Chicago 99th Street Station holiday homes
We found 3,385 holiday rentals — enter your dates for availability
If you are looking to stay near Chicago 99th Street Station (Beverly Hills), scroll through and discover private holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the amenities that you need and want, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Chicago 99th Street Station (Beverly Hills)
Showing deals for:3 Oct - 10 Oct
Image gallery for Beautiful Downtown 3BR with Free Parking
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Beautiful Downtown 3BR with Free Parking
Chicago, IL
7% off
Price is NZ$9,274
NZ$9,274
NZ$1,325 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(12 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
7% off
Price is NZ$14,193
NZ$14,193
NZ$2,028 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(8 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$9,059
NZ$9,059
NZ$1,294 per night
includes taxes & fees
Image gallery for 5 Star Upscale Entire Family Neighborhood Home
9.89.8 out of 10 rating
Exceptional
(27 reviews)
5 Star Upscale Entire Family Neighborhood Home
Berwyn, IL
8% off
Price is NZ$4,189
NZ$4,189
NZ$598 per night
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(39 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$7,094
NZ$7,094
NZ$1,013 per night
includes taxes & fees
Image gallery for Cozy, Comfortable and Convenient apartment. Close to everything!
9.89.8 out of 10 rating
Exceptional
(65 reviews)
Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park, IL
8% off
Price is NZ$2,977
NZ$2,977
NZ$425 per night
includes taxes & fees
Image gallery for Kasa | Relaxing Studio + Pet Friendly | Chicago
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Kasa | Relaxing Studio + Pet Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$4,444
NZ$4,444
NZ$635 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
1010 out of 10 rating
Exceptional
(10 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
8% off
Price is NZ$6,711
NZ$6,711
NZ$959 per night
includes taxes & fees
Image gallery for #1810 - Kasa Magnificent Mile Chicago
9.29.2 out of 10 rating
Wonderful
(9 reviews)
#1810 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,062
NZ$4,062
NZ$580 per night
includes taxes & fees
Image gallery for Luxury Designer Penthouse South | Pool | Gold Coast
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Luxury Designer Penthouse South | Pool | Gold Coast
Chicago, Illinois
8% off
Price is NZ$11,353
NZ$11,353
NZ$1,622 per night
includes taxes & fees
Image gallery for Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
1010 out of 10 rating
Exceptional
(16 reviews)
Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
Chicago, IL
7% off
Price is NZ$11,583
NZ$11,583
NZ$1,655 per night
includes taxes & fees
Image gallery for Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
1010 out of 10 rating
Exceptional
(5 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
8% off
Price is NZ$2,112
NZ$2,112
NZ$302 per night
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(54 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$6,951
NZ$6,951
NZ$993 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 03 - Terrace - River North
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Luxury Loft Collection 03 - Terrace - River North
Chicago, IL
8% off
Price is NZ$14,946
NZ$14,946
NZ$2,135 per night
includes taxes & fees
Image gallery for Kasa | Modern 2 BD + Near Local Eateries | Chicago
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Kasa | Modern 2 BD + Near Local Eateries | Chicago
Chicago, Illinois
8% off
Price is NZ$6,851
NZ$6,851
NZ$979 per night
includes taxes & fees
Image gallery for Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
1010 out of 10 rating
Exceptional
(18 reviews)
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Willowbrook, IL
8% off
Price is NZ$2,748
NZ$2,748
NZ$393 per night
includes taxes & fees
Image gallery for Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
Oak Park, Illinois
7% off
Price is NZ$2,793
NZ$2,793
NZ$399 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(14 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is NZ$12,085
NZ$12,085
NZ$1,726 per night
includes taxes & fees
Image gallery for Beautiful Unit CHI in Prime River North - 1
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Beautiful Unit CHI in Prime River North - 1
Chicago, Illinois
15% off
Price is NZ$6,411
NZ$6,411
NZ$916 per night
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(26 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,971
NZ$6,971
NZ$996 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
11% off
Price is NZ$12,078
NZ$12,078
NZ$1,725 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(14 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$8,405
NZ$8,405
NZ$1,201 per night
includes taxes & fees
Image gallery for Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
1010 out of 10 rating
Exceptional
(38 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
7% off
Price is NZ$4,096
NZ$4,096
NZ$585 per night
includes taxes & fees
Image gallery for Spacious 5 BR / King Size Beds + Private Parking!
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Spacious 5 BR / King Size Beds + Private Parking!
Chicago, IL
8% off
Price is NZ$9,555
NZ$9,555
NZ$1,365 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago 99th Street Station
Urban Home near 80/94
Sleeps 5 · 4 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Stunning 3 BR in prime Chicago location
Sleeps 5 · 3 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
106 reviews(106 reviews)
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
91 reviews(91 reviews)
Chic 3-bedroom apartment with WiFi and AC in delightful Chicago
Sleeps 10 · 3 bedrooms · 2 bathrooms
Beautiful Rustic Cabin for Two!
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Hammond Haven - Modern Comfort 4 Br/1.5 Bth
Sleeps 8 · 4 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value