Holiday rentals near Madison Street Theatre
We found 3,749 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Madison Street Theatre, scroll through and discover holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the amenities that you expect and more, which might include a hot tub and garden. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Madison Street Theatre
Showing deals for:26 Sept - 3 Oct
Image gallery for Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie, IL
10% off
Price is AU$7,414
AU$7,414
AU$1,059 per night
includes taxes & fees
Image gallery for Cozy, Comfortable and Convenient apartment. Close to everything!
9.89.8 out of 10 rating
Exceptional
(64 reviews)
Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park, IL
8% off
Price is AU$2,278
AU$2,278
AU$325 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
6% off
Price is AU$2,171
AU$2,171
AU$310 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$7,206
AU$7,206
AU$1,029 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 AU$3,900
AU$3,900
AU$557 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$7,405
AU$7,405
AU$1,058 per night
includes taxes & fees
Image gallery for The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
9.09.0 out of 10 rating
Wonderful
(6 reviews)
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
Chicago, IL
16% off
Price is AU$4,879
AU$4,879
AU$697 per night
includes taxes & fees
Image gallery for Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
Chicago, IL
7% off
Price is AU$9,585
AU$9,585
AU$1,369 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$2,926
AU$2,926
AU$418 per night
includes taxes & fees
Image gallery for Spacious, Sunny and Clean Apartment 25 min from Downtown Chicago
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Spacious, Sunny and Clean Apartment 25 min from Downtown Chicago
Berwyn, IL
8% off
Price is AU$2,282
AU$2,282
AU$326 per night
includes taxes & fees
Image gallery for Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Di
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Di
Chicago, IL
7% off
Price is AU$9,097
AU$9,097
AU$1,300 per night
includes taxes & fees
Image gallery for Luxury Designer Penthouse North - Pool - Gold Coast
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Luxury Designer Penthouse North - Pool - Gold Coast
Chicago, Illinois
8% off
Price is AU$9,121
AU$9,121
AU$1,303 per night
includes taxes & fees
Image gallery for Suburban FAB
1010 out of 10 rating
Exceptional
(7 reviews)
Suburban FAB
Schaumburg, IL
9% off
Price is AU$3,490
AU$3,490
AU$499 per night
includes taxes & fees
Image gallery for Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
1010 out of 10 rating
Exceptional
(11 reviews)
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Chicago, IL
7% off
Price is AU$4,833
AU$4,833
AU$690 per night
includes taxes & fees
Image gallery for #1402 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(25 reviews)
#1402 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$5,458
AU$5,458
AU$780 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Fast Wifi | Chicago
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Kasa | Family Friendly 3 BD + Fast Wifi | Chicago
Chicago, Illinois
8% off
Price is AU$9,407
AU$9,407
AU$1,344 per night
includes taxes & fees
Image gallery for Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
8.48.4 out of 10 rating
Very good
(10 reviews)
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Chicago, IL
7% off
Price is AU$2,774
AU$2,774
AU$396 per night
includes taxes & fees
Image gallery for Elegant 5400sqft Escape –5BR/4.5BA w/Spacious Yard - The Executive Residence
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Elegant 5400sqft Escape –5BR/4.5BA w/Spacious Yard - The Executive Residence
Prospect Heights, IL
8% off
Price is AU$7,863
AU$7,863
AU$1,123 per night
includes taxes & fees
Image gallery for Experience Chicago living near United Center
9.29.2 out of 10 rating
Wonderful
(25 reviews)
Experience Chicago living near United Center
Chicago, IL
7% off
Price is AU$2,060
AU$2,060
AU$294 per night
includes taxes & fees
Image gallery for Spacious 5-Bedroom Retreat in Forest Park
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Spacious 5-Bedroom Retreat in Forest Park
Forest Park, IL
32% off
Price is AU$4,671
AU$4,671
AU$667 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$6,076
AU$6,076
AU$868 per night
includes taxes & fees
Image gallery for Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
8.88.8 out of 10 rating
Excellent
(17 reviews)
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
Chicago, IL
7% off
Price is AU$2,576
AU$2,576
AU$368 per night
includes taxes & fees
Image gallery for Home Away From Home
1010 out of 10 rating
Exceptional
(9 reviews)
Home Away From Home
Chicago, IL
11% off
Price is AU$4,121
AU$4,121
AU$589 per night
includes taxes & fees
Image gallery for Wrigleyville Jungle House w/ game room basement party room for large groups!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Wrigleyville Jungle House w/ game room basement party room for large groups!
Chicago, IL
7% off
Price is AU$12,389
AU$12,389
AU$1,770 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Madison Street Theatre
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
320 reviews(320 reviews)
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
74 reviews(74 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
795 reviews(795 reviews)
Wrigleyville Suites
Sleeps 22 · 9 bedrooms
9.09.0 out of 10
Wonderfulwonderful
6 reviews(6 reviews)
Kasa South Loop Chicago
Sleeps 2 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
310 reviews(310 reviews)
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
171 reviews(171 reviews)
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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
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