Downtown Chicago vacation rentals

We found 860 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Downtown Chicago by choosing from 195 houses, 53 condos, and other vacation rentals. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you need and want for your stay, which might include air conditioning and a pool. What you'll find is a rental to meet everyone's needs, including options that are accessible or non-smoking.

Find out more about Downtown Chicago

Find out more about Downtown Chicago

Why visit Downtown Chicago

  1. Chicago Riverwalk: Enjoy leisurely strolls along the scenic waterfront with stunning views of the city.
  2. Magnificent Mile: Discover luxury shopping and breathtaking architecture on this iconic stretch.
  3. Cultural hubs: Immerse yourself in local art galleries and vibrant cultural experiences.
  4. Urban parks and beaches: Relax in beautiful parks and enjoy beach activities along Lake Michigan.
  5. Diverse neighborhoods: Explore charming areas with welcoming locals and romantic spots for all occasions.

Popular types of accommodation around Downtown Chicago

Planning a getaway to Downtown Chicago? The fun begins with finding the perfect place to stay! Explore a variety of popular vacation rentals, including apart hotels, stylish apartments, and cozy houses. Whether you’re looking for a holiday apartment or a beach house, Chicago accommodation offers something for everyone, complete with sought-after amenities to make your stay comfortable and enjoyable. Dive into your Chicago adventure today!

  • Apartments: The top choice for travelers, offering modern amenities and convenient locations in Downtown Chicago.
  • Houses: A great option for groups or families seeking a home-like atmosphere with all the comforts.
  • Condos: Stylish and spacious, these rentals provide a luxurious stay right in the heart of the city.
  • Cottages: A charming retreat, perfect for those looking for a cozy, quaint atmosphere.
  • Caravan Parks: An affordable and flexible option for travelers wanting a unique outdoor experience.**

Top attractions around Downtown Chicago

Downtown Chicago offers a vibrant mix of attractions perfect for family and city vacations. Visitors can explore urban parks, beaches, and modern universities while enjoying a rich cultural experience. Don't miss the Chicago Riverwalk, a great spot for leisurely strolls and scenic views. With plenty of activities and sights to discover, Downtown Chicago is sure to provide an unforgettable experience for travelers of all ages.

  1. Michigan Avenue: Known as the "Magnificent Mile," this vibrant street is lined with upscale shops, dining, and stunning architecture, offering a true taste of Chicago's urban lifestyle.
  2. Navy Pier: A bustling hub of entertainment, Navy Pier features beautiful lakefront views, art installations, and friendly locals, making it a perfect spot for leisure and fun.
  3. Millennium Park: This expansive urban park is ideal for families, offering outdoor art, lush gardens, and iconic attractions like the Cloud Gate, all within the city's heart.

Things to do recommended for couples

For a romantic getaway in Downtown Chicago, enjoy live music at the House of Blues or savor a meal at the Historic Michael Jordan Restaurant, perfect for couples. If you're up for a short drive, the Aragon Ballroom offers an entertaining experience just 6 miles away.

Things to do recommended for families

Families can catch an exciting game at Soldier Field, explore nature at Northerly Island Natural Area, or unwind at The East Bank Club. Each destination offers a unique experience, all within a short distance from Downtown Chicago, ensuring fun and relaxation for everyone.

Things to do recommended for groups

Experience the magic of live performances at the Chicago Theatre, indulge in shopping at the 900 North Michigan Shops, or enjoy a night of laughter at Second City, just a short drive from downtown. Each venue offers a unique vibe perfect for group enjoyment.

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

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, be sure to prioritize your preferences in the search filters. Here are some helpful Vrbo booking tips for you.

  • Traveling to Downtown Chicago with a group: Think about how many bedrooms you require, as well as additional features like a full kitchen or outdoor area for group activities. Luckily, you can easily narrow down your options for all these amenities and more on Vrbo.
  • Traveling to Downtown Chicago with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can be beneficial.
  • Taking your pets with you to Downtown Chicago: For many families, a vacation just wouldn’t be the same without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy 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 that offer discounts for month-long stays, 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Downtown Chicago

Exploring Downtown Chicago offers an unforgettable experience filled with vibrant urban landscapes and rich cultural vibes. Stroll along the iconic Magnificent Mile, where luxury shopping meets stunning architecture. Families will enjoy the friendly atmosphere and scenic parks, while art enthusiasts can immerse themselves in local galleries. With a variety of neighborhoods nearby, you'll find romantic spots and welcoming locals, making your vacation a perfect blend of adventure and relaxation in the heart of the Windy City.

  • Magnificent Mile: Magnificent Mile is a vibrant neighborhood located a mere 0.5 miles from Downtown Chicago, renowned for its upscale shopping and cultural experiences. This iconic stretch along Michigan Avenue boasts an impressive array of luxury boutiques, department stores, and dining options. Visitors can enjoy breathtaking views of the city skyline while exploring attractions like the John Hancock Center and the Chicago Riverwalk. The area is also home to various entertainment venues and events, making it a popular destination for families and city explorers alike.
  • The Loop: Situated just 0.5 miles from Downtown Chicago, The Loop serves as the city's bustling commercial heart. Known for its stunning architecture, this neighborhood features a mix of historic skyscrapers and modern buildings. The Loop is perfect for those looking to experience Chicago's vibrant arts scene, with numerous theaters showcasing everything from Broadway shows to local performances. Visitors can relax at Millennium Park, home to the famous Cloud Gate sculpture, and enjoy a variety of dining options that cater to every palate. The Loop truly encapsulates the essence of urban Chicago.
  • River North: Located 0.8 miles from Downtown Chicago, River North is a dynamic neighborhood famous for its art galleries, trendy restaurants, and nightlife. This area boasts a rich cultural scene, with numerous theaters and entertainment venues that attract visitors year-round. The bustling streets are lined with art installations and galleries, making it a haven for art enthusiasts. River North is also home to the iconic Merchandise Mart and offers easy access to the Chicago River, where visitors can enjoy scenic boat tours and picturesque views of the city.

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 January to February and November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.7°F (-3.5°C)Light RainMostly CloudyModerately LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyModerately LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyModerately HighSlightly High
June67.3°F (19.6°C)Light RainMostly SunnyModerately HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnyModerately HighAverage
August73.0°F (22.8°C)Light RainMostly SunnyAverageAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyModerately LowSlightly Low

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Save more with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash™ on your entire reservation. Being the planner definitely has its perks! When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash™ on qualifying bookings. Sign up today and start enjoying the savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board feature offers you a convenient way to plan your travels. You can start new trip ideas, pick up right where you left off, or easily manage and view your existing plans. All the properties you've saved or booked can now be accessed under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Settle into the Windy City

With its glittering skyscrapers, jaw-dropping Art Deco architecture, cavernous museums, and pristine parks, downtown Chicago is the thrilling epicenter of one of North America's most iconic major cities. From the cutting-edge galleries of River North, to the exclusive designer boutiques of the Magnificent Mile, to the chic bars and clubs of Rush Street, you'll find endless diversions here, whatever your idea of a good time may be. And with an array of alluring downtown Chicago vacation rentals to pick from, you can find a home-away-from-home, right in the heart of the action.

Amazing art all over downtown Chicago

You won't have to stray far from your downtown Chicago vacation rental to find awe-inspiring attractions. The Loop district is renowned for its eclectic public art installations, from Anish Kapoor's giant, bean-shaped steel sculpture, to Marc Chagall's surrealistic Four Seasons mosaic. For more masterpieces than you could ever hope to admire in a single sitting, head to the Art Institute of Chicago. One of the most prestigious museums in the United States, it's home to priceless works by the likes of Picasso, Edward Hopper, and Andy Warhol. For unbeatable panoramic views of the city, head up to the Skydeck of the vertigo-inducing Sears Tower.

Dine, drink, and dance in downtown Chicago

The Magnificent Mile is a shopaholic's mecca, home to a seductive array of department stores, fashion boutiques, and no-expense-spared flagship shops for many of the world's most popular retailers. Should you work up an appetite during your spree, you'll find an abundance of irresistible eateries nearby, where you can feast on everything from elegant fusion cuisine to decadent Chicago-style deep pan pizza. Once you've fueled up, it's time to explore the city's vibrant nightlife. Take it easy with an expertly mixed cocktail in a stylish jazz bar, or dance until the early hours in a pulsing house club.

Vibrant seasons in downtown Chicago

Chicago's climate is characterized by contrasts. Summer days tend to be long, hot and sunny, with humidity sometimes making things a little uncomfortable outside. June to August marks the city's peak visitor season, so downtown Chicago vacation rentals are naturally in high demand at this time of year. Fall can be a lovely time to visit, with milder temperatures and fewer out-of-towners jostling to see all the top sights. Spring weather is also usually pleasantly moderate, but rainfall in April and May can be high. Winters can be bitingly cold, with plenty of snowfall, so be sure to wrap up warm.

From pristine parks to blissful beaches

An abundance of pristine parks and green spaces make it easy to escape the hustle and bustle of this teeming metropolis. The Lurie Garden is a true urban oasis, where you can marvel at dazzling seasonal flower displays. Sprawling Lincoln Park is home to a beautifully maintained city zoo, where you can get up close and personal with everything from playful penguins to majestic African lions. If you're visiting during the warmer months, be sure to check out one of the glorious lakefront beaches, where you can lounge on golden sand whilst admiring the city skyline.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Downtown Chicago?
Apartments are the most popular style of vacation rental in Downtown Chicago, according to our data. Even if you’ve got a different idea about what you’d like, Vrbo has properties in loads of shapes and sizes. Explore our options to find your perfect pad.
How much does it cost to rent a vacation rental in Downtown Chicago?
Different things determine what you’ll pay for a vacation rental in Downtown Chicago, such as the season, length of stay and type of property. Still, all Vrbo homes have something in common — incredible value. Just enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in Downtown Chicago?
Prices for beach houses in Downtown Chicago can differ depending on the size and type of the property and when you’re traveling. Simply enter your travel dates into Vrbo and the number of guests to see available options and prices. From there you can use the filters to tailor your search by ratings, nearby activities, amenities and more.
Are there large group vacation rentals in Downtown Chicago?
With 22 Downtown Chicago vacation properties that can host a group of five or more people, you can invite a few extra buddies or family members along. Whether you’re planning an informal gathering or a celebratory event, we’ll help you book the perfect space to match the occasion.
Can I find two-bedroom vacation rentals in Downtown Chicago?
Downtown Chicago has 29 two-bedroom vacation properties for you to select from. Experience a vacation home with all the comfort and privacy you need at a fantastic price on Vrbo.
Are there vacation rentals with WiFi in Downtown Chicago?
Downtown Chicago has 63 vacation rentals with WiFi, so you can stay connected while you’re away. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movie blockbusters to posting pics on social media, these Vrbo homes make it a cinch to go online.
How old do you have to be to rent a vacation rental in Downtown Chicago?
The age limit can vary across properties on Vrbo, so be sure to look at the rules of the vacation rental in Downtown Chicago you’re considering. But typically, it’s 16, 18 or 21.
How long can I rent a vacation rental in Downtown Chicago for?
The length of time you can book a vacation rental in Downtown Chicago is up to the property. Simply enter your chosen travel dates to see a list of options offering extended stays. With tons of amenities like air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you’re sure to find someplace just right to call your home away from home in Downtown Chicago.
Does Vrbo offer discounts for vacation homes in Downtown Chicago?
Whether you’ve got your eye on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some fabulous bargains and discounts on Vrbo. From weekend retreats to extended vacations, we’ve got the ideal place for your next Downtown Chicago escape.

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