Discover a selection of 35 holiday rentals in Chicago, IL, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at £ 52 per night, and houses and flats & apartments are popular options for a stay in Chicago. Either way, you'll find a rental for everyone's needs.
Destination guide

The vibrant city of Chicago awaits you

Come and experience Chicago and its architecture, theatre scene and museums. Travellers especially like the skyscrapers, art and monuments in this cosmopolitan and scenic city. For a bit of culture, visit Art Institute of Chicago, Chicago Theatre or Field Museum of Natural History. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Things to do

Sightseeing in and around Chicago

Are you hoping to find attractions to visit while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Chicago a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Dave & Buster's (1.6 mi / 2.5 km)
  • Lincoln Park Zoo (3 mi / 4.8 km)
  • Oak Brook Golf Course (15.6 mi / 25.1 km)
  • Home Alone House (16.9 mi / 27.1 km)
  • Pinstripes (16.9 mi / 27.3 km)
  • The Glen Club (17.8 mi / 28.7 km)
Natural features

Exploring the natural features in Chicago

Whether you're an active traveller or just want to appreciate the scenery, Chicago is a great place to get out in nature. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (0.5 mi / 0.8 km)
  • Grant Park (0.6 mi / 0.9 km)
  • Burnham Park (1.3 mi / 2 km)
  • Ohio Street Beach (1.4 mi / 2.2 km)
  • Northerly Island (1.6 mi / 2.6 km)
  • Oak Street Beach (1.8 mi / 2.9 km)
How to get there

How to get to and around Chicago

Fly into Chicago O'Hare International Airport (ORD), the closest airport, located 15.7 mi (25.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago Midway Airport (MDW), which is 8.4 mi (13.6 km) away.

If you're travelling by train, Chicago Van Buren Street Station, Millennium Station and Chicago Union Station are the main stations in the area. It's easy to get around Chicago by catching a ride on the metro at Jackson Station (Blue Line), Jackson Station (Red Line) or Harold Washington Library Station.

What are the top holiday rentals in or near Chicago?

Whether you're after a cosy retreat for you and your special someone or somewhere spacious to fit the family, you'll find some top holiday rentals in and around Chicago. Here are a couple to get your inspiration flowing:

  • Around 9 miles from the centre of Chicago, you'll love staying at "Luxury Loyola 3 Bedroom, 2 Bath". It has 3 bedrooms and a range of conveniences like a living room and a nearby hospital.
  • Alternatively, unpack your bags at "Wrigleyville | Chicago Guest House | Not Just A Holiday Rental". Around 5 miles from the heart of Chicago, it has 3 bedrooms and comes with nearby birdwatching activities and an ice maker.

For even more great options, use the search bar at the top of the page to find the perfect Chicago holiday rental for you.

What are the top-rated holiday rentals for weekend getaways in or near Chicago?

Clock off on Friday and then forget about your worries. If you're chasing some fun and relaxation, these escapes in and near Chicago promise a memorable weekend getaway:

  • Located 1 mile to the north of the centre of Chicago, "53th Floor Magmile Penthouse - Views" is a favourite among nature buffs and adventurous types. Stay busy by exploring nearby attractions, including Raupp Memorial Museum and Ping Tom Memorial Park. Then, try some activities like cycling or basketball.
  • "52nd Floor Magmile Penthouse - Views" is another great setting for a fun few days away. Around 1 mile north of Chicago, use it as a base to do a little sailing or cycling. Howard Beach and Dupage County Historical Museum should also be on your to-do list if you stay here.

Can I find studio apartments for rent in and around Chicago?

Usually small, affordable and well located, it's not difficult to be charmed by a studio apartment. Make yourself comfortable in one of these options and experience the vibe of Chicago up close:

  • Make "52nd Floor Magmile Penthouse - Views" your home for a couple of days or more. This wonderful holiday rental features amenities including an outdoor pool and a microwave oven.
  • "51st Floor Magmile Penthouse - Views" is another fabulous option. Get comfy and take advantage of an outdoor pool, a fireplace and more.

With the money you save on your studio apartment, you can afford to explore even more of Chicago. Cultural sights like St. Mary's Cathedral and Bloomington Centre for the Performing Arts will help you get a better feel for the character of this destination.

Can I find short term rentals in or near Chicago?

Whether you're chasing a chic apartment or a house big enough to fit the family, you'll find the ideal place on Vrbo. Squeeze in a quick break at one of these retreats in or near Chicago:

  • If you can only spare a few nights, "52nd Floor Magmile Penthouse - Views" is a good choice. It's close to the centre of Chicago, so you'll be near lots of attractions.
  • Alternatively, book a few nights at "51st Floor Magmile Penthouse - Views". This centrally located property makes exploring the local sights easy.

What are the best romantic weekend getaways in or near Chicago?

Forget flowers and chocolates. Sometimes all you need is a weekend away, just you and your beloved. At Vrbo, we've got romantic getaways in and around Chicago that would make Cupid green with envy. Here are some we think you'll fall in love with:

  • Sneak off on Friday for a few nights of passion at "Luxury Loyola 3 Bedroom, 2 Bath". Around 9 miles from Chicago, it comes with lots of nice touches, including beauty services and a nearby marina.
  • Alternatively, spend your break drinking wine and canoodling at "Wrigleyville | Chicago Guest House | Not Just A Holiday Rental", around 5 miles from Chicago. Air conditioning and housekeeping services will help set the scene for romance.

Are there mansions for rent in or near Chicago?

If you're in search of somewhere to reconnect with loved ones this holiday, you're going to need somewhere spacious. These mansions for rent in or around Chicago will fit your entire crew while doing it in serious style:

  • Around 6 miles to the north of Chicago is "Beautiful 9bedroom Mansion With 4 Parking Spots. Walk To Wrigley Field And Lake Michigan". Along with its magnificent design, you'll also love its high-end amenities, such as a firepit and beauty services.
  • Alternatively, take your holiday up a notch and spend a few days at "Stone Mansion - 20 Free Parking Near Lake". It's located about 4 miles to the north of Chicago and comes with beauty services, a fireplace and more.

What's the best place to stay if you're looking to rent a house for a weekend in or near Chicago?

Around 0.1 miles northeast of Chicago, Central Chicago is an awesome spot to rent a holiday property for a weekend. Spend Saturday checking out the local sights and then Sunday putting your feet up. Near North Side is another favourite place to visit for a weekend away. It's around 1 mile north of Chicago.

What are the best large group holiday rentals in or near Chicago?

Share your trip and double the fun. Whether you're planning an active getaway with your besties or a family reunion, you'll have your pick of large group holiday rentals in and near Chicago:

  • You'll have plenty of space to sprawl out at "Sleep14 | 2 Downtown Penthouses | Vintage 5bd - +gym". Around 1 mile south of Chicago, this grand retreat has 5 bedrooms accommodating up to 14 guests. Top amenities include a kitchen and high-speed internet services.
  • "Stunning Designer Loft In Fulton Market" is another option that'll fit the whole gang. It's around 1 mile to the west of Chicago, has 5 bedrooms and sleeps up to 24 guests. A kitchen and an oven are among the things that'll help make your group getaway even more memorable.

What are the best houses for rent with a pool in or near Chicago?

A pool is often an all-important amenity when deciding where to spend your holiday, especially if you're getting away with the kids. Check out these houses with a pool in or near Chicago and fill your days with frolicking and fun:

  • Pack your swimming gear and book a few days at "Wrigleyville | Chicago Guest House | Not Just A Holiday Rental". There are plenty of other convenient amenities here, including a fridge and childrens activities.
  • Spend lazy days splashing around or enjoying peaceful moments beside the water at "Stunning House In The Heart Of Old Town". This property is another favourite and offers childrens activities, a kitchen and more.

Don't know how to pack for your Chicago getaway? This popular destination has a humid continental climate. In the summer months, expect average temperatures of between 65null and 75null. Look up our selection of Chicago holiday rentals by using the search bar at the top of the page. Simply adjust the filters to get more inspiration on where to stay.

What are the best large family holiday rentals in or near Chicago?

Whether your ideal escape is out in the country or by the beach, you'll have a lot more fun if you share it with loved ones. Stay in one of these large family holiday rentals in or near Chicago and bring the entire crew along:

  • Get your group under the same roof at "Wrigleyville | Chicago Guest House | Not Just A Holiday Rental", which has 3 bedrooms sleeping up to 8 guests. This retreat is around 5 miles to the north of Chicago and comes with amenities such as towels and a stair gate.
  • "Views, Pool, Fireplace, Fitness Centre" is another excellent option. It's around 1 mile to the north of Chicago, has 3 bedrooms and accommodates up to 8 people. Handy amenities here include a balcony and a dishwasher.

When you're ready to leave the house and explore, there are lots of family-friendly attractions nearby to keep everyone happy and entertained. Peoria Zoo, Children's Discovery Museum and Miller Park Zoo should be at the top of your to-do list.

Explore destinations around Chicago

Pulaski Park
181 holiday rentals
United Center
102 holiday rentals
388 holiday rentals
River North
628 holiday rentals
Rogers Park
97 holiday rentals
Humboldt Park
102 holiday rentals
Rush and Division
371 holiday rentals
The Loop
818 holiday rentals
Old Town Chicago
345 holiday rentals
404 holiday rentals
Gold Coast
363 holiday rentals
80 holiday rentals
West Town
944 holiday rentals
Theatre District
385 holiday rentals
16 holiday rentals
Grand Boulevard
35 holiday rentals
Old Town Triangle
87 holiday rentals
Lake View East
214 holiday rentals
University Village / Little Italy
113 holiday rentals
East Village
159 holiday rentals