Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

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Top guest favourite

Private room in Elmhurst

4.99 out of 5 average rating, 218 reviews

Chic Oasis near Downtown Chicago

Open the classic wooden shutters and let in the morning sun at this peaceful abode in the suburbs. The kitchen fridge and small appliances, family room, upstairs laundry, and basement game tables. We enjoy hosting our guests and are happy to help with any information and/or suggestions to make their visit as enjoyable as possible. Located in a quiet suburb, there's a park with tennis courts and a playground within walking distance. A short Uber or taxi ride reaches dozens of excellent restaurants and shops in locations such as the cozy downtown Elmhurst area. We are 10 minutes away from public transportation from Elmhurst to downtown Chicago. If you have a vehicle, parking is inexpensive at the Elmhurst train station. If you do not have a vehicle, we recommend taking Uber or Lyft to the Elmhurst train station. If you are planning to drive into the city of Chicago, we recommend using either SpotHero or ParkWhiz parking apps. We will try to make your stay as comfortable as possible. If you have any special needs or requests, please let us know and we will do our best to accommodate you.

Top guest favourite

Flat in Chicago

5 out of 5 average rating, 36 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

Private room in Evanston

4.94 out of 5 average rating, 197 reviews

Welcoming Evanston Home

We have a newly renovated suite awaiting your stay, perfect for one guest. This dedicated entry, private room + bathroom, and tree-lined street are in our quiet neighborhood in beautiful Evanston, just north of Chicago. As international travelers ourselves, we love hosting others from near or far! Enjoy a short walk to cafes, stores, mall shopping, parks, and restaurants. Easy free parking, convenient Uber / Lift rides, and public transportation are also here to make your stay enjoyable.

Flat in South Loop

4.72 out of 5 average rating, 247 reviews

Kasa | 1BD, 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.

Guest favourite

Private room in North Riverside

4.93 out of 5 average rating, 218 reviews

The Albany Park Room at the Cape Cod in Riverside

The Cape Cod in Riverside is 10 miles from downtown Chicago, accessible via METRA and CTA Blue Line. It's a block from a trail entrance, a mile from Brookfield Zoo, and close to Riverside's historic downtown and Loyola University Medical Center. O'Hare Airport is 18 miles away, and Midway is 9 miles. The Albany Park Room, one of two Airbnb listings, is on the second floor and accommodates two guests. The property supports sustainability with partial solar energy for heat and hot water.

Superhost

Flat in Grant Park

4.73 out of 5 average rating, 161 reviews

Sentral Studio Apt in South Loop Chicago

Experience a lifestyle where everything you need is right at your fingertips in the vibrant heart of Downtown Chicago. Explore the area effortlessly: ✔ Breathtaking views of Lake Michigan and the Chicago skyline ✔ Close to major business hubs and the Loop District ✔ Enjoy a walk along the scenic Lakefront Trail ✔ A lively array of world-class museums, gourmet restaurants, and iconic architecture ✔ Quick access to Millennium Park, the Art Institute of Chicago, and Grant Park

Guest favourite

Flat in Berwyn

5 out of 5 average rating, 7 reviews

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. This serene one-bedroom, one-bath suite offers a peaceful retreat, inspired by the calming essence of jade. The space features a sleek, airy design with thoughtful touches to make you feel right at home. Fully equipped kitchen, cozy living area, the bedroom invites restful nights, while the spa-like bathroom offers a moment of quiet indulgence. Perfect for a restful getaway or a productive stay.

Top guest favourite

Flat in Lower West Side

4.99 out of 5 average rating, 235 reviews

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Top guest favourite

Guest house in Andersonville

5 out of 5 average rating, 10 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.

Guest favourite

Shared room in East Rogers Park

4.83 out of 5 average rating, 174 reviews

05a. Common Room King

We have a King-sized bed in a Common Room. This is in a shared common room space. Up to 3 other guests my be booked in this room. The room has limited storage and NO DOOR. This space is best for those with little to no bags. Breakfast is included in your stay. We keep the pantry stocked with eggs, bacon, milk, orange juice, jam, bread, fruit, pancake mix, coffee and tea. Any of these items can be used to make yourself breakfast in the morning.

Flat in Streeterville

4.71 out of 5 average rating, 301 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 South Shore

5 out of 5 average rating, 7 reviews

Zen's ~ Quiet, Near Beach/Golf, DT, 1425 sq ft

Discover this renovated historical Chicago bungalow nestled in the cultural South Shore neighborhood. ~ Michelle Obama's childhood home and school are nearby ~ The block is the origin of the Back Alley Jazz community festival ~ Museum of Science & Industry ~ Garden of the Phoenix ~ Nature trails & Beaches ~ Jackson Park Golf Course ~ South Shore Cultural Center ~ Nearby access to bus/train, beaches, and free street parking