipses. Seven of them on four continents, from Wyoming to a fishing town in Chile. Banks days off through the on-call rota and books the trips years ahead, because eclipse dates do not move.

            Trip Grapevine earns a commission on bookings made through the links on this page. It costs you nothing, and it does not change the order of the list, which is set by the measurements above.