Condo vacation rentals in Chicago River

A spacious living area features a large sectional sofa arranged around a modern coffee table. Artwork adorns the wall above, with soft lighting enhancing the ambiance. A patterned area rug adds texture to the hardwood floor, while natural light enters through the adjacent windows.

4.94 out of 5 average rating, 112 reviews

Two Floor Luxury 3 Bedroom Condo in Old Town

Enjoy comfort, privacy, and elevated city living in this spacious three-bedroom, top-floor duplex apartment, located next door to The Sono Chicago in the heart of Old Town Chicago. Ideal for families, groups, or extended stays, this home offers generous space, abundant natural light, and a quiet retreat above the neighborhood. Spanning two levels on the top floor, the apartment features inviting living areas, a fully equipped kitchen, and three private outdoor decks, creating multiple spaces to

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A comfortable living room is showcased with a grey sofa adorned with decorative pillows. A round coffee table sits on a patterned rug, and a green vintage cabinet adds a pop of color. Bright light enters through open doorways, leading to a dining area beyond.

4.97 out of 5 average rating, 149 reviews

Large Remodeled Home in Lincoln Park, Sleeps 12!

Stay in this thoughtfully remodeled home in Lincoln Park. Sleeps 12 w/ complimentary access to 3 parking spots! Enjoy the spacious layout, massive bedrooms, 2 private decks, and front yard w/ a grill. You will be steps from the North & Clybourn Red Line station, Divvy stations, Binny's, Whole Foods, Trader Joe's, Steppenwolf Theatre, so many incredible restaurants! Our home is (conveniently!) located next to train tracks. If you are a light sleeper, this urban location might not be for you.

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A modern chef's kitchen is shown, featuring an island with seating for four. Sleek dark cabinetry contrasts with light countertops and stainless steel appliances. A bowl of fruit adds a touch of color, while glass pendant lights provide illumination above the island.

4.95 out of 5 average rating, 182 reviews

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

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A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.

4.98 out of 5 average rating, 170 reviews

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

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A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.

Condo in Little Italy

4.92 out of 5 average rating, 282 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

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4.81 out of 5 average rating, 219 reviews

Condo in West Side

Charming Condo near U.C./Loop/McCormick Place

Our spacious 3-bedroom, 2-bathroom condo is designed for comfort and convenience. Perfect for extended stays, it features a dedicated workspace with a desk and office chair, plus an in-unit washer and dryer. Two bedrooms offer cozy queen beds, while the third has a comfortable futon. The master bath is large enough for multiple people to get ready at once, and the fully stocked kitchen is ready for your culinary creations. Enjoy extra privacy in your secluded space within the building.

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A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.

4.89 out of 5 average rating, 194 reviews

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

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4.82 out of 5 average rating, 260 reviews

The living room features a wall-mounted television above a wooden console, surrounded by decor and framed photos. Comfortable seating includes gray armchairs and a sectional sofa, offering a relaxed setting. Natural light brightens the space through nearby windows, enhancing the airy atmosphere.

Condo in West Town

Chicago River West 4 Bedroom / 3 Bathroom

Two-level River West home great for travelers who want to see the best of Chicago (its neighborhoods!). The living room is a converted store front, so you benefit from airy ceilings and tons of natural light, which carries into the kitchen - between that and the new appliances, cooking here is a blast. The 4 bedrooms and 3 bathrooms are spread out over both floors, so it's ideal for families and groups of friends - book today!

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4.96 out of 5 average rating, 120 reviews

Two Bedroom w Porch in Wicker Park

Spacious two bedroom apartment with custom wood shelving and hard wood floors. Bay windows and great natural light. Gorgeous furnished porch for when the weather is nice. Quiet, tree lined street that's close to all the best bars and music venues. Short walk to Milwaukee avenue, two blocks from the Division Street blue line station which runs direct from O'hare, only two stations to downtown.

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An open kitchen and dining area features exposed wooden beams and stylish light fixtures. A modern dining table with black chairs provides seating, while a lounge chair is positioned nearby. Decorative plants and art add warmth to the contemporary space.

4.96 out of 5 average rating, 157 reviews

Modern Izakaya Studio in Wicker Park

The Izakaya Studio is a sleek, design-forward space in the heart of Wicker Park, with a secret whisky room inside. Inspired by the intimate atmosphere of a Japanese izakaya: warm, curated, a little unexpected. The kind of place where you settle in, pour something good, and stop thinking about your plans for a while. Spacious for a studio, and comfortable enough for a longer stay in Chicago.

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A spacious living area features a comfortable sectional sofa, a wooden dining table with matching chairs, and a cozy reading nook with an armchair. Large windows allow natural light to fill the room, which includes a decorative fireplace and tasteful artwork on the walls.

5.0 out of 5 average rating, 185 reviews

Stunning Wicker-Park Flat with Parking!

Enjoy a stylish experience at this centrally-located gem. Beautifully renovated 3 bedroom, 2 bath full floor flat. While quietly situated on the 3rd floor, you can walk out your front steps to all that Wicker Park and Division street has to offer. Coffee shops, bars, unlimited restaurants, green space, farmers market, gyms, grocery stores, and so much more. Easy and nearby public transit.

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