Old Town Accommodations
9.8
Fireplace/Heating
Pet Friendly
Kitchen
Air Conditioner
10.0- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
10.0- Fireplace/Heating
Balcony/Terrace
Parking- Air Conditioner
8.4- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
9.6
Breakfast- Parking
- Air Conditioner
- Internet
10.0- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
9.6
Spa- Fireplace/Heating
- Balcony/Terrace
View
10.0- Spa
- Fireplace/Heating
Ocean View- Balcony/Terrace
9.5- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
10.0- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
9.3- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
10.0
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Why Choose Rent By Owner for your Old Town Accommodations?
What makes our Accommodations special?
Popular Areas for Old Town Accommodations
Where are the best neighborhoods to stay in Old Town?
Staying in Old Town offers a charming array of neighborhoods where you can enjoy easy access to vibrant local culture and historic architecture. This area is perfect for those seeking a lively atmosphere combined with the convenience of nearby shops and dining options. Whether you're exploring the streets or relaxing in a nearby park, you'll find the ideal setting to experience the best of Chicago.
Downtown Chicago
Staying in this area offers convenient access to the city's central attractions and vibrant urban life, making it an ideal base for exploring all that the region has to offer.
View 1316+ Rentals in Downtown ChicagoRiver North
Located close to the heart of the city, River North features lively art galleries and trendy dining spots, perfect for those wanting to experience the energetic side of Chicago.
View 344+ Rentals in River NorthLincoln Park
This neighborhood provides a scenic setting with spacious parks and recreational activities nearby, suitable for visitors seeking a more relaxed and nature-oriented stay.
View 130+ Rentals in Lincoln ParkNear North Side
Offering proximity to shopping districts and cultural landmarks, this area is ideal for travelers eager to immerse themselves in Chicago's dynamic lifestyle.
View 564+ Rentals in Near North SideGold Coast
Known for its historic architecture and upscale ambiance, the Gold Coast delivers a luxurious experience right at the doorstep of the city's most refined attractions.
View 32+ Rentals in Gold CoastMid-North District
This neighborhood combines historic charm with modern amenities, providing a welcoming environment for those wanting to explore Chicago’s diverse neighborhoods.
View 4017+ Rentals in Mid-North DistrictSheffield Neighbors
With its vibrant nightlife and unique local eateries, Sheffield Neighbors is perfect for visitors looking to experience Chicago’s eclectic and lively scene.
View 4082+ Rentals in Sheffield NeighborsOld Town Triangle
The historic charm and cozy streetscapes here make it an appealing choice for travelers wanting an authentic Chicago experience within walking distance of major sites.
View 40+ Rentals in Old Town TriangleBest Times to Visit Old Town
When should you plan your Accommodations stay?
To make the most of your visit, consider planning your vacation during the quieter shoulder seasons or local festival times when the area's authentic charm can be fully appreciated without the peak season crowds.
Peak Season Highlights
Summer (June to August)
During the summer months, you'll experience warm weather ideal for exploring the area's vibrant streets and outdoor attractions.
Fall (September to November)
Autumn offers pleasant temperatures and colorful scenery, making it a popular time for visitors seeking a picturesque urban experience.
Off-Season Highlights
Winter (December to February)
Visit during winter for fewer crowds and cozy indoor activities, though be prepared for colder weather.
Early Spring (March to April)
As nature begins to awaken, the region sees fewer visitors, offering a quieter atmosphere before the peak spring season kicks in.
Weekly Weather Forecast for Old Town
How to Book Your Old Town Accommodations
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Old Town
Common Accommodations Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to a private outdoor patio or balcony for relaxing outdoors.
- Take advantage of nearby parks or green spaces for gardening or outdoor activities.
- Benefit from communal outdoor seating areas perfect for socializing and enjoying the fresh air.
- Discover outdoor grilling facilities to host cookouts during your stay.
- Experience convenient bicycle parking or storage for exploring the local neighborhood.
- Utilize outdoor fitness spaces or walking paths available in the region for active pursuits.
- Make the most of scenic views from rooftop terraces or outdoor balconies that overlook the area.
Top Attractions Around Old Town
What attractions are nearby?
Within this vibrant area, you can enjoy a variety of activities including exploring local shops, dining at renowned restaurants, and experiencing cultural events that highlight the unique charm of Old Town, making it an ideal destination for those seeking both relaxation and entertainment during their stay in Chicago.
Family Activities
- Chicago History Museum Engage your family in the rich history of the area through interactive exhibits and educational programs that bring the past to life.
- Lincoln Park Zoo Visit this free and family-friendly zoo nestled nearby, offering a diverse array of animals and fun, educational experiences for all ages.
- Farmers Markets Explore stalls filled with fresh produce and local treats at the neighborhood farmers markets, perfect for a leisurely family outing.
- Pottery & Art Studios Participate in creative workshops designed for families, allowing you to make memorable keepsakes together in this artistic region.
Adult Activities
- Architectural Riverwalk Tour: Experience a guided walk along the picturesque Chicago River, taking in stunning skyline views and learning about the area's historic architecture.
- Fine Dining Experiences: Indulge in the region’s renowned culinary scene by visiting upscale restaurants that offer a sophisticated atmosphere perfect for adult outings.
- Art Galleries and Museums: Discover contemporary art and cultural exhibits at local galleries and museums, providing enriching experiences just minutes from your stay.
- Nightlife and Live Music Venues: Enjoy evenings filled with live performances at trendy bars and music venues that showcase the vibrant atmosphere of the area.
Other Places to Stay in Old Town, IL
House of Glunz
Second City
Old Town Triangle
Old Town Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Take the time to discover the area’s renowned restaurants and cafes to enjoy authentic culinary experiences that showcase the region's flavor.
- Visit close-by attractions early in your stay: Planning visits to popular spots during your initial days ensures you experience the best before peak times or crowds arrive.
- Use public transportation or walk: To make the most of your trip, utilize accessible transit options and explore on foot for a more immersive experience of this destination.
- Book accommodations with convenience in mind: Choosing properties that are centrally located allows easy access to the region’s highlights and enhances your overall visit.
Transportation Options
- Chicago Transit Authority (CTA) Trains: This regional transit system offers convenient access to various neighborhoods and attractions, making it easy to explore the area from your accommodations.
- Bus Services: Several bus routes serve the region, providing flexible transportation options for getting around Old Town and connecting to other parts of the city.
- Divvy Bike Sharing: For a more active way to explore, the bike-sharing program offers numerous stations nearby, allowing you to navigate the area at your own pace.
- Taxis and Ride-Sharing Services: Reliable options like taxis and ride-shares ensure seamless door-to-door travel, ideal for quick trips or when carrying luggage.
Local Customs Options
- Traditional Neighborhood Festivities: Celebrating local holidays and festivals is a cherished tradition that provides insight into the community’s cultural heritage here.
- Respect for Historic Architecture: Maintaining the integrity of the area's historic buildings reflects a deep respect for its architectural heritage and contributes to the neighborhood’s charm.
- Community Engagement: Participating in neighborhood gatherings and local events fosters connections with residents and enriches your experience in this vibrant region.
- Politeness and Courtesy: Courteous interactions and friendly greetings exemplify the warm hospitality characteristic of this destination.
Frequently Asked Questions about Old Town Accommodations
1. What are the top Accommodations in Old Town?
There are a lot of options in Old Town. If you plan on staying in the Old Town area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Accommodations in Old Town:
- 5 Bedroom Huge House in Best Location Parking Fireplace Back Yard
- Large Condo with Outdoor Deck in Historic Chicago District home
- Go Grand in This Massive Old Town Mansion - Sleeps 22! apts
- Old Town Chicago at it's finest! Pet Friendly & Recently Renovated Top-Floor Condo Has Everything You Need for a Perfect Windy City Getaway condo
- Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! condo
- Charming & Bright Multilevel Townhome with Parking
- 3 br Spacious Home in Ideal Location w Free Parking Back Yard Pets Welcome
- MTM Fully Furnished Rental in Old Town - 2 Beds
- THE COMPOUND Large Exquisite House Private Yard 'Best Location' Well Appointed
- Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
2. How many Accommodations are available in Old Town?
Currently, the total number of properties listed by RBO in 2026 is over 68 in the Old Town area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Old Town.
3. What is the cancellation policy for bookings in this area?
4. Are there any additional fees I should be aware of when booking here?
5. How do I find out about the amenities included with my booking?
6. Is it possible to modify or cancel my reservation if plans change?
7. What is the check-in and check-out process for accommodations in this area?
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