Holiday rentals in Chicago

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.

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.

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.

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.

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!

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

Cozy Coach House Retreat Near Downtown!

Fully remodeled coach house centrally located in Chicago! Most tourist attractions are within a 15 drive or less! Public transportation is within a 3 min walk. You'll also have access to the shared rooftop deck (Furniture available May 5th-Sept 30th). This cozy unit offers 1 Queen bed + 1 bath, 1 Queen size air mattress provided, fully stocked kitchen and spacious living room space! Free Street Parking in the Area

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.

At the junction of comfort and care

Your warmly-decorated guest room has a queen-size memory foam mattress for a good night’s sleep. A meticulously kept bathroom is adjacent to your room. Parking is free and easy. Downtown is 17 minutes by car along Chicago's lakefront and 50 minutes by public transit. Little India in our West Ridge neighborhood is a noteworthy dining destination. Enjoy basing your Chicago stay here!

S3 Private cozy room. NO parking. 15min to O'Hare

NO car. There is nowhere to park your car. Cozy room in the house. great place to relax before/after a long flight. 5 minutes from the house there are shops, cafes and restaurants, public transport. And the airport can be reached by taxi in 15 minutes or by bus in 1 hour The room has air conditioning, so you can always set a comfortable temperature for yourself.

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Coach House in Historic Old Town Chicago

Our coach house is the perfect place for your stay in Chicago. Located walking distance from restaurants, Lake Michigan, the beach and public transportation, it will make your stay in Chicago easy and eventful. We can tell you everything you need to know about the best places in the city. You'll feel right at home here on your Chicago adventure.