
Holiday houses in Lake View
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Top-rated holiday rentals in Lake View
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Christmas in the City- Holiday Duplex in Lakeview
Decorated thanksgiving-NYE. A front door walkup duplex condo in the heart of Lakeview neighborhood. A perfect cozy place for a holiday 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 planters full of wintery greenery.

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!

North Side Near Wrigley Lakeview Walk Everywhere!!
Located on a beautiful tree lined street one block from the thriving Southport Corridor, one of the hottest neighborhoods in Chicago. You'll love the convenience of being just steps from the Southport Brown Line "L" Stop, you can see the City without ever needing to drive. Steps to outstanding restaurants, bars and shopping. Going to Wrigley Field? Enjoy a 10 minute walk down some of the most beautiful streets in Chicago. Ideal for families seeking comfort, style and a convenient location.

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

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.

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.

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.

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.

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!

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.

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.
Popular amenities for Lake View holiday rentals
Other great holiday rentals in Lake View

Pristine Lakeview l Boystown l Wrigley HavenlBeach

Urban Jungle Oasis • Steps to Wrigley + CTA

Modern Studio on Broadway

2bd/2bath Urban Loft w/ 2 pkg spots 1 blk to train

Private Twin Bedroom with Private Bathroom

SuperHost with Private bedroom/bath/entry Lakeview

Great Location / Private Room in Lakeview

Private Cozy Cottage in Lincoln Park w/ Porch
When is the best time to visit Lake View?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $172 AUD | $164 AUD | $195 AUD | $201 AUD | $244 AUD | $266 AUD | $261 AUD | $284 AUD | $238 AUD | $235 AUD | $224 AUD | $214 AUD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about holiday rentals in Lake View

Total holiday rentals
Explore 640 holiday rentals in Lake View

Nightly prices starting at
Lake View holiday rentals start at $31 AUD per night before taxes and fees

Verified guest reviews
Over 53,090 verified reviews to help you choose

Family-friendly holiday rentals
330 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 240 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
380 properties have a dedicated workspace

Wi-Fi availability
640 of Lake View holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Lake View rentals

4.8 Average rating
Lake View stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Family-friendly rentals Lake View
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Willis Tower
- Museum of Science and Industry
- Illinois Beach State Park
- Washington Park Zoo
- The Beverly Country Club
- Raging Waves Waterpark
- The 606