Discover a selection of 1,000 vacation rentals in Near North Side, Chicago that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and parking. Prices start at $110 per night, and houses and condos are popular options for a stay in Near North Side. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Near North Side
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What are the top vacation rentals in or near Near North Side?

Whether you're searching for a cozy retreat for you and your sweetie or somewhere spacious to fit the family, you'll find some top vacation rentals in and around Near North Side. Here are a couple to get you thinking:

  • Make the most of amenities including a living room and a desk at "Luxury Loyola 3 Bedroom, 2 Bath". Located around 7 miles from Near North Side, this vacation rental has 3 bedrooms and is a hit with guests.
  • Alternatively, unpack your suitcase at "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental". Located around 4 miles from the heart of Near North Side, it has 3 bedrooms and comes with games and an ice maker.

For even more great options, use the search bar at the top of the page to find the perfect Near North Side vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Near North Side?

Those chores can wait, because weekends were made for fun. Take time out at one of these weekend getaways in and near Near North Side and make the most of all the fantastic things to do nearby:

  • Spend your whirlwind escape at "53th Floor Magmile Penthouse - Views", which is around 1 mile to the south of Near North Side. There's plenty of adventure and nature to discover around here. Try some hiking and biking and golf or just explore the sights of Ravisloe Country Club and Monument Park.
  • Alternatively, leave your worries behind at "52nd Floor Magmile Penthouse - Views". Stay in and put your feet up, or head out for some cycling and hiking and biking. When you're ready to explore some nearby attractions, plan a visit to Marion Mahoney Griffin Beach and Conway Farms Golf Club. This popular vacation rental is around 1 mile south of Near North Side.

Can I find studio apartments for rent in and around Near North Side?

Usually small in size, affordable and well located, it's easy to fall for the charms of a studio apartment. Get cozy in one of these options and experience the culture of Near North Side up close:

  • Unpack your bags at "52nd Floor Magmile Penthouse - Views". Amenities including an outdoor pool and a lake view will help you feel at home here.
  • Alternatively, slip into vacation mode at "51st Floor Magmile Penthouse - Views", which comes with conveniences including an elevator and heating.

When it's time to leave your studio apartment and discover the highlights, there's loads to keep you occupied around Near North Side. Into art and culture? Swing by Arie Crown Theater and Remy Bumpo Theatre Company.

Can I find short term rentals in or near Near North Side?

Every now and then, you just need to escape from it all, even if it's only for a few short days. Enjoy a nice mix of sightseeing and relaxation at one of these short-term rentals in or around Near North Side:

  • Close to the center of Near North Side, "51st Floor Magmile Penthouse - Views" is the perfect place for a short and sweet break. While you're about, be sure to visit top sights like Wrigley Field and McCormick Place.
  • "52th Floor Penthouse - Fireplace" is another tempting option. Remember to add Millennium Park and Willis Tower to your must-do list when you're ready to sightsee.

What are the best romantic weekend getaways in or near Near North Side?

Nothing says "I love you" quite like planning a romantic weekend together. If you'd like to spend a couple of nights away with your partner, we've got some romantic getaways in and around Near North Side that will set your heart aflutter:

  • Around 7 miles from Near North Side, "Luxury Loyola 3 Bedroom, 2 Bath" is the perfect place for lovestruck couples. Beauty services and a restaurant dining guide are just some of the amenities you'll find here.
  • Alternatively, spend your escape sipping wine and canoodling at "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental", around 4 miles from Near North Side. Air conditioning and housekeeping services will help set the mood for romance.

Are there mansions for rent in or near Near North Side?

Nothing says "best vacation ever" like staying in a mansion. Spoil the family with a memorable escape at one of these mansions for rent in and around Near North Side:

  • Approximately 4 miles to the north of Near North Side is "Beautiful 9bedroom Mansion With 4 Parking Spots. Walk To Wrigley Field And Lake Michigan". As well as its striking design, you'll be impressed by its high-end amenities, such as beauty services and a firepit.
  • Alternatively, score major Brownie points and settle into "Stone Mansion - 20 Free Parking Near Lake". It's located about 3 miles to the north of Near North Side and offers amenities like beauty services, a fireplace and more.

What are the best houses for rent with a pool in or near Near North Side?

A pool is often a must-have amenity for any good vacation. Enjoy hours of entertainment splashing about or simply unwinding by the water at one of these refreshing retreats in or near Near North Side:

  • Pack your swimsuit and goggles and enjoy a fun stay at "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental". Other amenities here include a garden and towels.
  • "Stunning House In The Heart Of Old Town" is another top-rated option. After you've enjoyed a relaxing dip with the kids, take advantage of other conveniences like towels and a barbecue grill.

What are the best large family vacation rentals in or near Near North Side?

A family get-together should be memorable. Whether you're planning some time away with the kids or a party with relatives, our large family vacation rentals in or near Near North Side offer a comfy home away from home with ample space for everyone:

  • Sleeping up to 8 guests in 3 bedrooms, "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental" is the ideal place to enjoy some family time. This retreat is 4 miles to the northwest of Near North Side and has creature comforts that include coffee and tea making facilities and outdoor furniture.
  • Another great option is "Views, Pool, Fireplace, Fitness Center". This vacation rental is 1 mile south of Near North Side and features a TV, a barbecue grill and more. With 3 bedrooms accommodating up to 8 people, you won't need to leave anyone off your guest list.

When you're ready to venture outside and explore, there are loads of family-friendly attractions nearby to keep everyone entertained. Skydeck Ledge, Navy Pier and John G. Shedd Aquarium should be on your must-do list.

Are there one-bedroom vacation rentals in or near Near North Side?

Often located in sought-after positions due to their compact size, a one-bedroom rental is a great choice for one or two travelers. Here's a quick taste of Vrbo's range in or near Near North Side:

  • Check out "52nd Floor Magmile Penthouse - Views", a fantastic centrally located one-bedroom vacation property. A sauna and a kitchen are just two of the amenities here.
  • Also within easy reach of all the excitement of Near North Side, "51st Floor Magmile Penthouse - Views" is another popular one-bedroom option. After a day of exploring, return and enjoy amenities like a fireplace and a swimming pool.

Can I find two-bedroom vacation rentals in or near Near North Side?

It's easy to arrange your dream getaway with Vrbo. Whether you'd like a comfy cabin or a trendy apartment, we've got lots of two-bedroom options in or near Near North Side: Here are just a few of our top choices:

  • "53th Floor Magmile Penthouse - Views" is an awesome choice for smaller groups. As well as two bedrooms, this relaxing stay offers handy amenities like a swimming pool and a fireplace.
  • "53/54th Floor Magmile Penthouse" is another terrific two-bedroom property in the Near North Side area. It comes packed with convenient amenities like a swimming pool and a fireplace.