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Downtown Chicago vacation rentals

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Popular amenities for Downtown Chicago vacation rentals

Self check-in
Monthly stays
Gym
BBQ grill
Laptop-friendly workspace

Downtown Chicago apartment rentals

Guest favorite
A cozy living area features a modern black sectional sofa adorned with colorful throw pillows. A large photograph of a city skyline hangs on the wall. A small coffee table rests on a patterned rug, while a desk and chair are positioned beside a plant and shelves.
Apartment in Chicago
4.97 out of 5 average rating, 109 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

Guest favorite
A well-lit living area features a comfortable sofa adorned with colorful cushions, accompanied by a plush armchair and a stylish coffee table. Soft lighting from two lamps enhances the cozy ambiance, while a small desk and chair provide a designated workspace against a bright window.
Apartment in Evanston
4.85 out of 5 average rating, 250 reviews

Adorable 1BR apartment near Northwestern

Guest favorite
A welcoming living space features a round dining table surrounded by four chairs, with a large artwork depicting trees on the wall. A light fixture hangs from the ceiling, and a mirror reflects the room. Natural light fills the area, enhancing the warm ambiance.
Apartment in Evanston
4.83 out of 5 average rating, 179 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Superhost
A modern living area features a beige sectional sofa and a round coffee table set on a patterned rug. A large flat-screen TV is mounted on the wall, and a potted plant adds a touch of greenery. Natural light illuminates the space.
Apartment in Chicago
4.82 out of 5 average rating, 185 reviews

New apartment

Superhost
An outdoor terrace is visible, featuring seating arrangements with two orange chairs and a fire pit. The view overlooks Lake Michigan, with the calming waves in the background. A pathway leads down to the water, surrounded by the building's architecture.
Apartment in Chicago
4.89 out of 5 average rating, 170 reviews

Executive Apartment on Lake Michigan with parking

Guest favorite
A spacious living area is furnished with a dark sectional sofa, accented by decorative pillows. A round coffee table rests on an area rug, while a television is placed on a dark wooden stand. Natural light filters through large windows with sheer curtains.
Apartment in Chicago
4.98 out of 5 average rating, 217 reviews

Chicago Airbnb Newly Remodeled 2-Unit Apartment!

Top guest favorite
A bright living room is highlighted by large windows that invite natural light. A comfortable brown leather sofa and a beige loveseat are positioned around a colorful area rug. A wooden coffee table and a wall-mounted TV complement the inviting space.
Apartment in Chicago
4.97 out of 5 average rating, 148 reviews

Inviting 2 Bedroom Apartment in Roscoe Village

Guest favorite
A modern kitchen is depicted with a stainless-steel refrigerator and oven, complemented by a tiled backsplash. Light cabinetry provides ample storage, while a cozy couch with a blue accent pillow offers a welcoming touch. Natural light brightens the space, enhancing the functionality.
Apartment in Chicago
4.94 out of 5 average rating, 145 reviews

Cozy 2 bdrm near McCormick Place & Wintrust Arena

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Downtown Chicago condo rentals

Superhost
Condo in Evergreen Park
4.81 out of 5 average rating, 118 reviews

Evergreen Park Condo with balcony and Jacuzzi tub

Guest favorite
A workspace area is showcased with a stylish glass desk and a woven chair. A lamp stands on the desk, providing light, while a round mirror hangs on the wall behind it. Textured stone and wooden floors add warmth to the space.
Condo in Chicago
4.87 out of 5 average rating, 236 reviews

A Stones Throw from U Chicago South Campus!

Guest favorite
Condo in Chicago
4.95 out of 5 average rating, 129 reviews

Entire 3Bed/2Bath Condo Near McCormick & Metro

Guest favorite
Condo in Chicago
4.89 out of 5 average rating, 113 reviews

Convenient & Spacious 3BR Condo w/Free Parking

Guest favorite
The historic brick building features a unique architectural style with a turret, large windows, and a vibrant sunset sky in the background. Ground-level storefronts are visible, highlighting a mix of commercial spaces. The presence of parked cars adds to the urban ambiance.
Condo in Chicago
4.91 out of 5 average rating, 104 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

Guest favorite
A modern three-story condominium is showcased, featuring a combination of dark and light brick with large windows. Soft lighting highlights the front entrance and landscaped gravel area, providing a contemporary appeal. Neighboring buildings are visible in the background, contributing to the urban atmosphere.
Condo in Chicago
4.91 out of 5 average rating, 159 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

Top guest favorite
A spacious bedroom is highlighted by a large bed with a soft gray blanket and multiple decorative pillows. Two windows allow natural light to fill the room, with a piece of framed artwork displayed on the wall. Wooden nightstands flank the bed.
Condo in Chicago
4.98 out of 5 average rating, 277 reviews

Near Lake Michigan & Wrigley Field

Guest favorite
Condo in Chicago
4.99 out of 5 average rating, 137 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

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Other great vacation rentals in Downtown Chicago

Superhost
Home in Chicago
4.93 out of 5 average rating, 44 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

Guest favorite
A panoramic view of the Chicago skyline is presented, featuring iconic buildings illuminated against a dramatic night sky. The Willis Tower stands tall, with its lights creating a vibrant display amidst the clouds. The landscape showcases a blend of urban architecture bathed in colorful hues.
Apartment in Chicago
4.85 out of 5 average rating, 131 reviews

Condo with private terrace, free WIFI and parking

Guest favorite
Apartment in Chicago
4.86 out of 5 average rating, 43 reviews

Elegant 4Bedroom with Free Parking in Albany Park

Superhost
A modern dining area is highlighted by a wooden table surrounded by four chairs. The open-concept layout connects to a stylish kitchen featuring dark cabinetry and stainless steel appliances. Natural light fills the space, reflecting off the hard surface flooring and a cozy living room in the background.
Apartment in Chicago
4.64 out of 5 average rating, 28 reviews

City Gem: Stylish 3BR for Urban Explorers

Superhost
The exterior of a three-story Art Deco building is showcased, featuring a light-colored brick facade and large, symmetrical windows. A wrought iron fence surrounds the property, with well-maintained greenery enhancing the entrance. The sky above offers a clear blue backdrop.
Condo in Chicago
4.81 out of 5 average rating, 32 reviews

Spacious condo with open floor plan and fireplace

Superhost
Home in Cicero
4.79 out of 5 average rating, 186 reviews

Spacious whole apt near shopping and city

Top guest favorite
Home in Lombard
5 out of 5 average rating, 27 reviews

Spacious Home in Chicago Suburbs

Top guest favorite
Home in Wood Dale
5 out of 5 average rating, 5 reviews

Home in the Woods!

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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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Downtown Chicago