Holiday rentals with a fireplace near Navy Pier

The Metropolitan Retreat (Fitness Center • Sauna)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Peaceful River West, free parking

This Apt can be rented separately or together with Comfy River West Apt. https://abnb.me/aoJ0F64vDY This one on the the 2nd floor and one directly above on the 3rd floor. Together they will sleep 8 guest. This beautiful 2BR, 1 BA has all new furniture, all new appliances, counter tops, vanity, mirrors. Free parking in a gated lot, Level 2 EV charging available for electric cars. Shared patio/gardens and grill. Fully stocked kitchen, private washer & dryer.

Downtown Guild #3 | Mag Mile Gold Coast The Lake!

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - Steps away from the John Hancock - Gym in the Basement - Amazing location w/ many shops & restaurants nearby - Fast WIFI - KING bed - Charming, vintage Chicago building Walk to nearly any attraction in central Chicago. Please read our FAQs to answer any questions before booking.

Modern 3BR with Private Rooftop & Free Parking

A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

2BR Retreat with a Fireplace in Gold Coast

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. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

2br/2ba, A+ location by Mag mile, views & spacious

Unbeatable location next to Water Tower Place, with lots of natural light and partial lake view in a quiet vintage building with lots of character. Walk to nearly any attraction in central Chicago. I'm happy to help with sightseeing advice and discounts on popular tourist attractions. (Guests love: Location, View, Comfortable room and bed, Friendly/helpful host, Flexible luggage policy, fast wifi)

Stunning Wicker-Park Flat with Parking!

Enjoy a stylish experience at this centrally-located gem. Beautifully renovated 3 bedroom, 2 bath full floor flat. While quietly situated on the 3rd floor, you can walk out your front steps to all that Wicker Park and Division street has to offer. Coffee shops, bars, unlimited restaurants, green space, farmers market, gyms, grocery stores, and so much more. Easy and nearby public transit.