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    Roscoe Village Inn

    5.0 (2 reviews)
    Open Open 24 hours
    Updated a few days ago

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    10 years ago

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    13 years ago

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    Roscoe Village Guesthouse

    Roscoe Village Guesthouse

    4.3(13 reviews)
    0.2 miRoscoe Village

    We spent the long July 4th weekend visiting Chicago, and stayed in #3. The space worked very well…read morefor two couples. The unit was very clean and very quiet. The beds were comfortable and the linens nice. The kitchen and bath were tastefully done with granite and nice fixtures. All was in working order. The location was perfect. A short walk to the Brown Line, easy on street parking, lots of fun places to eat nearby. West Roscoe had an upscale family neighborhood vibe. We ate at the Turkish place and the Vietnamese place - both very good. A note to anyone who books #3. Make sure that you are comfortable with 2 flights of steep stairs. Make sure you know how to reboot a WIFI. And, ask about the A/C which must be on some sort of preprogrammed setting. We happened to be there when it was quite hot, so we had to often set the A/C to manual to cool off. This condo was a great home base for our 4 day weekend. It's always fun to be able to come "home" after a long day of sightseeing and relax and enjoy each others company in a comfortable space.

    Five of us came to town for 5 days for our son's wedding, and stayed in one of the guesthouses…read more The location was convenient to all of our activities. The guesthouse was our "base of operations". The place was immaculate and had everything we seemed to need in the well appointed kitchen. I even put the backyard grill to good use one night. The beds were comfortable, bathrooms had plenty of hot water, parking was convenient, and lots of interesting restaurants within walking distance. The neighborhood was full of happy children, and we enjoyed a game of Frisbee in a nearby park. We go well acquainted with the #50 bus to get us anywhere in the city.The neighborhood was full of happy children, and we enjoyed a game of Frisbee in a nearby park. We go well acquainted with the #50 bus to get us anywhere in the city. Our "wired" set took full advantage of the fast wi-fi connection. I had wanted to stay in a hotel, but my wife thought this would be more "homey" and see was right, it was a great decision. The only downside to us was that the toaster seemed to be hard-wired to the smoke alarm, but once we figured out to turn the exhaust fan one before we did any cooking all was well.

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    Roscoe Village Guesthouse
    Roscoe Village Guesthouse
    Roscoe Village Guesthouse

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

    Urban Holiday Lofts

    3.2(50 reviews)
    2.3 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(109 reviews)
    1.7 miBucktown

    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!

    This place is fantastic. I always felt comfortable and welcomed the entire time here. Both Kay and…read moreAshlee made sure we felt important and went out of their way on several occasions to provide top notch hospitality. I had a garage spot, which was great, although there was always a spot on the street to park. The neighborhood is nice and we felt comfortable walking even into the evening. They provided a custom breakfast with daily specials. The omelets are fantastic - FYI. There really isn't anything that i would change. I will definitely be back and will recommend this spot to anyone visiting that doesn't want to maybe deal with downtown, but yet are super close if that's your end goal. Thank you, Ashlee and Kat! You two make the experience what it is for the guests! 5 stars

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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 Inn - guesthouses - Updated May 2026

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