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

Wrigley Field/Lakeview -Entire Home- Large Groups!

Clarendon Hills Top Floor

Belmont House, Classy & Chic/walk to Wrigley Field

Spacious House ~3min walk WrigleyField~Free Prkg

Home in DT Libertyville near Corp HQs & Naval Base

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

Entire 3 Bedroom Cozy Unit

Roxan Corner

Family frndly TwnHm by navy base

3-bedroom hillside property in woods with fireplace and lake view
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 | 842 Holiday Homes |
|---|---|
Lowest Price | NZ$169 |
Highest Price | NZ$437 |
Popular accommodation | Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed, Wrigley Field/Lakeview -Entire Home- Large Groups!, Clarendon Hills Top Floor, Belmont House, Classy & Chic/walk to Wrigley Field, Spacious House ~3min walk WrigleyField~Free Prkg, Home in DT Libertyville near Corp HQs & Naval Base, Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families , Entire 3 Bedroom Cozy Unit, Roxan Corner, Family frndly TwnHm by navy base , 3-bedroom hillside property in woods with fireplace and lake view, Charming ModernRetro Home! |
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