Holiday rentals in Chicago River

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Top-rated holiday rentals in Chicago River

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Top guest favourite

Flat in Chicago

5 out of 5 average rating, 280 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Top guest favourite

Flat in Chicago

5 out of 5 average rating, 50 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Guest favourite

Flat in Chicago

4.91 out of 5 average rating, 23 reviews

Panoramic 2BR Penthouse in the Sky | Roof Deck

This sunny top floor penthouse is in a perfect location with panoramic lakefront and city views in multiple directions. With over 1,300 square feet of space, 13+ foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of downtown Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed, ideal for families, business travelers, or couples traveling together. The building has an outdoor pool and an amazing outdoor rooftop ter

Top guest favourite

Guest house in Chicago

5 out of 5 average rating, 20 reviews

Andersonville Luxe Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape. The pool and spa are heated heated through 12/31.

Top guest favourite

Flat in Chicago

4.98 out of 5 average rating, 170 reviews

Elegant Suite in Gold Coast

Established in 1927 as the first headquarters for Elizabeth Arden in Chicago, the Walton Residence is located in the heart of the Gold Coast neighborhood of Chicago. Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***From Sept. to beginning of Dec. 2024, there will be repairs to the exterior of the building. We do not expect this to cause major interruptions to your stay.

Flat in Chicago

4.8 out of 5 average rating, 317 reviews

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Superhost

Flat in Chicago

4.82 out of 5 average rating, 791 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Top guest favourite

Flat in Chicago

4.97 out of 5 average rating, 35 reviews

Newly Remodeled in West Town

Charming one bedroom in prime West Town neighborhood. Located on a quiet, tree-lined street just blocks from trendy restaurants, bars and boutiques. Michelin Star Kasama is just a block away. Brand new kitchen & bathroom remodel. Fully stocked kitchen. The decor is entirely inspired by being cozy and relaxing with neutral tones. Private front yard sitting area is exclusive for the apartment and provides wonderful people and dog watching with a park right across the street.

Flat in Chicago

4.71 out of 5 average rating, 344 reviews

Sonder Onterie | King Studio Apartment

Welcome to Onterie, where modern style meets an unbeatable location in the heart of Chicago's Magnificent Mile. You'll have world-class shopping and award-winning dining at your fingertips. Each apartment includes a fully equipped kitchen, in-suite laundry, and a Roku to stream your favorite shows. Unwind in the outdoor courtyard, or find focus in our co-working space. Onterie offers the perfect blend of city and lakeside living.

Top guest favourite

Flat in Chicago

5 out of 5 average rating, 6 reviews

Chicago Vintage & Chic Living

Live like a true Chicagoan in this charming 2BR/1BA Gold Coast walk-up, built in 1881. Enjoy modern comforts like in-unit laundry, central air, cozy bedding, fluffy towels, and a record player. Relax on the huge terrace with lounge and dining space. Steps to the lakefront, top restaurants, coffee shops, and luxury shopping. Walk to Lincoln Park, the free zoo, and the Riverwalk. Historic charm meets unbeatable location!

Top guest favourite

Flat in Chicago

5 out of 5 average rating, 13 reviews

Sunny Studio w/ Skyline View and Parking

Stylish attic studio in vibrant Pilsen, featuring handmade furnishings and skylights that flood the space with light. Sleeps 3 with a queen bed and sleek lounge sofa. Enjoy stunning downtown views from the porch. Steps from 18th Street for top dining, nightlife, and a park with an outdoor pool. A bright, elevated retreat in a prime location. Parking available on premises upon request.

Superhost

Flat in Chicago

4.81 out of 5 average rating, 83 reviews

The Alton - Designer Flat by Mag Mile & the Lake

A design lover's dream. Spend your next trip (or staycation) in a beautifully remodeled luxury studio in Chicago's Gold Coast neighborhood. This listing is for a private studio in a multiple-unit building. ✔ Safe and vibrant neighborhood. ✔ Steps from Michigan Avenue, luxury shops, and the Lake ✔ Convenient parking options nearby. ✔ Easy self-check-in.