Downtown Chicago vacation rentals

We found 822 vacation rentals — enter your dates for availability

Discover a selection of 902 apartments, 52 condos, and other vacation rentals in Downtown Chicago that are perfect for your trip. 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.
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Find out more about Downtown Chicago

Why visit Downtown Chicago

  • Iconic Architecture: Marvel at Chicago's stunning skyscrapers and architectural wonders, including the Willis Tower and John Hancock Center.
  • Chicago Riverwalk: Enjoy leisurely strolls along the picturesque Riverwalk, lined with dining and entertainment options.
  • Cultural Attractions: Explore world-class museums and theaters, showcasing Chicago's rich cultural heritage.
  • Vibrant Neighborhoods: Discover diverse neighborhoods, each offering unique dining, shopping, and entertainment experiences.
  • Family-Friendly Activities: Engage in a variety of family-friendly attractions, parks, and interactive exhibits throughout the downtown area.

Popular types of accommodation around Downtown Chicago

If you're exploring vacation rentals in Downtown Chicago, you're in for a treat. Our most popular accommodations include stylish apartments, spacious houses, and modern condos. Whether you're looking for a cozy villa or a convenient hotel room, you'll find plenty of options that cater to your needs. Enjoy the vibrant city life while staying in comfort and style.

  • Apartments: The top choice for visitors to Downtown Chicago, offering a range of amenities and a home-like atmosphere.
  • Houses: A favored option for families or groups seeking more space and comfort during their stay.
  • Condos: Ideal for those wanting a stylish and modern living space in the heart of the city.
  • Cottages: A quaint choice for travelers looking for a cozy and charming getaway.
  • Villas: These luxurious accommodations provide a unique and upscale experience for discerning guests.**

Top attractions in and around Downtown Chicago

Downtown Chicago offers a vibrant mix of family-friendly activities and urban exploration. You'll find stunning skyscrapers, inviting urban parks, and bustling streets to enjoy. Popular attractions include sightseeing tours, the scenic Chicago Riverwalk, and unique shopping experiences. Whether you're seeking cultural insights or outdoor adventures, Downtown Chicago has something for everyone, making it an ideal destination for your vacation.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street is a shopper's paradise, featuring high-end retailers, vibrant restaurants, and stunning architecture that captures the city's energy.
  • Field Museum of Natural History: A treasure trove of culture and science, this museum showcases fascinating exhibits, including Sue, the world's largest dinosaur, making it perfect for families and curious minds.
  • Navy Pier: A lively waterfront destination, Navy Pier offers picturesque views of Lake Michigan, entertainment options, and a friendly atmosphere, making it a great spot to relax and enjoy the scenery.

Things to do recommended for couples

Experience romance in Downtown Chicago by taking a sunset cruise along the Riverwalk, savoring a candlelit dinner at a rooftop restaurant with skyline views, or exploring the art at Millennium Park. Don't forget to share a sweet treat at one of the city's famous dessert shops.

Things to do recommended for families

Families visiting Downtown Chicago can explore the interactive exhibits at the Chicago Children's Museum, enjoy a day at Navy Pier with its rides and attractions, and take a scenic boat tour on the Chicago River for a unique view of the city’s stunning architecture.

Things to do recommended for groups

Groups visiting Downtown Chicago can enjoy a guided architectural boat tour along the Chicago River, explore Millennium Park's iconic sculptures, and indulge in deep-dish pizza at famous pizzerias. Don't miss the vibrant atmosphere of Navy Pier with its entertainment and dining options for everyone in the group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip—whether you’re traveling with a group, with family, bringing pets, or seeking extended stays—be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Downtown Chicago with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group activities. Luckily, you can easily sort through all of these options, and plenty 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 suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Downtown Chicago: For many families, a vacation wouldn't be the same without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Downtown Chicago: If you're in search of vacation rentals offering 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Downtown Chicago

Downtown Chicago offers an exciting blend of urban vibes and scenic beauty, perfect for family-friendly adventures and city-themed vacations. Explore iconic attractions, indulge in diverse dining, and enjoy vibrant neighborhoods nearby. With a range of vacation rentals available, your stay will be both comfortable and convenient. Experience the friendly atmosphere and lively spirit of Chicago as you create unforgettable memories in this bustling metropolis.

  • Chicago: As a bustling metropolis, Chicago serves as the vibrant core of the Windy City experience. Visitors flock to this dynamic urban landscape for a variety of family-friendly activities, outdoor adventures, and captivating city-themed experiences. Explore the renowned shopping areas and catch a thrilling game at one of the sports facilities. The city's attractions, including urban parks and tourist precincts, make it a perfect destination for travelers looking to immerse themselves in both culture and recreation.
  • Magnificent Mile: Located a mere half-mile from Downtown Chicago, the Magnificent Mile is a shopper's paradise and a must-visit neighborhood. Here, families can enjoy outdoor strolls alongside stunning architecture while indulging in retail therapy at high-end shops and boutiques. The area is also home to numerous educational attractions and arena entertainment venues, making it an ideal spot for those seeking both leisure and learning. Notable landmarks nearby include urban parks and sports facilities, providing a well-rounded experience.
  • The Loop: Just a half-mile from Downtown Chicago, The Loop is the city’s central business district, teeming with energy and excitement. This vibrant neighborhood is perfect for families and city explorers alike, featuring a range of shopping options, theaters, and arena entertainment. Visitors can enjoy the local landmarks such as urban parks and sports facilities, along with a variety of dining and cultural experiences. The Loop is where the city's history and modernity beautifully converge, making it a highlight of any Chicago trip.

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 March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 CloudyModerately LowSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyModerately HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can help, as prices tend to change. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or organize your travel arrangements. You can easily access the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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 in Downtown Chicago?
In Downtown Chicago, apartments are the most popular vacation rental choice, with approximately 824 available throughout the bustling city center. These apartments are often located near iconic attractions such as Millennium Park, the Art Institute of Chicago, and the Magnificent Mile, providing easy access to the vibrant urban atmosphere. Most units come equipped with modern amenities, including fully equipped kitchens, comfortable living areas, and many feature stunning views of the city skyline.

For those seeking more space, there are several vacation houses available, ideal for families or groups needing extra room to relax. These homes typically offer multiple bedrooms, private outdoor areas, and additional amenities to enhance the stay.
Are there any beach house rentals in Downtown Chicago?
In Downtown Chicago, there are about 390 beach house rentals available, mainly concentrated in vibrant neighborhoods near the waterfront. These rentals typically offer a range of amenities, including fully equipped kitchens, spacious living areas, and often stunning views of Lake Michigan. Many properties feature outdoor spaces such as balconies or patios, great for enjoying the city's skyline and lakeside ambiance.
How much does it cost to rent a vacation home in Downtown Chicago?
Prices for vacation rentals in Downtown Chicago vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Downtown Chicago to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Downtown Chicago vacation house rentals?
You can find great discounts on house rentals in Downtown Chicago on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Downtown Chicago?
In Downtown Chicago, vacation rentals commonly feature a variety of sought-after amenities that cater to travelers' needs. Most properties include fully equipped kitchens, allowing guests to prepare their own meals, which is especially convenient for those looking to save on dining out. Additionally, many rentals are equipped with coffee and tea makers, superb for starting the day with a warm beverage. For fitness enthusiasts, access to fitness facilities is often available, enabling guests to maintain their workout routines during their stay.

Pet-friendly options are also prevalent, with several rentals permitting pets and accommodating service animals, making it easier for travelers to bring their furry companions along.
Can I find family house rentals in Downtown Chicago?
In Downtown Chicago, there are numerous family-friendly house rentals available—approximately 179 options to choose from. This vibrant area is filled with exciting attractions and activities for all ages. Many homes feature spacious living areas, fully equipped kitchens for convenient meal preparation, and separate bedrooms for added privacy. Visitors can also expect amenities such as Wi-Fi, air conditioning, and sometimes even private outdoor spaces for relaxation.

Families will appreciate proximity to iconic landmarks like Millennium Park, where they can enjoy outdoor art installations and playgrounds, or the Field Museum, which offers educational exhibits that captivate both kids and adults. The nearby Shedd Aquarium and Adler Planetarium add to the family-friendly atmosphere, providing great experiences just a short distance away.
Can I rent a vacation home with a pool or hot tub in Downtown Chicago?
In Downtown Chicago, travelers can find a variety of vacation homes available for rent that feature both pools and hot tubs, with around 458 options for homes with pools and 44 with hot tubs. The downtown area is known for its vibrant urban setting, offering amenities that cater to a range of preferences. Many of these rentals come equipped with features such as outdoor pools, private hot tubs, fitness facilities, and spacious living areas, making them ideal for relaxation and social gatherings.

Neighborhoods like the Loop and River North are popular choices, providing easy access to iconic attractions, dining, and nightlife. Guests can also expect fully equipped kitchens, modern furnishings, and convenient access to public transport, enhancing the overall experience of staying in this bustling city.
Are there any Downtown Chicago vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Downtown Chicago with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly vacation rentals in Downtown Chicago?
Yes, travelers can book pet-friendly vacation rentals in Downtown Chicago, with numerous options available to accommodate pets. In this bustling urban area, many rentals come with modern amenities such as fully equipped kitchens, high-speed internet, and comfortable living spaces.

Neighborhoods like the Loop and River North offer a vibrant setting with easy access to parks where pets can enjoy some outdoor time. Grant Park, nearby, features expansive green spaces, walking trails, and beautiful gardens, making it an ideal destination for pet owners. Additionally, many vacation rentals in these areas are close to pet-friendly cafes and shops, ideal for those traveling with furry companions.
Can I find long-stay vacation rentals in Downtown Chicago?
A long-stay vacation rental in Downtown Chicago is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Downtown Chicago for a vacation rental?
The best time to visit Downtown Chicago for a vacation rental is during the peak season from June to August. This bustling period attracts a vibrant mix of travelers eager to soak in the city's famous summer festivals, outdoor dining, and scenic lakeside activities. With warm temperatures averaging in the mid-70s to low 80s Fahrenheit, visitors can comfortably explore the iconic Millennium Park, enjoy leisurely strolls along the Riverwalk, or take in breathtaking views from the Skydeck at Willis Tower.

July, in particular, stands out as the most popular month. The city comes alive with events such as the Chicago Air and Water Show, which draws huge crowds and offers unforgettable sights. This is a fantastic time for those who enjoy a lively option filled with music, art, and culture.

If you're looking for a more budget-friendly experience, consider visiting in January, when the city is quieter and offers unique winter attractions. While temperatures can dip into the 20s Fahrenheit, the charm of the holiday lights, cozy indoor activities, and fewer crowds can make for a delightful experience.

Ultimately, the best time to visit Downtown Chicago really depends on your travel preferences—whether you want to dive into the energetic summer scene or enjoy a more laid-back winter ambiance.
Are there any remote work vacation rentals in Downtown Chicago?
In Downtown Chicago, there are numerous vacation rentals suitable for remote work, with around 366 options available. This vibrant urban area is known for its stunning skyline, cultural attractions, and dining experiences. Many of these rentals come equipped with essential amenities for remote workers, including high-speed internet, dedicated workspaces, and comfortable desks in the units.

Travelers can expect fully furnished apartments that provide a blend of comfort and functionality, allowing for an efficient work-from-home setup. Additionally, some properties may include Wi-Fi, ensuring reliable connectivity throughout the stay. The proximity to various coffee shops and co-working spaces in the Loop also enhances the remote work experience, offering alternative environments for productivity. In terms of local attractions, the area boasts iconic spots such as Millennium Park, the Art Institute of Chicago, and the Magnificent Mile, providing ample opportunities for relaxation and exploration after work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Downtown Chicago vacation rental?
Book your Downtown Chicago vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Downtown Chicago, Illinois, United States of America?
In Downtown Chicago, visitors can engage in a variety of attractions that showcase the city's rich culture and stunning architecture. The iconic Millennium Park is a must-visit, featuring the famous Cloud Gate sculpture, also known as "The Bean," and beautifully landscaped gardens. Just a short walk away, the Art Institute of Chicago houses an extensive collection of artworks, making it a cultural highlight of the downtown area.

Nearby, the Magnificent Mile offers a bustling shopping experience with a mix of high-end boutiques and popular retailers, as well as restaurants and cafes for dining. The historic Chicago Riverwalk is superb for leisurely strolls, offering scenic views of the city's skyline and access to boat tours.

For those interested in history, the Chicago Architecture Foundation Center River Cruise is a popular choice, providing insights into the city's architectural marvels. The Willis Tower, once known as the Sears Tower, features an observation deck with breathtaking views of the city from above.
Can I change or cancel my Downtown Chicago home rental booking on Vrbo?
To find Downtown Chicago vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Downtown Chicago vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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