
Apartment holiday rentals in Old Town
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Top-rated apartment rentals in Old Town
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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.

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!

Rare 1BR Lincoln Park Apt, close to everything!
Historical charm with modern updates in this 1 Bedroom Lincoln Park Condo. This is the perfect place to stay while you're in Chicago with it being steps away from Chicago's largest park, one of the country's oldest free zoos, nationally acclaimed dining, lakefront trails, museums, DePaul University and more. While you're at home, relax in the cozy living room, cook dinner in the full and updated kitchen, rinse off with the rainfall shower head, or get some rest on the queen bed in the bedroom.

Lincoln Pk-parking-wifi-King bd-crib-kid friendly
This wonderful 2 bedroom garden apartment in superhot Lincoln Park on a block where homes sell for 4 million to 12.5 million dollars. Walk score 97 The apartment was totally renovated adding new furniture, Flatscreen TVs in both bedrooms and Livingroom, a fully stocked kitchen, superfast wifi (150 Mbps) dedicated parking space, rooftop deck, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop is 2.5 blocks from the apartment. Go to the Cubs game/downtown.

Lincoln Pk-Kingbed-fast WIFI-Parking-crib-roofdeck
A Wonderful 2 bedroom Airbnb in the Superhot Lincoln Park neighborhood on a block where homes sell from 5 million to 12.5 million dollars. The apartment was totally renovated adding new furniture, 50-inch High-Definition Flatscreen in the Livingroom, a fully stocked kitchen, superfast wifi, parking space, rooftop deck, Patio, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop. Pack-in-play, highchair, kids. Millennium Pk, Navy Pier, Mag Mile, Museum.

Beautiful 2BR Apartment in Old Town
Want to experience Chicago neighborhood charms, there is no better place to start than the Old Town Historic District. This 2 bedroom apartment is part of a Victorian-era building while interior has been updated for modern style living. You can enjoy lake front trail in the Summer, Bears football in the Fall, year end holiday shopping in the Winter, and Blackhawks playoffs in the Spring. With both Red and Brown line only a few blocks away, getting around in Chicago does not get any easier.

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.

OLD TOWN GARDEN GETAWAY
Take it easy at this unique and tranquil getaway! Guests love this space because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Privacy is hard to beat in this beautiful courtyard! - Extremely Fast WiFi - Pillow-top Bamboo mattress and SMART TV in each bedroom - Exceptional workspace - 5-10 minute (0.4 mile) walk from Clark/Division red line station (CTA L) We look forward to hosting you!

Kasa | Explore the Neighborhood-Mag Mile | 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.

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!

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!

Chic 2BR Gem with Fireplace
Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. Perfect for both business and leisure travelers, our space combines modern comfort with the vibrant energy of one of the city's most coveted neighborhoods.
Popular amenities for Old Town apartment rentals
Weekly apartment rentals

LIVN West Loop Chicago Queen Studio Apartment

Large 4BR/3BA • Safe Old Town Location • Walk Ever

OldTown Gem 3BD/2BA/ Free Parking/Close to Beach

Large condo w/ amazing roof deck

Luxury Designer Apartment 803| Gold Coast/Old Town

Nice Large 1 BR Apartment in OldTown

Luxury 2BR Apartment in Downtown Chicago

Old town green palace
Private apartment rentals

Designer Garden Unit in Bridgeport

Fulton House #1 (2bd/ 1ba)

Stylish Gold Coast 3BR Apt | Walk to Grocery&Cafes

Cozy apartment in Lake View

Modern 1BR in top rated neighborhood• Walk to All

River North | Rooftop With In & Out Parking | 6

Location! HUGE Wicker Park Concrete Jungle ROAR

Modern Minimalist Studio | Heart of Gold Coast
Apartment rentals with a hot tub

Top Floor Views + Central Comfort

Super Paradise+65 Amenities*Downtown 15 Min

Skyline Oasis: City & Lake Views

Luxury 3BD Penthouse – Private Patio+Skyline Views

Level One Bedroom Suite | Fulton Market

Chic 1 BR w 1 G Parking| W Park Nightlife nearby

Belmont Pleasures - hot tub / arcade gaming room

City Skyline Suite (Indoor Pool • Fitness Center)
When is the best time to visit Old Town?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £85 | £85 | £103 | £98 | £125 | £147 | £147 | £140 | £140 | £133 | £96 | £92 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about flat rentals in Old Town

Total holiday rentals
Explore 20 holiday rentals in Old Town

Nightly prices starting at
Old Town holiday rentals start at £59 per night before taxes and fees

Verified guest reviews
Over 3,810 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Old Town holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Old Town rentals

4.8 Average rating
Old Town stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Pet-friendly rentals Old Town
- Family-friendly rentals Old Town
- Rentals with a fireplace Old Town
- Rentals with a washing machine and dryer Old Town
- House rentals Old Town
- Rentals with a patio Old Town
- Rentals with outdoor seating Old Town
- Flat rentals Chicago
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- Flat rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Brookfield Zoo
- Garfield Park Conservatory
- University of Chicago
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower




