Holiday Rentals in Evanston, IL

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Evanston, IL holiday rentals
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Best Holiday rentals and Airbnb offers in Evanston, IL

Dramatic Wrigley Loft +Private Rooftop, Center Of Wrigley, Ranked Guest Favorite - Evanston, IL
9.9 302 reviews
Evanston, IL
26/06 – 28/06
SG$2573/nighttotal: SG$5146 (2 )

Dramatic Wrigley Loft +Private Rooftop, Center Of Wrigley, Ranked Guest Favorite

4 7
apartment, Chicago
This spacious apartment is situated in Wrigleyville, a lively neighbourhood just a short walk from Wrigley Field, home to the Chicago Cubs, and within easy reach of bars and restaurants. It has excellent user, location and cleanliness ratings.
The apartment has four bedrooms and three bathrooms, spread over 214 square metres, offering ample space for large groups or families. Amenities include a private rooftop with skyline views, a fully equipped kitchen, a game room with a foosball table and arcade, a Jacuzzi, a spa, a fitness centre, and parking.
Quiet Unit Near Transportation! - Evanston, IL
10 2 reviews
Evanston, IL
10/07 – 11/07
SG$558/nightfor 1 night

Quiet Unit Near Transportation!

1 2
apartment, Skokie
This Skokie apartment is located just a short distance from the Skokie Public Library and the Skokie Theatre, offering easy access to cultural attractions and entertainment. The apartment enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The flat can accommodate up to four guests and features a well-equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. Guests can also enjoy air conditioning, a garden, and parking, making it a convenient and relaxing base for exploring Skokie.
Near Zoo & Beach • Reading Nook + Parking - Evanston, IL
Evanston, IL
10/07 – 11/07
SG$1606/nightfor 1 night

Near Zoo & Beach • Reading Nook + Parking

3 2
apartment, Chicago
This Lincoln Park flat is a short walk from Fullerton Beach and Lincoln Park Zoo, and within a few kilometres of Wrigley Field and 360 Chicago.
This 3-bedroom flat offers 93 square metres of space for up to 15 guests, with a fully equipped kitchen, free Wi-Fi, air conditioning, and private parking.
Gorgeous 7bd Home W/ Garage - Evanston, IL
8.8 6 reviews
Evanston, IL
26/06 – 28/06
SG$1462/nighttotal: SG$2924 (2 )

Gorgeous 7bd Home W/ Garage

1 7
apartment, Chicago
This Belmont Cragin property is situated approximately 5 kilometres from Milwaukee Avenue and under 10 kilometres from Wrigley Field and the Frank Lloyd Wright Historic District.
This seven-bedroom house, sleeping up to sixteen guests, boasts a fully equipped kitchen, private patio, free Wi-Fi, and is close to the Copernicus Centre and Walt Disney House.
Family Apartment W/ Deck + Yard Near Northwestern - Evanston, IL
9.7 124 reviews
Evanston, IL
30/06 – 03/07
SG$415/nighttotal: SG$1245 (3 )

Family Apartment W/ Deck + Yard Near Northwestern

2 2
apartment, Evanston
This apartment is located in Evanston, Illinois, just 8.2 kilometres from Wrigley Field and 17.7 kilometres from Lincoln Park Zoo, making it a convenient base for exploring the city. It has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The property has two bedrooms and can accommodate up to six guests in its 111 square metres of space. Amenities include a fully equipped kitchen, a private deck and yard, air conditioning, free Wi-Fi, and parking, ensuring a comfortable and enjoyable stay.
Newgard Nest | Walk To Loyola L Bright 2nd Fl Apt - Evanston, IL
10 4 reviews
Evanston, IL
01/08 – 08/08
SG$399/nighttotal: SG$2793 (7 )

Newgard Nest | Walk To Loyola L Bright 2nd Fl Apt

1 6
apartment, Chicago
This three-bedroom flat in Chicago's Rogers Park district is situated a short walk from Loyola University, the CTA Red Line, and Lake Michigan's beaches, providing convenient access to city transport and the waterfront.
This residence offers sleeping arrangements for up to eight guests, featuring a fully equipped kitchen, a private three-season sitting room, a shared fenced garden, a dedicated workspace, and a private garage parking spot.
A+amazing Beauty, Entire 2 Br Skokie Historic Stay - Evanston, IL
9.7 95 reviews
Evanston, IL
08/10 – 12/10
SG$274/nighttotal: SG$1096 (4 )

A+amazing Beauty, Entire 2 Br Skokie Historic Stay

2 1
apartment, Skokie
This historic flat is situated in Skokie, a short walk from a range of restaurants, shops and public transport links to Chicago.
The two-bedroom apartment boasts a fully equipped kitchen, a private laundry room, and free Wi-Fi, ideal for couples or solo travellers seeking a comfortable and convenient base in the area.
Spacious Rogers Park Apt Near Beach And Cta - Evanston, IL
9.6 65 reviews
Evanston, IL
28/09 – 26/10
SG$316/nighttotal: SG$8848 (28 )

Spacious Rogers Park Apt Near Beach And Cta

1 2
apartment, Chicago
This Chicago apartment is situated near Marion Mahony Griffin Beach, a short walk (less than 0.16 km) from the Red Line, offering easy access to the city centre.
The one-bedroom flat sleeps four, features a fully equipped kitchen with a Keurig coffee machine and in-building laundry facilities, plus a 65-inch Roku TV and fireplace; free street parking is available (easiest before 4 pm).
Cozy Neighborhood Escape: Near Northwestern-chicago-beaches & More - Evanston, IL
10 49 reviews
Evanston, IL
08/10 – 12/10
SG$799/nighttotal: SG$3196 (4 )

Cozy Neighborhood Escape: Near Northwestern-chicago-beaches & More

1 1
apartment, Evanston
This newly renovated one-bedroom flat is situated in Evanston's arts district, a short walk from local shops, restaurants, the lakefront, Northwestern University, and various large hospitals. It has received excellent reviews from previous guests.
The flat comfortably accommodates up to four guests and includes a fully equipped kitchen, a smart Roku TV, in-unit laundry facilities, free street parking, complementary coffee, and board games. Guests can enjoy a range of amenities and features, including a jacuzzi, a garden, and air conditioning.
Eco-friendly Coach House Near Chicago - Evanston, IL
9.2 20 reviews
Evanston, IL
10/07 – 12/07
SG$381/nighttotal: SG$762 (2 )

Eco-friendly Coach House Near Chicago

1 2
apartment, Wilmette
This charming coach house is located in central Wilmette, just a short walk from the downtown area, the Metro station, and Northwestern University. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The two-level layout offers a separate living space and sleeping area, comfortably accommodating up to three guests. The apartment comes equipped with WiFi, air conditioning, a private backyard, and a dedicated parking space, making your stay both convenient and enjoyable.
Edgewater Glen 3bd Cozy Retreat Sleeps 6 - Evanston, IL
9.7 6 reviews
Evanston, IL
01/08 – 08/08
SG$886/nighttotal: SG$6202 (7 )

Edgewater Glen 3bd Cozy Retreat Sleeps 6

3 6
apartment, Chicago
This three-bedroom flat is located in the Edgewater district of Chicago, offering convenient access to local shops, cafes, and parks within 500 meters.
This accommodation includes a shared garden, in-unit laundry, and exclusive discounts on local luxury experiences as part of TheDreamRentals offer, accommodating up to six guests.
Soft Palate & Warm Bricks At A Rogers Park Home - Evanston, IL
9.8 222 reviews
Evanston, IL
09/09 – 16/09
SG$563/nighttotal: SG$3941 (7 )

Soft Palate & Warm Bricks At A Rogers Park Home

1 5
apartment, Chicago
This apartment is situated in Rogers Park, a lively neighbourhood on Chicago's North Side, within easy walking distance of Lake Michigan, beaches, and both Loyola and Northwestern Universities. The apartment has been rated excellent for location, cleanliness, and user experience.
The apartment is suitable for up to five guests, with two bathrooms and a modern kitchen with stainless steel appliances. It offers a range of features including a terrace, a garden, a spa, free parking, and a keyless entry system.

Best family friendly Evanston, IL holiday rentals

Among the 314 accommodations in Evanston, IL, here are the 4 best family friendly rentals

Aurelien Spacious Apartments In The Heart Of Gold Coast - Evanston, IL
9.7 537 reviews
Evanston, IL
27/06 – 03/07
SG$1288/nighttotal: SG$7728 (6 )

Aurelien Spacious Apartments In The Heart Of Gold Coast

1 2
apartment, Chicago
This two-bedroom apartment is conveniently located in Chicago, just a short walk from Oak Street Beach and a mile from the city centre. It has received excellent ratings for location, cleanliness and user experience.
The apartment comes with a fully equipped kitchen, private bathroom and free Wi-Fi. You can also enjoy a range of amenities including a swimming pool, sauna, fitness centre and parking.
Chic 3br King Bed+work-friendly+ Firepit - Evanston, IL
8.8 3 reviews
Evanston, IL
27/06 – 03/07
SG$685/nighttotal: SG$4110 (6 )

Chic 3br King Bed+work-friendly+ Firepit

3 2
apartment, Chicago
This Chicago apartment, ideal for families, is situated in Irving Park, a 9-minute walk (approximately 0.8 km) from Milwaukee Avenue and a 5-minute drive (approximately 2.4 km) from Portage Park, offering easy access to Grayland train station (15 minutes or approximately 7.2 km away) for exploring the city.
The three-bedroom, one-bathroom property sleeps seven guests and boasts a fully equipped kitchen, private garden with fire pit, in-unit laundry, EV charging, and family-friendly amenities including a high chair, cot, and children's tableware.
Beautiful, Sunny 2nd Floor 3br/1ba W Free Parking - Evanston, IL
9.9 158 reviews
Evanston, IL
09/09 – 16/09
SG$309/nighttotal: SG$2163 (7 )

Beautiful, Sunny 2nd Floor 3br/1ba W Free Parking

1 5
apartment, Chicago
This Lincoln Square flat is situated near the Western Brown Line el station, a 3.2km walk from the Old Town School of Folk Music and 3.2km from Lake Michigan beaches, offering easy access to Wrigley Field (7 el stops away).
The three-bedroom, one-bathroom apartment sleeps six, features a fully equipped kitchen including a dishwasher, free parking, and original woodwork, plus is close to Lincoln Square's restaurants and shops.
Culinary Dream - Pizza Oven/bbq/smoker - Evanston, IL
9.9 81 reviews
Evanston, IL
09/09 – 16/09
SG$772/nighttotal: SG$5404 (7 )

Culinary Dream - Pizza Oven/bbq/smoker

1 5
apartment, Skokie
This Skokie Airbnb, situated in a quiet, safe northern suburb of Chicago, offers easy access to various Skokie attractions; precise distances require a specific address.
The fully renovated house comprises two separate, self-contained units sleeping up to 12 guests, boasting a custom-built cooking station with commercial-grade appliances, a pizza oven, smoker, BBQ, and a 90ft driveway providing ample parking.

Best Evanston, IL holiday rentals with parking

Victorian House In Heart Of Rogers Park - Evanston, IL
10 123 reviews
Evanston, IL
28/09 – 26/10
SG$510/nighttotal: SG$14280 (28 )

Victorian House In Heart Of Rogers Park

1 2
apartment, Chicago
This fully restored Victorian house in a quiet Chicago neighbourhood offers easy access to public transport, restaurants, and beaches.
The three-bedroom property, sleeping six, boasts a fully equipped kitchen, multiple TVs with streaming services, a private garden with a Weber gas grill, and high-end bathroom features including a claw-foot bathtub and rain showers.
Giant 5-bedroom Home W/ Pool Table, 15 Min To Wrigley & Downtown - Evanston, IL
10 1 review
Evanston, IL
10/07 – 12/07
SG$1881/nighttotal: SG$3762 (2 )

Giant 5-bedroom Home W/ Pool Table, 15 Min To Wrigley & Downtown

5 2
apartment, Chicago
This spacious 223 square metre five-bedroom, three-bathroom residence in Chicago's Irving Park district offers a classic early-1900s Craftsman Foursquare design and is a 3.2 to 4 kilometre Uber journey from landmarks including Wrigley Field, the city centre, and Soldier Field.
This family-friendly apartment accommodates up to 14 guests and features a fully-equipped chef's kitchen, a dedicated games room with a pool table and 75" smart TV, high-speed Wi-Fi, air conditioning, and parking, with a check-out time of 10:00 AM.
New 4br Home Near Lake | Northwestern | Parking - Evanston, IL
10 7 reviews
Evanston, IL
10/07 – 12/07
SG$974/nighttotal: SG$1948 (2 )

New 4br Home Near Lake | Northwestern | Parking

4 2
apartment, Evanston
This Evanston townhouse is located in the North Shore district, a 10-minute drive from Northwestern University and a 30-minute drive from downtown Chicago.
This family-friendly residence offers air conditioning, Wi-Fi, a fully equipped kitchen with a dishwasher and microwave, laundry facilities, parking, and can accommodate up to 8 guests across 4 bedrooms.
Retro Disco Cowboy Fun, Walk To Wrigley, Restaurants/bars! 15 Mins To Downtown! - Evanston, IL
9.6 8 reviews
Evanston, IL
01/08 – 08/08
SG$2861/nighttotal: SG$20027 (7 )

Retro Disco Cowboy Fun, Walk To Wrigley, Restaurants/bars! 15 Mins To Downtown!

6 6
apartment, Chicago
This six-bedroom house in Lakeview, Chicago, is located close to Wrigley Field and a short distance from Lake Michigan and Millennium Park.
The property, ideal for large groups, boasts a unique Disco Cowboy theme, six bedrooms, two bathrooms, and amenities including a fridge, microwave, dishwasher, and air conditioning; guests can enjoy nearby Wrigleyville's nightlife, subject to the property's strict quiet hours.

Frequently asked questions about holiday rentals in Evanston, IL

Destinations nearby

Best Evanston, IL holiday rentals with a balcony

Stunning 6 Br Home * Chicago * Centrally Located - Evanston, IL
9.6 177 reviews
Evanston, IL
26/06 – 28/06
SG$1564/nighttotal: SG$3128 (2 )

Stunning 6 Br Home * Chicago * Centrally Located

6 7
apartment, Chicago
This six-bedroom house is located in Albany Park, a family-friendly neighbourhood just 16 kilometres from downtown Chicago, 10 kilometres from Wrigley Field and 10 kilometres from O'Hare Airport. This property has been rated excellent for location, cleanliness and user satisfaction.
The house features large common areas, a chef's kitchen with a five-person island, and spacious bedrooms. This home boasts a fully equipped kitchen, a Jacuzzi, a garden, parking, air conditioning, a laundry room, fast Wi-Fi, Smart TVs, Sonos speakers, Alexa and comfortable bedding.
1 Mi To Metra: Estate W/ Theater, Game Room & More - Evanston, IL
10 1 review
Evanston, IL
27/06 – 03/07
SG$1843/nighttotal: SG$11058 (6 )

1 Mi To Metra: Estate W/ Theater, Game Room & More

4 2
apartment, Northbrook
This Northbrook holiday let is situated 3.2 kilometres from Glen Town Centre, offering convenient access to local shopping plazas, the Northbrook Metra Station for Chicago transit, and attractions such as the Chicago Botanic Garden.
This expansive 864 square metre residence accommodates up to eight guests, featuring four bedrooms, seven bathrooms, a home cinema, a games room with a pool table, a dedicated children's play area, a private home gym, and a large garden with outdoor seating and a fire pit.
Avenir West Loop Penthouses With Iconic City Views - Evanston, IL
9.9 32 reviews
Evanston, IL
27/06 – 03/07
SG$1894/nighttotal: SG$11364 (6 )

Avenir West Loop Penthouses With Iconic City Views

1 2
apartment, Chicago
Cloud9 - 730, a presidential penthouse apartment in Chicago, is situated approximately 2.6 to 3 km from Union Station, Water Tower Place, the Museum of Contemporary Art, and the Shops at Northbridge.
This pet-friendly dwelling boasts a terrace, garden, free parking, and Wi-Fi, offering comfortable accommodation with air conditioning, a seating area, and wardrobe in each unit.
Irving Park Updated Vintage Top Unit 2-flat - Evanston, IL
9.6 55 reviews
Evanston, IL
09/09 – 16/09
SG$289/nighttotal: SG$2023 (7 )

Irving Park Updated Vintage Top Unit 2-flat

2 5
apartment, Chicago
This Chicago apartment rental is situated in the Irving Park/Avondale neighbourhood, approximately 5.5 km from Wrigley Field and 8.5 km from Lincoln Park Zoo.
The 93-square-metre one-bedroom, one-bathroom flat sleeps up to 10 guests and offers free Wi-Fi, air conditioning, parking, and is pet-friendly.

Best Evanston, IL holiday rentals with air conditioning

Charming Home 5 Minutes From Ohare Airport - Evanston, IL
10 2 reviews
Evanston, IL
26/06 – 28/06
SG$1026/nighttotal: SG$2052 (2 )

Charming Home 5 Minutes From Ohare Airport

1 7
apartment, Chicago
This five-bedroom, three-bathroom flat is conveniently situated near O'Hare International Airport, offering a mere 5-minute commute and excellent access to Chicago's major highways and public transport network, making it an ideal base for exploring the city or travelling further afield.
This spacious accommodation comfortably hosts up to 14 guests, featuring air conditioning, a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, and a private 2-car garage, all within easy reach of shopping centres and restaurants.
1br Serene And Cozy Chicago Apartment - Manor 2 - Evanston, IL
8.2 4 reviews
Evanston, IL
10/07 – 12/07
SG$353/nighttotal: SG$706 (2 )

1br Serene And Cozy Chicago Apartment - Manor 2

1 2
apartment, Chicago
This one-bedroom flat in Chicago's Manor 2 district is located 5 kilometres from Wrigley Field and 7.5 kilometres from Loyola University Chicago.
This 67-square-metre apartment accommodates up to three guests and features a kitchen with a fridge and microwave, air conditioning, and complimentary WiFi.
Traveling Man Special Close To Everything - Evanston, IL
Evanston, IL
10/07 – 11/07
SG$400/nightfor 1 night

Traveling Man Special Close To Everything

1 2
apartment, Evanston
This one-bedroom flat in Evanston offers a central location, providing convenient access to Willmett and excellent train connectivity for effortless regional travel.
This apartment accommodates two guests and features air conditioning, a kitchen, and internet, making it an ideal and peaceful base for exploring Evanston and beyond.
3 Beds | 2 Bath | Spacious & Cozy Duplex Apartment - Evanston, IL
9.8 20 reviews
Evanston, IL
01/08 – 08/08
SG$932/nighttotal: SG$6524 (7 )

3 Beds | 2 Bath | Spacious & Cozy Duplex Apartment

1 6
apartment, Chicago
This three-bedroom, two-bathroom duplex apartment in Chicago's Albany Park neighbourhood is ideally located just a block from the Kimball Brown Line station, offering easy access to North Park University, Northeastern Illinois University, Wrigley Field (6.4 km), and downtown Chicago (a 15-minute drive).
The spacious property boasts in-unit laundry, a fully equipped kitchen with dishwasher, parking, central heating and air conditioning, smart home features and sleeps up to six guests, making it perfect for families or groups visiting the city.
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