Holiday houses in Old Town, Chicago

5 out of 5 average rating, 264 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

4.88 out of 5 average rating, 218 reviews

Lincoln Paradise– Steps to Park & Zoo!

This semi-basement apartment is located on a tree lined street full of gorgeous, historic buildings. With easy access to shopping, dining and drinking via Wells St & North Avenue- you'll love this location! Walking distance from Lincoln Park, the Lakefront, North Ave Beach, and the Lincoln Park Zoo. Feel right at home with the bright and welcoming layout, with every convenience of home provided. This garden unit is spacious, you'll have plenty of room to relax during your stay in the Windy City!

4.93 out of 5 average rating, 209 reviews

Apartment in Old Town

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Room for reg-size SUV in private driveway! - Luxurious interior design - Tranquil rooftop w/ grill - Fast WiFi - Pillow-top Bamboo mattress in each master en-suite - State of the art kitchen - Exceptional workspace - 5 minute walk from red line (CTA L) We look forward to hosting you!

4.96 out of 5 average rating, 113 reviews

English garden apt. in the heart of Lincoln Park

Welcome to this new, totally furnished apartment in the heart of East Lincoln Park…only a 3 minute walk to the Lincoln Park Zoo! Apartment has been completely renovated with high finishes throughout. Living room boasts a 50” television with Dish TV, internet and a queen sleeper sofa! Gourmet kitchen with granite counter tops with an eat-in bar height counter top. Truly gourmet kitchen! Bedroom with en-suite European styled bathroom. Wall mounted television in the bedroom. In unit laundry.

Apartment in Magnificent Mile

4.98 out of 5 average rating, 160 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.

4.98 out of 5 average rating, 124 reviews

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

4.98 out of 5 average rating, 111 reviews

Guest suite in Old Town

Travelers Retreat in Old Town Chicago

Our garden unit is decorated with treasured souvenirs, maps, art, and decor that we’ve collected from all over the world to create a travel inspired retreat for Airbnb guests. Located in Old Town, a walkable neighborhood with famed architecture, stellar dining, stand-up/sketch comedy, and local shopping. Walking distance to Brown (Sedgwick) and Red (North/Clybourn) line trains. Centrally located between Downtown/River North and Lakeview/Wrigleyville. Adjacent to Gold Coast & Lincoln Park.

4.96 out of 5 average rating, 431 reviews

Sophisticated Flat in Historic Building

Nestled in the charming Old Town Triangle of Chicago, this luxurious flat offers a seamless blend of historic charm and contemporary sophistication. With its soaring ceilings and elegant arched windows, this immaculate space boasts a truly captivating ambiance. Impeccably designed interiors ensure a truly indulgent stay, while the building's rich heritage adds an unforgettable sense of place. Treat yourself to the ultimate Chicago getaway and bask in the allure of this stunning residence.

4.9 out of 5 average rating, 295 reviews

Condo in Lincoln Park

Old Town Pied-à-Terre w/Pvt Terrace and Parking

Our bright modern 2 bedroom condo has 13 ft ceilings and an amazing private terrace. It's in the heart of Old Town, right on Wells St - steps outside the door are some of the city's best restaurants, cafes, and bars. Just a 5 minute walk to two world-renowned comedy clubs: Second City and Zanies. The Chicago History Museum, Lincoln Park Zoo, and the lake are a quick walk too. The Sedgwick CTA stop is nearby too! Please note: patio cushions are available May through October.

4.84 out of 5 average rating, 279 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

This cozy studio in the heart of Lincoln Park is just steps away from some of the best experiences that Chicago has to offer! Just a block from the Lincoln Park Zoo and near the great restaurants and bars of the neighborhood, there's something here for everyone. See a show at the world-famous Second City, take a quick ride up Clark St to see the Cubs play at historic Wrigley Field, or just stay in and relax, there's no wrong way to spend your time in the Windy City!

4.83 out of 5 average rating, 243 reviews

Spacious Luxury Townhouse - Old Town

Historic 3 bedroom home in Old Town! Comfortably sleeps 6, and access to 3 levels of living space. The massive rain shower in the master bath is my favorite part, but there's plenty of luxury here to enjoy. Plus, we're right in the heart of Old Town, just steps from all of the shops and restaurants on Wells Street, and a 5 minute walk to the Sedgwick Brown/Purple line stop - you can be in the Loop in 20 minutes! Book today!

4.86 out of 5 average rating, 305 reviews

Historic Old Town Flat - Minutes from Downtown!

Built in 1886, our "Boland House" offers guests a rare chance to stay in an architecturally significant residence on a beautiful tree-lined street in Historic Old Town district! The original owner was chief of plasterwork projects for the "White City's" 1893 World's Columbian Exposition - combined with modern day conveniences. If you've always wanted to stay in an authentic Chicago Victorian brownstone, you've found it!

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Popular amenities for Old Town, Chicago holiday rentals

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Wi-Fi

Pool

Free parking on premises

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Stay near Old Town, Chicago's top sights

Lincoln Park Zoo211 locals recommend

Magnificent Mile104 locals recommend

Museum Of Contemporary Art Chicago53 locals recommend

Other great holiday rentals in Old Town, Chicago

4.74 out of 5 average rating, 31 reviews

Apartment in Old Town

Oldtown Stylish cute studio

AndrewRating, 5 stars2 weeks ago

Hatice's place is in the perfect location. It is spacious and clean. She was a great communicator. I would stay there again.

5 out of 5 average rating, 4 reviews

Large condo w/ amazing roof deck

HeatherRating, 5 stars1 week ago

Loved our stay. Great location, very fun roof top. I wish we had longer to stay and shop. Had dinner at Armitage Alehouse and ice cream at Annettes. Highly recommend!! Made brunch one day and had everything we needed, very well equipped and the beds were SUPER comfy!

Apartment in Old Town

4.78 out of 5 average rating, 78 reviews

Studio w/ Large Terrace & Kitchenette, Lincoln Prk

RachelRating, 5 stars1 week ago

Absolutely loved staying here! Coffee on the deck, walking distance to the beach, Lincoln Park, restaurants, grocery stores and even downtown if youre up for a good walk. Ozlem responded to my questions immediately and even sent me a text or two to just check in and see how my stay was going. The place was clean and very comfortable. I would absolutely stay here again!!

4.92 out of 5 average rating, 13 reviews

Condo in Lincoln Park

Cozy Condo, Sleeps 2!

BriannaRating, 5 stars4 weeks ago

I enjoyed my stay. The neighborhood was walkable and quiet. Check-in went smoothly and there were no issues throughout my stay. Thomas was very communicative and responsive.

4.98 out of 5 average rating, 65 reviews

Condo in Old Town

Two Floor Luxury 3 Bedroom Condo in Old Town

BetsyRating, 5 stars4 weeks ago

What a gem - We loved our stay! Whenever you find a beautiful, comfortable, well appointed home in a GREAT location with a helpful, kind and responsive host it’s a huge win! This stay checked all of those boxes and will most definitely be on our ‘repeat properties’ list.

4.98 out of 5 average rating, 80 reviews

Opulent 3bdr2bth Old Town Luxury + Parking prmts

MehganRating, 5 stars4 weeks ago

Lovely space and a perfect location for exploring the city. Great restaurants within a short walk. Lincoln Park also just a short walk.

4.66 out of 5 average rating, 170 reviews

One-of-a-Kind Apartment In Old Town!

LeeRating, 5 stars1 month ago

Donald’s place was in a perfect location for our family to travel around the city. Extremely walkable to Lincoln Park as well as coffee shops, restaurants, and other amenities. The area was safe and cute to walk around with two small children. The team managing the Airbnb were also very diligent making sure that the pack n play met our expectations, reaching out personally to make sure we didn’t have any issues. The living room was comfortable and had everything we expected, making it a nice place to spend time and relax. The only thing unexpected to note is that the second bedroom is quite small, with not much room beyond the bed and a small desk. We were able to fit the pack n play but not much else. Overall that was manageable though and we had a lovely stay, I would definitely recommend this to others for value and location especially!