Holiday rentals in Downtown Chicago

A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.

5 out of 5 average rating, 77 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.

An outdoor pool is surrounded by a pavement area, featuring a few lounge chairs arranged along the sides. The building's modern architecture is visible in the background, with city high-rises and clear blue skies providing a vibrant setting.

5 out of 5 average rating, 38 reviews

The Stadium Overlook (Fitness Center • Sauna)

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. Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 1 bedroom apartment offers guests all the comforts of home, whether on the road for work or play.

5 out of 5 average rating, 5 reviews

Upscale High-Rise Apt · Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

Superhost

A modern kitchen area with an island and bar stools is shown, adjacent to a dining space with chic seating. A bright living area features a PAC-MAN arcade machine. The bathroom is visible, showcasing contemporary fixtures and a clean design. All spaces exude a cozy ambiance.

4.86 out of 5 average rating, 186 reviews

Cozy Beauty Sleeps 5 - 10 Min to Downtown PacMan

Luxurious 550 sqft 1BR 1BA located 10 min from Downtown! Stand up shower, games for adults & kids, cozy bedroom 2 Smart TVs, free wifi (600 mpbs speed) Grill + Patio Chairs Sleeps 4 comfortably, 1 full bed, 1 queen sleeper sofa, 1 air mattress Street parking can be very difficult!!! - permits provided Walking distance from famous 26th street, plenty of restaurants 3 miles from Little Italy and Chinatown 15 min drive from Millenium Park and Soldier Field Great for professionals and travelers.

4.97 out of 5 average rating, 59 reviews

A modern kitchen features sleek stainless steel appliances, white cabinetry, and a large island with a quartz countertop. Barstools are arranged along one side. A dining area with a circular mirror and plants is visible in the background, creating an open and inviting layout.

Apartment in Chicago

Fulton Market Masterpiece 2BR/2BA (+garage spot)

Welcome to this West Loop/Fulton Market Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Randolph St. - Close to every popular attraction that makes Chicago so great - Attached, garage parking spot! - Luxurious interior design - Tranquil patio off kitchen - Fast WiFi - Very comfortable sleeping! - State-of-the-art kitchen - Beautiful, primary en-suite! - 10 minute walk from green line (CTA L) We look forward to hosting you!

4.96 out of 5 average rating, 552 reviews

A contemporary loft bedroom features a spacious bed with a light grey quilt. Exposed brick walls complement framed vintage Chicago artwork. Soft lighting is provided by string lights near the window. A green plant adds a touch of nature, while dark wood accents create warmth.

Loft in Chicago

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.

A modern living room showcases large windows providing natural light and city views. A cozy sectional sofa is positioned adjacent to a sleek flat-screen TV, complemented by a dark coffee table and decorative elements. Exposed brick walls add character to the airy space.

4.94 out of 5 average rating, 82 reviews

River North | Rooftop With In & Out Parking | 6

Enjoy a stylish experience at this centrally-located place! ✨🏙️ Stunning 1,000 sq. ft. modern 2-bedroom, 2-bathroom unit—perfect for corporate travelers 💼 & families looking for a stylish escape in downtown Chicago. 🌆 🔥 Rooftop Patio w/ BBQ 🚗 Free In/Out Parking (5-min walk to garage) 🏠 2 Bedroom | 2 Bathroom 🛏️ 2 Queen Beds & Sleeper Sofa (Sofa Bed - Sleeps 1) 🛌 2 Inflatable Airbeds 👶 Portable Crib (For Mini Travel Companion) 🎬 Netflix, Hulu, Disney+, & Prime Included

4.89 out of 5 average rating, 152 reviews

A modern living area features a dark sofa adorned with colorful throw pillows. A wooden coffee table rests in front, and light streams in through large windows that offer views of the surrounding city. A dining table with chairs is visible in the background.

Apartment in Chicago

Downtown Park #11 - Mich Ave PH | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

4.96 out of 5 average rating, 257 reviews

An aerial view captures the airy living area featuring large glass doors that invite natural light. A modern gray sofa is positioned beside a round coffee table. The wood dining table in the foreground is surrounded by colorful chairs, enhancing the open layout of the space.

Apartment in Chicago

Updated Designer Duplex In Fulton Market W/parking

We completed our luxury renovation in kitchen, bathrooms, and patio with a fire pit! We hope you enjoy! The first thing you notice stepping into my house are the sky-high ceilings! Enormous floor to ceiling windows allow light to stream into the the 2 floor home. The stylish and very large terrace are great for summer nights. Walk out the front door & you are in the heart of restaurant row with all the best bars and restaurant in the city. Parking included!

A modern kitchen area features white cabinetry and stainless steel appliances, including a refrigerator and stove. A small wooden dining table is positioned against the wall, complementing the neutral tile floor and the soft lighting from recessed ceiling fixtures.

4.97 out of 5 average rating, 35 reviews

Cozy newly renovated apartment in Bridgeport

Welcome to your perfect home away from home in Bridgeport, Chicago 🏡 This newly renovated cozy 1-bedroom, 1-bathroom apartment offers a comfortable, inviting space just 10 mins to downtown Chicago. Located couple minutes from Chinatown Whether you're here to catch a White Sox game or immerse yourself in the vibrant local food scene and culture, this location is ideal for exploring the best of Chicago. FREE PARKING 🅿️ NO PARTIES.

5 out of 5 average rating, 6 reviews

Springfield Serenity

Welcome to Springfield Serenity, a modern two-bedroom retreat designed for calm and connection. Unwind in the serene meditation corner, enjoy a movie night or a round of Pac-Man in the cozy entertainment room, and relax in a space filled with soft tones of greenish-blue and gold. Whether you’re here to rest, reset, or explore, Springfield Serenity offers a peaceful, stylish escape that feels like home.

4.97 out of 5 average rating, 186 reviews

Elegant Suite in Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of May 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours***

Popular amenities for Downtown Chicago holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Downtown Chicago

4.85 out of 5 average rating, 13 reviews

Comfortable Private 1 bedroom

A cozy living area is furnished with a circular coffee table and a cushioned seating arrangement featuring light-colored upholstery. Soft natural light filters through sheer and patterned curtains, creating a comfortable environment for relaxation. A piece of wall art adds a touch of decoration.

4.76 out of 5 average rating, 50 reviews

Bees Knees - Room 3

4.69 out of 5 average rating, 369 reviews

B1 - Next to Downtown Chicago - Private Room

Hotel room in Chicago

4.65 out of 5 average rating, 133 reviews

Modern design with VU Skyward rooftop bar

Hotel room in Chicago

4.58 out of 5 average rating, 444 reviews

Lincoln Park gem with storied jazz & rock history

4.88 out of 5 average rating, 40 reviews

23rd Pl 2U