Holiday rentals in Downtown Chicago

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Top-rated holiday rentals in Downtown Chicago

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Superhost

Flat in Chicago

5 out of 5 average rating, 31 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.

Superhost

Flat in Chicago

4.98 out of 5 average rating, 161 reviews

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.

Superhost

Private room in Oak Park

4.73 out of 5 average rating, 298 reviews

Little Gem Double Rm Home Base for Chicago Trips!

Great home base for Chicago adventures & PREMIUM location in the epicenter of Oak Park - America's home of prairie architecture! Beautiful park/Frank Lloyd Wright homes are directly outside your door and you are only a 25-minute train ride to Millennium Park & all of Chicago! Eclectic garden level (shared) apartment decorated with fun and funky furnishings. Private Bedroom with new double size bed, deluxe bedding, towels. Shared bathroom, living room, and kitchenette. View my other 2 listings!

Superhost

Flat in Chicago

4.9 out of 5 average rating, 52 reviews

52nd Floor MagMile Penthouse VIEWS Fireplace Pool

Welcome to your dream home! You'll feel like royalty as you tower 52 stories above Downtown Chicago. Imagine waking up to floor-to-ceiling windows, an exquisite fireplace & ultimate luxury urban living. With Lake Michigan as your backdrop, the city and its skyline unfold before you. To the east, you have the elegance of North Michigan Avenue and to the west, the artsy sophistication of River North. Don't miss out on living the high life. Come and see this penthouse for yourself!

Superhost

Flat in Chicago

4.78 out of 5 average rating, 147 reviews

McCormick Place Studio/parking/sleeps up to 4

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • City view • Queen size bed + Queen size air mattress 2 extra guests • Comfortable stay for up to 4 guests at a time • Access to the Gym • Dedicated Internet • 4K smart HDTV(Netflix and Roku) • Fully equipped & stocked kitchen with complimentary Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

Superhost

Apartment in Chicago

4.9 out of 5 average rating, 296 reviews

Old Town Pied-à-Terre w/Pvt Terrace and Parking

Our bright modern 2 bedroom condo has 13 ft ceilings and an amazing private terrace. It's in the heart of Old Town, right on Wells St - steps outside the door are some of the city's best restaurants, cafes, and bars. Just a 5 minute walk to two world-renowned comedy clubs: Second City and Zanies. The Chicago History Museum, Lincoln Park Zoo, and the lake are a quick walk too. The Sedgwick CTA stop is nearby too! Please note: patio cushions are available May through October.

Loft in Chicago

4.99 out of 5 average rating, 109 reviews

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.

Superhost

Flat in Chicago

4.86 out of 5 average rating, 78 reviews

Penthouse near Fulton Market: 3BR Luxury

Book now your Chicago getaway for May or June and enjoy $200 in DoorDash credit for delicious food delivered right to your door. This limited-time offer makes your stay even better – don't miss out! Immerse yourself in the vibrant energy of Chicago at 'The Bow', our modern 3BR penthouse offering breathtaking views and a comfortable stay. Its prime location ensures you're just moments from the exciting culinary scene and the city's energetic main nightlife.

Guest house in Chicago

5 out of 5 average rating, 6 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.

Superhost

Flat in Chicago

4.94 out of 5 average rating, 54 reviews

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Flat in Chicago

4.79 out of 5 average rating, 29 reviews

Sonder Onterie | Two-Bedroom 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.

Flat in Chicago

5 out of 5 average rating, 12 reviews

Luxury Downtown Chicago 2BD-2BA View-Gym-Rooftop

Experience downtown Chicago living at its finest in this stunning 2-bedroom apartment in the heart of the Loop. Wake up to breathtaking city views and step out to world-class attractions just minutes from your door. Enjoy in-unit laundry, gigabit Wi-Fi, free parking, and luxe building amenities, including a rooftop lounge, and gym. Perfect for business or leisure!