Downtown Chicago vacation rentals

Why visit Downtown Chicago

1. Iconic Skyscrapers: Marvel at the stunning skyline featuring famous buildings that define Chicago's architectural landscape.
2. Beautiful Urban Parks: Enjoy lush green spaces like Grant Park and Millennium Park, perfect for relaxation and outdoor activities.
3. Cultural Experiences: Immerse yourself in the rich history and vibrant arts scene through museums and galleries.
4. Trendy Neighbourhoods: Explore diverse areas like the Loop and River North, filled with shops, dining, and nightlife.
5. Family-Friendly Activities: Discover engaging attractions suitable for all ages, ensuring fun for the whole family.

Popular types of accommodation around Downtown Chicago

Planning a getaway to Downtown Chicago? You're in for a treat! Discover a variety of accommodation options, including stylish apartments, cozy houses, and modern condos. Whether you're seeking vibrant downtown apartments or welcoming vacation rentals, you'll find the perfect place to unwind. Explore your options for accommodations in Chicago and experience the charm of the Windy City like never before!

• Apartments: The top choice for visitors in Downtown Chicago, offering modern amenities and a vibrant city living experience.
• Houses: A great option for those seeking spacious accommodations, perfect for families or groups wanting a home-like atmosphere.
• Condos: Popular for their stylish designs, these rentals provide a blend of comfort and convenience in the heart of the city.
• Cottages: A quaint option for a peaceful retreat, ideal for those looking to unwind while enjoying the urban landscape.
• Villas: Luxurious spaces that offer an upscale experience for travelers wanting a more lavish stay.**

Top attractions around Downtown Chicago

Downtown Chicago is perfect for family-friendly, outdoor, and city-themed vacations. Visitors can enjoy iconic skyscrapers, beautiful urban parks, and historic buildings that reflect the city's rich culture. Whether you're seeking cultural experiences, family activities, or stunning cityscapes, there's something for everyone. Don't forget to explore vacation rentals in Chicago for a comfortable stay while you discover all that this vibrant city has to offer.

1. Navy Pier: A lively jetty featuring stunning urban scenery, artistic displays, and a friendly atmosphere. Enjoy waterfront dining, amusement rides, and cultural events.
2. Michigan Avenue: A bustling street renowned for its vibrant city vibes, lined with upscale shops, dining, and iconic architecture, perfect for strolling and exploring.
3. Grant Park: An expansive urban park ideal for families, offering outdoor recreational activities, beautiful gardens, and city views, making it a perfect spot for relaxation.

Things to do recommended for couples

For a romantic getaway in Downtown Chicago, enjoy a lively night at the House of Blues or savor a delightful meal at the Historic Michael Jordan Restaurant, perfect for couples. If you're up for a short drive, the Aragon Ballroom offers fantastic concerts just 9.7km away.

Things to do recommended for families

Your family will have a fantastic time visiting Soldier Field for an exciting sports experience, exploring the serene Northerly Island Natural Area for relaxation, and enjoying wellness activities at The East Bank Club, all conveniently located within 3.2km of Downtown Chicago.

Things to do recommended for groups

Experience the vibrant culture at the historic Chicago Theatre, enjoy shopping at the bustling Chicago Place Mall, and explore the upscale 900 North Michigan Shops for a perfect blend of family fun and entertainment in Downtown Chicago.

What do I need to keep in mind when booking a vacation around Downtown Chicago

If you're travelling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips for you.

• Traveling to Downtown Chicago with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Thankfully, Vrbo allows you to refine your search to include all of these options and more.
• Traveling to Downtown Chicago with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with finding suitable amenities, like private swimming pools. Additionally, it’s wise to think about how close you are to attractions that cater to families.
• Taking your pets with you to Downtown Chicago: For many families, a trip isn't truly complete without their furry companion by their side. If this resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Downtown Chicago: If you're in search of vacation rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Downtown Chicago

Downtown Chicago offers a vibrant mix of urban charm and artistic flair, perfect for families and outdoor enthusiasts alike. Explore iconic landmarks, lush parks, and trendy neighbourhoods that showcase the city's unique atmosphere. From the stunning skyline to the bustling business district, you'll find the best places to stay and experience the essence of Chicago. Enjoy the perfect blend of culture, scenery, and family-friendly activities that make this destination a top choice for your vacation.

• The Loop: The Loop is the vibrant heart of Chicago, located a mere 805m from Downtown. It's known for its stunning architecture and bustling atmosphere. Here, travellers can immerse themselves in family-friendly activities, enjoy outdoor spaces, and experience the dynamic city life. Popular venues include shopping areas, theatre districts, and the United Center, which hosts exciting events. Highlights in The Loop include the iconic Millennium Park, where you can take a selfie with the famous Cloud Gate sculpture, and the serene Grant Park, perfect for a leisurely stroll.
• Magnificent Mile: Also situated just 805m from Downtown, the Magnificent Mile is a shopper’s paradise and a must-visit for those seeking a blend of family fun, city experiences, and outdoor leisure. This bustling avenue is lined with an array of high-end shops, restaurants, and educational attractions. Key highlights include the historic Water Tower and the Chicago Sports Museum, which celebrates the city's rich sports culture. The vibrant atmosphere makes it an ideal spot for leisurely walks, shopping sprees, and enjoying the city's skyline.
• River North: Located 1.3km from Downtown, River North is a trendy neighbourhood that draws visitors with its artistic flair and lively scene. Known for its family-friendly environment and outdoor offerings, it features a mix of shopping areas, theatres, and entertainment venues. Artistic highlights include the renowned Chicago Riverwalk and various galleries showcasing local talent. The proximity to the Esplanade offers a picturesque setting for relaxation, while the vibrant nightlife ensures that there's always something exciting happening.

Best time to go to Downtown Chicago

If you're planning a trip to Downtown Chicago, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like December to February tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly Cloudy	Moderately Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Moderately Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Average	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Average
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Average
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Average
December	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Moderately Low	Average

Booking with Vrbo is simple

Are you hoping to save on your upcoming adventure? Keep in mind that being flexible with your travel dates can lead to significant savings, as prices often vary. Additionally, opting for a longer stay typically allows you to enjoy even greater discounts. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient space to plan new adventures, pick up right where you left off, or manage and arrange your travel plans. You can easily access properties you’ve saved or booked in the Potential, Upcoming, or Current Trips sections. To start using Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.