Holiday rentals near Anna and Frederick Douglass Park
We found 3,080 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals close to Anna and Frederick Douglass Park that provide the perfect home base for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you need and want for your stay, which might include parking and a garden. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Anna and Frederick Douglass Park
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 AU$8,375
AU$8,375
AU$1,196 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
8% off
Price is AU$12,728
AU$12,728
AU$1,818 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 AU$8,216
AU$8,216
AU$1,174 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 AU$6,542
AU$6,542
AU$935 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 AU$6,174
AU$6,174
AU$882 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 AU$4,039
AU$4,039
AU$577 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 AU$3,849
AU$3,849
AU$550 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 AU$3,726
AU$3,726
AU$532 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 AU$2,756
AU$2,756
AU$394 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 AU$10,526
AU$10,526
AU$1,504 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 AU$10,567
AU$10,567
AU$1,510 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 AU$13,449
AU$13,449
AU$1,921 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 AU$6,200
AU$6,200
AU$886 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 AU$11,250
AU$11,250
AU$1,607 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 AU$6,261
AU$6,261
AU$894 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 AU$5,894
AU$5,894
AU$842 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 AU$6,391
AU$6,391
AU$913 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 AU$11,247
AU$11,247
AU$1,607 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 AU$7,328
AU$7,328
AU$1,047 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 AU$2,603
AU$2,603
AU$372 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
8% off
Price is AU$3,757
AU$3,757
AU$537 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 AU$8,959
AU$8,959
AU$1,280 per night
includes taxes & fees
Image gallery for Lakefront property , minutes from McCormick Place and Downtown Chicago.
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Lakefront property , minutes from McCormick Place and Downtown Chicago.
Chicago, IL
11% off
Price is AU$6,413
AU$6,413
AU$916 per night
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.49.4 out of 10 rating
Exceptional
(27 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
9% off
Price is AU$2,978
AU$2,978
AU$425 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Anna and Frederick Douglass Park
Showing deals for: 2 Oct - 5 Oct
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sleeps 4 · 1 bedroom
8.48.4 out of 10
Very goodvery good
314 reviews(314 reviews)
The current price is AU$1,485
AU$1,485
for 3 nights, 1 room
AU$495 per night
includes taxes & fees
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
172 reviews(172 reviews)
The current price is AU$1,250
AU$1,250
for 3 nights, 1 room
AU$417 per night
includes taxes & fees
Small hidden Gem
Sleeps 4 · 2 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
8 reviews(8 reviews)
The current price is AU$868
AU$868
for 3 nights, 1 apartment
AU$289 per night
includes taxes & fees
Rare Gem! Indoor Pool, Rooftop Deck, Close to Magnificent Mile
Sleeps 2 · 1 bedroom · 1 bathroom
8.08.0 out of 10
Very goodvery good
77 reviews(77 reviews)
The current price is AU$1,289
AU$1,289
for 3 nights, 1 room
AU$430 per night
includes taxes & fees
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
192 reviews(192 reviews)
The current price is AU$1,573
AU$1,573
for 3 nights, 1 room
AU$524 per night
includes taxes & fees
Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago
Sleeps 3 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
The current price is AU$941
AU$941
for 3 nights, 1 apartment
AU$314 per night
includes taxes & fees
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