Old Town, Chicago vacation rentals

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Top-rated vacation rentals in Old Town, Chicago

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Superhost

Condo in Lincoln Park

Exclusive Condo Steps from Old Town + Lincoln Park

Enjoy a lively experience at this renovated condo located in the heart of Old Town. There are endless choices of shopping, restaurants and bars nearby. We are centrally located and walking distance from the North/Clybourn Red Line stop, which makes us the perfect location to explore Chicago! Also check out our "Neighborhood Foodie Guide" for some of the local favorites. This is especially an ideal space and location if you're looking to revamp your "work-from-home" for a weekend or longer!

$182 per night

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Apartment in Lincoln Park

Sophisticated Flat in Historic Building

Nestled in the charming Old Town Triangle of Chicago, this luxurious flat offers a seamless blend of historic charm and contemporary sophistication. With its soaring ceilings and elegant arched windows, this immaculate space boasts a truly captivating ambiance. Impeccably designed interiors ensure a truly indulgent stay, while the building's rich heritage adds an unforgettable sense of place. Treat yourself to the ultimate Chicago getaway and bask in the allure of this stunning residence.

$177 per night

Superhost

Apartment in Lincoln Park

Lincoln Park / Old Town, Roomy Nook

Location! On the edge of Old Town / Lincoln Park, literally. The location cannot be beat. Tree-lined sidewalks, brick buildings; taking a stroll in the neighborhood is a must. We are < 2 miles north of the heart of downtown Chicago, 10- minute walk to the lake, < 5 minute walk to a multitude of cafes, restaurants and boutiques. Come relax in the middle of the city in a surprisingly quiet and peaceful flat.

$142 per night