Vacation rentals near Theatre on the Lake
We found 3,737 vacation rentals — enter your dates for availability
Choose the perfect private vacation rental that's near Theatre on the Lake. Vacation homes provide the amenities you need and want for your family, friends, or furry companion, like WiFi and cable TV. At the end of the day, you'll be able to choose a rental that has what everyone needs, including a place that is accessible or non-smoking.
Vacation rentals with weekly discounts - Theatre on the Lake
Showing deals for:Nov 14 - Nov 21
Image gallery for HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
9.29.2 out of 10 rating
Wonderful
(50 reviews)
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Chicago, IL
18% off
Price is CA $249
CA $249
CA $2,568 total
CA $2,568 total
includes taxes & fees
Image gallery for Beautiful, Remodeled Penthouse Unit in Old Town!
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Beautiful, Remodeled Penthouse Unit in Old Town!
Chicago, IL
5% off
Price is CA $493
CA $493
CA $4,952 total
CA $4,952 total
includes taxes & fees
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 $450
CA $450
CA $4,504 total
CA $4,504 total
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(16 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, IL
10% off
Price is CA $725
CA $725
CA $7,159 total
CA $7,159 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
28% off
Price is CA $2,976
CA $2,976
CA $28,064 total
CA $28,064 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, IL
10% off
Price is CA $448
CA $448
CA $4,427 total
CA $4,427 total
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.89.8 out of 10 rating
Exceptional
(12 reviews)
3BR Luxury Modern Apartment
Chicago, IL
10% off
Price is CA $444
CA $444
CA $4,535 total
CA $4,535 total
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(57 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, IL
10% off
Price is CA $498
CA $498
CA $4,903 total
CA $4,903 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, IL
10% off
Price is CA $606
CA $606
CA $6,109 total
CA $6,109 total
includes taxes & fees
Image gallery for Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
9.09.0 out of 10 rating
Wonderful
(15 reviews)
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
Chicago, IL
10% off
Price is CA $916
CA $916
CA $9,024 total
CA $9,024 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 $2,684 total
CA $2,684 total
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
(6 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
10% off
Price is CA $197
CA $197
CA $1,726 total
CA $1,726 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 $4,366 total
CA $4,366 total
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, IL
10% off
Price is CA $359
CA $359
CA $3,572 total
CA $3,572 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 $3,070 total
CA $3,070 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 $4,700 total
CA $4,700 total
includes taxes & fees
Image gallery for Brownstone in Gold Coast - Downtown
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Brownstone in Gold Coast - Downtown
Chicago, IL
20% off
Price is CA $129
CA $129
CA $1,494 total
CA $1,494 total
includes taxes & fees
Image gallery for Spacious Home/King Bed/Fast Wi-Fi/Free Parking/Fenced Yard/Only 2 Steps to Enter
9.69.6 out of 10 rating
Exceptional
(49 reviews)
Spacious Home/King Bed/Fast Wi-Fi/Free Parking/Fenced Yard/Only 2 Steps to Enter
Worth, IL
7% off
Price is CA $283
CA $283
CA $2,617 total
CA $2,617 total
includes taxes & fees
Image gallery for NEW LUXURY PENTHOUSE CONDO
1010 out of 10 rating
Exceptional
(186 reviews)
NEW LUXURY PENTHOUSE CONDO
Chicago, IL
5% off
Price is CA $477
CA $477
CA $4,888 total
CA $4,888 total
includes taxes & fees
Image gallery for 3BR Prime Hyde Park Location Near University of Chicago and Dining
1010 out of 10 rating
Exceptional
(5 reviews)
3BR Prime Hyde Park Location Near University of Chicago and Dining
Chicago, IL
7% off
Price is CA $314
CA $314
CA $3,249 total
CA $3,249 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 $174
CA $174
CA $1,827 total
CA $1,827 total
includes taxes & fees
Image gallery for Trendy|Comfortable|1BR|Lincoln Square
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Trendy|Comfortable|1BR|Lincoln Square
Chicago, IL
10% off
Price is CA $329
CA $329
CA $3,287 total
CA $3,287 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
(62 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 $4,294 total
CA $4,294 total
includes taxes & fees
Image gallery for Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Chicago, IL
10% off
Price is CA $177
CA $177
CA $1,826 total
CA $1,826 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Theatre on the Lake
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
464 reviews(464 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
337 reviews(337 reviews)
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
187 reviews(187 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
83 reviews(83 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
871 reviews(871 reviews)
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sleeps 8 · 1 bedroom
7.87.8 out of 10
Goodgood
129 reviews(129 reviews)
Top rated rentals - Theatre on the Lake
Rooftop is perfect, great location
1010 out of 10
Exceptionalexceptional
186 reviews(186 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
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