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    Roscoe Village Guesthouse

    4.3 (13 reviews)
    Open 9:00 am - 2:00 AM (Next day)

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    Review Highlights - Roscoe Village Guesthouse

    Stayed for a weekend getaway at the guest house in Old Town Chicago while we were visiting friends that lived in Lincoln park and other areas near by.

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    Urban Holiday Lofts - Common area "Sky Lounge" Urban Holiday Lofts

    Urban Holiday Lofts

    3.2(50 reviews)
    2.1 miWicker Park, West Town

    Halfway through the stay - things may change but, given many negative reviews, I thought I'd offer…read moremy initial take. It's in a cool neighborhood with great food and right next to the blue line. The price is great. Place is older but they are trying and there aren't any real problems. Walls are thin, heat doesn't always make it to the end of the line but it's very safe, very comfortable, clean. It's nicer than, say, most Airbnb's I've stayed at. Not as nice as a hotel but I'm happy with it and don't see the problems some people posted about. It's a specific place for a specific purpose and I'd recommend it for that. I wouldn't recommend it as a cheap hotel alternative. I would recommend it as a solid Airbnb option or upper-end hostile. Staff is fine, they aren't trained four seasons customer service staff so they aren't going to do well with conflict you throw at them but if you're polite and respectful they are right back at you. I am happy to be here.

    I'm always surprised whenever my friends are surprised by the fact that I choose to stay at hostels…read morewhen I travel, whether it's within the states or around the world. All the hostels I've ever stayed at have been clean, friendly, accommodating, and very affordable--Urban Holiday Lofts is no exception. My friend booked this place on hostelworld, which contains all the information you need to get to the hostel. For the phone addicts, it's also searchable on Google maps. This place awesomely reimburses you for the cost of your CTA ticket to the hostel (a heads up: it's $5 from the O'Hare International Airport). Also, true to the description, they charge an additional 16.4% tax when you arrive to pay for your stay. Jason, who is very sociable and has a good sense of humor, was at the front desk when I checked in. Whoever checks you in gives you a great list of eateries and bars in the area (along with a list of rules) and a short tour of the hostel. My bed was in the standard 6-room female dorm, which had 3 bunk beds and no A/C (they had a ceiling fan and a heating system). My floor had 4 bathrooms, which can be congested during the evenings when everyone wants to shower. There's washers and dryers on-site that will cost you $1.50 each, and you can purchase detergent from the front desk. Complimentary breakfast is from 8 - 10 AM, and it consists of bagels, cereal (Aldi's version of Frosted Flakes and Raisin Bran), bread, milk, coffee, and tea. Breakfast is hosted in the upstairs common space, which also has two computers for general use. Towels are provided, and lockers are available in the shared dorm rooms ($1 lock rental for your entire stay). And I should mention that the location of this hostel is bombdotcom. Though not in the heart of downtown, Wicker Park has great nightlife, and the CRT Blue Line, from which this hostel is 5 minutes away, runs 24/7. 24 frickin' 7. Oh, before you leave, drop by the nearby Aldi grocery store to pick up some awesomely named German chocolate at awesomely affordable prices. Just beware of the weight of all that chocolate in your bag and how that could detrimentally affect your back. Don't say I didn't warn you.

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    Urban Holiday Lofts - Bathroom at Urban Holiday Lofts

    Bathroom at Urban Holiday Lofts

    Urban Holiday Lofts - 2 Person Private Room

    2 Person Private Room

    Urban Holiday Lofts - Private Ensuite Room At Urban Holiday Lofts Hostel

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    Private Ensuite Room At Urban Holiday Lofts Hostel

    Ray's Bucktown Bed and Breakfast - from scrach strawberry compote

    Ray's Bucktown Bed and Breakfast

    4.9(110 reviews)
    1.5 miBucktown

    Ray's Bucktown B&B is an absolute gem. The neighborhood, the staff, the breakfast, the whole damn…read morepackage. It has character. It makes you feel like you're on an adventure. There's a warmth here. And that's something even the snazziest of hotels can't promise. Don't get me wrong, I enjoy bougie hotels too, but this place has a story. The dry sauna and steam room were more than enough comfort, and while we couldn't enjoy the roof deck due to storms, it looked like the perfect place to chill. Our room was spotless, we had plenty of space, and the jacuzzi tub was the cherry on top. Breakfast is included, and the food from that kitchen was stellar. They had an entire separate vegan menu. I was super into the local kombucha and fermented hot sauce options, and the vegan French toast and tofu scramble were spot on. There are always snacks and beverages available around the clock, too. So fear not, my fellow snackers. As far as the vibe, let's just say the founder must have made randomness their full-time job. There is art all over the place, plus collections of all shapes and sizes. Two dozen antique cameras? Got it. 15 or so vintage thermoses on a shelf? Yep. Rock collections, statues, maps, and more? There is just stuff to look at EVERYWHERE. And I mean that in the best way possible. My wife booked us a little one-night getaway, and Ashley and the team made the whole thing a treat. Smooth sailing from start to finish, friendly, accommodating, and the room was our cozy little home away from home, even if only for a night. Completely walkable to all kinds of fun and shopping. Zero complaints. I can't say I've been to a place like Ray's before. It's a community. Just check the common rooms where you'll find board games, books about art and the neighborhood, and people just chilling out. It's unique, and we need more uniqueness these days. Ray's is the kind of place I love to recommend. Anyone can grab a hotel, but this type of visit is something much more memorable.

    A solid place to stay when in Chicago! We were fortunate to have a garage spot, but there's lots of…read morefree parking surrounding the place. Very friendly staff and a quirky vibe - perfect for people who want something more relaxed. Breakfast is included and you order off a menu they give you. Very good! They also have free snacks! We were in the Skylight Room which I liked - access to the roof deck, felt pretty private. You do hear the kitchen though I. The morning, but there is an additional door to close if needed. It's sort of like staying at a friend's house great for those who want to be in a classic Chicago neighborhood instead of downtown. Would recommend!

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    Ray's Bucktown Bed and Breakfast - Relax in our common area

    Relax in our common area

    Ray's Bucktown Bed and Breakfast - Sundays mean eggs Benedict with homemade hollandaise sauce!

    Sundays mean eggs Benedict with homemade hollandaise sauce!

    Ray's Bucktown Bed and Breakfast - Skylight Room, split level, queen bed AND full futon, private ensuite bathroom

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    Skylight Room, split level, queen bed AND full futon, private ensuite bathroom

    Roscoe Village Guesthouse - guesthouses - Updated July 2026

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