Vacation 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.

New Build in Pilsen! Spacious 2 Bed 2 Bath Unit

Experience upscale city living with @TheDreamRentals in this stylish 2-bedroom, 2-bath Airbnb located in Chicago’s vibrant Tri-Taylor neighborhood. This modern retreat features sleek interiors, spacious bedrooms with queen beds, a fully equipped gourmet kitchen, and designer finishes throughout. Enjoy high ceilings, large windows, and smart amenities just minutes from downtown, the United Center, and the Illinois Medical District. Perfect for professionals, couples, or small groups seeking comf

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.

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

Spacious Hotel Room in The Loop

Just steps away from the famed shopping on State Street, this boutique hotel is located inside the Nederlander Theater building in the Chicago Loop Theater District. The hotel features on-site dining, state-of-the-art business services and modern guest rooms with free WiFi. Every room at Cambria Hotel Chicago Loop/Theater District provides a 49-inch flat-screen HDTV and a large work space with a desk and ergonomic chair. Select rooms also offer plush lounge seating.

The Chicago Cozy Brick Retreat

This unit offers a charming blend of modern amenities and historic charm. This thoughtfully designed unit features an open-concept living space with exposed brick walls and stylish furnishings. The fully equipped kitchen boasts new appliances, perfect for culinary adventures. The comfortable bedroom, with a cozy bed and ample storage, ensures a restful stay. The sleek bathroom includes contemporary fixtures and a walk-in shower. Street parking is easily available.

Egyptian Room - Free Parking, 1 block to CTA

Comfortable lower level bedroom with a pillow top king bed, granite topped desk, and smart tv makes this room a super cozy retreat, You will have full access to the kitchen cooking and free Keurig coffee. You have a private mini fridge in your room for food storage. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms. Easy unmetered street parking is readily available for those coming by car.

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.

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!

Private studio near Wrigley

Getting to all major destinations is key while also coming back to a quiet neighborhood. Only a few steps from public transportation. The unit is attached to a single family home with your own private entrance and access to the backyard that has a gas grill and fire pit (and pups at times that like to play fetch). I am a 1 mile walk to Wrigley Field. Also had a pull out couch if need additional sleeping space.

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.