Vacation rentals near Pegasus Players
We found 3,684 vacation rentals — enter your dates for availability
Choose the perfect private vacation rental that's close to Pegasus Players. Vacation homes provide the best amenities for your stay with friends, family, or just your pet, such as a garden and pool. At the end of the day, you'll find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Vacation rentals with weekly discounts - Pegasus Players
Showing deals for:Nov 7 - Nov 14
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10 rating
Exceptional
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
10% off
Price is CA $451
CA $451
CA $4,507 total
CA $4,507 total
includes taxes & fees
Image gallery for Beautiful, Remodeled Penthouse Unit in Old Town!
9.49.4 out of 10 rating
Exceptional
(24 reviews)
Beautiful, Remodeled Penthouse Unit in Old Town!
Chicago, IL
5% off
Price is CA $530
CA $530
CA $5,346 total
CA $5,346 total
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(15 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
10% off
Price is CA $872
CA $872
CA $8,449 total
CA $8,449 total
includes taxes & fees
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10 rating
Exceptional
(22 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
10% off
Price is CA $3,722
CA $3,722
CA $34,671 total
CA $34,671 total
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
10% off
Price is CA $515
CA $515
CA $5,063 total
CA $5,063 total
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(41 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
10% off
Price is CA $440
CA $440
CA $4,150 total
CA $4,150 total
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
10% off
Price is CA $591
CA $591
CA $5,965 total
CA $5,965 total
includes taxes & fees
Image gallery for Modern 3BR Penthouse in the Loop | Roof Deck
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Modern 3BR Penthouse in the Loop | Roof Deck
Chicago, IL
10% off
Price is CA $730
CA $730
CA $7,215 total
CA $7,215 total
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(56 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
10% off
Price is CA $573
CA $573
CA $5,656 total
CA $5,656 total
includes taxes & fees
Image gallery for Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
1010 out of 10 rating
Exceptional
(32 reviews)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie, IL
10% off
Price is CA $778
CA $778
CA $6,743 total
CA $6,743 total
includes taxes & fees
Image gallery for Gorgeous N. Kenwood/Hyde Park
8.08.0 out of 10 rating
Very good
(7 reviews)
Gorgeous N. Kenwood/Hyde Park
Chicago, IL
10% off
Price is CA $288
CA $288
CA $2,952 total
CA $2,952 total
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
9.69.6 out of 10 rating
Exceptional
(28 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
10% off
Price is CA $352
CA $352
CA $3,506 total
CA $3,506 total
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, Illinois
10% off
Price is CA $539
CA $539
CA $5,425 total
CA $5,425 total
includes taxes & fees
Image gallery for Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
1010 out of 10 rating
Exceptional
(6 reviews)
Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
Chicago, IL
10% off
Price is CA $231
CA $231
CA $2,686 total
CA $2,686 total
includes taxes & fees
Image gallery for Cheerful 4 bedroom smart home w/ indoor fireplace
8.08.0 out of 10 rating
Very good
(14 reviews)
Cheerful 4 bedroom smart home w/ indoor fireplace
Chicago, IL
5% off
Price is CA $399
CA $399
CA $4,369 total
CA $4,369 total
includes taxes & fees
Image gallery for Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
1010 out of 10 rating
Exceptional
(42 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
19% off
Price is CA $301
CA $301
CA $3,072 total
CA $3,072 total
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.49.4 out of 10 rating
Exceptional
(32 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
10% off
Price is CA $279
CA $279
CA $2,823 total
CA $2,823 total
includes taxes & fees
Image gallery for Historic 1920s Private Bungalow Near Logan Square!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Historic 1920s Private Bungalow Near Logan Square!
Chicago, IL
10% off
Price is CA $465
CA $465
CA $4,703 total
CA $4,703 total
includes taxes & fees
Image gallery for New Garden Studio near Wrigley/DePaul/Dwtn
9.49.4 out of 10 rating
Exceptional
(16 reviews)
New Garden Studio near Wrigley/DePaul/Dwtn
Chicago, IL
10% off
Price is CA $210
CA $210
CA $2,192 total
CA $2,192 total
includes taxes & fees
Image gallery for NEW LUXURY PENTHOUSE CONDO
1010 out of 10 rating
Exceptional
(185 reviews)
NEW LUXURY PENTHOUSE CONDO
Chicago, IL
5% off
Price is CA $477
CA $477
CA $4,891 total
CA $4,891 total
includes taxes & fees
Image gallery for 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
1010 out of 10 rating
Exceptional
(60 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago, IL
10% off
Price is CA $434
CA $434
CA $4,297 total
CA $4,297 total
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(19 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
10% off
Price is CA $822
CA $822
CA $8,331 total
CA $8,331 total
includes taxes & fees
Image gallery for Experience Chicago living near United Center
9.29.2 out of 10 rating
Wonderful
(26 reviews)
Experience Chicago living near United Center
Chicago, IL
10% off
Price is CA $175
CA $175
CA $1,828 total
CA $1,828 total
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
10% off
Price is CA $714
CA $714
CA $7,067 total
CA $7,067 total
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Pegasus Players
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
457 reviews(457 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
334 reviews(334 reviews)
Prime Location! Indoor Pool, Near Millenium Park, Shedd Aquarium, Willis Tower
Sleeps 2 · 1 bedroom · 1 bathroom
7.87.8 out of 10
Goodgood
82 reviews(82 reviews)
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
181 reviews(181 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
856 reviews(856 reviews)
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sleeps 4 · 1 bedroom
8.28.2 out of 10
Very goodvery good
337 reviews(337 reviews)
Top rated rentals - Pegasus Players
Rooftop is perfect, great location
1010 out of 10
Exceptionalexceptional
185 reviews(185 reviews)
Spent 4 nights, we had everything we needed, plus nice extra touches. Location is central and close to some great neighborhoods. Jessica was very responsive and even accommodated an early check-in for a bit extra. Would definitely stay here again.
Alex P.
Stayed May 2024
Friend trip to Chicago
1010 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
We were a group of 8 40+ yr old females. We all found the house very very clean and comfortable. We spent most of our time downtown so didn’t get a chance to explore the neighborhood too much, though we felt very safe at all times.
I would recommend this property to all.
Sarah M.
Stayed Oct 2023
Great place!
1010 out of 10
Exceptionalexceptional
295 reviews(295 reviews)
It was a great place to stay!!
Gordon S.
Stayed Mar 2020
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, yards and more
More for lessMore space, more privacy, more amenities — more value