Lakeview Holiday Rentals
Condo
- Chicago
- ·
- Lake View East
- 0.17 mi to center
10.0Exceptional
(63 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
Hot Tub
Parking
Balcony/Terrace
Kitchen
US $527/Night
7 Nights - US $3,690
Apartment
- Chicago
- ·
- Lake View East
- 0.30 mi to center
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
Internet
Child Friendly
US $256/Night
7 Nights - US $1,792
House
10.0Exceptional
(28 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
Air Conditioner
US $531/Night
7 Nights - US $3,717
Condo
10.0Exceptional
(56 Reviews)
2 Bedrooms
2 Baths
5 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $476/Night
7 Nights - US $3,332
Apartment
- Chicago
- ·
- Lake View East
- 0.18 mi to center
10.0Exceptional
(4 Reviews)
6 Bedrooms
2 Baths
20 Guests
3498.27 ft²
Private Beach
EV Charge Station- Parking
Ocean View
US $482/Night
7 Nights - US $3,371
Apartment
10.0Exceptional
(55 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $536/Night
7 Nights - US $3,749
Apartment
- Chicago
- ·
- Wrigleyville
- 0.16 mi to center
10.0Exceptional
(52 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $644/Night
7 Nights - US $4,510
Condo
10.0Exceptional
(36 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $392/Night
7 Nights - US $2,742
Condo
10.0Exceptional
(34 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $520/Night
7 Nights - US $3,637
Luxury Holiday Rentals in Lakeview
Over 507+ Luxury Holiday Rentals in or Near Lakeview
House
4 Bedrooms
2 Baths
10 Guests
2497.23 ft²
- Parking
- Internet
- Child Friendly
Security/Safety
US $3,786/Night
7 Nights - US $26,500
House
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
7.4Very Good
(3 Reviews)
9 Bedrooms
4 Baths
22 Guests
4200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,239/Night
7 Nights - US $15,671
House
10.0Exceptional
(60 Reviews)
6 Bedrooms
5 Baths
17 Guests
5000 ft²
Oceanfront- Hot Tub
- Parking
Spa
US $2,178/Night
7 Nights - US $15,245
House
10.0Exceptional
(62 Reviews)
4 Bedrooms
2 Baths
10 Guests
4000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,823/Night
7 Nights - US $12,759
Bed & Breakfast
5 Bedrooms
3 Baths
12 Guests
1200 ft²
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $1,660/Night
7 Nights - US $11,621
House
10.0Exceptional
(26 Reviews)
5 Bedrooms
3 Baths
16 Guests
- Oceanfront
- Parking
- Ocean View
View
US $1,529/Night
7 Nights - US $10,705
House
- Chicago
- ·
- Wrigleyville
- 0.14 mi to center
9.8Exceptional
(30 Reviews)
3 Bedrooms
2 Baths
8 Guests
1600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,445/Night
7 Nights - US $10,114
New
Apartment
- Chicago
- ·
- Wrigleyville
- 0.27 mi to center
10.0Exceptional
(2 Reviews)
9 Bedrooms
5 Baths
16 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $1,309/Night
7 Nights - US $9,161
Apartment
10.0Exceptional
(1 Review)
4 Bedrooms
1 Bath
12 Guests
1700.7 ft²
- View
- Air Conditioner
- Internet
Sports/Activities
US $1,265/Night
7 Nights - US $8,855
Top-Rated Holiday Rentals with a Pool in Lakeview
Over 20+ The Best Private Villas and Holiday Rentals in Lakeview with a Pool
Apartment
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
13 Guests
Private Pool- Hot Tub
- Parking
Pool
US $913/Night
7 Nights - US $6,392
Condo
9.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
7 Guests
1200 ft²
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $425/Night
7 Nights - US $2,972
Apartment
7.8Very Good
(10 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Breakfast
- Pool
- Kitchen
- Air Conditioner
US $96/Night
7 Nights - US $672
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
US $234/Night
7 Nights - US $1,638
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
US $221/Night
7 Nights - US $1,546
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
US $214/Night
7 Nights - US $1,495
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
US $190/Night
7 Nights - US $1,327
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Pool
- Kitchen
- Air Conditioner
- Child Friendly
US $157/Night
7 Nights - US $1,099
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
US $157/Night
7 Nights - US $1,096
Pet-Friendly Holiday Rentals in Lakeview
Over 200+ Pet-Friendly Holiday Rentals in or Near Lakeview
Apartment
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
10.0Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $542/Night
7 Nights - US $3,793
Apartment
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
10.0Exceptional
(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
1205.56 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $480/Night
7 Nights - US $3,361
Bed & Breakfast
8.0Excellent
(659 Reviews)
1 Bedroom
1 Bath
- Parking
- Internet
- Pet Friendly
- Security/Safety
US $223/Night
7 Nights - US $1,564
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
6 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $402/Night
7 Nights - US $2,811
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
20 Guests
2497.23 ft²
- Private Beach
- Parking
- Ocean View
- Balcony/Terrace
US $622/Night
7 Nights - US $4,357
Apartment
- Chicago
- ·
- Wrigleyville
- 0.27 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
6 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $350/Night
7 Nights - US $2,450
Condo
9.6Exceptional
(25 Reviews)
2 Bedrooms
2 Baths
4 Guests
1070 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $234/Night
7 Nights - US $1,638
Apartment
9.6Exceptional
(18 Reviews)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $284/Night
7 Nights - US $1,987
Apartment
9.6Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
10 Guests
969 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $417/Night
7 Nights - US $2,922
Large Holiday Rentals and Private Villas in Lakeview
Over 71+ Large Holiday Rentals and Private Villas in or Near Lakeview
Apartment
9.6Exceptional
(5 Reviews)
1 Bedroom
1 Bath
12 Guests
1001 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $483/Night
7 Nights - US $3,383
Apartment
- Chicago
- ·
- Wrigleyville
- 0.20 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
2497.23 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $799/Night
7 Nights - US $5,594
Condo
10.0Exceptional
(129 Reviews)
3 Bedrooms
3 Baths
10 Guests
2200 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $420/Night
7 Nights - US $2,937
Apartment
- Chicago
- ·
- Wrigleyville
- 0.23 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
12 Guests
23680.6 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,018/Night
7 Nights - US $7,129
Apartment
10.0Exceptional
(117 Reviews)
4 Bedrooms
3 Baths
16 Guests
2300 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $892/Night
7 Nights - US $6,243
Apartment
- Chicago
- ·
- Wrigleyville
- 0.15 mi to center
10.0Exceptional
(65 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,067/Night
7 Nights - US $7,471
Apartment
- Chicago
- ·
- Lake View East
- 0.14 mi to center
10.0Exceptional
(55 Reviews)
4 Bedrooms
2 Baths
20 Guests
2300 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $352/Night
7 Nights - US $2,464
House
- Chicago
- ·
- Lake View East
- 0.28 mi to center
10.0Exceptional
(51 Reviews)
6 Bedrooms
2 Baths
20 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $687/Night
7 Nights - US $4,807
House
- Chicago
- ·
- Lake View East
- 0.15 mi to center
10.0Exceptional
(33 Reviews)
4 Bedrooms
2 Baths
20 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $346/Night
7 Nights - US $2,421
Wheelchair Accessible Holiday Homes in Lakeview
Over 59+ Wheelchair Accessible Holiday Homes in or Near Lakeview
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
6.0Good
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
800 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $397/Night
7 Nights - US $2,778
Apartment
7.6Very Good
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
548.96 ft²
- Air Conditioner
- Internet
Wheelchair Accessible
US $68/Night
7 Nights - US $476
Hotel
- Chicago
- ·
- Wrigleyville
- 0.20 mi to center
9.6Exceptional
(1005 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Air Conditioner
US $410/Night
7 Nights - US $2,868
New
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
1 Bedroom
1 Bath
2 Guests
500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $272/Night
7 Nights - US $1,902
Apartment
6.3Good
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
548.96 ft²
- Air Conditioner
- Internet
- Wheelchair Accessible
US $66/Night
7 Nights - US $462
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
2 Bedrooms
2 Baths
4 Guests
1208 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $223/Night
7 Nights - US $1,562
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
1 Bedroom
1 Bath
4 Guests
500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $221/Night
7 Nights - US $1,547
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
2 Bedrooms
2 Baths
4 Guests
958 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $173/Night
7 Nights - US $1,208
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
2 Bedrooms
2 Baths
4 Guests
1025 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $172/Night
7 Nights - US $1,205
Lakeview Private Villas and Holiday Homes Under $200
Over 152+ Lakeview Private Villas and Holiday Homes Under $200
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
1 Bedroom
1 Bath
2 Guests
655 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $141/Night
7 Nights - US $990
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
505.9 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $174/Night
7 Nights - US $1,216
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
1 Bedroom
1 Bath
2 Guests
655 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $140/Night
7 Nights - US $978
Apartment
9.8Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
6 Guests
947.22 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $133/Night
7 Nights - US $932
Apartment
1 Bedroom
1 Bath
2 Guests
700 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $137/Night
7 Nights - US $957
Apartment
1 Bedroom
1 Bath
2 Guests
700 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $134/Night
7 Nights - US $938
Apartment
1 Bedroom
1 Bath
2 Guests
700 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $127/Night
7 Nights - US $888
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
1 Bedroom
1 Bath
2 Guests
475 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $95/Night
7 Nights - US $668
Instantly Bookable Holiday Homes in Lakeview
Over 259+ Instantly Bookable Holiday Homes in or Near Lakeview
Apartment
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
647 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $352/Night
7 Nights - US $2,465
Apartment
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Pet Friendly
- Child Friendly
US $186/Night
7 Nights - US $1,304
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $352/Night
7 Nights - US $2,464
New
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
849 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $268/Night
7 Nights - US $1,874
Apartment
9.8Exceptional
(34 Reviews)
2 Bedrooms
1 Bath
4 Guests
754 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $254/Night
7 Nights - US $1,778
Apartment
9.8Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $276/Night
7 Nights - US $1,930
Condo
9.6Exceptional
(37 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $294/Night
7 Nights - US $2,060
Apartment
9.6Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $346/Night
7 Nights - US $2,419
Apartment
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
9.4Exceptional
(65 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $221/Night
7 Nights - US $1,548
Book a Last Minute Place to Stay in Lakeview
About Casai's Private Villas and Holiday Rentals in Lakeview
Discover more than 516 vacation rentals available in Lakeview. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Lakeview.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Lakeview, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Lakeview. On average, places to stay near Lakeview offer 905.73 ft², with nightly prices averaging US $543.
With Casai, finding and comparing holiday rentals in Lakeview is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Show more
Show less
Top Accommodation Types in Lakeview
| Type | Count |
|---|---|
| Holiday Apartments | 385 |
| Vacation Homes | 47 |
Use these Quick Filters to Find a Holiday Rental in Lakeview
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Lakeview.
Weather in Lakeview, IL
View the weather forecast for Lakeview before booking your Lakeview Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Other Places to Stay in Lakeview, IL
Frequently Asked Questions About Lakeview?
What are the top holiday rentals in Lakeview?
With numerous options available in Lakeview, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Lakeview:
- Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
- Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE
- 5 Bedroom Wrigleyville experience right by stadium
- EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
- PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
- Luxurious Four-Level Home with Personal Touches Everywhere
- Wrigleyville Private Guesthouse
- Chic Urban Retreat Near Wrigley Field w/Parking
- Wrigleyville Inn - Unit 3
Which holiday homes in Lakeview are best for families?
If you're searching for a family-friendly holiday home in Lakeview, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Lakeview:
- Entire Apt in Heart of Chicago
- Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S
- Best Western Plus Hawthorne Terrace Hotel
How many Casai.com holiday rentals are available in Lakeview?
As of 2026, Casai boasts over 516 properties listed in the Lakeview area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Lakeview.
Nearby Neighborhood (13)
| Neighborhood | Property Count |
|---|---|
| Lincoln Park Vacation Rentals in Chicago, Illinois | 132 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 52 |
| North Center Vacation Rentals in Chicago, Illinois | 45 |
| Lake View East Vacation Rentals in Chicago, Illinois | 41 |
| Uptown Vacation Rentals in Chicago, Illinois | 35 |
| Sheffield and DePaul Vacation Rentals in Chicago, Illinois | 33 |
| Wrightwood Neighbors Vacation Rentals in Chicago, Illinois | 3484 |
| Ravenswood Vacation Rentals in Chicago, Illinois | 1335 |
| Park West Vacation Rentals in Chicago, Illinois | 3594 |
| Roscoe Village Vacation Rentals in Chicago, Illinois | 1948 |
| West Lakeview Vacation Rentals in Chicago, Illinois | 2224 |
| Boystown Vacation Rentals in Chicago, Illinois | 1706 |
| West DePaul Vacation Rentals in Chicago, Illinois | 3258 |
Map
