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Pet-friendly vacation rentals in South Loop, Chicago

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in South Loop, Chicago

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest suite in McKinley Park

4.84 out of 5 average rating, 202 reviews

Vintage Suite Home Chicago by Sox/Park/Transit

Guest suite in an 1890 Worker's Cottage with plenty of character, originally built for laborers in the Chicago Stockyards. This quiet neighborhood is a respite from city buzz, just 20 min from the Loop. Your space has great natural light, 2 comfy beds (1 folds to a couch), private bath, flexible work/dining area, super-fast WiFi, and a kitchen with all the essentials. Private entry via back door. Free parking. Get downtown in 4 stops by train or any of 5 nearby buses. Se habla español.

Mar 30 – Apr 6

G$19,454 GYD per night

Home in Berwyn

4.91 out of 5 average rating, 242 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

Sep 8 – 15

G$20,014 GYD per night

Apartment in Chicago

4.95 out of 5 average rating, 109 reviews

Comfortable, modern apartment 20 Min from Downtown

Welcome to Chicago! Whatever reason brings you to my lovely city, I'm sure my house will suit your every need. There are three units with separate entrees, out of which the first unit is for your own use; second unit is rented occasional. I live in the garden apartment, but will be rarely home. This modern unit has: -2 bedrooms 1 queen & 1 double bed -2 full bathroom -washer and a dryer -fully equipped kitchen - Wi Fi -50'' flat screen TV -central Air/Heat - back yard with porch -free parking

Feb 1 – 8

G$24,122 GYD per night

Apartment in West Town

4.98 out of 5 average rating, 221 reviews

Ukrainian Village Garden Retreat

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

Aug 23 – 30

G$45,829 GYD per night

Guest suite in Logan Square

4.97 out of 5 average rating, 226 reviews

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

Sep 10 – 17

G$23,963 GYD per night

Guest suite in Chicago

4.97 out of 5 average rating, 239 reviews

Stylish Studio in Historic Logan Square

Brand new, unique garden studio (4 steps down), located in the heart of the highly desirable Logan Square neighborhood. This luxurious space with heated floors & a spa inspired bathroom is situated on the Historic Logan Boulevard, 2 blocks from the CTA Blue Line which runs between downtown & O'Hare airport. The suite has a private entrance & access to a fabulous shared backyard space. The owner's treehouse deck can be reserved by request. Convenience & excitement are easily accessible!

Sep 21 – 28

G$31,910 GYD per night

Condo in West Loop

4.96 out of 5 average rating, 178 reviews

Updated Designer Duplex In Fulton Market W/parking

UPDATE: We just completed our luxury renovation March 2023! New kitchen, bathrooms, and patio with a firepit. We hope you enjoy! The first thing you notice stepping into my house are the sky-high ceilings! Enormous floor to ceiling windows allow light to stream into the the 2 floor home. The stylish and very large terrace are great for summer nights. Walk out the front door & you are in the heart of restaurant row with all the best bars and restaurant in the city. Parking included!

Jan 8 – 15

G$105,167 GYD per night

Apartment in Roscoe Village

4.96 out of 5 average rating, 238 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

Dec 2 – 9

G$21,803 GYD per night

Guest suite in Bridgeport

4.94 out of 5 average rating, 126 reviews

Comfortable & Cozy in Bridgeport

Cozy in-law apartment (garden-level) in Chicago's Bridgeport neighborhood. Great for a couple, a single person that is "working from home," or young friends. Unique touches like local art (including a hand-painted shower curtain), equipped kitchen, and a mini library out front in case you forgot your book! In a nice, quiet neighborhood that is close to Chinatown, Pilsen, Sox Park, Midway, and McCormick Place. Chicago Registration Number: R21000062030

Jul 20 – 27

G$24,175 GYD per night

Apartment in Lincoln Square

4.96 out of 5 average rating, 323 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

Nov 20 – 27

G$27,308 GYD per night

Condo in Chicago

4.97 out of 5 average rating, 331 reviews

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

Sep 23 – 30

G$30,754 GYD per night

Apartment in Logan Square

4.93 out of 5 average rating, 208 reviews

Cozy Private Coach House

This is a cozy 1 bedroom unit in a private coach house. Excellent location in the middle of trendy Logan Square! Please Inquire about winter time longer stays! Stays 30+ days avoid local taxes! I have a 28 night minimum in the winter, until the end of February or possibly March. But I recommend putting in at least 30 days to avoid those taxes!

Sep 2 – 9

G$29,808 GYD per night

Vacation rentals for every style

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Popular amenities for South Loop, Chicago pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Avondale

4.86 out of 5 average rating, 215 reviews

The Avondale Guesthouse

Apr 20 – 27

G$34,015 GYD per night

Home in North Park

4.95 out of 5 average rating, 129 reviews

Chicago Riverhouse summer on our patio!

Feb 13 – 20

G$55,080 GYD per night

Home in Forest Park

4.91 out of 5 average rating, 224 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Jun 23 – 30

G$32,102 GYD per night

Home in Chicago

4.93 out of 5 average rating, 327 reviews

Amazing Penthouse Skyline Views!

Mar 20 – 27

G$142,394 GYD per night

Home in Lincoln Park

4.82 out of 5 average rating, 140 reviews

Historic Old Town, Fabulous 4 Bedroom Home

G$78,566 GYD per night

Home in Lincoln Park

4.81 out of 5 average rating, 197 reviews

Spacious Luxury Townhouse - Old Town

Oct 5 – 12

G$190,606 GYD per night

Home in Logan Square

4.98 out of 5 average rating, 132 reviews

Southwestern Penthouse TRES | Sleeps 12

Feb 21 – 28

G$89,249 GYD per night

Home in Avondale

4.93 out of 5 average rating, 210 reviews

Luxe 6BR House *Trendy Logan Square *Garage Access

Dec 21 – 28

G$170,838 GYD per night

Pet-friendly home rentals with a pool

Apartment in Chicago

4.79 out of 5 average rating, 159 reviews

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

Jan 13 – 20

G$68,647 GYD per night

Apartment in Old Town

4.87 out of 5 average rating, 110 reviews

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

Jul 7 – 14

G$164,301 GYD per night

Apartment in The Loop

4.89 out of 5 average rating, 9 reviews

Safe Downtown Penthouse Lake Views #1|Gym, Parking

Jun 5 – 12

G$106,341 GYD per night

Apartment in Logan Square

4.91 out of 5 average rating, 32 reviews

Luxe Suite + Spa House Retreat! Pets Welcome

Jan 26 – Feb 2

G$32,662 GYD per night

Apartment in West Loop

5.0 out of 5 average rating, 10 reviews

Skyline Oasis: City & Lake Views

Jun 27 – Jul 4

G$87,437 GYD per night

Apartment in East Rogers Park

5.0 out of 5 average rating, 8 reviews

Cozy studio near Michigan lake

Jun 30 – Jul 7

G$26,205 GYD per night

Apartment in Magnificent Mile

5.0 out of 5 average rating, 7 reviews

Luxury Designer Penthouse South |Pool| Gold Coast

Nov 6 – 13

G$146,182 GYD per night

Apartment in Rosemont

4.9 out of 5 average rating, 20 reviews

Relaxing Standard Room l Free Airport Shuttle

Jul 7 – 14

G$37,448 GYD per night

Private, pet-friendly home rentals

Apartment in Chicago

4.89 out of 5 average rating, 340 reviews

Sunny Logan Square Artists' home

Jan 30 – Feb 6

G$22,836 GYD per night

Apartment in Pilsen Historic District

4.9 out of 5 average rating, 154 reviews

Spacious unique artist's home in Pilsen

Oct 24 – 31

G$40,875 GYD per night

Guest suite in Chicago

4.93 out of 5 average rating, 354 reviews

Peaceful Portage Park Apartment

Apr 18 – 25

G$22,427 GYD per night

Apartment in Pilsen Historic District

4.84 out of 5 average rating, 106 reviews

Spacious 2BR near downtown Chicago

Jul 9 – 16

G$36,173 GYD per night

Apartment in Chicago

4.88 out of 5 average rating, 190 reviews

Comfort zone

Apr 17 – 24

G$25,759 GYD per night

Apartment in Wicker Park

4.84 out of 5 average rating, 480 reviews

Relaxed Bucktown/Wicker Park 1B Apt

Oct 2 – 9

G$23,395 GYD per night

Apartment in Irving Park

4.91 out of 5 average rating, 226 reviews

Skylights, King Bed, 2 bedrooms

Mar 5 – 12

G$23,018 GYD per night

Apartment in Chicago

4.87 out of 5 average rating, 304 reviews

Unwind in the Garden of an elegant, Modern Home

Dec 4 – 11

G$37,714 GYD per night

Quick stats about vacation rentals that are pet-friendly in South Loop, Chicago

Total rentals
120 properties
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Rentals with a pool
60 properties have a pool
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
4K reviews
Nightly prices starting at
G$14,605 GYD before taxes and fees

Destinations to explore