Downtown Chicago holiday rentals

We found 737 holiday rentals — enter your dates for availability
Discover a selection of 908 apartments, 53 flats and other holiday rentals in Downtown Chicago that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include parking and a pool. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

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Why visit Downtown Chicago

  • Iconic Skyscrapers: Marvel at the stunning architecture of renowned skyscrapers that define Chicago's skyline.
  • Millennium Park: Enjoy the blend of art and nature in this vibrant urban park, featuring public art installations and beautiful green spaces.
  • Cultural Richness: Experience the city's rich culture through historic buildings and local art galleries scattered throughout the neighbourhood.
  • Outdoor Activities: Delight in various outdoor activities, including walking, cycling, and enjoying the scenic views along the waterfront.
  • Family-Friendly Atmosphere: Discover a welcoming environment perfect for families, with numerous attractions and experiences for visitors of all ages.

Popular types of accommodation around Downtown Chicago

You have decided on a trip to Downtown Chicago, and now comes the fun part – choosing where you're going to stay. Enjoy the city's vibrant attractions, iconic landmarks and diverse experiences, all while staying in a stylish apartment, cosy private holiday home or modern condo. Discover available apartments and holiday rentals that offer the perfect blend of comfort and convenience during your visit to Downtown Chicago, Chicago, Illinois, United States of America.

  • Apartments: A popular choice for visitors seeking comfort and convenience in Downtown Chicago, offering a range of styles and amenities.
  • Private Holiday Homes: Ideal for families or groups, these homes provide a homely atmosphere with ample space and privacy.
  • Condos: Modern and often centrally located, condos offer stylish living with easy access to city attractions.
  • Villas: Spacious accommodations that provide a luxurious experience, perfect for those seeking a more upscale stay.
  • Cottages: Charming and cosy, these quaint properties offer a unique retreat while still being close to the vibrant city life.**

Top attractions in Downtown Chicago

Downtown Chicago is a vibrant neighbourhood perfect for families and outdoor enthusiasts. Visitors can marvel at iconic skyscrapers, enjoy lush urban parks, and explore historic buildings that reflect the city's rich culture. The area offers a wealth of attractions and experiences, making it ideal for those seeking a city-themed holiday. Don't miss the opportunity to immerse yourself in the lively atmosphere and discover the heart of Chicago.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street features high-end shopping, dining, and iconic architecture, providing a vibrant city atmosphere perfect for urban exploration.
  • Navy Pier: A lively destination on Lake Michigan, Navy Pier offers stunning waterfront views, amusement rides, and various dining options, making it a great spot for leisure and entertainment.
  • Millennium Park: This urban oasis hosts a variety of art installations, gardens, and outdoor concerts, making it a delightful family-friendly space for relaxation and cultural experiences.

Things to do recommended for couples

Seeking a romantic getaway in Downtown Chicago? Enjoy a leisurely walk along the picturesque Riverwalk, share a sunset at Millennium Park, or indulge in a candlelit dinner at a rooftop restaurant, soaking in breathtaking views of the skyline. It's the perfect setting for a memorable couple's retreat.

Things to do recommended for families

Families will revel in the interactive exhibits at the Chicago Children's Museum and enjoy delightful strolls along the scenic Millennium Park, where art and nature intertwine.

Things to do recommended for groups

Groups visiting Downtown Chicago can enjoy an architectural boat tour along the Chicago River, explore Millennium Park's iconic Cloud Gate sculpture, and indulge in deep-dish pizza at a local eatery, all while taking in the vibrant atmosphere of this bustling city.

*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

If you're travelling with a group, as a family, bringing along your pets, or seeking longer stays, it's important to filter your options based on your specific priorities. Here are some helpful booking tips for using Stayz.

  • Traveling to Downtown Chicago with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Fortunately, you can easily filter for all these options and more on Stayz.
  • Traveling to Downtown Chicago with young kids: Traveling with young children can be demanding. You must prioritise their comfort and safety, as well as provide age-appropriate facilities, such as a private swimming pool. It’s also advisable to consider your nearness to family-friendly attractions.
  • Taking your pets with you to Downtown Chicago: For some, a family holiday isn’t complete without the presence of their four-legged friend. If this resonates with you, explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Downtown Chicago: If you're in search of holiday rentals that offer 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 preferences such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Downtown Chicago

Downtown Chicago offers a vibrant blend of urban energy and scenic beauty, making it an ideal destination for families and outdoor enthusiasts alike. Visitors can revel in breathtaking city views while exploring iconic landmarks such as Millennium Park, where art and nature converge. With its central location, Downtown Chicago serves as a gateway to various attractions, providing a friendly atmosphere that showcases the city's rich culture and lively spirit.

  • Chicago: As a sprawling metropolis, Chicago serves as the vibrant core of Downtown Chicago, attracting visitors with its rich mix of family-friendly activities, outdoor spaces, and urban experiences. The city is renowned for its iconic shopping districts and entertainment venues, including theatres and sports facilities. Key landmarks such as the historic stadiums and beautifully designed urban parks offer an excellent opportunity for relaxation and recreation. Stroll along the waterfront or take in the stunning skyline as you discover the diverse culture and history that this remarkable city has to offer.
  • Magnificent Mile: Located a mere 805m from Downtown Chicago, the Magnificent Mile is a bustling neighbourhood known for its upscale shopping and vibrant atmosphere. Visitors flock here for a family-friendly experience, with an array of outdoor activities and educational attractions. This lively area is home to numerous shopping centres, entertainment venues, and cultural sites. Don't miss the chance to explore the nearby urban parks and sports facilities, which provide a perfect backdrop for leisurely strolls or family picnics, making it an ideal destination for both tourists and locals alike.
  • The Loop: Also situated 805m from Downtown Chicago, The Loop is the city’s historical and commercial heart. It is celebrated for its captivating blend of family-oriented activities, outdoor spaces, and engaging cultural experiences. The neighbourhood is dotted with a variety of shopping spots, theatres, and entertainment facilities. Prominent attractions such as urban parks and sports stadiums are within easy reach, allowing visitors to immerse themselves in the dynamic environment. Enjoy the architectural marvels and cultural offerings that make The Loop a must-visit part of your Chicago adventure.

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 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 CloudyAverageSlightly 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 CloudyModerately LowAverage

Booking with Stayz is a breeze

Are you planning to save on your upcoming holiday? Try being flexible with your travel dates as prices can vary. Additionally, booking a longer stay often results in significant savings. To discover the ideal Stayz property that fits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides an excellent platform for you to plan new journeys, manage your existing arrangements, or review and organise your bookings. The properties you’ve saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

When is the best time to visit Downtown Chicago for a holiday rental?
The peak season for visiting Downtown Chicago spans from June to August, with July being the most popular month for travellers. This vibrant time of year sees the city bustling with activity, as visitors flock to enjoy warm temperatures averaging 20 to 30 degrees Celsius. The outdoor festivals, concerts, and events create an electric atmosphere, making it an ideal time for those seeking a lively holiday experience.During these summer months, Chicago offers an array of outdoor activities, from exploring Millennium Park to taking scenic walks along the waterfront. With so much to see and do, it's a superb opportunity for those who appreciate convenience and quality in their travel experiences.If you're looking for a more budget-friendly option, consider visiting in January. While the weather is cooler, with temperatures often dipping below freezing, this time of year allows for a quieter exploration of the city's attractions. You can enjoy the stunning architecture without the crowds and take advantage of lower rental rates.Ultimately, the best time to visit Downtown Chicago hinges on your preferences for a bustling atmosphere filled with summer energy or a more tranquil experience during the winter months.
What are the top attractions in Downtown Chicago, Illinois, United States of America?
In Downtown Chicago, visitors can immerse themselves in a variety of attractions that showcase the city's rich culture and architecture. The iconic Millennium Park is a must-visit, featuring the famous Cloud Gate sculpture, often referred to as "The Bean," and the serene Lurie Garden. Just a short walk away, the Art Institute of Chicago houses an impressive collection of artworks, including pieces by Grant Wood and Georgia O'Keeffe.The Magnificent Mile offers a bustling shopping experience, lined with luxury boutiques and high-end department stores, alongside stunning architectural landmarks such as the Tribune Tower. For those interested in history, the Chicago Riverwalk provides beautiful views and access to various dining options along the water.Navy Pier is another highlight, where families can enjoy attractions like the Ferris wheel, theatres, and an array of restaurants. Additionally, the nearby Museum Campus features the Field Museum and the Shedd Aquarium, making it an ideal spot for those interested in science and marine life.
Are all fees included in the Downtown Chicago holiday homes prices shown on Stayz?
Stayz 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.
Are there any Downtown Chicago holiday homes with parking?
Stayz offers a wide selection of holiday homes in Downtown Chicago with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Downtown Chicago holiday homes?
You can find great discounts on holiday homes in Downtown Chicago on Stayz, 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.
Can I change or cancel my Downtown Chicago holiday home booking on Stayz?
To find Downtown Chicago holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Downtown Chicago?
A long-stay holiday home in Downtown Chicago is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Downtown Chicago holiday home?
Book your Downtown Chicago holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Downtown Chicago?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Downtown Chicago to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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