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Pet-friendly holiday rentals in Downtown Chicago

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Downtown Chicago

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

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Flat in Park Ridge

4.78 out of 5 average rating, 422 reviews

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level Condo one bedroom one bath. The Condo is very large for a one bedroom. Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. Perfect place to relax Perfect and safe place to rest . 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10 min from Chicago outlets etc. It is not a party room . No parties or large gathering .... Garden Apartment

Guest favourite

Flat in Chicago

4.98 out of 5 average rating, 131 reviews

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

Guest favourite

Guest suite in Chicago

4.93 out of 5 average rating, 401 reviews

Peaceful Portage Park Apartment

You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

Guest favourite

Flat in Chicago

4.98 out of 5 average rating, 128 reviews

Elegant Suite in Gold Coast

Established in 1927 as the first headquarters for Elizabeth Arden in Chicago, the Walton Residence is located in the heart of the Gold Coast neighborhood of Chicago. Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***From Sept. to beginning of Dec. 2024, there will be repairs to the exterior of the building. We do not expect this to cause major interruptions to your stay.

Loft in Chicago

4.79 out of 5 average rating, 221 reviews

Fun Dtown Penthouse #4 | Park, Museums +gym

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ It's Unique! ✅ High loft ceilings ✅ FAST WIFI ✅ Spacious layout ✅ Comfy beds ✅ Central Location ✅ Private Balcony! ✅ Close proximity to Grant Park, Soldier Field, Museums, and more! You are a short walk to Millennium/Grant Park, Skydeck, Shedd Aquarium, Adler Planetarium & many dining + shopping options!

Guest favourite

Flat in Chicago

4.9 out of 5 average rating, 169 reviews

Cozy and Comfy 1BR Apartment in Logan Square!

Welcome to Chicago! Our 1-bedroom/1 bathroom apartment unit is perfect for getaway to Chicago. It's professionally designed with modern furniture and located in the trendy Logan Square neighborhood. Designated parking spot is NOT available, but there is plenty of street parking. NOTE: -This is a basement unit with a low ceiling ( HEIGHT: 5.9 ft.). ONLY SUITABLE FOR SOMEONE AROUND or UNDER 5.8 FT. -There are two windows in the bedroom and two windows in the living room for natural light.

Guest favourite

Flat in Chicago

4.9 out of 5 average rating, 386 reviews

Sunny Logan Square Artists' home

2nd floor classic Chicago 2flat with lots of light. 3 bedrooms available, with 2 additional sofabeds. Great if you and family/group of friends are in town for an event and want to stay together. Grocery store 1.5 blocks away. Quiet street. Parking is decent. New bath has all marble walls, extra long/deep tub and rain shower. 1 mile walk to the Logan Square CTA Blue Line and Logan Square brunch/night-life. 5 min walk to Metra. Walk to 606 trail. Chicago Registration Number: R24000117459

Guest favourite

Flat in Chicago

4.9 out of 5 average rating, 175 reviews

Huge Pet Friendly East Albany Park Apartment

Enjoy staying in a classic Chicago 2-flat w/vintage charm and modern amenities. This sunny top floor unit has an updated kitchen & bath w/everything you need including in-unit laundry & Central Air. Experience life on the border of 2 great neighborhoods, Albany Park & Ravenswood Manor. Walk to Kedzie & Lawrence for diverse cuisine or walk to Lincoln Square. Take the Kedzie Brown Line to Lakeview & Lincoln Park. $75/pet/per stay. $25/person/night after 2 guests. Check-in/out @11am/@4pm.

Guest favourite

Flat in Chicago

4.95 out of 5 average rating, 283 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".,

Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 104 reviews

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen

Welcome to our charming home in the peaceful yet centrally located Buena Park neighborhood, housed in an updated antique building. This prime location offers easy access to the Red and Purple train lines, as well as multiple bus routes, making it easy to explore Chicago. You’ll be within walking distance of Wrigley Field, Clark St. bars, Montrose Beach, Lakeview, Boystown, and the iconic Green Mill. A perfect blend of quiet comfort and proximity to Chicago’s best attractions.

Guest favourite

Flat in Chicago

4.96 out of 5 average rating, 361 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.

Guest suite in Chicago

4.88 out of 5 average rating, 112 reviews

Cozy one-bedroom suite in the heart of West Loop

Enjoy your trip to Chicago in the heart of Fulton Market in this cozy, one-bedroom guest suite. Whether you’re visiting friends or here for business, this guest suite is the perfect space to unwind at the end of the day. Grab dinner at Chicago’s top-rated restaurants in Fulton Market and West Loop, all within a 10 minute walk. Go out for the night at some of Chicago’s best bars and nightlife.

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Popular amenities for Downtown Chicago pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 356 reviews

Amazing Penthouse Skyline Views!

Guest favourite

Home in Oak Park

4.88 out of 5 average rating, 113 reviews

Urban Chic 3beds w/2bath + free parking & W/D

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 157 reviews

Chicago River House -Large private entire home

Guest favourite

Home in Chicago

4.94 out of 5 average rating, 127 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

Home in Bolingbrook

4.92 out of 5 average rating, 125 reviews

The Sunshine Spot

Guest favourite

Home in Chicago

4.95 out of 5 average rating, 142 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

Guest favourite

Home in Chicago

4.82 out of 5 average rating, 226 reviews

Spacious Luxury Townhouse - Old Town

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 112 reviews

2BD/1 BA with summer patio in quiet Roscoe Village

Pet-friendly home rentals with a pool

Serviced apartment in Chicago

4.76 out of 5 average rating, 71 reviews

Level ◆ Brand New Luxe One Bedroom

Apartment in Chicago

New place to stay

voco: Balcony & City View

Flat in Chicago

4.64 out of 5 average rating, 67 reviews

Gold Coast Dream: Sleek Studio/Perfect City Vibes”

Flat in Chicago

4.7 out of 5 average rating, 116 reviews

Play in the Windy City and rest by the “606”

Flat in Des Plaines

4.85 out of 5 average rating, 41 reviews

Spacious 2BR/Free Parking/Central Location/O'Hare

Flat in Chicago

4.82 out of 5 average rating, 222 reviews

Spectacular Corner 2BR Penthouse in the Loop | Roo

Flat in Chicago

4.81 out of 5 average rating, 63 reviews

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!

Guest favourite

Flat in Chicago

4.94 out of 5 average rating, 16 reviews

Modern unit in Bridgeport-Chicago

Private, pet-friendly home rentals

Guest favourite

Guest suite in Chicago

4.9 out of 5 average rating, 198 reviews

Chicago Living: Your Home Away From Home

Guest favourite

Guest suite in Chicago

4.97 out of 5 average rating, 277 reviews

Stylish Studio in Historic Logan Square

Guest favourite

Apartment in Chicago

4.89 out of 5 average rating, 106 reviews

Unique 2BR/2BA FREE Parking/WI-FI Minutes From DT

Flat in Chicago

4.91 out of 5 average rating, 44 reviews

Loop Loft-Subway & Art Institute

Guest favourite

Flat in Forest Park

4.85 out of 5 average rating, 228 reviews

Home in Forest Park downstairs.

Guest favourite

Apartment in Chicago

4.92 out of 5 average rating, 221 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Guest favourite

Flat in Berwyn

4.91 out of 5 average rating, 342 reviews

Private apartment with retro vibe

Guest favourite

Flat in Chicago

4.93 out of 5 average rating, 111 reviews

CitySlickers Crash Pad /Free Parking /No Clean Fee

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