Pet-friendly vacation rentals in The Loop

★Bright & Bold 1BR in Roscoe Village + Fireplace★

At this swanky home, you'll love the bold finishes, in-suite laundry, and private fully-equipped kitchen. Located in “village within the city” known for its charming and laidback vibe, you're near a nice array of casual taverns, independent shops, and cute cafes. Kick back on the couch over a good Netflix show, sleep in on an ultra-comfortable memory foam bed, or create a spa-like experience in the bathroom with rainfall shower, favorite tunes on the Bluetooth speaker, and ultra-soft towels.

Unmatched Urban Retreat Close to 18th Strip & Loop

This stylish Airbnb in the very popular Pilsen neighborhood is perfect for small and large travel groups. There are 2 bedrooms with queen size beds, and the couch folds out for an additional sleeping area. The 2 full bathrooms will have everything you need to get ready to hit the town. The tall ceilings make this space for larger than life, and the unique décor gives this Airbnb a great urban feel. The fully equipped kitchen and updated appliances are perfect for those quiet nights in.

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.

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Kasa | Walk to Lincoln Park Zoo | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because: -Central Location near public transit (no car needed!) -FAST WIFI -En-suite Laundry -Lake & Park are outside our front door -Comfy Queen beds -1 Closed & 1 Loft style bedroom -Shared Rooftop Deck with stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you're interested in booking, see our FAQs below.

Logan Square Video Game Loft

Treat yourself to a unique stay in this hip video game themed studio. Enjoy the comfort of this large, bright space—and the games and artwork on display—during your trip. Explore the happening neighborhood scene in the Logan/Bucktown/Wicker Park area via the 606 walking trail (right outside the door) or walk two blocks to the Blue Line el stop for easy access to downtown or the airport. *Please be sure to review the Other Things to Note section as well as our house rules.

Old Irving Park- Sweet Garden Suite with Spa

Enjoy our unique, recently renovated, garden suite (basement). Every corner, a pleasant surprise in Old Irving, you will be surrounded by cafes, breweries, and restaurants. You'll have the best of both worlds - the conveniences of the city combined with the charm of a tucked-away garden oasis. Steps away from the train, there is direct train transit to ORD) + downtown. If you do decide to drive, the drive is 15 minutes downtown. Oh did we mention we have a hot tub...

Private, spacious studio close to Medical District

Fully equipped 900 sf garden apartment in owner occupied building. Private exterior entrance with smart lock. Open floor plan with large kitchen. Energy efficient, very clean and exceptionally comfortable with radiant floor heating. Free and plenty of street parking available. Easy access to Mt. Sinai (less than 1/2 mile) the Illinois Medical District (2 miles), and McCormick Place (5 miles). Ideal for medical students.

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!

Elegant Suite in Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of May 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours***

Eddy Street Upstairs Apartment

Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!