Chicago Holiday Homes
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Featured Holiday Homes in Chicago

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

A Home Away From Home!

Breathtaking home close to Schaumburg, Chicago

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

4BR Retreat w/ Theater, Game Room & Backyard

✽ Charming Cottage ✽ close to College/Town/Station

4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.

Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

Belmont House, Classy & Chic/walk to Wrigley Field
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$241 |
Highest Price | NZ$1,446 |
Popular accommodation | Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed, A Home Away From Home!, Breathtaking home close to Schaumburg, Chicago, Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater, HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony, 4BR Retreat w/ Theater, Game Room & Backyard, ✽ Charming Cottage ✽ close to College/Town/Station, 4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom., Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG, Belmont House, Classy & Chic/walk to Wrigley Field, Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown |
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