Holiday rentals in Wrigleyville, Chicago

4.97 out of 5 average rating, 215 reviews

Modern vintage chic steps from Wrigley Field!

Vintage touches and modern updates in the heart of Wrigleyville! Includes off street parking. Close enough to see Wrigley Field from the building, yet the block is charming and quiet. Close to the lake and Boystown. The vintage DNA is beautifully respected while updates provide the modern amenities you expect when traveling. Large deck. You will love the exposed brick and original millwork while enjoying huge new windows, an open floor plan, chef's kitchen, stylish decor, and spa like bathroom.

4.85 out of 5 average rating, 255 reviews

Guest suite in Lake View

Wrigleyville/Boystown/Entire Private Floor!

1000 sq ft-entire private floor & door access. The perfect Wrigleyville/Boystown/Lake location. Zip to downtown Chicago in minutes via cab or public transportation options. Our friendly neighborhood is packed with fun bars, fabulous restaurants, unique boutiques & great music venues. Enjoy pool, ping pong and pinball and our 65" 4K flat screen TV or a seat at the bar. A Queen bed, 2 single beds in the main room, steam shower and bathroom. We have a mini fridge, microwave, coffee and home gym.

4.98 out of 5 average rating, 258 reviews

Home in Lake View

Wrigleyville Southport Studio

This Wrigleyville studio is the best of urban living combined with a tranquil retreat. With vintage, mahogany paneled walls and a comfy king size bed this apartment has everything! Free coffee, tea, snacks and dedicated work space. The Southport Corridor is blocks away with restaurants, bars and shopping. Free street parking and 4 blocks to El/ Brown/Purple/ Red line trains. Wrigley Field, Metro and Vic is 4 blocks away. This garden studio is the perfect retreat in the heart of Chicago!

4.97 out of 5 average rating, 301 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

4.89 out of 5 average rating, 224 reviews

Flat in Wrigleyville

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.

5 out of 5 average rating, 107 reviews

Steps away from Wrigley Field!!

The Wrigley Home is a newly renovated 2-bedroom with spacious living room & dining room. Ideal location for groups & families as this family-friendly neighborhood is walking distance to train stops (Addison- Red Line & Southport- Brown Line), retail shops, bars, restaurants, parks, and more! You will feel like home with a large sofa, fireplace, dining room table, brand new kitchen appliances, the amenities of home, pack and play, high chair, stroller, toys, backyard for grilling, etc.

4.96 out of 5 average rating, 511 reviews

Loft in Lake View

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

4.99 out of 5 average rating, 287 reviews

A Whimsical Fairy-tale Loft in Ravenswood Chicago

Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co. and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

4.99 out of 5 average rating, 119 reviews

Home in Wrigleyville

Whole apartment! 2 Bed/2 bath steps from Wrigley!!

Newly rehabbed urban nest among the tree-lined streets of beautiful East Lakeview. Literally 60 seconds to Wrigley Field, close to bars, restaurants, El train/busses, and lakefront. You’ll have loads of space in this 2 bed, 2 bath, plus office and large laundry room with FREE full size W/D. Free parking passes! Owner lives near by and is happy to help with anything you need to make your trip the best it can be. Flexible check in/out times upon request.

Guest suite in North Center

4.97 out of 5 average rating, 120 reviews

Modern Garden Apartment in Lincoln Square

Welcome to our stylish and updated one-bedroom apartment located in a classic brick building in Lincoln Square. Perfect for solo travelers or couples, the space features a comfortable queen bed and a bright, modern interior. Just a short walk to the Brown Line and steps from Lincoln Square’s cozy shops, top-rated restaurants, and vibrant local culture. Wrigley Field, downtown attractions, and Lske Michigan are easily accessible by bike or train.

Superhost

Flat in Wrigleyville

4.8 out of 5 average rating, 438 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.

Apartment in Wrigleyville

4.98 out of 5 average rating, 116 reviews

Wrigleyville Inn. Historic Greystone, Free Parking

Have fun with the whole family at this stylish place. Completely rehabbed 3 bedroom 2 bathroom high-end 2nd-floor condo in a historic greystone building, 5 minutes walk to Wrigley Field. And only 2 minutes walk to Clark or Halsted Streets. New open back porch for your enjoyment. Free parking included. Old Grey Lady being reborn. Total gut rehab of classic Chicago 3 flat.

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Popular amenities for Wrigleyville, Chicago holiday rentals

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Other great holiday rentals in Wrigleyville, Chicago

5 out of 5 average rating, 132 reviews

Private room in Uptown

Easily accessible Uptown room

MarinaRating, 5 stars3 weeks ago

We absolutely loved starting at Cameron’s place! It was so clean, beautiful and in the perfect location for us. Cameron was so kind and helpful and really set the bar for what an Airbnb host should be. We would definitely book to stay there again!

Private room in Lake View

4.95 out of 5 average rating, 164 reviews

Private Queen Bedroom with Private Bathroom

NatalieRating, 5 stars5 days ago

Tim and Barbara have created the best AirBnB we've ever experienced! They have thought of everything to make guests feel welcome and comfortable. Our top two items are always safety and cleanliness, and both of those were a 10/10. So, all of the other little details they've added are like icing on the cake. From the welcome tour, a little snack basket in the room, a guidebook and maps on hand to give us ideas plan our days, quick responses to every communication, and just being friendly, inviting hosts, our first big trip to Chicago couldn't have been any better. We hope to stay here again in the future!

Private room in Lake View

4.92 out of 5 average rating, 103 reviews

Convenient Location / Private Room (Queen Bed)

JackRating, 5 stars6 days ago

Tim’s stay was neat and exactly as described. He was very thorough in regards to details surrounding check in and various policies and procedures. Very polite and clean!

5 out of 5 average rating, 6 reviews

Flat in Wrigleyville

Prime Location! 2BR Near Wrigley

YiceRating, 5 stars1 week ago

A really good experience living here

5 out of 5 average rating, 13 reviews

*Best of Northalsted*

AmyRating, 5 stars2 weeks ago

Carlos was such a fabulous host! The place is so spacious! We loved the location close to Wrigley. Enjoyed the coffee shop close by and going to Lark for a drink and sing some Karaoke. Hope to come back in the future!

5 out of 5 average rating, 12 reviews

A Walk To Wrigley

IbrahimRating, 5 stars1 week ago

Had a great stay! The place was beautiful—clean, stylish, and super comfortable. Loved the location—easy to get around the city and right next door to a lively bar, which added to the fun vibes. Overall, awesome energy, great host, and would definitely stay again.

Private room in Wrigleyville

4.94 out of 5 average rating, 34 reviews

Modern condo in Wrigeleyville and Boystown

TaliaRating, 5 stars2 weeks ago

We were really happy with our stay. The place is really clean and spacious and the location is great. Chialung is also really nice. We would definitely come back if we're back in Chicago.