Chicago holiday homes

We found 4,236 holiday rentals — enter your dates for availability

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April 2025

May 2025

Discover a selection of 1276 homes, 2473 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:18 Jul - 25 Jul

Exceptional

(20 reviews)

Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

Chicago, IL

8% off

NZ$11,931 per night

includes taxes & fees

Enter into our large 1800 sq. ft. condo, featuring a game room. Perfect for you!

Exceptional

(27 reviews)

City Center, River North Condo HUGE 3BR, Patio, Parking(2x)

Chicago, IL

12% off

NZ$2,192 per night

includes taxes & fees

Wake up to nice natural light though the large windows

Exceptional

(14 reviews)

Kasa | Family Friendly 3 BD + Game Room Access | Chicago

Chicago, Illinois

8% off

NZ$1,532 per night

includes taxes & fees

The apartment is flooded with beautiful light from multiple sides

Exceptional

(38 reviews)

Stunning Corner 2BR in the Loop | City & Lake Views

Chicago, Illinois

7% off

NZ$1,099 per night

includes taxes & fees

Open living room and dining space with lake views and great light

Exceptional

(31 reviews)

Modern Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, Illinois

7% off

NZ$1,103 per night

includes taxes & fees

Exceptional

(20 reviews)

Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago

Chicago, Illinois

8% off

NZ$1,532 per night

includes taxes & fees

Our apartments have a 4.87 rating across all booking channels for 180,000+ nights hosted, and counting

Exceptional

(9 reviews)

Kasa | Inviting 1 BD + Game Room Access | Chicago

Chicago, Illinois

8% off

NZ$807 per night

includes taxes & fees

Exceptional

(39 reviews)

Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, Illinois

7% off

NZ$1,118 per night

includes taxes & fees

Exceptional

(25 reviews)

Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, Illinois

7% off

NZ$1,202 per night

includes taxes & fees

Exceptional

(80 reviews)

SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE

Chicago, IL

8% off

NZ$1,070 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Chicago

Wrigley Field

Find the best place to stay - Chicago

Rare Gem! Indoor Pool, Rooftop Deck, Close to Magnificent Mile

Sleeps 2 · 1 bedroom · 1 bathroom

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking

Sleeps 5 · 2 bedrooms · 2 bathrooms

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. Michigan Avenue and Navy Pier 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:

Dave & Buster's (1.4 mi / 2.3 km)
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)
Adagio Teas (14.1 mi / 22.6 km)
The Dome at the Parkway Bank Sports Complex (14.4 mi / 23.2 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 home?

Among the most sought-after neighbourhoods to enjoy a holiday home in Chicago is Near North Side. When you stay here, you’ll be near top attractions like Navy Pier and Chicago Childrens Museum.

What is the most popular type of holiday home accommodation in Chicago?

The most desirable types of holiday homes in Chicago are apartments. After something a little different? Bookabach has plenty of options to match our guests’ diverse needs, so you’ll see holiday properties in all shapes and sizes. The perfect home away from home is waiting for you — get yours today.

How much does it cost to rent a holiday home in Chicago?

The average price for a holiday home in Chicago can vary based on factors like property type, length of stay and time of year. Whether you’re thinking about a sprawling villa with a pool or a quaint cabin ideal for just you and the kids, just enter your dates of travel to see stays that offer great value.

How much does it cost to rent a beach house in Chicago?

The average price for a holiday home by the beach in Chicago depends on when you’re going and the type and size of property you’re searching for. You can find prices easily and quickly on Bookabach by entering your dates of travel. Then use the filters to select the number of bedrooms and amenities important to you, such as a pool, air conditioning and WiFi.

Are there pet-friendly holiday homes in Chicago?

With 2,074 properties that allow pets, your furry buddy can join in the fun on your Chicago getaway. Use our filter tool to search our pet-friendly holiday homes and find a stay that’ll set tails wagging on Bookabach.

Can I rent a house with a pool in Chicago?

Add a whole other level of fun to your getaway by booking one of the 392 houses with a private pool in Chicago. Use our search filter to find properties with pools on Bookabach, then spend your days splish-splashing around in a swimming pool that’s just for you.

What are popular home amenities in Chicago?

A firepit, nearby museums and a barbecue grill head the list of most popular home amenities in Chicago. Whether you plan to travel solo, with a partner or a bunch of friends, Bookabach will help you find a holiday home that suits your style with a load of extras you’ll love.

Are there large group holiday homes in Chicago?

Take your pick of 185 holiday properties in Chicago that can host 10 or more people. Whether you’re planning a holiday with extended family or an event like a birthday party, there’s enough space to get your group together under the same roof.

Are there holiday homes in Chicago that welcome kids?

With 2,058 family-friendly holiday homes to select from in Chicago, there’s never been a better time to introduce your little ones to the magic of travel. Just check our “Properties good for families” filter box to look for stays loaded with amenities perfect for holidaying families, such as kitchens, outdoor spaces, entertainment areas and hot tubs.

What are the top attractions for families in Chicago?

Keep your kids busy at these fabulous family-friendly attractions in Chicago:

Navy Pier
Chicago Riverwalk
Shedd Aquarium

Are there one-bedroom holiday homes in Chicago?

Yes, you can pick from 670 one-bedroom homes in Chicago. Whether you’d like a comfy cottage or a cabin, our one-bedroom properties are perfect if you don’t require tons of space. One of the best parts about having your own digs? You’ll never need to share your adventure with strangers.

Can I find two-bedroom holiday homes in Chicago?

You can select from 568 two-bedroom holiday homes in Chicago. Give the kids the second room or fill it with a couple of your best buddies. There’s ample space for whoever’s lucky enough to be joining your adventure.

Are there holiday homes with WiFi in Chicago?

Chicago has 685 holiday homes with WiFi, so you’ll be able to stay connected when you’re away. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movies with the family to posting pics on social media, these Bookabach homes make it easy to get online.

How can I find holiday homes with air conditioning in Chicago?

Chicago has 1,970 holiday homes where you’ll be able to relax in air-conditioned comfort. To find a stay on Bookabach featuring this amenity, choose your travel dates and use the convenient filters to select the “air conditioning” box.

How old do you have to be to rent a holiday home in Chicago?

You should check with the Chicago holiday home you’re considering on Bookabach as the age limit differs. However, it’s typically 16, 18 or 21.

How long can I rent a holiday home in Chicago for?

The length of time you can rent a holiday home in Chicago differs according to the property. Simply enter your preferred travel dates to view a list of options offering extended stays. With tons of features such as air conditioning and kitchens, as well as some offering weekly or monthly discounted prices, you’re sure to discover a perfect place to call your home away from home in Chicago.