Holiday rentals near Theatre on the Lake
We found 3,638 holiday rentals — enter your dates for availability
Choose the perfect holiday home within easy reach of Theatre on the Lake. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Theatre on the Lake
Showing deals for:19 Sept - 26 Sept
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$9,697
AU$9,697
AU$1,385 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$11,495
AU$11,495
AU$1,642 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$2,958
AU$2,958
AU$423 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(17 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$3,602
AU$3,602
AU$515 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Game Room Access | Chicago
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Kasa | Family Friendly 3 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is AU$9,835
AU$9,835
AU$1,405 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$6,851
AU$6,851
AU$979 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
9.69.6 out of 10 rating
Exceptional
(38 reviews)
Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
Chicago, IL
7% off
Price is AU$10,984
AU$10,984
AU$1,569 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 902 - Terrace - River North
8.88.8 out of 10 rating
Excellent
(5 reviews)
Luxury Loft Collection 902 - Terrace - River North
Chicago, Illinois
8% off
Price is AU$10,465
AU$10,465
AU$1,495 per night
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(29 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, Illinois
7% off
Price is AU$8,182
AU$8,182
AU$1,169 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$9,612
AU$9,612
AU$1,373 per night
includes taxes & fees
Image gallery for Stunning Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Stunning Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is AU$6,830
AU$6,830
AU$976 per night
includes taxes & fees
Image gallery for Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(34 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is AU$5,652
AU$5,652
AU$807 per night
includes taxes & fees
Image gallery for Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
9.49.4 out of 10 rating
Exceptional
(31 reviews)
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
Chicago, IL
7% off
Price is AU$7,599
AU$7,599
AU$1,086 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
(52 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is AU$7,331
AU$7,331
AU$1,047 per night
includes taxes & fees
Image gallery for Spacious 3 bedroom in ideal Roscoe village location
1010 out of 10 rating
Exceptional
(44 reviews)
Spacious 3 bedroom in ideal Roscoe village location
Chicago, IL
7% off
Price is AU$3,387
AU$3,387
AU$484 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 02 - Terrace - River North
1010 out of 10 rating
Exceptional
(18 reviews)
Luxury Loft Collection 02 - Terrace - River North
Chicago, IL
8% off
Price is AU$10,621
AU$10,621
AU$1,517 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
Chicago, Illinois
8% off
Price is AU$9,835
AU$9,835
AU$1,405 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$3,602
AU$3,602
AU$515 per night
includes taxes & fees
Image gallery for Kasa | Inviting 1 BD + Game Room Access | Chicago
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Kasa | Inviting 1 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is AU$5,138
AU$5,138
AU$734 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$3,602
AU$3,602
AU$515 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
Chicago, Illinois
8% off
Price is AU$9,835
AU$9,835
AU$1,405 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is AU$3,031
AU$3,031
AU$433 per night
includes taxes & fees
Image gallery for Unbeatable Top Floor: Views, Central, Modern
1010 out of 10 rating
Exceptional
(5 reviews)
Unbeatable Top Floor: Views, Central, Modern
Chicago, IL
7% off
Price is AU$6,105
AU$6,105
AU$872 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is AU$8,674
AU$8,674
AU$1,239 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Theatre on the Lake
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
167 reviews(167 reviews)
Bridgeport Place -free parking, McCormick-Sox Park
Sleeps 4 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
2-bedroom haven near Ohare with Wi-Fi, AC in fabulous Bellwood
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
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