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Vacation rentals in Downtown Chicago

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Downtown Chicago vacation rentals

Self check-in
Gym
BBQ grill
Laptop-friendly workspace
Wifi

Downtown Chicago apartment rentals

Superhost
A modern kitchen area features a compact island with a sleek sink and metallic fixtures. A round dining table with black-and-white polka dot chairs sits against a light pink floral accent wall. Warm lighting enhances the inviting ambience of the space.
Apartment in Chicago
4.83 out of 5 average rating, 360 reviews

*Entire City Apartment 1 block to Train Park Free

Top guest favorite
A green sofa is positioned in a bright living area, accompanied by a round coffee table. A decorative bowl and a potted plant sit atop the table, while a piece of wall art featuring a tree landscape adds character. Natural light enters through nearby windows.
Apartment in Chicago
4.99 out of 5 average rating, 253 reviews

Modern Apt with style & comfort in Pilsen Chicago

Guest favorite
A vintage-style sign featuring bold red and white lettering, stating 'Bohemian Lodge no 17' against a dark brown background. Decorative elements include images of beer glasses and whimsical knot designs, creating a nostalgic atmosphere.
Apartment in Chicago
4.85 out of 5 average rating, 308 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Guest favorite
A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.
Apartment in Chicago
4.92 out of 5 average rating, 136 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Superhost
A modern living area features a comfortable sofa adorned with neutral and textured cushions. A large mirror reflects natural light, highlighting the floor-to-ceiling windows that offer expansive city views. Stylish plants and sleek furniture enhance the contemporary design.
Apartment in Chicago
5 out of 5 average rating, 6 reviews

Downtown Chicago Retreat 2BD/2BA Views+Gym+Rooftop

Guest favorite
A spacious light-filled game area is highlighted by a ping pong table at the center. Large windows frame the room, offering views of the outside. A comfortable seating area is visible alongside a decorative plant and wall-mounted mirrors, contributing to a relaxed environment.
Apartment in Chicago
4.97 out of 5 average rating, 111 reviews

King Bed • No Stairs • Ping-Pong • United Center

Guest favorite
A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.
Apartment in Oak Park
4.86 out of 5 average rating, 689 reviews

Rockin' 2Bed steps to shops/food/train

Guest favorite
A modern lounge area is highlighted by large floor-to-ceiling windows, offering expansive views of the Chicago skyline. Two round, cozy chairs are positioned near a small round table, complemented by a plush sofa. Green plants add a touch of nature to the space.
Apartment in Chicago
5 out of 5 average rating, 22 reviews

14th Floor 3Bd 3Bth Unit w/ Gym, Pool, &Amenities

Downtown Chicago condo rentals

Guest favorite
The living area features exposed brick walls and hardwood floors, with an arrangement of seating including a red armchair and a cozy sofa. A glass coffee table sits on a plush area rug. A wall-mounted flat-screen TV is present, alongside indoor plants and decorative elements.
Condo in Chicago
4.99 out of 5 average rating, 300 reviews

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

Guest favorite
A bright living area features large windows that offer city views. Comfortable seating arrangements include a pair of teal sofas and a wooden armchair. A coffee table sits at the center on a soft area rug, accompanied by a flat-screen TV mounted on a nearby wall.
Condo in Evanston
4.95 out of 5 average rating, 119 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Superhost
A modern kitchen is highlighted by white cabinetry and stainless-steel appliances, including a gas stove and microwave. A black countertop provides ample workspace. A dining area with a wooden table and chairs is visible, complemented by a large window allowing natural light to fill the space.
Condo in Chicago
4.93 out of 5 average rating, 265 reviews

The Upscale Getaway Near Downtown

Guest favorite
The living room features a comfortable sofa embellished with decorative pillows and a cozy throw. A gallery wall, adorned with framed photographs, adds visual interest. A wooden coffee table rests in front of the sofa, complemented by accent lighting on either side.
Condo in Chicago
4.96 out of 5 average rating, 148 reviews

East Lakeview Designer Condo with 2 Bd, 2 Bath

Guest favorite
A vibrant living area is highlighted by a deep blue sofa and a colorful area rug. A large wall-mounted television is positioned across from the seating, and modern artwork decorates the walls. The adjoining kitchen is visible in the background, showcasing sleek cabinetry and new appliances.
Condo in Chicago
4.85 out of 5 average rating, 227 reviews

3D Tour! Designer Condo near Logan Square

Guest favorite
An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.
Condo in Chicago
4.97 out of 5 average rating, 161 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Guest favorite
A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.
Condo in Chicago
4.93 out of 5 average rating, 265 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Top guest favorite
A modern living area features a spacious couch with a textured throw, positioned near a wall-mounted TV above a sleek fireplace. Large sliding glass doors lead to an outdoor patio, revealing a view of the vibrant neighborhood.
Condo in Chicago
4.98 out of 5 average rating, 131 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Other great vacation rentals in Downtown Chicago

Top guest favorite
Apartment in Chicago
5 out of 5 average rating, 15 reviews

Chicago Vintage & Chic Living

Guest favorite
A spacious living area features high ceilings with a skylight and large windows, offering ample natural light. A comfortable green sofa and a black armchair are positioned near a coffee table. A fireplace and a television are visible, with scenic views seen through the glass doors.
Apartment in Chicago
4.96 out of 5 average rating, 28 reviews

Sunny Penthouse - Oakwood Beach

Apartment in Chicago
4.9 out of 5 average rating, 142 reviews

Steps to Nightlife • Pool Table + Deep Tub

Top guest favorite
A comfortable living area features a dark sectional sofa positioned around a round coffee table. A wall-mounted television is displayed above a modern electric fireplace. Natural light enters through a small window, while a plant and a workspace are subtly included in the room.
Guesthouse in Chicago
5 out of 5 average rating, 25 reviews

Garden Retreat in Historic Bronzeville

A modern living area featuring large windows that provide plenty of natural light and city views. A spacious gray sofa is paired with a sleek side table and a small plant. A dining table with several chairs is visible in an adjacent area, enhancing the inviting layout.
Apartment in Chicago
4.71 out of 5 average rating, 150 reviews

Sonder South Wabash | 1BR w/ Balcony City View

Top guest favorite
Two hanging chairs are positioned on a covered patio, surrounded by lush greenery and decorative plants. A small garden structure adds privacy, while the floor features a vibrant red surface. Ambient light filters through the overhead structure, creating a relaxed outdoor space.
Home in Chicago
5 out of 5 average rating, 20 reviews

Chicago Row House Garden Apartmt

Top guest favorite
An open concept living area is captured, showcasing a modern kitchen with stainless steel appliances and gray cabinetry. A cozy sofa with textured cushions faces a large window, allowing natural light to fill the space. A sleek dining table is positioned nearby.
Apartment in Chicago
5 out of 5 average rating, 58 reviews

Fantastic West Loop 2 bedroom

The exterior of a historic four-story building showcases intricate stonework and arched windows. Two blue doors with glass inserts serve as the main entrance, framed by a wooden porch that leads to the entrance. The surrounding greenery adds a touch of nature.
Loft in Chicago
4.7 out of 5 average rating, 155 reviews

Studio with View of Skyline in Heart of Pilsen

Frequently Asked Questions

  • How is the weather in Downtown Chicago?

    Downtown Chicago experiences a diverse climate. Summers can be hot, typically reaching 85°F (29°C), while winter temperatures can drop to around 20°F (-6°C), often accompanied by snow. The transitional seasons, spring and fall, offer more moderate weather, making them pleasant times to visit.

  • What are some of the best things to do in Downtown Chicago?

    There's no shortage of activities in Downtown Chicago. Explore the Art Institute of Chicago, walk alongside the Chicago River, or enjoy a stroll in Millennium Park. You can also marvel at the city's skyline from the Willis Tower's Skydeck or take a boat cruise on Lake Michigan.

  • What is the best time of year to visit Downtown Chicago?

    The summer months, from June to August, are a great time to explore Downtown Chicago as the city comes alive with a range of cultural events including Lollapalooza, the Chicago Air and Water Show, and the Jazz Festival. However, the city also offers distinctive charm during the winter season, with events like the Magnificent Mile Lights Festival and the Winter WonderFest.

  • What are the best places to stay in Downtown Chicago?

    Guests enjoy staying in several areas in Downtown Chicago. The Loop, Chicago's central business district, is known for its bustling atmosphere and close proximity to many attractions. River North, with its art galleries and fashion outlets, is also popular. Streeterville, near Navy Pier and Magnificent Mile, is another preferred location.

  • What are the best places to visit in Downtown Chicago?

    There are many popular places to visit in Downtown Chicago. These include the Navy Pier, with its iconic Ferris wheel, the Art Institute of Chicago, known for its impressive collection, and the historic Chicago Theatre. Don't miss a walk down the Magnificent Mile for shopping and dining.

  • What are some hiking trails in Downtown Chicago?

    While Downtown Chicago is primarily urban, there are lovely trails to explore. The 18-mile (29 km) Lakefront Trail along Lake Michigan is a favorite among locals and visitors. The Chicago Riverwalk also provides a scenic urban hike through the heart of the city.

  • What are some family activities to do in Downtown Chicago?

    Families in Downtown Chicago can explore a multitude of engaging activities. Visit the Shedd Aquarium or the Field Museum for an educational outing, enjoy outdoor fun at Maggie Daley Park, or discover the wonders of space at the Adler Planetarium.

  • What are some of the best day trip ideas in Downtown Chicago?

    For day trips, consider exploring the natural beauty of the Chicago Botanic Garden or the historical architecture in Oak Park, both within a short drive from Downtown. Alternatively, the Indiana Dunes National Park, 50 miles (80 km) away, offers an escape to nature.

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