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    Best Weekend Cottages Chicago Near Me

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    1. Claremont Cottages - Near West Side

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    Address: Chicago, IL 60612

    2. Chicago Guest House - Chicago

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    19 reviews
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    Address: 1216 W Newport Ave, Chicago, IL 60657

    Telephone: (312) 952-5150

    Business type: Vacation home rental agency

    Business: Three exclusive Wrigleyville Guest Houses. Luxury vacation rentals where you will experience the feeling of having your own home away from home in Chicago! Enjoy the private space with beautiful gardens and free parking. Walk to Wrigley Field, shops, restaurants, live entertainment and more!

    3. Roscoe Village Inn - North Center

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    Roscoe Village Inn
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    Address: 3515 N Seeley Ave, Chicago, IL 60618

    Telephone: (312) 301-5916

    Business type: Vacation home rental agency

    Business: Roscoe Village Inn; upscale vacation rentals on Chicago's trendy northside. Warm and cozy--thoughtfully furnished and fully equipped with everything you need to feel at home in Chicago whether it be for a few day or extended stay. Reserve your guesthouse in Roscoe Village today! 312-301-5916
    4worldlovers:
    weekend cottages chicago Roscoe Village Inn

    ​​Stroll down Roscoe and you’ll see why ‘The Village’ is such a popular destination for locals & tourists alike looking for a unique & unconventional urban setting! You'll enjoy dining at the gastropubs and cozy cafes and shopping at the multitude of independently owned shops and unique boutiques. Roscoe Street is always alive with weekly events at the local establishments. Come summer it also hosts family friendly street festivals serving great food and live entertainment. ​​

    4. Chicago's Best Vacation Rentals - Chicago

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    Chicago's Best Vacation Rentals
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    Address: 512 W 37th St, Chicago, IL 60609

    Schedule: Temporarily closed

    Telephone: (773) 680-0775

    Business type: Vacation home rental agency

    5. Apartment - Near North Side

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    Apartment
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    Address: 30 W Erie St, Chicago, IL 60654

    Business type: Lodge

    6. Vaystays - Near North Side

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    Vaystays
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    Address: 222 W Ontario St #320, Chicago, IL 60654

    Schedule: Opens at 8:00 AM

    Telephone: (312) 878-4572

    Business type: Vacation home rental agency

    4worldlovers: Whether you've got a group of couples, your family, or several generations of family members, we’ve got the place for you at the best price.

    Payments are handled securely via credit card, your funds are held in escrow, and owners are not paid until the rental is delivered to your satisfaction.

    Get the most out of the weekend by staying where the action is. Many homes are steps to the stadium, and you can sort results by distance to the game.

    Our property owners are vetted, every home is professionally cleaned, and we’re standing by to assist you during your stay.

    Your university trip is more than a game or graduation ceremony. It's a reunion, religious experience, and rite of passage all rolled into one. There are hundreds of exclusive property owners on the "Home Team" in college football destinations across the nation ready to host your entire group under one roof. Whether you're creating your first listing or trying to pick the perfect home for your group, we've got you covered.

    7. Chicago Guest House - Chicago

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    9 reviews
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    Address: 1330 W Henderson St, Chicago, IL 60657

    Telephone: (312) 952-5150

    Business type: Guest house

    8. Beach House Chicago - Rogers Park

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    Beach House Chicago
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    Address: 7609 N Eastlake Terrace, Chicago, IL 60626

    Schedule: Opens at 9:00 AM

    Telephone: (708) 613-0188

    Business type: Vacation home rental agency

    Business: Beach House Chicago is your vacation rental and event space on Lake Michigan.

    9. Chicago Vacation Rentals - Near North Side

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    Chicago Vacation Rentals
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    Address: 1400 N Halsted St, Chicago, IL 60642

    Telephone: (312) 867-7407

    Business type: Vacation home rental agency

    4worldlovers: If you’re heading to Chicago and looking to be near downtown but want a more neighborhood experience with friendly, knowledgeable transcontinental hosts, our home off Halsted just might be the perfect fit for you.

    The neighborhood is great: Vibrant and alive, with plenty to do, to eat, to drink & to be entertained by: Plus, everything you need is right here: We've got the second largest Whole Foods market around the corner with it's fabulous food court (5 dining options) and tables along the riverfront, a great neighborhood pub & wine bar, as well as Mariano's Market and a Super Target for shopping.

    We are located within easy reach of everything, no car is needed, but if you are driving in, we can offer up to two parking spaces (there is a fee/night per space, must be for the duration).

    Check with us for availability (and be sure to let us know your dates, the number of guests) we'll get back to you quickly. Note that pricing is based on the number of guests.

    Missing friends and family who live in Chicago? This is THE place to stay to visit them.

    10. Kings Tower chicago - Chicago

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    Kings Tower chicago
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    Address: 5849 S Michigan Ave, Chicago, IL 60637

    Telephone: (773) 812-2771

    Business type: Bed & breakfast

    11. Chicago Guest House - Chicago

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    80 reviews
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    Address: 3715 N Lakewood Ave, Chicago, IL 60613

    Telephone: (312) 952-5150

    Business type: Guest house

    12. Caps Cottage Grove - Greater Grand Crossing

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    Caps Cottage Grove
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    Address: 7701 S Cottage Grove Ave, Chicago, IL 60619

    Telephone: (773) 846-6708

    Business type: Cottage


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