Chicago holiday homes

We found 4,533 holiday rentals — enter your dates for availability
Discover a selection of 933 homes, 1779 apartments and other holiday rentals in Chicago that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a fireplace. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Chicago (and vicinity)

Showing deals for:1 Jan - 8 Jan

Interior
Our downtown Townhouse is in an amazing location
It is huge! With lots of areas for relaxing and entertaining
Dining
Exceptional
(92 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
NZ$12,702
for 7 nights, 1 home
NZ$1,815 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Outdoors at night
River North Luxury Living
French Bistro and Wine Bar - right downstairs
Interior
Exceptional
(106 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
NZ$6,711
for 7 nights, 1 apartment
NZ$959 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Children’s area
Interior
Exterior
Exterior detail
Exceptional
(29 reviews)

6 Bedrm/3 Bath Spring Retreat, Hot Tub, Fireplace

West Chicago

8% off
NZ$13,080
for 7 nights, 1 home
NZ$1,869 per night
includes taxes & fees
6 Bedrm/3 Bath Spring Retreat, Hot Tub, Fireplace
Living area
Dining
Interior
Private kitchen
Exceptional
(17 reviews)

Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks

Burr Ridge

8% off
NZ$6,976
for 7 nights, 1 home
NZ$997 per night
includes taxes & fees
Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks
Living area
Property grounds
Private kitchen
Room
Exceptional
(8 reviews)

Rare Historic One Bedroom Carriage House in Downtown Glen Ellyn

Glen Ellyn

8% off
NZ$2,913
for 7 nights, 1 room
NZ$416 per night
includes taxes & fees
Rare Historic One Bedroom Carriage House in Downtown Glen Ellyn
Room
Dining
Living area
Private kitchen
Exceptional
(7 reviews)

Modern 4-bedroom house in peaceful Westmont area

Westmont

8% off
NZ$5,749
for 7 nights, 1 home
NZ$821 per night
includes taxes & fees
Modern 4-bedroom house in peaceful Westmont area
Interior
Breakfast bar seating also available
Open concept kitchen
Fully fenced yard - perfect for fur babies
Exceptional
(23 reviews)

Wonderful in Wood Dale, right by O’Hare airport!

Wood Dale

12% off
NZ$5,869
for 7 nights, 1 home
NZ$838 per night
includes taxes & fees
Wonderful in Wood Dale, right by O’Hare airport!
Interior
Private kitchen
Room
Dining
Exceptional
(10 reviews)

Prime Location - Cozy Naperville HomeStay - GameRoom

Naperville

8% off
NZ$4,045
for 7 nights, 1 home
NZ$578 per night
includes taxes & fees
Prime Location - Cozy Naperville HomeStay - GameRoom
Interior
Exterior
Terrace/patio
Dining
Exceptional
(14 reviews)

Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12

Chicago

7% off
NZ$9,623
for 7 nights, 1 apartment
NZ$1,375 per night
includes taxes & fees
Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12
Dining
Interior
Living area
Room
Exceptional
(25 reviews)

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Berwyn

8% off
NZ$2,990
for 7 nights, 1 apartment
NZ$427 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Room 2 Queen bed black out curtains vintage snd Original art and a TV
Polk Street
Stop by say Hello to Dave our neighbor at his newest hipest Italian eatery
Open Concept Living Room
Exceptional
(315 reviews)

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Chicago

7% off
NZ$3,497
for 7 nights, 1 apartment
NZ$500 per night
includes taxes & fees
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Kitchen (upstairs)
Downstairs living area
Fun Mirror Wall Upstairs
Upstairs queen bedroom 2
Exceptional
(100 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
NZ$17,875
for 7 nights, 1 apartment
NZ$2,554 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Bedroom 1 (King Size) + 55Inch TV
Living Room
Front Yard View
Kitchen
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

7% off
NZ$9,034
for 7 nights, 1 home
NZ$1,291 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Living area
Interior
Private kitchen
Dining
Wonderful
(41 reviews)

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Berwyn

8% off
NZ$3,531
for 7 nights, 1 apartment
NZ$504 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Interior
Living area
Exterior detail
Room
Exceptional
(8 reviews)

Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago

Chicago

10% off
NZ$4,093
for 7 nights, 1 apartment
NZ$585 per night
includes taxes & fees
Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago
Dining
Room
Interior
Living area
Exceptional
(29 reviews)

3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi

Waukegan

7% off
NZ$2,562
for 7 nights, 1 apartment
NZ$366 per night
includes taxes & fees
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Enjoy your stay in the well appointed living room with a 55" Roku Smart TV
5 minutes drive to McCormick Place (0.9 miles)
Upscale kitchen with an equally spacious dining room
Upscale kitchen with an equally spacious dining room
Wonderful
(9 reviews)

23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown

Chicago

7% off
NZ$4,248
for 7 nights, 1 apartment
NZ$607 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Room
Private kitchen
Exterior detail
Dining
Exceptional
(69 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off
NZ$5,983
for 7 nights, 1 apartment
NZ$855 per night
includes taxes & fees
Steps from the “L” train to Wrigley & Downtown
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
NZ$12,157
for 7 nights, 1 home
NZ$1,737 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Living area
Dining
Room
Living area
Wonderful
(21 reviews)

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Berwyn

8% off
NZ$3,220
for 7 nights, 1 apartment
NZ$460 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Bedroom 1
Living room
Available parking on premises for up to 2 vehicles.
Private kitchen
Exceptional
(42 reviews)

Entire 3 Bedroom Cozy Unit

Waukegan

8% off
NZ$2,780
for 7 nights, 1 home
NZ$397 per night
includes taxes & fees
Entire 3 Bedroom Cozy Unit
Exterior
Private kitchen
Smart tv and wifi available
Full size bed, smart tv closet
Exceptional
(29 reviews)

Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed

Chicago

8% off
NZ$2,718
for 7 nights, 1 home
NZ$388 per night
includes taxes & fees
Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed
Dining
Exterior detail
Property grounds
Private kitchen
Exceptional
(12 reviews)

Historic feel, Modern comfort Walk to parks and food in beautiful Chicago

Chicago

6% off
NZ$2,498
for 7 nights, 1 apartment
NZ$357 per night
includes taxes & fees
Historic feel, Modern comfort Walk to parks and food in beautiful Chicago
Private kitchen
Living area
Room
Exterior
Excellent
(10 reviews)

High-end 2Bdrm Garden Apt. Where Comfort Meets Style

Chicago

7% off
NZ$3,192
for 7 nights, 1 apartment
NZ$456 per night
includes taxes & fees
High-end 2Bdrm Garden Apt. Where Comfort Meets Style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to vibrant Chicago

Take a holiday to Chicago and enjoy the area's theatre scene, architecture and museums. This city is cosmopolitan and scenic, recognised for its art, monuments and entertainment. Navy Pier and Michigan Avenue are a couple of places to search for that perfect souvenir. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Chicago

Are you hoping to discover attractions to visit during your stay? Venture out of your holiday home and check out everything that makes Chicago a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Lincoln Park Zoo (2.8 mi / 4.5 km)
  • Galloping Ghost (12.5 mi / 20.1 km)
  • Harborside International Golf Center (13 mi / 21 km)
  • The Dome at the Parkway Bank Sports Complex (14.4 mi / 23.2 km)
  • Oak Brook Golf Course (15.7 mi / 25.3 km)
  • The Glen Club (17.7 mi / 28.5 km)

Exploring the natural features in Chicago

Whether you're an outdoor enthusiast or just want to take in the scenery, Chicago is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (0.3 mi / 0.5 km)
  • Grant Park (0.7 mi / 1 km)
  • Maggie Daley Park (0.5 mi / 0.8 km)
  • Ohio Street Beach (1.2 mi / 1.9 km)
  • Burnham Park (1.4 mi / 2.2 km)
  • Oak Street Beach (1.6 mi / 2.5 km)

Transport options to and around Chicago

Fly into Chicago Midway Airport (MDW), the closest airport, located 8.6 mi (13.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago O'Hare International Airport (ORD), which is 15.7 mi (25.3 km) away.

If you're travelling by train, Millennium Station, Chicago Van Buren Street Station and Chicago Union Station are the main stations that serve the city. It's easy to get around Chicago by jumping on the metro at Monroe Station (Red Line), Monroe Station (Blue Line) or Adams-Wabash Station.

Frequently asked questions

What is the best area to stay in Chicago when booking a holiday rental?
When considering the best area to stay in Chicago for a holiday rental, you might want to explore the vibrant neighbourhood of Lincoln Park. This area is known for its lush parks, including the expansive Lincoln Park itself, which offers picturesque walking paths and the Lincoln Park Zoo, a delightful attraction that's free to visitors. The neighbourhood is also home to an array of charming boutiques, trendy restaurants, and lively bars, making it superb for those looking to immerse themselves in local culture.Another excellent choice is the Loop, which is the city's bustling downtown area. Staying here means you'll be in close proximity to iconic attractions such as Millennium Park, where you can admire the famous Cloud Gate sculpture, and the Art Institute of Chicago, renowned for its impressive collection of artworks. The Loop is filled with a variety of holiday rental options, ranging from modern apartments to historic buildings, providing plenty of choices to suit different preferences.Both Lincoln Park and the Loop offer a wealth of amenities and attractions, ensuring a memorable stay in Chicago.
Where are the best areas for renting a beach house in Chicago?
For renting a beach house in Chicago, the areas along the Lake Michigan shoreline are particularly appealing. The neighbourhood of Rogers Park, located on the city's far north side, offers a variety of beachside properties that provide easy access to the expansive and scenic beaches. Many of these rentals come equipped with amenities such as outdoor decks, barbeque facilities, and spacious living areas, great for families or groups looking to enjoy the summer sun.Moving south, the area around the popular North Avenue Beach in Lincoln Park is another great option. Here, you can find modern apartments and charming bungalows that often feature balconies with lake views, fully equipped kitchens, and proximity to local parks and attractions. This vibrant neighbourhood is also close to the Lincoln Park Zoo and the Chicago History Museum, offering plenty of activities for visitors.Additionally, the South Shore neighbourhood offers beach houses near the picturesque Jackson Park and the historic Museum of Science and Industry. Properties in this area typically include amenities like private patios and easy access to the beach, making them great for those who wish to explore both the sandy shores and the cultural landmarks nearby.
What is the most popular type of holiday rental accomodation in Chicago?
In Chicago, apartments are the most popular type of holiday rental, with around 10,104 available across the city. These rentals are commonly found in vibrant neighbourhoods such as River North, Lincoln Park, and the Loop, providing easy access to iconic attractions like Millenium Park, the Art Institute, and Navy Pier. Most apartments come equipped with modern amenities, including fully furnished kitchens, spacious living areas, and often in-unit laundry facilities, making them ideal for both short and extended stays.For those seeking more space, approximately 4,184 holiday houses are also available, which typically feature multiple bedrooms, private outdoor areas, and BBQ facilities—great for families or groups looking to enjoy a cozy feel.
Are there any family house rentals in Chicago?
In Chicago, there is a wide selection of family-friendly house rentals, with approximately 1,589 options available throughout the city. Neighbourhoods such as Lincoln Park and Wicker Park are particularly popular among families due to their spacious homes and proximity to various attractions.Properties in Lincoln Park often come with multiple bedrooms, fully equipped kitchens, and inviting outdoor spaces, superb for children to play. Visitors can easily access the Lincoln Park Zoo, which is a delightful outing for families, as well as the beautiful Lincoln Park Conservatory.Meanwhile, Wicker Park offers a mix of modern and vintage homes, featuring amenities like game rooms, laundry facilities, and sometimes even private gardens. This area is known for its vibrant arts scene and lively dining options, providing plenty of entertainment for all ages.
Can I rent a holiday home with a pool or hot tub in Chicago?
In Chicago, there are numerous holiday homes available for rent that feature pools and hot tubs, with around 617 options to choose from. The city offers a variety of neighbourhoods where these properties can be found, including the vibrant Near North Side, known for its bustling atmosphere and proximity to Lake Michigan, and the more relaxed Lincoln Park, which provides a family-friendly environment with parks and local attractions.Travellers can expect a range of amenities in these rentals, including private pools, spacious hot tubs, and outdoor lounging areas, making them ideal for relaxation and social gatherings. Many properties also come equipped with fully stocked kitchens, allowing for convenient meal preparation, and some may feature additional perks like barbecue grills and access to communal fitness facilities.
Are there pet-friendly house rentals in Chicago?
In Chicago, there are numerous pet-friendly house rentals available, with a count exceeding 1900 options. Areas like Lincoln Park and the West Loop are particularly appealing for those travelling with pets. In Lincoln Park, holiday homes often feature modern amenities such as fully equipped kitchens, spacious living areas, and sometimes outdoor spaces where pets can roam. The proximity to Lincoln Park itself, which includes walking trails and gardens, provides ample opportunities for leisurely strolls with your furry companions.The West Loop is another vibrant neighbourhood that offers a variety of pet-friendly rentals. Many of these properties boast rooftop decks and fitness centres, ensuring a comfortable stay. Grant Park, located nearby, offers expansive green spaces superb for exercising pets, along with cultural attractions that enhance your visit.For those seeking a more suburban feel, areas like Forest Park feature homes with larger yards and private patios, ideal for pets to enjoy. Additionally, nearby parks and nature reserves provide further opportunities for outdoor activities.
Are there any remote work holiday rentals in Chicago?
In Chicago, there is an impressive selection of remote work holiday rentals, with around 11,304 options available throughout the city. Areas such as the Loop and River North are particularly popular for their vibrant setting and proximity to key attractions. Many of these properties offer essential amenities for remote workers, including high-speed internet, dedicated workspaces, and comfortable office chairs, making it easy to stay productive during your stay.Travellers can expect a variety of accommodation types, from modern apartments with stunning skyline views to charming lofts in historic buildings. Most rentals come equipped with Wi-Fi, allowing for seamless connectivity, and many properties include features like fully equipped kitchens, laundry facilities, and access to communal spaces such as gyms or rooftop terraces.For those looking to take breaks from work, Chicago's cultural offerings are just a stone's throw away, with museums, parks, and a lively dining scene nearby. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Chicago?
In Chicago, popular rental amenities include kitchens, which allow guests to prepare their own meals, and coffee and tea makers for a comforting start to the day. Many properties are also pet-friendly, accommodating those travelling with furry companions, and service animals are permitted as well. Onsite parking is another sought-after feature, making it convenient for visitors who arrive by car.
When is the best time to visit Chicago for a holiday rental?
The best time to visit Chicago for a holiday rental is during the peak season from May to July. This lively period attracts a diverse crowd of travellers looking to immerse themselves in the city's vibrant culture, stunning architecture, and numerous festivals. July, in particular, stands out as the most popular month, filled with outdoor events, concerts, and activities that make the most of the warm summer weather.During these months, you can expect pleasant temperatures averaging between 20 to 30 degrees Celsius, ideal for exploring Chicago's renowned parks, such as Grant Park and Millennium Park, where you can enjoy outdoor concerts and art installations. The city's magnificent skyline offers a great backdrop for sightseeing, and you can easily stroll along the iconic Lake Michigan waterfront.For those seeking a more budget-friendly travel experience, consider visiting Chicago in December. It's cooler, with temperatures often hovering around freezing (0 to 5 degrees Celsius), the holiday season brings a unique charm to the city. You can enjoy festive decorations, Christmas markets, and the enchanting atmosphere of winter events without the bustling crowds of the peak season.Ultimately, your choice of when to visit Chicago should reflect your preference for a vibrant, energetic summer experience or a quieter, more festive winter adventure.
What are the top attractions in Chicago?
In Chicago, visitors can take part in a variety of attractions spread across its vibrant neighbourhoods. The Loop is the city's bustling heart, where you can find the iconic Willis Tower and Millennium Park, known for its famous Cloud Gate sculpture, often referred to as "The Bean." Nearby, the Art Institute of Chicago showcases an impressive collection of artworks, making it a must-visit for art enthusiasts.In the Near North Side, the Magnificent Mile offers a shopper's paradise with high-end boutiques and dining options, while the historic Water Tower adds a touch of architectural charm to the area. For a taste of Chicago's rich history and culture, head to the Museum Campus, which houses the Field Museum, Shedd Aquarium, and Adler Planetarium, all within walking distance of each other.Lincoln Park is another highlight, featuring the expansive Lincoln Park Zoo and beautiful gardens, great for a leisurely day outdoors. The trendy neighbourhood of Wicker Park is known for its hip boutiques, music venues, and vibrant street art, making it a favourite spot for younger crowds.
Are all fees included in the 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 Chicago holiday homes with parking?
Bookabach offers a wide selection of holiday homes in 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 Chicago holiday homes?
You can find great discounts on holiday homes in 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 Chicago holiday home booking on Bookabach?
To find 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 Chicago?
A long-stay holiday home in 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 Chicago holiday home?
Book your 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 Chicago?
Prices for holiday homes in 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 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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