Apartment vacation rentals in Chicago

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Top-rated apartment rentals in Chicago

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Top guest favorite

Apartment in Lincoln Park

5 out of 5 average rating, 269 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.

Guest favorite

A comfortable seating area features a spacious beige sectional couch adorned with patterned pillows. A coffee table is positioned on a light-colored area rug, complemented by a lamp and decorative items. Natural light enters through a window above the couch, enhancing the room's neutral tones.

Apartment in Portage Park

4.86 out of 5 average rating, 133 reviews

Classic Chicago Bungalow Garden Unit 1bdrm 1 bath

Classic Chicago Bungalow garden unit apartment furnished with a queen bed, living room, and everything you & your guests need to enjoy your stay in Chicago! Make yourself at home once you arrive. Traditional cable TV is not included in your stay, we do provide a smart tv, Feel free to use with YOUR own login and enjoy! Located in Chicago northwest side. Use Addison and Cicero as your cross street to determine gps and location. Your space is separate with no shared common areas. Owner lives above

Guest favorite

An inviting studio space features warm wooden paneling and a dark couch. A coffee table with magazines and guidebooks is centrally positioned. Soft lighting is provided by wall sconces, and a bed is visible in the background, accented by a colorful wall art piece.

Apartment in Logan Square

4.91 out of 5 average rating, 432 reviews

The Grotto of Logan Square

Garden unit, great for a small group looking for a base while they explore the city. 10 min walk from Logan Square Blue Line, restaurants, galleries, coffee shops and clubs. Explore the city from one of its best neighborhoods! In your downtime the space offers several chicago guide books and magazines. There is a Fire stick in the TV that has most major media apps installed. The alarm clock is also a speaker for your phone to plug into. Please make sure you read the amenities and house manual.

Top guest favorite

The bedroom is designed with a spacious bed centered against an accent wall featuring geometric patterns. A plush bench is positioned at the foot of the bed. Warm lighting illuminates the room, complemented by rich curtains and wooden flooring.

Apartment in Magnificent Mile

4.98 out of 5 average rating, 162 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.

Superhost

A well-maintained outside space features a neatly trimmed grassy area along a pathway, flanked by vibrant greenery and flowering plants. On one side, a wooden deck with railings enhances the exterior of the two-story building, while a fence provides privacy.

Apartment in Chicago

4.89 out of 5 average rating, 186 reviews

Royal Coach House Cottage

Royal Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Our space is quite cozy, quaint and ideal for relaxation, peace & quiet. Flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants. Seconds from park, walking track and playground. Minutes from downtown and Magnificent Mile. Local transportation accessible including bicycle rental.

Guest favorite

A bright and airy attic space is characterized by soaring white shiplap walls and rustic wood flooring. A comfortable sectional sofa and lounge chair are positioned around a glass coffee table. Natural light floods in through multiple skylights, illuminating the cozy bedroom area visible in the background.

Apartment in Avondale

4.97 out of 5 average rating, 163 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

Top guest favorite

A bright hallway is illuminated by natural light, showcasing a mix of art and plants. Shelves with various glassware and plants line one wall, while framed artwork featuring mountains and landscapes adds character. Light wooden flooring runs throughout the space.

Apartment in Humboldt Park

4.99 out of 5 average rating, 142 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Superhost

An open basement space is showcased, featuring a gray futon with decorative pillows and a colorful throw. A wall shelf holds a world map and books. The cozy sleeping area includes a spacious bed with bedside lamps, while a patterned rug adds warmth to the floor.

Apartment in Logan Square

4.92 out of 5 average rating, 129 reviews

Logan Square Garden Sanctuary

This house is located in historic Logan Square. The space is a newly renovated basement unit of an owner-occupied two-flat. It's right next to Palmer Square which is a two acre park with a jogging path, kids area, and benches. It's a perfect place to have a picnic or meet with friends. The neighborhood is very walking-friendly and there's tons of great shops and restaurants in the area. The unit has an open floor-plan with a comfy memory foam bed, futon, a full bathroom, and kitchenette.

Top guest favorite

The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.

Apartment in West Town

4.97 out of 5 average rating, 538 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Superhost

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

Apartment in Near North Side

4.82 out of 5 average rating, 757 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 favorite

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Apartment in Belmont Cragin

4.98 out of 5 average rating, 123 reviews

Belmont Pleasures - hot tub / arcade gaming room

Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether you’re looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.

Guest favorite

A modern kitchen features sleek black cabinetry and appliances, complemented by a contrasting white countertop. Stylish stools are arranged around a small kitchen island. The wall is adorned with a framed painting, while decorative items are displayed on open shelves above the countertop.

Apartment in Pilsen Historic District

4.87 out of 5 average rating, 272 reviews

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.