Discover Your Perfect Downtown Chicago Vacation Homes

Best Vacation Homes in Downtown Chicago

See More Downtown Chicago Vacation Rentals

Downtown Chicago Luxury Rentals

See More Downtown Chicago Luxury Vacation Rentals
Find More Downtown Chicago Villas, Resorts, & Rentals on BedroomVillas

Downtown Chicago Pet Friendly Vacation Rentals

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9.6 (166 Reviews)
Apartment
Kasa River North Chicago
  • Air Conditioner
  • Pet Friendly
  • Pool
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10.0 (4 Reviews)
Apartment
Stylish 1BR in West Loop
  • Air Conditioner
  • Pet Friendly
  • TV
View Availability
See More Pet-Friendly Vacation Rentals in Downtown Chicago on PetFriendly.io

Why Choose Rent By Owner for your Downtown Chicago Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Downtown Chicago Vacation Rentals

Where are the best neighborhoods to stay in Downtown Chicago?

When choosing where to stay in Downtown Chicago, you’ll find a variety of vibrant neighborhoods that offer unique access to the city’s best attractions and amenities. This bustling area is known for its diverse neighborhoods, each with its own distinct character—whether you're seeking the energetic downtown core, the historic charm of nearby districts, or modern city living. By selecting a vacation rental in Downtown Chicago, you ensure easy connectivity to major business hubs, entertainment venues, and cultural sites, making your visit both convenient and memorable. Trust in these well-situated neighborhoods to provide a seamless experience during your Chicago adventure.

Magnificent Mile

This vibrant area offers exceptional shopping, dining, and entertainment options, making it an ideal base for exploring the best of downtown Chicago. Staying here puts you close to iconic landmarks and the bustling city life.

View 4128+ Rentals in Magnificent Mile

The Loop

Known as the heart of Chicago’s business district, this neighborhood provides convenient access to cultural attractions and historic architecture, perfect for travelers seeking a lively urban experience.

View 761+ Rentals in The Loop

River North

Famous for its art galleries, trendy restaurants, and nightlife, this area is great for those who want to immerse themselves in Chicago’s creative scene while enjoying easy access to downtown sights.

View 446+ Rentals in River North

Lincoln Park

A picturesque neighborhood offering lush green spaces and a relaxed atmosphere, ideal for visitors wanting a more tranquil stay within reach of the city's premier attractions.

View 161+ Rentals in Lincoln Park

South Loop

This culturally rich district combines historic sites with proximity to major museums and parks, making it a great choice for travelers eager to explore Chicago’s history and natural beauty.

View 387+ Rentals in South Loop

West Loop

Renowned for its culinary scene and modern lofts, this neighborhood caters to visitors looking for a stylish, food-focused stay in close proximity to downtown Chicago.

View 201+ Rentals in West Loop

Near North Side

Offering upscale accommodations and boutique shopping, this area is perfect for those wanting a luxurious experience near the city’s premier attractions.

View 784+ Rentals in Near North Side

Gold Coast

This historic neighborhood features elegant architecture and high-end shopping, making it an excellent choice for travelers seeking sophisticated accommodations in the heart of the city.

View 46+ Rentals in Gold Coast

Best Times to Visit Downtown Chicago

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit this vibrant destination can enhance your experience, allowing you to enjoy the local atmosphere and events at their best while securing the perfect vacation rentals in the region.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, the area experiences warm weather and vibrant city events, making it an ideal time for sightseeing and outdoor activities.

Average Temperature Daytime: high 80s to low 90s °F - Nighttime: mid 60s to low 70s °F
autumn
Fall (September to November)

Autumn in this destination offers cooler temperatures and stunning fall foliage, attracting visitors seeking scenic views and cultural festivals.

Average Temperature Daytime: mid 60s to mid 70s °F - Nighttime: mid 50s to mid 60s °F

Off-Season Highlights

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Winter (December to February)

Winter brings colder weather and fewer crowds, providing a peaceful atmosphere for those who enjoy a quieter stay and festive holiday markets.

Average Temperature Daytime: mid 30s to mid 40s °F - Nighttime: mid 20s to mid 30s °F
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Spring (March to May)

Springtime offers mild temperatures and blooming landscapes, making it a pleasant period for exploring the area without the peak season crowds.

Average Temperature Daytime: mid 50s to mid 60s °F - Nighttime: mid 30s to mid 40s °F

Weekly Weather Forecast for Downtown Chicago

How to Book Your Downtown Chicago Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Downtown Chicago

More Top-Rated Vacation Rentals in Downtown Chicago Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Access to outdoor communal spaces such as rooftop terraces with panoramic city views.
  • On-site secure parking facilities for convenient and safe vehicle storage.
  • Outdoor grilling areas or barbecue stations for relaxing meals outdoors.
  • Options for bike storage or bike-sharing stations to explore the local area actively.
  • Near public parks or green spaces ideal for outdoor leisure and recreation.
  • Patio or balcony spaces that provide a private outdoor setting within your rental unit.
  • Swimming pools or splash pads available for cooling off during warm days in this vibrant region.

Top Attractions Around Downtown Chicago

What attractions are nearby?

While staying here, you can explore a variety of nearby activities such as visiting renowned museums, enjoying world-class dining, and taking in scenic views along the waterfront, all within easy reach of your vacation rentals in the heart of downtown Chicago.

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Family Activities

  • Visit Millennium Park: Enjoy iconic art installations like Cloud Gate and relax in this urban oasis right at the heart of the city.
  • Explore Shedd Aquarium: Discover a fascinating array of marine life, perfect for family-friendly adventures in the region.
  • Experience the Field Museum: Immerse yourself in natural history exhibits that captivate visitors of all ages right here in downtown.
  • Stroll along Navy Pier: Take in scenic views, enjoy kid-friendly attractions, and indulge in local dining along this popular area.
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Adult Activities

  • Visit Millennium Park: Enjoy the stunning outdoor art, gardens, and the iconic Cloud Gate sculpture right in the heart of this vibrant area.
  • Explore the Art Institute of Chicago: Immerse yourself in world-class artworks and exhibitions housed within a historic downtown setting.
  • Take an architecture river cruise: Discover the area's remarkable skyline and architectural history aboard a guided boat tour along the Chicago River.
  • Experience nightlife along the Magnificent Mile: Indulge in upscale dining, lively bars, and boutique shopping just steps from your downtown Chicago vacation rentals.

Other Places to Stay in Downtown Chicago, IL

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Near North Side
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The Loop
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River North
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Streeterville
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West Loop
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Rush and Division
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Gold Coast
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West Loop Gate
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Downtown Chicago Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take advantage of the area's renowned dining scene by visiting nearby eateries to enjoy authentic regional flavors and enhance your culinary experience.
  • Utilize Public Transit: Maximize your time by using the region's efficient public transportation options to easily access key attractions from your vacation rentals in Downtown Chicago.
  • Plan Your Sightseeing: Schedule visits to popular destinations in the area early in the day to avoid crowds and make the most of your sightseeing opportunities.
  • Discover Hidden Gems: Venture beyond the main tourist spots to uncover local shops, unique landmarks, and cultural experiences that offer a true taste of this vibrant destination.

Transportation Options

  • Chicago Transit Authority (CTA) L Train: This extensive rail system offers quick, reliable access to many neighborhoods and attractions throughout the city, making it an ideal transportation option for exploring here.
  • Divvy Bike Share: With numerous stations across the area, Divvy provides a convenient and eco-friendly way to enjoy scenic rides through downtown and its surroundings.
  • Metra Commuter Rail: Connecting this region to suburbs and nearby towns, Metra is perfect if you're planning day trips outside the city center.
  • Taxis and Rideshare Services: Popular options like taxis and apps such as Uber and Lyft offer door-to-door convenience for getting around within this vibrant destination.

Local Customs Options

  • Greeting Etiquette: In this vibrant area, a friendly nod or a firm handshake is customary when meeting locals, reflecting the region's welcoming spirit.
  • Dining Customs: When dining in the neighborhood, it's common to enjoy shared plates and to tip generously for attentive service, aligning with local hospitality standards.
  • Respect for Music and Art: Appreciating jazz clubs and art galleries is a significant part of the area's culture, so engaging respectfully and supporting local artists enhances your experience here.
  • Public Behavior: Maintaining a polite and considerate demeanor in busy public spaces is appreciated, especially during community events and local gatherings in this destination.

Frequently Asked Questions About Downtown Chicago?

1. What are the top vacation rentals in Downtown Chicago?

There are a lot of options in Downtown Chicago. If you plan on staying in the Downtown Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Downtown Chicago:

2. How many vacation rentals have private pools in Downtown Chicago?

There are 68 vacation rentals with private pools near Downtown Chicago. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Downtown Chicago are best for families?

If you are looking for a family-friendly vacation home in Downtown Chicago, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Downtown Chicago:

4. How many Rentbyowner vacation rentals are available in Downtown Chicago?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 2397 in the Downtown Chicago area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Downtown Chicago. 

5. What is the cancellation policy for vacation rentals in Downtown Chicago?

Cancellation policies vary depending on the individual property listing. To understand the specific terms, review the cancellation details provided in the listing or contact the property owner directly.

6. How do I secure my booking for a vacation rental in this area?

Bookings are confirmed once you complete the reservation process and any required payment. For detailed instructions, refer to the booking steps outlined in the listing or reach out to the property owner for assistance.

7. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning charges, service fees, or taxes are often included in the total price displayed during checkout. For precise fee details, consult the listing information or contact the property owner before finalizing your reservation.

8. What amenities are typically included in vacation rentals in downtown Chicago?

Most listings feature amenities like Wi-Fi, kitchen facilities, and linens. To see what’s available for a specific property, review the amenities section of the listing or contact the owner directly for more details.

9. Is there parking available with vacation rentals in this part of the city?

Parking options vary by property; some offer dedicated spots, while others may not include parking. Please check the parking details in the listing or contact the owner beforehand to confirm availability and any associated costs.