Downtown Chicago holiday homes

We found 770 holiday rentals — enter your dates for availability
Discover a selection of 906 apartments, 52 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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    Enjoy full kitchens, laundry, pools, gardens and more

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Why visit Downtown Chicago

  • Iconic skyscrapers: Marvel at the stunning architecture and towering buildings that define the Chicago skyline.
  • Cultural experiences: Enjoy a rich array of museums, theatres, and galleries that showcase the city's vibrant arts scene.
  • Urban parks: Relax in beautiful green spaces offering scenic views and recreational activities amidst the urban landscape.
  • Diverse dining: Savor a variety of culinary delights, from local favourites to international cuisine, in lively eateries.
  • Dynamic atmosphere: Experience the energetic vibe of Downtown, with friendly locals and bustling streets perfect for exploration.

Top attractions in and around Downtown Chicago

Downtown Chicago offers a vibrant mix of experiences, from towering skyscrapers to charming urban parks and historic buildings. Ideal for family, outdoor, and city-themed holidays, visitors can enjoy cultural attractions and engaging city experiences that capture the essence of this dynamic neighbourhood, all within the heart of the city.

  • Navy Pier: A vibrant jettyPier in Downtown Chicago offering urban scenery and a friendly atmosphere, perfect for enjoying city views and lively strolls.
  • Grant Park: This urbanPark in Downtown Chicago provides a family-friendly outdoor space with a true city vibe, ideal for picnics and leisurely walks.
  • Adler Planetarium and Astronomy Museum: Located a short distance from Downtown Chicago, this spacePark offers entertaining exhibits and family-focused experiences centred on astronomy.

Things to do recommended for couples

Looking for a romantic getaway in Downtown Chicago? Explore the stunning Millennium Park, take a scenic river cruise at sunset, or enjoy a cosy dinner at one of the city's rooftop restaurants, delighting in breathtaking views of the skyline together.

Things to do recommended for families

Families will delight in exploring the interactive exhibits at the Museum of Science and Industry, or enjoying a day at Millennium Park, where kids can splash in the Crown Fountain and play on the playground. Don’t forget to take in the stunning views from the Skydeck.

Things to do recommended for groups

Groups in Downtown Chicago can immerse themselves in the city's vibrant culture by exploring historic neighbourhoods, enjoying diverse cuisines, and taking a scenic river cruise along the Chicago River. Experience local art, bustling markets, and lively music scenes for a memorable visit.

*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

Whether you're journeying with a group, travelling with your whanau, bringing your pets along, or seeking extended stays, be sure to select filters that reflect your needs. Here are some tips for booking on Vrbo.

  • Traveling to Downtown Chicago with a group: Consider the number of bedrooms required, along with amenities like a fully equipped kitchen or an outdoor area for group gatherings. Luckily, you can filter for these features and many others on Vrbo.
  • Traveling to Downtown Chicago with young kids: Traveling with young ones can be demanding. You need to prioritise their comfort and safety, along with suitable amenities like a private pool. It's also wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Downtown Chicago: Some families just aren’t complete without their furry mate tagging along. If that sounds like you, have a look at Vrbo properties that welcome pets. Many of these homes offer pet-friendly amenities like feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Downtown Chicago: If you’re in search of holiday 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 even a private pool in your search criteria.

Where to stay near Downtown Chicago

Downtown Chicago offers an urban haven with stunning city views and rich history. Ideal for family, outdoor, and city-themed holidays, visitors can explore vibrant streets on foot, experiencing the dynamic atmosphere and friendly locals. The area boasts iconic urban scenery, with attractions celebrated for their heritage and modern charm. It’s a perfect destination for those seeking a blend of business energy and laid-back city vibes.

  • Chicago: As a sprawling city with Downtown Chicago at its heart, Chicago offers a vibrant mix of family-friendly and outdoor city experiences. Visitors can explore a variety of attractions including expansive shopping areas and bustling arena entertainment facilities, with theatres adding a touch of cultural flair. Notable nearby landmarks include a renowned sports facility stadium, a tourist precinct rich in history, and a welcoming urban park, making it an ideal urban adventure.
  • Magnificent Mile: Located 805m from Downtown Chicago, the Magnificent Mile neighbourhood beckons with its dynamic blend of attractions. This area is popular among families and those seeking an outdoor, city-themed experience. Here, travellers can enjoy a mix of shopping and educational venues alongside arena entertainment facilities. The neighbourhood is also close to a historic tourist precinct, a prominent sports facility stadium, and a scenic urban park, offering a well-rounded exploration experience.
  • The Loop: Situated just 805m from Downtown Chicago, The Loop neighbourhood is a hub of activity and charm. It caters to families and visitors looking for an outdoor, urban experience. The area is characterised by its array of shopping venues, lively arena entertainment facilities, and theatres that highlight the local culture. With a nearby tourist precinct, a refreshing urban park, and a notable sports facility stadium, The Loop provides an engaging and diverse travel experience.

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.

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

Booking with Vrbo is a breeze

Are you keen to save some cash on your next adventure? One effective strategy is to stay flexible with your travel dates, as prices can vary quite a bit. Additionally, opting for 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 holiday rental.

Vrbo Trips: Planning as easy as it gets

Here’s the paraphrased version in a reliable and supportive tone of voice: Vrbo’s innovative Trip Board offers you a dedicated space to start planning new adventures, pick up where you left off, or easily organise your travel plans. Any properties you’ve saved or booked before are now neatly categorised as Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Downtown Chicago holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Downtown Chicago to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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