Vacation rentals near Monument Park
We found 1,072 vacation rentals — enter your dates for availability
Discover a selection of vacation rentals near Monument Park that provide the perfect home base for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the best amenities for spending time at your vacation home, which might include WiFi and a pool. No matter what you're looking for, you're sure to find a rental for everyone's needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Monument Park
Showing deals for:Nov 7 - Nov 14
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 $230
CA $230
CA $2,677 total
CA $2,677 total
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, IL
8% off
Price is CA $207
CA $207
CA $1,818 total
CA $1,818 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 $464
CA $464
CA $4,687 total
CA $4,687 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 $300
CA $300
CA $3,062 total
CA $3,062 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
(33 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
10% off
Price is CA $278
CA $278
CA $2,814 total
CA $2,814 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 $208
CA $208
CA $2,179 total
CA $2,179 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 $1,822 total
CA $1,822 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 $361
CA $361
CA $3,592 total
CA $3,592 total
includes taxes & fees
Image gallery for Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown
1010 out of 10 rating
Exceptional
(5 reviews)
Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown
Chicago, IL
15% off
Price is CA $348
CA $348
CA $3,373 total
CA $3,373 total
includes taxes & fees
Image gallery for ✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨
8.08.0 out of 10 rating
Very good
(9 reviews)
✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨
Evanston, IL
10% off
Price is CA $444
CA $444
CA $4,047 total
CA $4,047 total
includes taxes & fees
Image gallery for Cozy 2BR/1BA Garden Apartment Near Lincoln Square
8.48.4 out of 10 rating
Very good
(11 reviews)
Cozy 2BR/1BA Garden Apartment Near Lincoln Square
Chicago, IL
10% off
Price is CA $108
CA $108
CA $1,735 total
CA $1,735 total
includes taxes & fees
Image gallery for Cheerful 3 bedroom. Feels like home.
1010 out of 10 rating
Exceptional
(9 reviews)
Cheerful 3 bedroom. Feels like home.
Chicago, IL
19% off
Price is CA $208
CA $208
CA $2,156 total
CA $2,156 total
includes taxes & fees
Image gallery for Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
8.88.8 out of 10 rating
Excellent
(19 reviews)
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
Chicago, IL
10% off
Price is CA $197
CA $197
CA $2,049 total
CA $2,049 total
includes taxes & fees
Image gallery for ❤️🔥MAGNIFICENT NEW Home w/8 Beds & Free Parking❤️🔥
9.69.6 out of 10 rating
Exceptional
(35 reviews)
❤️🔥MAGNIFICENT NEW Home w/8 Beds & Free Parking❤️🔥
Chicago, IL
15% off
Price is CA $646
CA $646
CA $6,221 total
CA $6,221 total
includes taxes & fees
Image gallery for Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking
9.29.2 out of 10 rating
Wonderful
(12 reviews)
Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking
Chicago, IL
20% off
Price is CA $251
CA $251
CA $2,555 total
CA $2,555 total
includes taxes & fees
Image gallery for ⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
9.89.8 out of 10 rating
Exceptional
(7 reviews)
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
Chicago, IL
10% off
Price is CA $430
CA $430
CA $4,253 total
CA $4,253 total
includes taxes & fees
Image gallery for Cozy 4-bedroom house in adorable Evanston with WiFi, AC
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Cozy 4-bedroom house in adorable Evanston with WiFi, AC
Evanston, IL
10% off
Price is CA $380
CA $380
CA $3,658 total
CA $3,658 total
includes taxes & fees
Image gallery for Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!
Chicago, IL
10% off
Price is CA $1,484
CA $1,484
CA $14,395 total
CA $14,395 total
includes taxes & fees
Image gallery for Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood
1010 out of 10 rating
Exceptional
(14 reviews)
Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood
Evanston, IL
15% off
Price is CA $228
CA $228
CA $2,287 total
CA $2,287 total
includes taxes & fees
Image gallery for Finished Basement in Historic Oak Park with 2 cats
8.48.4 out of 10 rating
Very good
(5 reviews)
Finished Basement in Historic Oak Park with 2 cats
Oak Park, IL
15% off
Price is CA $93
CA $93
CA $1,204 total
CA $1,204 total
includes taxes & fees
Image gallery for Luxe Duplex - Private Gym -Huge Yard -King Beds Garage Parking-EV Charger- Crib
9.69.6 out of 10 rating
Exceptional
(16 reviews)
Luxe Duplex - Private Gym -Huge Yard -King Beds Garage Parking-EV Charger- Crib
Chicago, IL
34% off
Price is CA $258
CA $258
CA $2,715 total
CA $2,715 total
includes taxes & fees
Image gallery for Special Skevanston Space 2mi to Northwestern University & beach
9.09.0 out of 10 rating
Wonderful
(19 reviews)
Special Skevanston Space 2mi to Northwestern University & beach
Evanston, IL
10% off
Price is CA $195
CA $195
CA $1,764 total
CA $1,764 total
includes taxes & fees
Image gallery for 6 Bedrooms Home Suburbs of Chicago
9.89.8 out of 10 rating
Exceptional
(7 reviews)
6 Bedrooms Home Suburbs of Chicago
Northbrook, IL
10% off
Price is CA $2,442
CA $2,442
CA $20,069 total
CA $20,069 total
includes taxes & fees
Image gallery for Stunning & Spacious 7BD Home with garage!
8.48.4 out of 10 rating
Very good
(5 reviews)
Stunning & Spacious 7BD Home with garage!
Chicago, IL
10% off
Price is CA $653
CA $653
CA $6,717 total
CA $6,717 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Monument Park
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
460 reviews(460 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
335 reviews(335 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
182 reviews(182 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
862 reviews(862 reviews)
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sleeps 4 · 1 bedroom
8.28.2 out of 10
Very goodvery good
339 reviews(339 reviews)
Top rated rentals - Monument Park
Beautiful
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Really nice place, slept 10 very comfortably, clean
Joe T.
Stayed Dec 2024
Excellent Chicago-area accommodations
1010 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
This apartment has plenty of room for four adults and is very well-maintained. It's equipped with everything your need for a comfortable stay, is very clean, and is located conveniently near restaurants and shopping.
Jennifer E.
Stayed Sep 2024
Great spot for a stay in Chicago
1010 out of 10
Exceptionalexceptional
179 reviews(179 reviews)
Clean, organized and efficient, thanks!
Peter W.
Stayed Sep 2022
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