Chicago Vacation Rentals

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Best Chicago Vacation Rentals

Staying in Chicago vacation rentals provides convenience with proximity to major attractions and affordable options for families. From unique experiences in downtown to urban retreats in diverse neighborhoods, options are plentiful.

8.2

Good

(902 Reviews)

+ 97 photos

The Palmer House Hilton

17 East Monroe Street
Free Wi-Fi in public areas
Baggage storage
Locker room
24-hour reception
24-hour security
Bar/ Lounge area
Restaurant
Welcome drink
Coffee shop
Fitness center
Indoor swimming pool
Massage
Spa & wellness center
Elevator
Business center
Express check-in/ -out
Children's menu
Cribs
Wheelchair access
Pets allowed
Air conditioning
No smoking on site
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The Palmer House Hilton, a remarkable 4-star establishment located just 1 block from Millennium Park, offers elegant accommodations featuring views of the city. It houses 1641 rooms and provides amenities like an on-site fitness center and spa services for guests. Besides, the Lockwood restaurant serves daily American cuisine while the Lobby Bar is perfect for crafted cocktails. Situated near the Monroe Red Line subway station, it allows quick travel to Chicago's attractions, including Navy Pier just 2 miles away.

Price comparison

Average Price 293 US$

8.4

Good

(643 Reviews)

+ 97 photos

The Drake Hotel

140 East Walton Place
Free Wi-Fi in public areas
Baggage storage
24-hour reception
24-hour security
Bar/ Lounge area
Restaurant
Welcome drink
Coffee shop
Fitness center
Jacuzzi
Laundry
Flat-screen TV
Elevator
Business center
Express check-in/ -out
Beach access
Video games
Cribs
Wheelchair access
Pets allowed
Air conditioning
No smoking on site
Show more + Show less -
The Drake Hotel is a prestigious 4-star hotel with scenic views of Lake Michigan, located only 3 minutes from Oak Street Beach. Known for its elegantly designed rooms, it features an afternoon tea service and is just a short distance from Navy Pier, bringing guests closer to local attractions. Each of the 535 rooms comes with deluxe bedding and marble bathrooms. On-site, you can explore shops, enjoy live entertainment, and dine in excellent restaurants like Pelago Ristorante.

Price comparison

Average Price 474 US$

7.8

Good

(1020 Reviews)

+ 97 photos

Hilton Chicago

720 South Michigan Avenue
Free Wi-Fi in public areas
Baggage storage
Locker room
24-hour reception
24-hour security
Bar/ Lounge area
Restaurant
Welcome drink
Snack bar
Coffee shop
Picnic area/ Tables
Fitness center
Sauna
Laundry
Flat-screen TV
Elevator
Business center
Express check-in/ -out
Sun loungers
Children's menu
Cribs
Wheelchair access
Pets allowed
Air conditioning
No smoking on site
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Hilton Chicago, located within walking distance of the culturally rich Millennium Park, features stunning views overlooking Grant Park and Lake Michigan. This hotel offers numerous dining options including the popular 720 South Bar & Grill serving local cuisine. Each of the 1544 rooms comes equipped with modern amenities, and guests can take advantage of leisure facilities including the indoor pool and fitness center.

Price comparison

Average Price 279 US$

8.3

Good

(912 Reviews)

+ 97 photos

Hyatt Regency Mccormick Place Chicago

2233 South Martin Luther King Dr
Wi-Fi
Baggage storage
Locker room
24-hour reception
Bar/ Lounge area
Restaurant
Welcome drink
Snack bar
Coffee shop
Fitness center
Jacuzzi
Sauna
Laundry
Elevator
Business center
Express check-in/ -out
Cycling
Golf course
In-room breakfast
Children's menu
Board games
Wheelchair access
No pets allowed
Air conditioning
No smoking on site
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Hyatt Regency Mccormick Place boasts direct connections to the McCormick Place Convention Center and features spacious rooms with contemporary designs and high-tech amenities such as 42-inch flat-screen TVs. Guests can take advantage of a fitness center, indoor swimming pool, and a variety of business services. The hotel's location allows easy access to attractions like Soldier Field and Navy Pier.

Price comparison

Average Price 252 US$

8.7

Good

(1667 Reviews)

+ 97 photos

Hyatt Regency Chicago

151 East Wacker Drive
Wi-Fi
Baggage storage
24-hour reception
24-hour security
Bar/ Lounge area
Restaurant
Welcome drink
Coffee shop
Fitness center
Laundry
Flat-screen TV
Elevator
Business center
Express check-in/ -out
Children's menu
Cribs
Wheelchair access
No pets allowed
Air conditioning
No smoking on site
Show more + Show less -
Hyatt Regency Chicago is the largest hotel in the city, located just steps from the Magnificent Mile. It offers a variety of on-site dining options including Stetsons Modern Steak + Sushi and Market Chicago, open 24 hours for convenience. Accommodations feature eco-friendly rooms equipped with modern technology, and guests can unwind in the 24-hour fitness center. It's also a short walk from the Art Institute of Chicago and Museum of Science and Industry.

Price comparison

Average Price 346 US$

Not every trip needs a standard hotel room.

Among them: Apartment or Holiday home.

Each suits a different kind of trip.

Chicago Beachfront Rentals

Beachfront rentals in Chicago provide an ideal escape for those looking to enjoy the sun and sand. The proximity to Lake Michigan enhances the recreational experience and offers stunning views.

8.4

Good

(31 Reviews)

+ 97 photos

House 5863- Chicago'S Premier Bed And Breakfast

5863 N Glenwood Avenue
Free Wi-Fi in rooms
24-hour security
Snack bar
Picnic area/ Tables
Flat-screen TV
Adults only
Shared kitchen
Express check-in/ -out
VIP check-in/ -out
Beach access
Board games
No pets allowed
Air conditioning
No smoking on site
Show more + Show less -
House 5863- Chicago's Premier Bed And Breakfast is a charming 4-star Bed and Breakfast located near Foster Beach, just 1.5 miles away. The accommodations feature a variety of private rooms equipped with modern amenities like flat-screen TVs and air conditioning. Guests can enjoy a continental breakfast and relax in the garden or terrace. With Loyola University Chicago located just 1 mile from the property, it's a convenient stay for guests visiting the area.

Price comparison

Average Price 239 US$

9.0

Good

(82 Reviews)

+ 43 photos

The Greenleaf House

1320 West Greenleaf Avenue
Wi-Fi
Off-site parking lot
Baggage storage
Locker room
24-hour security
Picnic area/ Tables
Flat-screen TV
Electric kettle
Shared kitchen
Darts
Cycling
Fishing
Diving
Wind surfing
Golf course
Tennis court
Bowling
Beach access
Sun loungers
Children's play area
Board games
Pets allowed
Air conditioning
No smoking on site
Show more + Show less -
The Greenleaf House offers a beachside stay in Chicago's Rogers Park district, just 0.5 miles from Loyola Beach. Guests can enjoy a laid-back atmosphere with comfortable accommodations and amenities including a tennis court. The property also provides free Wi-Fi and is located near local shops and restaurants.

Price comparison

Average Price 73 US$

Logan Square Vacation Rentals

Staying in Logan Square offers a suburban feel within the city, popular for its vibrant streets filled with art and culture. This area features restaurants and parks.

9.5

Good

(138 Reviews)

+ 97 photos

Ray'S Bucktown Bed And Breakfast

2144 North Leavitt
Wi-Fi
Free parking
Baggage storage
Snack bar
Picnic area/ Tables
Steam room
Spa center
Laundry
Flat-screen TV
Shared kitchen
Business center
Express check-in/ -out
In-room breakfast
Children's play area
Children's menu
Playpen
Cribs
Board games
Wheelchair access
Pets allowed
Air conditioning
No smoking on site
Show more + Show less -
Ray's Bucktown Bed and Breakfast is a welcoming 3-star property located within close proximity to Lincoln Park Zoo and Wrigley Field. This bed and breakfast offers air-conditioned rooms with modern amenities, free Wi-Fi, and private bathrooms. Guests can enjoy a delicious breakfast with various options daily and have access to the garden and a sauna. Located just a few miles from major attractions, it provides easy transport options.

Price comparison

Average Price 154 US$

8.4

Good

(148 Reviews)

+ 97 photos

The Hotel & Athletic Club At Midtown

2444 North Elston Avenue
Wi-Fi
Free parking
24-hour reception
24-hour security
Babysitting/Child services
Seasonal outdoor pool
Indoor swimming pool
Air conditioning
Children's play area
Kids club
Children's menu
Cribs
Sun loungers
Beach umbrellas
Fitness center
Pedicure
Manicure
Jacuzzi
Facial
Waxing
Back massage
Head massage
Full body massage
Beauty treatment
Steam room
Treatment room
Tennis court
Yoga class
Flat-screen TV
Elevator
VIP check-in/ -out
Poolside snack bar
Restaurant
Welcome drink
Snack bar
Coffee shop
Baggage storage
Locker room
No pets allowed
No smoking on site
Show more + Show less -
The Hotel & Athletic Club At Midtown offers a unique experience with full access to the Midtown Athletic Club, featuring indoor and outdoor pools, fitness facilities, and spa services. Located just 2 miles from Wrigley Field and 2 miles from Lincoln Park Zoo, this hotel is ideal for active guests. Each air-conditioned room includes a flat-screen TV and a seating area, providing comfort after a long day of exploration.

Price comparison

Average Price 219 US$

+ 33 photos

Logan Sq 2Br W Roof Gym 1 Block To L Chi-480

2340 N California Ave, Chicago, Il 60647, Usa
Wi-Fi
Dryer
Cookware/ Kitchen utensils
Show more + Show less -
Logan Sq 2BR w Roof Gym 1 Block to L CHI-480 is a fully equipped apartment located close to the California subway station. It features modern décor, a shared lounge, and free Wi-Fi. Each apartment includes a kitchen making it suitable for family stays, and is nearby parks and dining options, providing a comforting experience in the city.

Price comparison

+ 44 photos

Logan Square 2Br W Pool Lounge Gym Nr L Chi-869

2522 N Milwaukee Ave, Chicago, Il 60647, Usa
Wi-Fi
Dryer
Cookware/ Kitchen utensils
Show more + Show less -
Logan Square 2Br W Pool Lounge Gym Nr L Chi-869 is situated about 4 miles from Wrigley Field, featuring stylish decor and amenities. It includes a fully equipped kitchen and easy access to a communal pool and lounge space. The property is close to major transit routes ensuring convenient travel throughout the area.

Price comparison

Vacation Rentals Chicago Lakefront

Lakefront vacation rentals allow guests to immerse in the beauty of Lake Michigan while enjoying modern accommodations close to urban attractions.

8.6

Good

(288 Reviews)

+ 97 photos

Renaissance Chicago Downtown Hotel

1 West Upper Wacker Drive
Free Wi-Fi
Baggage storage
Locker room
24-hour reception
24-hour security
Bar/ Lounge area
Restaurant
Welcome drink
Snack bar
Coffee shop
Fitness center
Indoor swimming pool
Laundry
Flat-screen TV
Elevator
Canoeing
Wheelchair access
Pets allowed
Air conditioning
No smoking on site
Show more + Show less -
Renaissance Chicago Downtown Hotel is conveniently located near the Chicago River. It features a rooftop bar for guests to enjoy cocktails while taking in the scenic views. An indoor heated pool and fitness center are available to ensure a comfortable stay.

Price comparison

Average Price 139 US$

7.3

Good

(1980 Reviews)

+ 97 photos

Best Western Chicago Downtown-River North

125 W Ohio Street
Wi-Fi
Baggage storage
Locker room
24-hour reception
Bar/ Lounge area
Restaurant
Fitness center
Indoor swimming pool
Rooftop pool
Elevator
Sun loungers
No pets allowed
Air conditioning
No smoking on site
Show more + Show less -
Best Western Chicago Downtown-River North is located in vibrant downtown Chicago, just blocks from the Magnificent Mile and offers a rooftop deck with skyline views. It features an indoor pool. On-site dining options include Pizzeria Ora, serving Chicago-style pizza.

Price comparison

Average Price 89 US$

7.6

Good

(1741 Reviews)

+ 97 photos

Best Western Grant Park Hotel

1100 S Michigan Avenue
Free Wi-Fi in rooms
24-hour reception
Restaurant
Welcome drink
Fitness center
Laundry
Elevator
Express check-in/ -out
Cribs
No pets allowed
Air conditioning
No smoking on site
Show more + Show less -
Best Western Grant Park Hotel offers an excellent location directly across from Grant Park, providing easy access to several local attractions. The restaurant offers a mixture of American and Italian cuisine, with room service available for convenience. Each room also comes with complimentary Wi-Fi and essential amenities.

Price comparison

Average Price 86 US$

8.3

Good

(5921 Reviews)

+ 97 photos

Warwick Allerton Chicago

701 N Michigan Ave
Free Wi-Fi in rooms
Baggage storage
24-hour reception
24-hour security
Bar/ Lounge area
Welcome drink
Coffee shop
Fitness center
Laundry
Flat-screen TV
Elevator
Business center
Express check-in/ -out
Cribs
Board games
No pets allowed
Air conditioning
No smoking on site
Show more + Show less -
Warwick Allerton Chicago is located in the heart of downtown, combining historic architecture with modern style. Guests can enjoy on-site dining and experienced service along with banquet facilities for events. The hotel's proximity to Navy Pier and Millennium Park allows for easy exploration of attractions.

Price comparison

Average Price 71 US$

8.1

Good

(650 Reviews)

+ 97 photos

Crowne Plaza - Chicago West Loop By Ihg

25 South Halsted Street
Free Wi-Fi in public areas
Baggage storage
24-hour reception
Bar/ Lounge area
Restaurant
Snack bar
Coffee shop
Fitness center
Flat-screen TV
Elevator
Business center
Express check-in/ -out
VIP check-in/ -out
In-room breakfast
Beach access
Private beach
Children's buffet
Cribs
Pets allowed
Air conditioning
No smoking on site
Show more + Show less -
Crowne Plaza - Chicago West Loop By Ihg Hotel is strategically located adjacent to the United Center. Each guest room is equipped for business or leisure with work desks and coffee-making facilities. Dining options include Dine restaurant serving American cuisine for all meals.

Price comparison

Average Price 99 US$

Vacation Rentals Lincoln Park Chicago

Lincoln Park accommodations provide easy access to diverse dining and recreational spaces, along with a community-oriented atmosphere.

7.8

Good

(889 Reviews)

+ 97 photos

Hotel Versey Chicago Lincoln Park

644 West Diversey Parkway
Wi-Fi
Baggage storage
24-hour reception
Flat-screen TV
Elevator
Cribs
Board games
Wheelchair access
Pets allowed
Air conditioning
No smoking on site
Show more + Show less -
Hotel Versey Chicago Lincoln Park is a boutique hotel just 2 miles from Wrigley Field, providing guests with access to a 50-inch flat-screen TV and a Nespresso coffee machine in every room. With a focus on local culture, it boasts convenient access to fitness facilities nearby and is well-positioned within the Lincoln Park neighborhood, near shops and dining.

Price comparison

Average Price 77 US$

9.2

Good

(35 Reviews)

+ 97 photos

Villa D' Citta

2230 North Halsted Street
Wi-Fi
Baggage storage
Outdoor dining area
Welcome drink
Aerobics
Jacuzzi
Flat-screen TV
Elevator
Cookware/ Kitchen utensils
VIP check-in/ -out
Hiking
Cycling
Golf course
Tennis court
Bowling
In-room breakfast
Children's buffet
No pets allowed
Air conditioning
No smoking on site
Show more + Show less -
Villa D' Citta is a charming 4-star bed and breakfast situated within walking distance of North Avenue Beach and Lincoln Park Zoo. The property features air-conditioned accommodations with unique decor and modern comforts. Enjoy a complimentary continental breakfast, while the garden and hot tub add a touch of relaxation for all guests.

Price comparison

Average Price 228 US$

8.0

Good

(4841 Reviews)

+ 97 photos

Chicago Getaway Hostel

616 West Arlington Place
Laundry
Flat-screen TV
Business center
Tennis court
Game room
24-hour reception
Non-smoking property
Show more + Show less -
Chicago Getaway Hostel situated in Lincoln Park offers an inviting and social environment, ideal for budget-conscious travelers. It features convenient access to transit options for easy exploration of the city. Accommodations vary from shared dorms to private rooms.

Price comparison

Average Price 32 US$

6.6

Good

(477 Reviews)

+ 97 photos

Hotel Lincoln

1816 North Clark Street
Wi-Fi
Baggage storage
24-hour reception
Bar/ Lounge area
Restaurant
Welcome drink
Coffee shop
Picnic area/ Tables
Fitness center
Flat-screen TV
Elevator
Dryer
Business center
Express check-in/ -out
Cycling
Golf course
Children's menu
Cribs
Wheelchair access
Pets allowed
Air conditioning
No smoking on site
Show more + Show less -
Hotel Lincoln, located directly across from Lincoln Park, is just 10 minutes from Lincoln Park Zoo. This boutique hotel features modern updates along with vibrant decor throughout its 193 guestrooms. It offers a rooftop bar to enjoy cocktails while overlooking the park.

Price comparison

Average Price 85 US$

7.8

Good

(13 Reviews)

+ 13 photos

Webster House

402 W. Webster
Wi-Fi
Dryer
Cookware/ Kitchen utensils
Air conditioning
Paid shuttle service
Flat-screen TV
Laundry
VIP check-in/ -out
Cycling
Canoeing
Fishing
Wind surfing
Golf course
Tennis court
Bowling
Squash
Outdoor dining area
Picnic area/ Tables
Beach access
Children's play area
Board games
Baggage storage
Pets allowed
24-hour security
No smoking on site
Show more + Show less -
Webster House provides a peaceful escape situated within walking distance of Lincoln Park Zoo and offers beautiful garden views. It features one-bedroom accommodations complete with self-catering facilities. The property enjoys a location advantageous for access to local beaches and parks.

Price comparison

Average Price 230 US$

Incorporating history and architecture, Chicago has over 200 years of rich heritage, visible in landmarks such as the Art Institute, one of the oldest and largest art museums in the United States. The city's innovative skyline features iconic structures like the Willis Tower, while its vibrant culinary scene is highlighted by famous dishes like deep-dish pizza and Chicago-style hot dogs. The city's diverse atmosphere is complemented by its extensive hotel offerings, with options that cater to business and leisure travelers alike. Proximity to attractions like Millennium Park and the Field Museum ensures visitors have ample opportunity to experience the city's culture. With over 100 hotels in downtown Chicago, top-rated accommodations such as the Palmer House Hilton and The Drake offer modern amenities and easy access to public transport.

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