Discover a selection of 1,000 vacation rentals in Wicker Park, 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 parking and WiFi. Prices start at $69 per night, and houses and condos are popular options for a stay in Wicker Park. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Wicker Park
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What are the top vacation rentals in or near Wicker Park?

Whatever your vacation needs, you'll find a rental property in or around Wicker Park that fits you like a glove. Take a peek at these favorites:

  • "Luxury Loyola 3 Bedroom, 2 Bath" is a favorite with guests. Around 6 miles from Wicker Park, it has 3 bedrooms and loads of handy amenities, including a boat and an electric kettle.
  • Another great option is "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental", which is around 2 miles from Wicker Park. With 3 bedrooms, a fridge and a TV, it has everything you need to keep you comfortable and content.

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

What are the top-rated vacation rentals for weekend getaways in or near Wicker Park?

Clock out on Friday afternoon and then forget the real world. If you're craving some fun and relaxation, these properties in and around Wicker Park are the perfect weekend getaway:

  • "53th Floor Magmile Penthouse - Views" is a popular option around 2 miles southeast of central Wicker Park. You don't need to go far to find a memorable experience around this vacation rental. Pull out your map and head for Gleneagles Country Club and Deer Grove Forest Preserve. Activities like basketball and windsurfing will add a nice touch to your whirlwind stay.
  • Alternatively, take some time out at "52nd Floor Magmile Penthouse - Views". Approximately 2 miles southeast of Wicker Park, activities around here include sailing and golf. More into sightseeing? Don't miss Canalport Riverwalk Park and Arrowhead Golf Club.

Can I find studio apartments for rent in and around Wicker Park?

Experience the vibe and culture of Wicker Park from the privacy and comfort of a studio apartment. Whether you're eager to kick back on your own or have fun with a few friends, we'll help you find the ideal studio apartment for rent in or near Wicker Park:

  • Explore your surroundings and then sleep soundly at "52nd Floor Magmile Penthouse - Views". This vacation rental is a great base for discovering the sights and offers amenities including off-street parking options and a bicycle.
  • Alternatively, escape to "51st Floor Magmile Penthouse - Views", which comes with conveniences such as an outdoor pool and a microwave oven.

When it's time to step foot outside your studio apartment and go exploring, there's plenty to keep you amused around Wicker Park. Enjoy cultural attractions? Swing by DePaul Art Museum and ArchiTech Gallery.

Can I find short term rentals in or near Wicker Park?

Short-term rentals aren't hard to find in and around Wicker Park. Chill out for a night or two in an upmarket bed & breakfast, a studio apartment or a roomy home. Whatever type of rental you'd like, you'll have plenty to select from with Vrbo. Here are some of our faves:

  • If you'd like to be close to the action, "51st Floor Magmile Penthouse - Views" will be just the ticket. It's within reach of the center of Wicker Park and a superb base to check out attractions like Wrigley Field and McCormick Place.
  • Eat, sleep and explore from "52th Floor Penthouse - Fireplace", another good option. Millennium Park and Willis Tower should be on your itinerary when you're ready to see the sights.

What are the best romantic weekend getaways in or near Wicker Park?

Nothing says "I love you" like a romantic weekend escape. If you'd like to spend a couple of evenings away with your sweetheart, we've got some romantic getaways in and around Wicker Park that will sweep you off your feet:

  • Located around 6 miles from Wicker Park, "Luxury Loyola 3 Bedroom, 2 Bath" is a perfect place for starry-eyed lovebirds. Beauty services and a nearby marina are just some of the many amenities here.
  • Alternatively, spend your escape drinking wine and canoodling at "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental", around 2 miles from Wicker Park. Air conditioning and outdoor furniture will help ramp up the romance.

Are there mansions for rent in or near Wicker Park?

Nothing screams "best vacation evvv-er" like staying in a mansion. Spoil the family with an unforgettable getaway at one of these mansions for rent in or near Wicker Park:

  • Approximately 4 miles to the north of Wicker Park is "Beautiful 9bedroom Mansion With 4 Parking Spots. Walk To Wrigley Field And Lake Michigan". As well as its grand design, you'll also love its first-class amenities, such as beauty services and a chef.
  • Another great pick is "Stone Mansion - 20 Free Parking Near Lake". Around 3 miles to the northeast of Wicker Park, this swanky vacation rental is the crème-de-la-crème of homes and comes with beauty services, a fireplace and more.

What are the best large group vacation rentals in or near Wicker Park?

Big groups mean huge fun. They also mean finding someplace that'll effortlessly fit your crew. Check out our large group vacation rentals in or around Wicker Park and get everybody together under the same roof:

  • A nice range of amenities including a fireplace and a kitchen make "Aloha 2. 0 Tropical 5 Bed In Wicker Park" a top pick for groups. This property has 5 bedrooms and accommodates up to 15 guests. From the center of Wicker Park, it's around 0.1 miles away to the east.
  • Nothing takes priority over hanging out with the people you love, and "Lac Mondesir Monflanquin Villa T2 2p5p" makes it easy to do that. Located around 1 mile to the northwest of Wicker Park, as many as 15 people can stay in this vacation rental which has 4 bedrooms. A garden and a kitchen are among the various amenities at hand here.

What are the best houses for rent with a pool in or near Wicker Park?

Having access to a pool is always a nice perk when you're on vacation, especially if you're bringing the kids. Have fun splashing the days away at one of these houses with a pool in or near Wicker Park:

  • 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 stair gate and a kitchen.
  • "Private Historic Coach House Wicker Park" is another great option. After you've enjoyed a dip with the fam, make the most of other conveniences like a kitchen and towels.

What are the best large family vacation rentals in or near Wicker Park?

It's always more fun to share the great times with the people you care about the most. Whether you're planning a family break or getting away with good friends, Vrbo has a large vacation rental that's right for you. These are two of our best in and around Wicker Park:

  • About 2 miles to the north of Wicker Park, "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental" has 3 bedrooms and can sleep up to 8 guests. It comes with a host of amenities, including a kitchen and a fridge.
  • Another great option is "Views, Pool, Fireplace, Fitness Center". This property is 2 miles southeast of Wicker Park and features a swimming pool, childrens activities and more. With 3 bedrooms accommodating up to 8 people, you won't have to leave anyone off your guest list.

When you're ready to leave the house and explore, there are lots of family-friendly attractions nearby to keep everyone happy and entertained. Skydeck Ledge, Navy Pier and John G. Shedd Aquarium should be on your list.

What are the best large houses to rent with indoor pools in or near Wicker Park?

Add a serve of indulgence to your vacation by staying someplace with a private indoor pool. These gorgeous large houses in or near Wicker Park have a swimming space that's just for you, along with tons of room for whoever is fortunate enough to be joining you:

  • With 4 bedrooms that can fit up to 7 people, "Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool" is the perfect place to spend time with your friends or family. Make use of this getaway's host of amenities, such as a firepit and a swimming pool.
  • Another enticing property is "3b/2. 5ba Luxury Penthouse With Views". With 3 bedrooms sleeping up to 8 guests, you can invite your entire crew to stay, hang out and swim. A lake view and a swimming pool are other amenities you'll find here.

For even more options, use the search bar at the top of the page and adjust the filters to find the Wicker Park vacation rental that's perfect for your needs.