Apartment vacation rentals in Wrigleyville, Chicago

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Top-rated apartment rentals in Wrigleyville, Chicago

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Guest favorite

Rental unit in Roscoe Village

4.9 out of 5 average rating, 400 reviews

Relax and Enjoy Chicago in an Updated and Private Apartment in Roscoe Village

We converted our garden unit into a great space for travelers, we updated everything with you in mind, features high end appliances, full kitchen, 1 king and 1 queen pullout, heated floors, and free wifi. There are only 2 beds. We also have a landscaped backyard and grill access if requested If you need anything please let me know ahead of time Roscoe Village is often thought of as a small town inside the big city. It is one mile west of Wrigley Field and two miles west of the lakefront.

Guest favorite

Rental unit in Lake View

4.93 out of 5 average rating, 197 reviews

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown

Welcome to our family-friendly & cozy 1-bedroom/1 bathroom apartment! We are walking distance from Wrigley Field, Montrose Beach, Andersonville restaurants, Green Mill Jazz Club, Riviera, Lincoln Square, Target and grocery. Close to Red, Purple & Brown CTA trains and 22, 78 bus lines to reach airports & top sights. Street parking is open & free (check signage!) We are a smoke-free home directly across from a school with playground in a very quiet & safe neighborhood: Ravenswood/Uptown.

Guest favorite

Rental unit in Lake View

4.97 out of 5 average rating, 276 reviews

The Garden on Wayne

Located in one of the top 3 neighborhoods in Chicago, a great spot for a couple, a small family, business travel or a weekend with the girls. Close to high end shopping, a world famous and historic theatre and dozens of restaurants, our quaint garden apartment offers a quiet spot in a great area for weekending - and is also the midpoint between O'Hare and Downtown. The Lakefront is a quick 20-minute walk; the Lincoln Park Zoo is 20 minutes in an Uber. Please see below for further detail

Guest favorite

Rental unit in Wrigleyville

4.9 out of 5 average rating, 204 reviews

A Novel Situation at Wrigley

This is such a lovely spot and I think you will quite like it. The space features wonderful large windows in all of rooms and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a five minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. It's about a ten minute walk to all of the 'Boystown' nightlife. There is no parking available with the apartment.

Guest favorite

Rental unit in Roscoe Village

4.96 out of 5 average rating, 278 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

Guest favorite

Rental unit in Lake View

4.85 out of 5 average rating, 229 reviews

Private Queen Bedroom and En Suite Bath

Visiting Chicago? Stay in true Windy City style by joining us in our historic 3-flat in the Lakeview neighborhood on Chicago's North Side within walking distance of Wrigley Field and the popular Southport Corridor of restaurants, bars and shops. We love hosting and can help you tailor an exploration of our city that is perfect for your interests or occasion. Walking access to the Red and Brown Elevated lines and buses at the end of the block can get you throughout Chicagoland.

Guest favorite

Rental unit in Lake View

4.97 out of 5 average rating, 362 reviews

Charming, Spacious 3BR Lakeview Apt Near Transit

This newly remodeled 3-bedroom unit with 1-bath apartment is perfect for both leisure & business travelers. Located on a safe, tree-lined street, in the Lakeview neighborhood, with a completely private entrance of it's own. We are just a 5 minute walk away from the CTA Irving Park Brown Line, which will get you downtown in less than 20min. We are also conveniently close to Wrigley Field, Lake Michigan, Bus Stops, and other great neighborhood shops, restaurants, and nightlife.

Guest favorite

Rental unit in Lake View

4.87 out of 5 average rating, 123 reviews

The Wrigley Escape - Sleeps 1-4

Located steps away from Wrigley Field. 5 min = 2 1/2 blocks. = 0.2 miles. Can you get any closer? This beautifully furnished unit sits comfortably in Wrigleyville and sleeps up to 4 guests. Need to work, play, maybe a little of both? Your Wrigleyville unit has the best of what you are looking for. On historic Addison Ave, you can hop, skip, and jump out the door to see a baseball game, concert, go to bars, restaurants, shops, coffee shops, and outdoor life ! Let's Play Ball!

Guest favorite

Rental unit in Lake View

4.97 out of 5 average rating, 146 reviews

Walk to Wrigley * Garage Parking* Peaceful Patio

Relax in our comfortable apartment after exploring Wrigley or visiting one of the many bars and restaurants nearby. The apartment boasts 3 bedrooms with large living spaces in the Kitchen, Living Room, and Dining Room. In the summer you can enjoy our beautiful backyard patio with the option to grill or relax before the Cubs game. If you feel like exploring more of Chicago, the brown line is a short 10 minute walk away and there are always Uber’s or Lyft’s available.

Guest favorite

Rental unit in Uptown

4.96 out of 5 average rating, 284 reviews

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

Guest favorite

Rental unit in Lake View

4.93 out of 5 average rating, 188 reviews

Penthouse Near Wrigley Field

This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.

Guest favorite

Rental unit in Wrigleyville

4.8 out of 5 average rating, 417 reviews

'Secret Garden' Apartment in Wrigleyville

Small garden unit in the heart of Wrigleyville. Steps from both Wrigley and Boystown. The apartment has a queen bed in the bedroom and a sitting area with a TV and mini-dining area. In addition, the apartment has mini fridge, microwave, coffee machine w/ pods, and small dining table. There is no kitchen; fortunately Chicago has a multitude of amazing restaurants to choose from! Includes full bathroom with shower and linens.