
Vacation rentals in Old Town
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Top-rated vacation 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.

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!

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.

Family-Friendly 2BD/2BA Prime Location (+parking)
Getaway to this authentic Old Town apartment! 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 - Master en-suite w/ all the bells/whistles! - Extremely Fast WiFi - Pillow-top Bamboo mattresses - Charming neighborhood - 5-10 minute walk from red line (CTA L) We look forward to hosting you!

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.

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport fireplace is not operational.

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt
Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

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

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.

Modern Luxury In Old Town - Sleeps 4
Stay in one of the best neighborhoods in Chicago - Old Town! Recently renovated spacious top floor condo with all modern amenities, in a classic 19th century Chicago home in one of the best parts of the city with access to dining, bars, entertainment and more. Ideal for traveling families and friends, and plenty of Chicago culture nearby, from nearly every era. A neighborhood bar with Frank Sinatra's favorite ribs! Michelin-starred restaurants!

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!

Cheerful 3 story townhouse Old Town/LP
Discover a luxurious three-story townhouse, ideally located for exploring Chicago's Lincoln Park Zoo, Lake Michigan, Magnificent Mile, Old Town, and Lincoln Park's vibrant dining and shopping. Enjoy a complimentary designated parking spot. Please note: due to a host's medical condition, we cannot accommodate service animals that are cats or dogs. A fee applies for more than two guests.
Popular amenities for Old Town, Chicago vacation rentals
Private Old Town, Chicago vacation rentals

Flat in Lincoln Park 2-Flat Central to Everything

Archways at the Lincoln Park Zoo 2bed/2ba

Cool Quiet Coach House, Private Access + Patio

East Lakeview Designer Condo with 2 Bd, 2 Bath

Lakeview Loft-Vintage Chicago, Modern Amenities

Large Remodeled Home in Lincoln Park, Sleeps 12!

Unwind in Style Steps from the Magnificent Mile

Old Town/Lincoln Park Luxury Home Garage & Rooftop
Old Town, Chicago apartment rentals

Wicker Park Walk-Up Condo

A Vintage Pink House in the Heart of Chicago

Bucktown Brick Cottage Apartment

Cozy Lincoln Park Studio - Steps to Zoo!

Dugout in Wrigleyville

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Spacious & private! Free parking! Great location!

Great Location! Gold Coast! 07
Private Old Town, Chicago apartments

Penthouse Near Wrigley Field

Beautiful (No Chores & No Cleaning Fees)

Prime Lincoln Park Views + Modern Amenities Await

Coach House in Historic Old Town Chicago

The Picasso: #1 Chicago Location

The Noble Farmhouse, w/ Garden in West Town

Peaceful River West, free parking

Lincoln Park Charm + On site Parking Included!
Quick stats about vacation rentals in Old Town
Total rentals
70 properties
Nightly prices starting at
€ 51 before taxes and fees
Total number of reviews
7.1K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Destinations to explore
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606