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4 Places to Stay in Chicago That Aren’t Your Typical Hotel

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Looking to experience Chicago like a local? Forego staying on the Magnificent Mile and unpack your suitcase somewhere more unique.
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Exclusive Logan Square Urban Enclave

With just 6 rooms Longman & Eagle books up fast but if you can snag a room you’ll love the vibrant artistic spaces. Each of the 6 rooms is completely unique sporting mix tapes and custom artwork and installations.  If you’re the type of person who wants to be in the center of the party – this is the right choice for you – Longman & Eagle’s rooms are above their occasionally raucous and always delicious tavern and restaurant.
2657 N. Kedzie Ave
Chicago, IL 60647
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The Drake Experience but not at The Drake

OK, we get it, you want to stay Downtown– in the olive pit in the middle of the freakin’ olive. We don’t blame you, the Magnificent Mile isn’t called magnificent for no reason. Do yourself a favor and don’t pay The Drake prices and deal with The Drake crowds – head a few blocks over to The Tremont Chicago instead. Located in the heart of Chicago’s Gold Coast neighborhood, The Tremont is a boutique hotel with contemporary décor.
100 East Chestnut
Chicago, IL 60611
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Hip Hostel

Forget everything you think you know about hostels because The Freehand is not your average hostel experience. Hosted in a classic 1927 building with a relaxed community vibe and dynamic food and beverages –The Freehand is in the heart of River North a quick jaunt away from Chicago’s best art galleries. As a bonus, the Freehand’s in-the-know event coordinator has expertly curated outings and activities that Freehand guests can join.
19 East Ohio Street
Chicago, IL 60611
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Villa D’ Citta

There’s truly nothing else like this luxurious Italian bed and breakfast in Chicago. Nestled in the gorgeous Lincoln Park neighborhood you can experience old world comfort along with some of Chicago’s best shopping and dining just a few steps away. Top notch service, top notch breakfast, and did we mention the outdoor patio with Jacuzzi?
2230 N. Halsted Street
Chicago, IL 60614