
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!

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!

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.

Victorian Guest Suite in Old Town
This private guest suite is the restored 1st floor of my Victorian era single family home. The space has a private ground floor entrance with small patio, located in the “Old Town Historic District”. Decor is Mid Century Modern. Located 1 block north of Sedgwick train station, bus stop across the street, 5 minute walk to the lake, 1/2 hour lakeside walk to downtown. Great restaurants nearby. Only registered guests are allowed on the premises. Please see booking requirements in house rules

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.

Old Town/Gold Coast Masterpiece (+private rooftop)
Chicago's top getaway spot! 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 - Privacy is hard to beat in this beautiful courtyard! - Luxurious interior design - Spacious rooftop for lounging - Extremely Fast WiFi - Pillow-top Bamboo mattresses - State-of-the-art kitchen - Exceptional workspace - 5-10 minute walk from red line (CTA L) We look forward to hosting you!

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.

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!
Popular amenities for Old Town apartment rentals
Weekly apartment rentals

Wicker Park Walk-Up Condo

Hip Chicago Condo in fun shopping and dining area

Hancock Lookout|Steps to Beach&Transit, CHI Views

The Alton - Designer Flat by Mag Mile & the Lake

Large condo w/ amazing roof deck

Cozy apartment in the heart of Lincoln Park

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

The Picasso: #1 Chicago Location
Private apartment rentals

Private Balcony/1 Garage Parking/Skyline Rooftop

Lovely apt with 2 br suites and large living areas

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

Sleek 2 Bed, 2 Bath Condo in Trendy Fulton Market

Amazing Andersonville! 1 King 1 Queen 2BR Apt.

1 BR w/ Rooftop & Wrigley Views!

Old town green palace

Bosworth Living in Wicker Park
Apartment rentals with a hot tub

Top Floor Views + Central Comfort

Level Junior Two Bedroom Suite | Fulton Market

Luxury 3BD Penthouse – Private Patio+Skyline Views

Skyline Oasis: City & Lake Views

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

Belmont Pleasures - hot tub / arcade gaming room

Checkerboard Studio, Private Outdoor Hot Tub, Yard

Modern 2BR South Loop Apt, McCormick & Wintrust
When is the best time to visit Old Town?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $163 AUD | $163 AUD | $198 AUD | $188 AUD | $241 AUD | $283 AUD | $282 AUD | $269 AUD | $269 AUD | $255 AUD | $184 AUD | $177 AUD |
| 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 apartment rentals in Old Town

Total holiday rentals
Explore 30 holiday rentals in Old Town

Nightly prices starting at
Old Town holiday rentals start at $113 AUD per night before taxes and fees

Verified guest reviews
Over 3,720 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Old Town holiday rentals include Wi-Fi access

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

4.7 Average rating
Old Town stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Rentals with outdoor seating Old Town
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- Rentals with a washing machine and dryer Old Town
- Rentals with a fireplace Old Town
- Rentals with a patio Old Town
- Family-friendly rentals Old Town
- Apartment rentals Chicago
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- Apartment 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
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Wilmot Mountain Ski Resort
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo




