Holiday rentals in West Side

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in West Side

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Private room in Evanston

4.94 out of 5 average rating, 209 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.

Superhost

Private room in Chicago

4.82 out of 5 average rating, 521 reviews

Florence Room - 3min to CTA, Free Parking, Roomy

The Florence room is one of three rooms in the grotto. The room has a king size bed and full size sofa sleeper for a maximum guest count of 4. You will have access to the kitchen for the microwave, toaster, and stove, along with free Keurig coffee. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms.There is a private mini fridge in your room for food storage. The house is one block from the Kedzie Green line rail station.

Superhost

Private room in North Riverside

4.91 out of 5 average rating, 312 reviews

The Sable Creek Room at the Cape Cod in Riverside

Welcome to your home away from home! 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 Loyola University Medical Center. Conveniently located, it’s 18 miles from O’Hare Airport and 9 miles from Midway. The Sable Creek Room, one of two Airbnb listings, is the only bedroom on the main floor and accommodates two guests. The property partially uses solar energy.

Guest favourite

Home in Oak Park

4.97 out of 5 average rating, 144 reviews

Quiet & Just Outside of Chicago w/ Free Parking

Our Oak Park, recently remodeled garden unit is 3 blocks to the train with free parking in upscale, safe, walkable Oak Park. Enjoy some time in our little urban farm. Check out the gardens and visit our 6 friendly hens. This non-smoking studio with a kitchenette is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties, 4 guests max. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

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

4.68 out of 5 average rating, 346 reviews

Sonder Market Hall | King Studio Apartment

Overlooking Union Park, Market Hall is the perfect blend of city and seclusion. You’ll have leafy green views, paved walking trails, and endless global cuisine options on Randolph Street. Each room includes a fully equipped kitchen, in-suite laundry, and a Roku for streaming. And take advantage of the free weights or machines in the fitness center. The West Loop is a trendy hot spot for foodies and entertainment seekers. Enjoy the best of the Windy City at Market Hall.

Superhost

Private room in Chicago

4.82 out of 5 average rating, 205 reviews

ChicagoRiver Double Room

Nicely decorated Private (10x11 sq ft) Room w/designated work station, well-lit, *shared common bathroom* (other guests may be in the premises). This is NOT a full condo rental; just 1 room. Quiet & clean, 2 miles from downtown, walking distance to dozens of restaurants in Taylor Street & Little Italy. Perfect location in a quiet neighborhood, but still close to the city to enjoy food& music festivals, free concerts in Grand Park, Museums, Broadway shows, etc

Guest favourite

Flat in Berwyn

5 out of 5 average rating, 16 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 Chicago

4.99 out of 5 average rating, 243 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

Home in Chicago

5 out of 5 average rating, 13 reviews

Chicago Row House Garden Apartmt

This stylish urban garden apartment is a comfortable stay just a few blocks from the United Center and 1 mile from the very popular West Loop and Fulton Market areas! Street parking is readily available and free! We are a 3 mile straight shot down to Millennium Park in the Loop. Take the “L”, bike or walk there and hit Greek Town, the Lyric Opera, the Sears (Willis) Tower, the Art Institute and the Bean (Cloud Gate) along the way!

Flat in Chicago

4.59 out of 5 average rating, 81 reviews

Cozy Basement Apartment - Great Location!

Check out our garden apartment on the border of Logan Square & Humboldt Park! It's right off the 606 Trail (which will lead you east to Bucktown & Wicker Park). Also, it is a short walk to either Humboldt Park or Logan Square. The layout - 1 spacious bedroom, full kitchen, private entrance, dining area and more. We're close to the Blue Line, so it's convenient to get here from O'Hare, & to the Loop!

Superhost

Hotel room in Rosemont

4.89 out of 5 average rating, 366 reviews

Relaxing Standard Room l Free Airport Shuttle

Explore the charming neighborhood of Rosemont just outside our doors. Attractions await you: ✔ Offers a 24-hour front desk, airport transfers, an ATM and free WiFi throughout the property. ✔ Enjoy indoor pool or use the business centre that offers printing, copying and fax services. ✔ Breakfast included. Monday to Friday from 6:30AM to 9:30AM, and on Saturday and Sunday from 7:30AM to 10:30AM.