Holiday houses in Lake View, 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, 92 reviews

Pristine Lakeview| Boystown |Wrigley Haven |Beach

In the heart of historic trendy Boystown and Wrigleyville, this fully furnished quiet 1 BR/1 BA apartment with an equipped kitchen is in a vibrant culturally diverse neighborhood. 5 Minutes' drive to Downtown. It is steps from the beach, lakefront parks, and Belmont Harbor, and is within walking distance to many restaurants, boutique shops, amazing nightlife, many local theaters, and home of the World Series Champs, the CUBS. Enjoy 65inches Samsung QLED Tv Netflix, Hulu, Apple Music Fast Wi-Fi

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!

4.96 out of 5 average rating, 510 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.

4.97 out of 5 average rating, 392 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.

Apartment in Lincoln Square

4.86 out of 5 average rating, 363 reviews

Renovated Designer Flat in Heart of Lincoln Square

Kick back with a fresh coffee and enjoy the designer touches of this renovated apartment, including marble worktops, wood floors and 1920s exposed brickwork. There are great courtyard views, while the memory foam mattress and super-sized sofa add real comfort. Lincoln Square is a quaint, family-friendly neighborhood. There's abundant German influence here, and great shops, restaurants, and bars line Lincoln Avenue. Downtown is 20 mins by train. Wrigley Field is close too.

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.

Apartment in Wrigleyville

4.97 out of 5 average rating, 91 reviews

Beautiful Remodel in Sought After Wrigleyville

Modern comfort meets unbeatable location in this freshly renovated 1BR/1BA Wrigleyville gem. Enjoy the "new unit" feel with fresh paint, new appliances, and soaring 10-ft ceilings. Nestled in Lakeview, you're steps from top restaurants, bars, theaters, and iconic attractions. Perfect for travelers seeking style, convenience, and a true Chicago experience. Public transit is a block away and Spothero parking behind the building.

Apartment 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.

4.95 out of 5 average rating, 121 reviews

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

4.91 out of 5 average rating, 11 reviews

Designer 1 Bed, 1 Free Parking

Kick back and relax in this stylish 1BR, 1BA condo in Lakeview, Chicago. Located on the 1st floor, it features a king bed, a 65" TV in the living room, fast WiFi, elevator access, and easy self check-in. 1 FREE parking space included! You're just 5 mins to Wrigley Field, 7 mins to Lincoln Park Zoo, 10 mins to Downtown & Millennium Park, and 15 mins to Navy Pier. Book your stay today!

4.99 out of 5 average rating, 637 reviews

Condo in Lake View

Urban Comfort in the Heart of Chicago

This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and a newly remodeled en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

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Other great holiday rentals in Lake View, Chicago

4.96 out of 5 average rating, 190 reviews

Private room in Evanston

Welcoming Evanston Home

JoshuaRating, 5 stars2 weeks ago

Jennifer was a very hospitable host and I had a very pleasant stay. The room was very clean and quiet!

5 out of 5 average rating, 5 reviews

Modern & Well-Located 1BR Apt

KristinaRating, 5 stars3 days ago

Great location in the heart of Boystown! 10-minute walk to the Red Line and easy stroll to Wrigley. Vin was proactive and left great instructions on how to get into the apartment. Very clean as well!

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 stars2 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

4.96 out of 5 average rating, 50 reviews

The Cornelia: Your own bathroom & parking included

PeterRating, 5 stars2 weeks ago

The hosts were excellent and provided great service. The location is ideal - easy to reach by public transport and only a 3 minute walk to bars/ shops and restaurants. The place was perfect for a solo traveller like myself

4.81 out of 5 average rating, 413 reviews

Private room in Chicago

Loft Style Private Apt (1 Room- 420 Friendly)

AaronRating, 5 stars1 week ago

clean, affordable, quiet. no trouble getting in or leaving. host is is cool and accommodating. 5 stars, book with confidence.

Private room in Wrigleyville

4.94 out of 5 average rating, 34 reviews

Modern condo in Wrigeleyville and Boystown

TaliaRating, 5 stars1 week 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.