Chicago Holiday Homes
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Holiday Homes in Chicago

Clarendon Hills Top Floor

Lincoln Park Living - Suite 2!

Great 3 bedroom rental unit near Logan Square

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

4BR Retreat w/ Theater, Game Room & Backyard

Cheerful 4 bedroom smart home w/ indoor fireplace

Cozy 3-bedroom house in family-oriented Melrose Park.

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

Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Holiday Accommodation Chicago
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Chicago are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Chicago itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Chicago holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Chicago, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Chicago with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Chicago Holiday Homes essential information
Accommodation | 936 Holiday Homes |
---|---|
Lowest Price | NZ$255 |
Highest Price | NZ$1,062 |
Popular accommodation | Clarendon Hills Top Floor, Lincoln Park Living - Suite 2!, Great 3 bedroom rental unit near Logan Square, Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed, 4BR Retreat w/ Theater, Game Room & Backyard, Cheerful 4 bedroom smart home w/ indoor fireplace, Cozy 3-bedroom house in family-oriented Melrose Park., SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE, Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square, Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, Luxury Home Away From Your Home, Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families |
More accommodations in Chicago
Top trending hotels in Chicago

Congress Plaza Hotel
More destinations for you
- Hotels in Orland Park
- Hotels in Albany Park
- Hotels in Northlake
- Hotels in Countryside
- Hotels in San Francisco
- Hotels in Miami
- Hotels in Downtown Chicago
- Hotels in North Pullman
- Hotels in Boston
- Bannockburn Pet Friendly Hotels
- Hotels in Dallas
- Bannockburn Luxury Hotels
- Hotels in Seattle
- Hotels in Washington
- Hotels in New York
- Hotels in Nashville
- Hotels in Orlando
- Hotels in Glenview
- Hotels in Las Vegas
- Hotels in Elmhurst
- New York Apartment Hotels
- Hotels in Los Angeles
- Hotels in Houston
^Eligibility requirements and conditions apply