The Gap Pet Friendly Vacation Rentals
Apartment
- Chicago
- ·
- Bridgeport
- 0.64 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
3 Guests
Kitchen
Air Conditioner
Internet
Pet Friendly
US $247/Night
7 Nights - US $1,727
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
8 Guests
8611.13 ft²
EV Charge Station
Parking- Air Conditioner
- Internet
US $437/Night
7 Nights - US $3,061
Apartment
9.4Exceptional
(469 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
Balcony/Terrace- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,302
Condo
9.8Exceptional
(28 Reviews)
3 Bedrooms
2 Baths
6 Guests
1750 ft²
Child Friendly
US $234/Night
7 Nights - US $1,639
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
796.53 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $429/Night
7 Nights - US $3,001
New
Condo
9.2Exceptional
(17 Reviews)
3 Bedrooms
1 Bath
6 Guests
1000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $354/Night
7 Nights - US $2,475
New
House
- Chicago
- ·
- Back of the Yards
- 0.85 mi to center
5 Bedrooms
1 Bath
9 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $117/Night
7 Nights - US $817
Apartment
10.0Exceptional
(23 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $286/Night
7 Nights - US $2,004
Condo
- Chicago
- ·
- South Loop
- 0.39 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
3 Baths
6 Guests
1000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $533/Night
7 Nights - US $3,733
Pet-Friendly Vacation Rentals in The Gap
Over 525+ Pet-Friendly Vacation Rentals in or Near The Gap
Condo
- Chicago
- ·
- South Loop
- 0.68 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
5 Guests
689 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $531/Night
7 Nights - US $3,720
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
8 Guests
796.53 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $817/Night
7 Nights - US $5,722
Apartment
9.2Exceptional
(1195 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
Pool- Balcony/Terrace
- Kitchen
US $234/Night
7 Nights - US $1,637
Apartment
- Chicago
- ·
- Lower West Side
- 1.59 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $399/Night
7 Nights - US $2,790
Apartment
- Chicago
- ·
- Near South Side
- 0.39 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,176/Night
7 Nights - US $8,231
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
583 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $90/Night
7 Nights - US $631
Apartment
9.8Exceptional
(60 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $396/Night
7 Nights - US $2,773
Condo
- Chicago
- ·
- South Loop
- 0.43 mi to center
9.8Exceptional
(51 Reviews)
2 Bedrooms
2 Baths
6 Guests
958 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $494/Night
7 Nights - US $3,459
Apartment
- Chicago
- ·
- South Loop
- 0.44 mi to center
9.8Exceptional
(35 Reviews)
2 Bedrooms
3 Baths
6 Guests
958 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $533/Night
7 Nights - US $3,733
Luxury Places to Stay in The Gap
Over 516+ Luxury Places to Stay in or Near The Gap
New
Apartment
2 Bedrooms
2 Baths
8 Guests
1205.56 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $6,350/Night
7 Nights - US $44,450
Hotel
8.9Fabulous
(209 Reviews)
4 Baths
349.83 ft²
- EV Charge Station
- Parking
- Balcony/Terrace
- Air Conditioner
US $2,333/Night
7 Nights - US $16,331
Apartment
10.0Exceptional
(1 Review)
5 Bedrooms
6 Baths
16 Guests
3165 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,319/Night
7 Nights - US $16,235
Hotel
- Chicago
- ·
- Near South Side
- 0.34 mi to center
3 Baths
1101.51 ft²
- EV Charge Station
- Parking
- Balcony/Terrace
- Air Conditioner
US $2,250/Night
7 Nights - US $15,750
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
4 Baths
12 Guests
2303.48 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $2,198/Night
7 Nights - US $15,383
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
3 Baths
12 Guests
1851.39 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $2,119/Night
7 Nights - US $14,833
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
9.6Exceptional
(11 Reviews)
3 Bedrooms
2 Baths
8 Guests
2368.06 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $1,466/Night
7 Nights - US $10,262
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
9.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
10 Guests
2152.78 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $1,225/Night
7 Nights - US $8,576
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
7.0Very Good
(2 Reviews)
6 Bedrooms
3 Baths
12 Guests
2604.87 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $1,224/Night
7 Nights - US $8,566
Top-Rated Vacation Rentals with a Pool in The Gap
Over 104+ Top-Rated Vacation Rentals with a Pool in or Near The Gap
Hotel
8.7Fabulous
(1896 Reviews)
8 Baths
862.91 ft²
Private Pool- Parking
- Pool
- Balcony/Terrace
US $246/Night
7 Nights - US $1,720
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.6Fabulous
(284 Reviews)
1 Bath
301.39 ft²
- Private Pool
Oceanfront- Parking
- Pool
US $291/Night
7 Nights - US $2,035
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.5Fabulous
(750 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $229/Night
7 Nights - US $1,604
Hotel
8.3Excellent
(360 Reviews)
5 Baths
363.82 ft²
- Private Pool
- Oceanfront
- Pool
Ocean View
US $198/Night
7 Nights - US $1,384
House
- Chicago
- ·
- Grand Boulevard
- 0.32 mi to center
8.3Excellent
(12 Reviews)
6 Bedrooms
5 Baths
15 Guests
3196.88 ft²
- Parking
- Pool
- Balcony/Terrace
View
US $657/Night
7 Nights - US $4,597
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
7.7Very Good
(348 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $162/Night
7 Nights - US $1,133
Condo
- Chicago
- ·
- University Village / Little Italy
- 0.42 mi to center
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $355/Night
7 Nights - US $2,482
Apartment
- Chicago
- ·
- South Loop
- 0.40 mi to center
3 Bedrooms
2 Baths
6 Guests
1511 ft²
- Pool
Spa- Kitchen
- Air Conditioner
US $307/Night
7 Nights - US $2,147
Apartment
- Chicago
- ·
- South Loop
- 0.40 mi to center
2 Bedrooms
1 Bath
4 Guests
972 ft²
- Pool
- Spa
- Kitchen
- Air Conditioner
US $303/Night
7 Nights - US $2,121
Large Vacation Homes & Villas in The Gap
Over 34+ Large Vacation Homes & Villas in or Near The Gap
House
10.0Exceptional
(15 Reviews)
5 Bedrooms
3 Baths
8 Guests
4000 ft²
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $902/Night
7 Nights - US $6,312
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
10 Guests
1194.79 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $549/Night
7 Nights - US $3,845
Apartment
3 Bedrooms
1 Bath
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $309/Night
7 Nights - US $2,163
House
- Chicago
- ·
- Bridgeport
- 0.76 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
12 Guests
1100 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $733/Night
7 Nights - US $5,131
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
9.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
1194.79 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $828/Night
7 Nights - US $5,794
House
- Chicago
- ·
- Bridgeport
- 0.27 mi to center
9.6Exceptional
(24 Reviews)
4 Bedrooms
2 Baths
12 Guests
2000 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $421/Night
7 Nights - US $2,948
Apartment
- Chicago
- ·
- Lower West Side
- 0.54 mi to center
9.6Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $272/Night
7 Nights - US $1,906
Apartment
8.8Fabulous
(3 Reviews)
5 Bedrooms
3 Baths
12 Guests
2085 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $496/Night
7 Nights - US $3,472
Apartment
8.0Excellent
(1 Review)
3 Bedrooms
1 Bath
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $418/Night
7 Nights - US $2,926
Wheelchair Accessible Vacation Homes in The Gap
Over 274+ Wheelchair Accessible Vacation Homes in or Near The Gap
Condo
- Chicago
- ·
- South Loop
- 0.44 mi to center
9.8Exceptional
(31 Reviews)
2 Bedrooms
2 Baths
6 Guests
958 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $533/Night
7 Nights - US $3,733
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- View
- Air Conditioner
- Internet
- Pet Friendly
US $441/Night
7 Nights - US $3,089
Hotel
- Chicago
- ·
- Indian Village
- 0.09 mi to center
8.0Excellent
(1000 Reviews)
1 Bath
Breakfast- Parking
- Kitchen
- Air Conditioner
US $140/Night
7 Nights - US $979
Condo
- Chicago
- ·
- South Loop
- 0.43 mi to center
9.8Exceptional
(28 Reviews)
2 Bedrooms
2 Baths
6 Guests
958 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $522/Night
7 Nights - US $3,654
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Air Conditioner
- Internet
- Pet Friendly
Wheelchair Accessible
US $351/Night
7 Nights - US $2,454
Apartment
9.8Exceptional
(19 Reviews)
2 Bedrooms
1 Bath
6 Guests
1109 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $812/Night
7 Nights - US $5,687
Apartment
9.6Exceptional
(80 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $433/Night
7 Nights - US $3,028
Apartment
9.6Exceptional
(67 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $327/Night
7 Nights - US $2,289
Condo
- Chicago
- ·
- Printers Row
- 0.25 mi to center
9.6Exceptional
(33 Reviews)
2 Bedrooms
2 Baths
6 Guests
689 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $533/Night
7 Nights - US $3,733
The Gap Petfriendly and Airbnb Homes Under $200
Over 197+ The Gap Petfriendly and Airbnb Homes Under $200
Condo
6.0Good
(1 Review)
2 Bedrooms
2 Baths
3 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $130/Night
7 Nights - US $908
Apartment
- Chicago
- ·
- South Loop
- 0.22 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
441.32 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $185/Night
7 Nights - US $1,295
Condo
- Chicago
- ·
- Grand Boulevard
- 0.49 mi to center
1 Bedroom
1 Bath
- Kitchen
- Internet
- Pet Friendly
- Child Friendly
US $180/Night
7 Nights - US $1,259
Apartment
- Chicago
- ·
- South Loop
- 0.40 mi to center
2 Bedrooms
2 Baths
4 Guests
1161 ft²
- Pool
- Spa
- Kitchen
- Air Conditioner
US $200/Night
7 Nights - US $1,399
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
9.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
796.53 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $171/Night
7 Nights - US $1,197
Apartment
1 Bedroom
1 Bath
2 Guests
600 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $199/Night
7 Nights - US $1,393
Apartment
- Chicago
- ·
- South Loop
- 0.40 mi to center
2 Bedrooms
2 Baths
4 Guests
962 ft²
- Pool
- Spa
- Kitchen
- Air Conditioner
US $189/Night
7 Nights - US $1,322
Apartment
1 Bedroom
1 Bath
2 Guests
600 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $180/Night
7 Nights - US $1,260
Apartment
- Chicago
- ·
- South Loop
- 0.22 mi to center
1 Bedroom
1 Bath
2 Guests
446 ft²
- Pool
- Spa
- Kitchen
- Air Conditioner
US $175/Night
7 Nights - US $1,226
Instantly Bookable Vacation Homes in The Gap
Over 274+ Instantly Bookable Vacation Homes in or Near The Gap
Apartment
- Chicago
- ·
- Bronzeville
- 0.39 mi to center
9.8Exceptional
(30 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $223/Night
7 Nights - US $1,561
Apartment
- Chicago
- ·
- Bridgeport
- 0.52 mi to center
9.8Exceptional
(7 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $252/Night
7 Nights - US $1,765
Apartment
- Chicago
- ·
- Printers Row
- 0.13 mi to center
9.6Exceptional
(22 Reviews)
1 Bedroom
1 Bath
7 Guests
710 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $331/Night
7 Nights - US $2,314
Apartment
- Chicago
- ·
- Printers Row
- 0.12 mi to center
9.6Exceptional
(17 Reviews)
1 Bedroom
1 Bath
7 Guests
710 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $532/Night
7 Nights - US $3,727
Condo
9.4Exceptional
(41 Reviews)
2 Bedrooms
2 Baths
8 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $431/Night
7 Nights - US $3,019
Apartment
- Chicago
- ·
- Printers Row
- 0.13 mi to center
9.4Exceptional
(16 Reviews)
1 Bedroom
1 Bath
7 Guests
710 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $556/Night
7 Nights - US $3,890
Apartment
9.4Exceptional
(14 Reviews)
1 Bedroom
1 Bath
4 Guests
334 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $251/Night
7 Nights - US $1,754
Apartment
9.4Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
8 Guests
1012 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $350/Night
7 Nights - US $2,450
Condo
9.4Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
7 Guests
1098 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $496/Night
7 Nights - US $3,469
Book a Last Minute Place to Stay in The Gap
About The Gap Vacation Rentals
There are more than 1444 places to stay in The Gap and many that are available that welcome pets. These options include dog-friendly hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many pet-friendly places to stay in The Gap.
Are you seeking a last-minute pets-allowed hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With PetFriendly The Gap, you can quickly compare different options to find the hottest deals with a single click. Looking for pet travel at a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near The Gap. Places to stay near The Gap are 791.82 ft² on average, with prices averaging US $453 a night.
PetFriendly makes it easy to find and compare hotels, resorts, and holiday rentals in The Gap with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your pet-friendly place to stay today.
Show more
Show less
Top Dog Hotels, Pet-Friendly Vacation Rentals, and Places to Stay in The Gap
| Type | Count |
|---|---|
| Holiday Apartments | 1034 |
| Vacation Homes | 137 |
| Villas | 2 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in The Gap
★ Pro Tip: PetFriendly™ has the best results when it comes to finding places to stay that accept pets anywhere around the world. Travelers can find and compare over 10 million listings from all over the world. Use the intelligent Filter feature to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, inns, resorts, and more. Enjoy Pet Travel without Hassle in The Gap.
Weather in The Gap, IL
View the weather forecast for The Gap before booking your hotel or rental.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Other Places to Stay in The Gap, IL
Frequently Asked Questions About The Gap?
What are the top vacation rentals in The Gap?
Find the best options in or near The Gap for pet-friendly travel. If you are planning a trip or vacation in The Gap, consider a week or two at exciting pets-allowed hotels, resorts, or other suggested properties best known as Top Vacation Rentals and Places to Stay in The Gap:
- Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
- Family Friendly 2-Bedroom w/Kitchen & Laundry
- Large historic home minutes from downtown Chicago and the lakefront.
- Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Cozy Downtown MICH AVE #7 | gym+rooftop
- Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool
- Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
- Cozy 2BR South Loop Condo with Optional Parking and Gym Near McCormick Place, Public Transit & City Hotspots
- Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines
- Bridgeport Basecamp Comfy Peaceful Sleeps 10+
Which vacation homes in The Gap are best for families?
Are you looking for a family-friendly and pet-friendly hotel, resort, or vacation home in The Gap? Check these highly-rated pet accommodations and places to stay with excellent reviews for families or groups staying in The Gap:
- Downtown Penthouse #1 | Vintage 2bd (+Gym)
- McCormick Place 2BR Spacious Corner Unit with Optional Parking Sleeps 6 Guests Near Soldier Field and Grant Park
- Downtown Park #11 - Mich Ave PH | gym+rooftop
How many PetFriendly vacation rentals are available in The Gap?
PetFriendly™ updates its properties regularly to bring you a great selection of places to stay with their pet policies clearly spelled out. At present, the total number of active properties listed by PetFriendly in 2026 is over 1444 in the The Gap area, and still growing every day. When we combine listings from multiple websites and travel providers, PetFriendly can provide you with a huge selection of the best places to stay that welcome pets in The Gap.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Bronzeville Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 64 |
| Douglas Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 32 |
| Lake Meadows Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 1403 |
People Also Ask
Map
