Old Town Chicago vacation rentals
Find the best place to stay - Old Town Chicago
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Photo gallery for New 3BR Residence Adjacent to Wrigley Field - Outdoor Patio - BBQ Grill
New 3BR Residence Adjacent to Wrigley Field - Outdoor Patio - BBQ Grill
Photo gallery for Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
Photo gallery for Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Photo gallery for Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Photo gallery for Stylish Corner 2BR in the Loop | City & Lake Views
Stylish Corner 2BR in the Loop | City & Lake Views
Find spaces that suit your style
Top rated rentals - Old Town Chicago
Photo gallery for Luxury SOHO Styled Two-Level Townhouse | Old Town
Great for families
Photo gallery for Luxury House in the heart of Old Town with Parking
Simply Perfect
Photo gallery for Lovely 4 Bedroom Spot located in Charming Old Town
Perfect City Apartment!
Photo gallery for GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
Great location just off Old Town!
Photo gallery for Ideal Old Town Location, 5 min walk to public transportation, 10 min to Wells St
Wonderful apartment in Old Town
Photo gallery for MTM Fully Furnished Rental in Old Town - 2 Beds
Long Term Stay
Photo gallery for MTM Fully Furnished Rental in Old Town - 2 beds
Great place
Photo gallery for Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Perfect girls trip getaway!
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental accommodation in Old Town Chicago?
According to our research, houses are considered the most popular type of property in Old Town Chicago. But as you might expect, everyone's idea of an awesome stay differs. Vrbo has vacation homes in a variety of shapes and sizes, so you're sure to find the best fit for your needs.
How much does it cost to rent a vacation rental in Old Town Chicago?
Property type, length of stay and time of year are among the factors that can determine the price of a vacation home. Simply click on your dates of travel to find your dream escape. From cozy country cottages to sprawling luxury villas, all Vrbo vacation rentals offer incredible value.
How much does it cost to rent a beach house in Old Town Chicago?
The average price for a vacation rental close to the beach in Old Town Chicago will depend on when you'll be there and the style and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering the dates you'll be traveling. Then use our filters to pick the number of bedrooms and amenities important to you, like a pool, air conditioning and WiFi.
Are there pet-friendly vacation rentals in Old Town Chicago?
Yes. There are. You can choose from 25 stays that welcome pets in Old Town Chicago on Vrbo. Our furry kids also deserve a getaway, so simply use our search function for pet-friendly vacation rentals to book a place where Rover can join in the fun.
What are popular rental amenities in Old Town Chicago?
When it comes to rental amenities that guests prefer in Old Town Chicago, a fireplace, nearby museums and a firepit rank the highest. With Vrbo vacation rentals, you'll discover options to fit your style and taste, whether you're traveling with relatives, friends or even pets.
Are there large group vacation rentals in Old Town Chicago?
Old Town Chicago has 10 vacation rentals that can host 10 or more guests. These properties come with the space and privacy you need to share good times with loved ones.
Are there vacation rentals in Old Town Chicago that welcome kids?
Bring the entire family together for an adventure in Old Town Chicago at one of our 25 family-friendly vacation properties. A lot of these stays provide conveniences that are ideal for trips with the kids, including full kitchens, living rooms and entertainment units. Just click on the "Properties good for families" filter and decide on your favorite.
What are the top attractions for families in Old Town Chicago?
There's a ton of amazing things to do and see with the family in Old Town Chicago, including:
- Navy Pier
- Chicago Riverwalk
- Shedd Aquarium
Are there one-bedroom vacation rentals in Old Town Chicago?
Yes, you'll find five one-bedroom properties in Old Town Chicago to pick from. A one-bedroom vacation home is a superb choice if it's just you and your sweetheart or if you're vacationing alone. Toss in more space, privacy and convenience compared to a regular hotel, and you've got yourself a getaway to remember.
Can I find two-bedroom vacation rentals in Old Town Chicago?
You can pick from six two-bedroom vacation homes in Old Town Chicago. Give your little ones the second room or maybe fill it with a couple of your best friends. There's enough space for whoever's fortunate enough to come along for the ride.
Are there vacation rentals with WiFi in Old Town Chicago?
Whether you want to keep up with world events, look over emails or post a pic to social media, there are 16 vacation homes with WiFi in Old Town Chicago. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Old Town Chicago?
Decide on your travel dates and then use our filters to search for vacation rentals with ac in Old Town Chicago on Vrbo. With 23 air-conditioned properties available here, you can look forward to a comfortable and cool stay.