Apartment vacation rentals in Lake View

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

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

Lakeview Charmer -with parking!

Walk to Wrigley 4 blocks away: 15 min walk; 3 minute drive. Walk to The Vic (around the corner), the lake, several theaters, many restaurants, RedLine el (1 block) takes you north to Evanston, south to Loop, to Sox. Park your car behind the building. A Garden 2 BR (one semi-private; see pics) with 2 queen beds. With rollaway and couch, could accommodate up to 6. We also have a fold up crib. FYI: NO Smoking inside or on the patio. No animals. See pic on patio: el is a few doors west.

Cozy Bedroom in Wrigleyville (Entire Apt)

You can’t beat this location! Right in the middle of Boystown and steps from Wrigley Field, you’ll be surrounded by some of the city’s best bars, restaurants, and nightlife. Cubs Stadium is just one block away, and the Addison Red Line station is a quick 5-minute walk, making it easy to explore all of Chicago. No shared space: Due to updated COVID-19 policies, this unit is now 100% private. Once you book, the entire place is yours and the additional listing will be blocked immediately.

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.

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., Cash's Kitchen 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.

Charming suite 3 blocks from Wrigley Field

Your Wrigleyville get-away destination awaits! Spend a fun, baseball themed weekend within 3 blocks of Wrigley Field on this quaint neighborhood block. Walking distance to dozens of bars and restaurants in Lakeview & 3 blocks from the "El" CTA train Brown & Red lines. This suite sleeps 4 people comfortably and is perfect for families. A full kitchen, desk, coffee station, Wifi, and smart TV can be your home away from home. Book your weekend now for the next homestand or concert!

CASA NEWPORT

Second floor, one bedroom apartment, with an additional queen pullout couch located in a beautiful historic district in Lakeview. Just steps away from Halsted street/Boystown/Wrigley field. Conveniently located to shopping, restaurants, subway (EL) and grocery stores. Close to lakefront, jogging path and bike path. Complementary street parking passes available. The apartment does NOT have airconditioning. It does have a window unit in the bedroom from April to September.

Spacious 2 Bedroom in the heart of Lakeview!

Come enjoy this warm and spacious 2br/1ba vintage apartment in the heart of Lakeview! 10 Minute walk to Wrigley Field and steps away from many dining and shopping options. Fully stocked kitchen, dining room (seats six), decorative fireplace, TV w/ Fire Stick, two bedrooms with queen beds, office space for working remote, and large private deck with gas grill. Very close to Lake Shore Drive, short walk to the Belmont L, and easy access to many buses. Two night minimum stay.

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.

Sleek and cool garden loft in East Lakeview

Cool loft 1 bedroom, queen bed in bedroom, 2nd queen bed in living area. Contemporary custom kitchen with quartz counters and stainless appliances. In unit laundry with central heat and air. Within walking distance to Lake Michigan, Belmont Station, Wrigley Field, Briar Street Theater, The Vic, Belmont Theater District, too many restaurants to mention and lots of retail shopping. 24 hour Starbucks nearby, Free Wifi and Netflix

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.