Apartment holiday rentals in Lake View, Chicago

4.91 out of 5 average rating, 99 reviews

Wrigleyville Condo 2 Blks from Lake & Train

I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red line & 2 blks from the lake. Easy proximity 4 blks to Wrigley Field & restaurants/nightlife in Wrigleyville & Boystown. Amazing restaurant next door w/back patio- El Mariachi w/the freshest chips & guacamole! Starbucks, playground, and Divvy Bike station at the corner. 1 mi to Montrose Beach. All downtown sight-seeing easily accessible from Lake Shore Dr or red line 2 blks away.

Superhost

Apartment in Uptown

4.91 out of 5 average rating, 163 reviews

Stunning, Spacious, & Sunny 2bed Uptown Condo

Welcome to your home away from home in Uptown! My bright and inviting condo offers a perfect blend of comfort and convenience, with your own sunny living room to relax, fully-equipped kitchen and formal dining room, spacious private bedroom, serene sunroom with full bed for extra guests, and a workspace for business travelers. Short walk from the lakefront and Montrose Beach, and a 6-minute walk to the Wilson Red Line, this location is excellent for exploring all that Chicago has to offer.

4.99 out of 5 average rating, 181 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

4.96 out of 5 average rating, 121 reviews

Apartment in Uptown

Large 3BD/2.5 BA by Lakefront - Long stays welcome

Beautiful and spacious, lovingly rehabbed Chicago Greystone with backyard perfect for grilling & relaxing. Unit is great for a family or business stays. The unit offers a large open floor-plan with a chef's kitchen, spacious bedroom suites on each floor plus additional bedroom/half bath. Private deck off main bedroom suite. Has large backyard space - rare for the neighborhood. 0.6mile walk to lakefront/park 20 minute walk to Cubs Park Easy access to lake, harbor, Divvy bike rentals

4.99 out of 5 average rating, 158 reviews

Interior Designer’s 2bd 2bath w Private Backyard

A front door walkup duplex condo in the heart of Lakeview neighborhood. A perfect home away from home for a business trip or cozy winter getaway. Surrounded by restaurants, bars and shops & just steps from the Wellington brown line train stop. Luxurious amenities such as designer toiletries, cooking oils/spices, cafe du monde coffee and various teas. Walk to nearby Wrigley, Lake, Lincoln Park Zoo or enjoy a cozy fire in private backyard adorned with platters full of wintery greens

4.98 out of 5 average rating, 107 reviews

Designer Lakeview Haven. Private Rooftop Oasis!

Beautiful 2 bedroom, 2.5 bath condo on tree lined street in charming Lakeview. Only a 2 minute walk to the Paulina Brown line stop and 20 minute walk to Wrigley Field, I’m nestled between the Southport Corridor and Roscoe Village. Short walk to Starbucks, City Target, Walgreens, Whole Foods and multiple local restaurants and bars. Hop on the train and be downtown in 20 minutes. I have 3 floors of bright and spacious living with a gorgeous furnished rooftop with city views.

4.92 out of 5 average rating, 349 reviews

Apartment in North Side

Susie's Space. 2BR easy parking & pet friendly

Sunny and spacious, 2 bedroom apartment in Avondale near the Green Exchange/ Greenhouse Loft Flexible, self check-in Easy street parking (with provided permits) Pet fee $80 per pet Bedroom 1 with a king sized bed Bedroom 2 with a full bed Air conditioning and ceiling fans Soft linens and towels Separate dining room Fully equipped kitchen Free WIFI Smart TV for streaming Garden in back with a fire pit and charcoal grill Laundry room in basement

4.95 out of 5 average rating, 109 reviews

Apartment in Wicker Park

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Superhost

4.78 out of 5 average rating, 167 reviews

Modern Wrigley Oasis with Parking!

Beautifully designed in the heart of Wrigley. Steps away from Wrigley Field, bars, restaurants and shops! This modern oasis comes with TWO tandem parking spaces! This unit is epic. Enjoy Wrigley in style! Please note: this unit is immediately next to the Brown train line. It can be heard but it is not disruptive or an inconvenience. We just want to make sure people are aware before booking.

Apartment in Wrigleyville

4.98 out of 5 average rating, 117 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.

4.98 out of 5 average rating, 376 reviews

Sunny Apartment Just 2 Blocks from Wrigley and Boystown

Located on a quiet, tree-lined street, the apartment sits on the second storey of a classic Chicago house in Lakeview—a vibrant lakefront community with arts and culture, green space, eateries, boutiques, nightlife, and transportation options. Street parking passes available upon request. Less than five minute walk to red line El (subway train) stop and several bus lines.