Holiday Homes in Chicago
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Holiday Homes in Chicago
Featured Holiday Homes in Chicago
Lincoln Park Living - Suite 2!
Lincoln Park Living - Suite 2!
10.0 out of 10, Exceptional, (2)
Luxury Downtown Penthouse with Private Rooftop!
Luxury Downtown Penthouse with Private Rooftop!
10.0 out of 10, Exceptional, (4)
Your Next Vacation Home
Your Next Vacation Home
10.0 out of 10, Exceptional, (9)
The price is NZ$497
includes taxes & fees
28 May - 29 May
Save an average of 15% on thousands of hotels when you're signed in
Breathtaking Downtown Penthouse B - Sleeps 11
Breathtaking Downtown Penthouse B - Sleeps 11
10.0 out of 10, Exceptional, (2)
✽ Charming Cottage ✽ close to College/Town/Station
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (30)
The price is NZ$477
includes taxes & fees
20 May - 21 May
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, (13)
The price is NZ$696
includes taxes & fees
21 May - 22 May
Freshly Remodeled Cozy Home
Freshly Remodeled Cozy Home
10.0 out of 10, Exceptional, (15)
Updated Forest Park 3 BR Bungalow
Updated Forest Park 3 BR Bungalow
10.0 out of 10, Exceptional, (82)
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
10.0 out of 10, Exceptional, (149)
Cozy, King bed with heated bathroom!
Cozy, King bed with heated bathroom!
9.8 out of 10, Exceptional, (8)
Breathtaking home close to Schaumburg, Chicago
Breathtaking home close to Schaumburg, Chicago
9.8 out of 10, Exceptional, (37)
Charming Oak Park Home w/ Private Fire Pit!
Charming Oak Park Home w/ Private Fire Pit!
9.8 out of 10, Exceptional, (8)
Beautiful, Remodeled Penthouse Unit in Old Town!
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, (8)
The price is NZ$384
includes taxes & fees
19 May - 20 May
Elegant Mayor's Manor in Central Chicago - 9 Beds
Elegant Mayor's Manor in Central Chicago - 9 Beds
9.6 out of 10, Exceptional, (8)
national historic home near downtown airports no parties no events
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
The price is NZ$564
includes taxes & fees
19 May - 20 May
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (70)
Prime location Historic Chicago Townhouse
Prime location Historic Chicago Townhouse
9.4 out of 10, Exceptional, (59)
LUXE 3 BR, 2 BA + Hot Tub
LUXE 3 BR, 2 BA + Hot Tub
9.2 out of 10, Wonderful, (9)
The price is NZ$444
includes taxes & fees
19 May - 20 May
Luxury Home Away From Your Home
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other property types in Chicago
Sentral Michigan Avenue
Sentral Michigan Avenue
9.2 out of 10, Wonderful, (400)
The price is NZ$288
includes taxes & fees
27 May - 28 May
Kasa Magnificent Mile Chicago
Kasa Magnificent Mile Chicago
9.2 out of 10, Wonderful, (222)
Sonder South Wabash
Sonder South Wabash
8.8 out of 10, Excellent, (295)
The price is NZ$372
includes taxes & fees
28 May - 29 May
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Chicago Holiday Homes information
Number of reviews | 243 |
---|---|
Accommodation | 480 Holiday Homes |
Lowest Price | NZ$282 |
Highest Price | NZ$696 |
Recent Reviews in ChicagoExpedia verified reviews
5/5 Excellent
"Very nice, beautiful hotel. The staff is amazing, both friendly and professional. My only issue was the shower, which we found lacking in both temperature and water pressure. It wasn’t a major problem, and somewhat understandable given the age of the hotel. Otherwise, it was a great stay."
A verified traveller stayed at Congress Plaza Hotel
Posted 2 days ago
Popular Destinations
More accommodation types in Chicago
All Accommodation Types
Be inspired: Top Holiday Homes destinations in 2024
- New Zealand Holiday Houses
- Auckland Holiday Houses
- Hanmer Springs Holiday Houses
- Rarotonga Holiday Houses
- Queenstown Holiday Houses
- Gold Coast Holiday Houses
- Rotorua Holiday Houses
- Taupo Holiday Houses
- Nelson Holiday Houses
- Christchurch Holiday Houses
- Wellington Holiday Houses
- Fiji Holiday Houses
- Wanaka Holiday Houses
- Kaikoura Holiday Houses
- Akaroa Harbour Holiday Houses
- Tauranga Holiday Houses
- Mount Maunganui Holiday Houses
- Dunedin Holiday Houses
- Hamilton Holiday Houses
- Napier Holiday Houses