This Avondale property, situated 24km from O'Hare International Airport and two blocks from a highway, offers easy access to Chicago's attractions and the neighbourhood's restaurants. Sleeping sixteen guests comfortably across eight bedrooms and six bathrooms, this spacious house boasts two fully equipped kitchens, three gathering areas, a garden, and two garage parking spaces.
9.6 274 reviews
Chicago, IL
24/07 – 27/07
NZ$1794/nighttotal: NZ$5382 (3 )
Cubbies Dream! Half A Block To Wrigley! You Can Feel The Excitement In The Air On Game Days! By Allset Turnover
2 6
apartment , Chicago
This Wrigleyville apartment is situated a mere 0.8 kilometres from Wrigley Field and a short walk from the 'L' train, offering easy access to Chicago's iconic baseball stadium and excellent transport links. The two-bedroom, two-bathroom flat sleeps up to six guests comfortably, features a private deck with pre-game views of Wrigley Field, and includes amenities such as a fully equipped kitchen, Wi-Fi, and pet-friendly options (one pet allowed, additional fee applies).
10 58 reviews
Chicago, IL
18/06 – 20/06
NZ$755/nighttotal: NZ$1510 (2 )
Feelin’ Nauti • 1br + Parking Near Wrigley
1 2
apartment , Chicago
This Chicago apartment, ideally situated in Wrigleyville, is a short 0.97 km walk from the Addison Brown Line 'L' train station and within easy reach of Wrigley Field, Lincoln Park Zoo, and the Southport Corridor. The self-contained ground-floor flat offers one bedroom, one bathroom, and sleeps two guests, boasting a full kitchen with complimentary coffee, free parking, and complimentary access to The Metropolitan co-working space in the Willis Tower.
9.7 7 reviews
Chicago, IL
21/08 – 01/09
NZ$397/nighttotal: NZ$4367 (11 )
The Parkside Perch (Fitness Center • Lounge)
1 2
apartment , Chicago
This one-bedroom flat is located in Chicago's Loop district, offering access to theatres, shops, restaurants, nightlife, parks, and Lake Michigan. This suite accommodates up to four guests and includes a kitchen with a fridge, freezer, microwave, and dishwasher, alongside building amenities such as a swimming pool and fitness centre.
9.0 2 reviews
Chicago, IL
19/06 – 21/06
NZ$1028/nighttotal: NZ$2056 (2 )
Garden 1br Condo W/ Free Parking & Comfy Double Bed
1 2
apartment , Chicago
This one-bedroom flat is situated in Humboldt Park, just an 800-metre walk from the 606 Trail, with easy access to Humboldt Park and Garfield Park, offering a peaceful neighbourhood with a variety of restaurants and cafes. It has consistently received very good ratings from previous guests. The 46 square metre flat can comfortably accommodate up to three guests and includes a well-equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, parking, and internet access. Additional features include a portable sound machine, starter supplies, and a shared parking space in a rear lot.
9.8 48 reviews
Chicago, IL
04/08 – 08/08
NZ$308/nighttotal: NZ$1232 (4 )
Tree-lined Street Near The Lake!
1 2
apartment , Chicago
This Chicago garden flat is located in a tree-lined residential neighbourhood, approximately 0.8km from Lake Michigan beaches and close to public transport, restaurants, and a supermarket. The one-bedroom, one-bathroom apartment sleeps two guests and features a private terrace, garden, full kitchen with dishwasher, and potential use of a pool table; enjoy easy access to local amenities and a tranquil escape from the city centre.
9.6 33 reviews
Chicago, IL
28/06 – 01/07
NZ$320/nighttotal: NZ$960 (3 )
Livn West Loop Chicago Classic Studio Apartment
1 2
studio , Chicago
This stylish loft-style apartment is located in Chicago's West Loop, a short walk from Union Station and the Willis Tower. This family-friendly studio offers a full kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, and an in-unit washer and dryer, accommodating up to two guests.
9.7 169 reviews
Chicago, IL
24/07 – 26/07
NZ$352/nighttotal: NZ$704 (2 )
Charming/cozy Chicago Bungalow Garden Unit 1br/1ba
1 2
apartment , Chicago
This Portage Park garden flat is situated in Chicago's Northwest Side, offering a quiet retreat. The self-contained one-bedroom apartment sleeps four, features in-unit laundry, Netflix, and complimentary on-street parking, plus a private entrance and self check-in.
This five-bedroom apartment is located in the quiet Brighton Park neighbourhood, just a short distance from downtown Chicago, Chinatown, McCormick Place, and major sports stadiums. The apartment is highly rated, receiving excellent reviews for cleanliness and location. The apartment is perfect for large groups, comfortably sleeping up to 16 guests in a range of sleeping arrangements. Guests will enjoy the modern amenities, including a fully equipped kitchen, secure parking, and a large back patio, making it an ideal choice for families or groups of friends.
9.5 363 reviews
Chicago, IL
08/07 – 13/07
NZ$221/nighttotal: NZ$1105 (5 )
Italian Garden Apt/kids Friendly/great Location!!
1 2
apartment , Chicago
This Chicago apartment rental, situated in a family home, offers a self-contained space with convenient on-street parking or nearby parking within 0.16 km. The one-bedroom flat sleeps up to five guests, featuring a queen-size bed, sofa bed, and twin foldaway beds, a kitchenette with microwave and fridge, plus free Wi-Fi and an outdoor play area.
9.3 6 reviews
Chicago, IL
08/07 – 12/07
NZ$360/nighttotal: NZ$1440 (4 )
2br Stay Near Mccormick W/ Kitchen
1 3
apartment , Chicago
This modern two-bedroom flat is located in Chicago's South Loop, offering easy access to McCormick Place (approximately 1.6 kilometres away), Lake Michigan, and downtown Chicago (around 3.2 kilometres by Uber). This apartment accommodates up to six guests and features a fully equipped kitchen, air conditioning, reliable Wi-Fi for remote working, and access to a two-level fitness centre and rooftop deck with grills.
Chicago, IL
01/08 – 31/10
NZ$245/nighttotal: NZ$22295 (91 )
Relax In West Town - In-unit Laundry And Pet Friendly! By Allset Turnover
1 1
apartment , Chicago
This West Town flat, a couple of kilometres from the Loop and Navy Pier, offers easy access to the Blue and Green 'L' lines and is conveniently located near Lake Michigan. The one-bedroom apartment sleeps three, features a terrace, parking, and a kitchen with a fridge, microwave, and dishwasher, and is close to numerous restaurants and shops.
Best family friendly Chicago, IL accommodations
Among the 11918 accommodations in the area, here is the list of the 4 best family friendly ones
9.8 48 reviews
Chicago, IL
09/10 – 13/10
NZ$5543/nighttotal: NZ$22172 (4 )
Unique Luxury Fulton Market Penthouse - Sleeps 32
4 2
apartment , Chicago
This penthouse loft is located in the Fulton Market district of Chicago, just a short walk from the city's bustling nightlife, restaurants, and cultural scene. The apartment has received excellent ratings for its cleanliness, location and user experience. The apartment is spacious and unique, with two side-by-side lofts offering over 7,000 square feet of space. Guests can enjoy a chef's kitchen, a dedicated elevator entrance, nine bedrooms, 7.5 bathrooms, modern design and free onsite garage parking.
9.9 130 reviews
Chicago, IL
12/08 – 15/08
NZ$620/nighttotal: NZ$1860 (3 )
Trendy West Town Flat - 2 Bed / 1.5 Bath W Parking
2 4
apartment , Chicago
This two-bedroom apartment is located in West Town, Chicago, just 4.2 km from Water Tower Chicago and 4.3 km from Union Station, offering easy access to both downtown attractions and the lively West Loop neighbourhood. The apartment has received excellent ratings for its location, cleanliness, and overall user experience. The apartment offers a patio for relaxing and enjoying the Chicago weather. Modern amenities include a well-equipped kitchen with a dishwasher, oven, and microwave, as well as complimentary Wi-Fi, bed linen, towels, and laundry service. On-site parking is also available for guests arriving by car.
Chicago, IL
28/06 – 05/07
NZ$688/nighttotal: NZ$4816 (7 )
Spacious 3br Condo With Skyline Views Near Mccormick Place & Soldier Field
3 5
apartment , Chicago
This three-bedroom Chicago apartment, situated in the Near South Side, is ideally located near McCormick Place convention centre and a short walk from a subway station, offering easy access to the Museum Campus and the city centre. The 88-square-metre (947 square feet) property boasts a spacious layout, comfortably sleeping up to eight guests, and includes amenities such as a fully equipped kitchen, on-site gym, and EV charging stations; nearby attractions include Soldier Field and the Art Institute of Chicago.
9.7 66 reviews
Chicago, IL
21/07 – 01/08
NZ$446/nighttotal: NZ$4906 (11 )
Private Parking, Comfy Bed
1 2
apartment , Berwyn
This Berwyn apartment, ideally located for exploring the area, is an 8-minute walk from local restaurants and amenities, and within a 16-kilometre drive of Oak Park, Little Village, and Chicago's medical district. The one-bedroom flat offers a queen-size bed, sleeps four guests, includes free on-site parking, fast Wi-Fi, a 50-inch smart TV with streaming services, and a fully equipped kitchen; shared laundry facilities are also available.
Best Chicago, IL accommodations with a kitchen
9.4 9 reviews
Chicago, IL
23/07 – 25/07
NZ$802/nighttotal: NZ$1604 (2 )
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
3 6
apartment , Chicago
This spacious three-bedroom apartment, sleeping 8-10, is situated in Brighton Park, Chicago, approximately 5km from Little Italy, Chinatown, and the city centre. The 86 square metre property boasts a fully equipped kitchen, multiple smart TVs, free Wi-Fi, and a shared, fenced backyard, with family-friendly amenities including arcade games and a travel cot.
9.5 2 reviews
Chicago, IL
24/07 – 27/07
NZ$1041/nighttotal: NZ$3123 (3 )
Modern And Bright 2br On Michigan Ave With Optional Parking And Gym Access Near Soldier Field & Grant Park
2 8
apartment , Chicago
This family-friendly Chicago apartment, situated approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of the Art Institute of Chicago and the Chicago Symphony Orchestra, offers convenient access to major cultural attractions. The 84-square-metre property features a spacious two-bedroom, two-bathroom layout sleeping up to eight guests, complete with a fully equipped kitchen, complimentary Wi-Fi, private parking, and a patio offering city views; a fitness centre is optionally available.
9.7 332 reviews
Chicago, IL
19/09 – 22/09
NZ$451/nighttotal: NZ$1353 (3 )
Cozy Lincoln Park Studio - Steps To Zoo!
1 2
apartment , Chicago
This Chicago studio apartment is ideally located in Lincoln Park, a block from Lincoln Park Zoo and within easy reach of Wrigley Field and The Second City. The self-contained apartment sleeps three, features a kitchenette with fridge and microwave, air conditioning, a garden, parking and excellent guest reviews; nearby attractions include numerous restaurants and bars.
9.8 9 reviews
Chicago, IL
22/06 – 24/06
NZ$473/nighttotal: NZ$946 (2 )
Indulging 2br Apartment In Festive Boystown - Buckingham 1
2 2
apartment , Chicago
This Boystown apartment in Chicago is situated near Wrigley Field (a 2.4km walk), Fullerton Beach (2.3km), and within a few kilometres of Lincoln Park Zoo, 360 Chicago, the Water Tower, and the Museum of Contemporary Art. The two-bedroom flat offers self-catering facilities including a dishwasher and washing machine, free Wi-Fi, and sleeps up to four guests, ideal for families or groups exploring Chicago's North Side attractions.
Frequently asked questions about accommodations in Chicago, IL
What are the top attractions and must-see sites in Chicago, IL?
Chicago is packed with iconic sights. You've got to see the Willis Tower (formerly Sears Tower) for amazing city views, stroll along Navy Pier for a classic Chicago experience, and check out Millennium Park, where you'll find the iconic Cloud Gate sculpture, affectionately known as 'The Bean'.
Which cultural festivals and seasonal events should visitors attend in Chicago, IL?
Chicago comes alive with events throughout the year. The Chicago Blues Festival in June is a must for music lovers, while the Taste of Chicago in July is a foodie's paradise. For a festive atmosphere, head to the Christkindlmarket in December, a charming German Christmas market.
What are the best accommodations with a pool in Chicago, IL?
What are the most convenient modes of transportation within Chicago, IL?
The Chicago Transit Authority (CTA) is your best bet for getting around. The 'L' train system is efficient and covers most of the city. For shorter distances, consider the CTA buses, which are also reliable. If you're feeling adventurous, try Divvy, the city's bike-sharing programme.
What are the best accommodations with a jacuzzi in Chicago, IL?
What outdoor activities and adventures are popular in and around Chicago, IL?
Chicago offers plenty of outdoor fun. Lincoln Park Zoo is a great free option for families. For a scenic stroll, head to the Lakefront Trail, which runs along Lake Michigan. If you're looking for a more adventurous experience, rent a kayak or paddleboard and explore the Chicago River.
What are the best accommodations for families and kids in Chicago, IL?
What types of accommodations are available in Chicago, IL?
Chicago has a wide range of accommodation options to suit every budget. From luxury hotels in the Gold Coast to budget-friendly hostels in Wicker Park, you'll find something to fit your needs. For a unique experience, consider staying in a historic hotel like the Palmer House Hilton.
What are the best pet friendly accommodations in Chicago, IL?
The best time to visit Chicago depends on your preferences. Spring and autumn offer mild weather and fewer crowds. Summer is bustling with festivals and outdoor activities, but it can be hot and humid. Winter brings snow and festive events, but temperatures can drop below freezing.
What are the best accommodations with parking in Chicago, IL?
What local dishes and culinary experiences are a must-try in Chicago, IL?
Chicago is a foodie's paradise. Try a deep-dish pizza, a Chicago classic, and don't forget to grab a hot dog from a street vendor. For a more upscale experience, head to one of the city's many Michelin-starred restaurants.
In which part of Chicago, IL should you consider renting accommodation?
The best neighbourhood for you depends on your interests. If you want to be close to the action, consider staying in River North or the Loop. For a more relaxed vibe, try Wicker Park or Lincoln Park. For a taste of history, check out the Gold Coast or the Magnificent Mile.
Destinations nearby
Best Chicago, IL accommodations with a pool
Among the 11918 accommodations in the area, here is the list of the 4 best ones with a pool
9.2 25 reviews
Chicago, IL
01/09 – 31/10
NZ$221/nighttotal: NZ$13260 (60 )
Charming 1 Bdr In Great Location
1 2
apartment , Chicago
This one-bedroom Chicago apartment is ideally situated in the heart of the city, a short walk from Michigan Avenue and a plethora of shops, restaurants, and public transport options. The apartment boasts a modern open kitchen with stainless steel appliances, a comfortable king-size bed, a spacious walk-in closet, and access to a swimming pool, gym, laundry room, and a movie room, making it ideal for a couple's city break.
9.8 72 reviews
Chicago, IL
27/07 – 30/07
NZ$1291/nighttotal: NZ$3873 (3 )
Exclusive 3br With Views, Ideal For Tourists
1 3
apartment , Chicago
This three-bedroom, two-bathroom Chicago Loop apartment offers stunning skyline views and is situated steps from Millennium Park and the Chicago Riverwalk. The 6-guest property boasts a well-equipped kitchen with top-brand appliances, a heated indoor pool, access to a Sky Lounge with fitness facilities, and sound-engineered windows for a peaceful stay; private parking is available at an extra cost.
10 9 reviews
Chicago, IL
01/12 – 03/01
NZ$177/nighttotal: NZ$5841 (33 )
Experience Chicago - Perfect For Work And Leisure
1 1
apartment , Chicago
This luxurious Chicago condo is situated on the Magnificent Mile, offering unparalleled access to high-end shopping and dining, and is within easy reach of public transport. The 32nd-floor apartment boasts a king-sized bed, fully equipped kitchen, and accommodates up to three guests, with a fitness centre, swimming pool, and stunning city views among its amenities.
Chicago, IL
21/08 – 02/10
NZ$566/nighttotal: NZ$23772 (42 )
Amazing Streeterville 2br W/ Gym & Pool, Ohio St Beach, By Blueground
2 1
apartment , Chicago
This Downtown Chicago flat is ideally located less than 1 km from Lincoln Park, Michigan Avenue, and Lake Michigan, with Navy Pier and State Street also within a 2.4 km radius, offering easy access to public transport via nearby Grand and Chicago Red Line stations. The 120 square metre apartment boasts two bedrooms, two bathrooms, and sleeps four, featuring a fully equipped kitchen, in-building amenities including a swimming pool and fitness centre, plus on-site barbecues and optional housekeeping.
Neighborhoods and points of interest in Chicago, IL
Best Chicago, IL accommodations with parking
10 4 reviews
Chicago, IL
30/06 – 31/07
NZ$484/nighttotal: NZ$15004 (31 )
Cozy 2bd 2ba Apt! Steps To Lake With Gym & Parking
1 1
apartment , Chicago
This Edgewater flat offers excellent access to downtown Chicago, Loyola University and the lakefront beaches, situated a short walk from the Granville Red Line station and the lakefront parks and beaches. This two-bedroom flat accommodates four guests with a king and queen-size bed, featuring a fully equipped kitchen, in-unit laundry, air conditioning, and complimentary garage parking, all within an excellent rated property.
9.8 16 reviews
Chicago, IL
14/07 – 18/07
NZ$510/nighttotal: NZ$2040 (4 )
Edgewater Apt With Free Parking, Gym, City Living
1 4
apartment , Chicago
This stylish 2-bedroom, 2-bathroom flat is situated in Chicago's Edgewater district, offering convenient access to local eateries, Lake Michigan's beaches, and the expansive Lincoln Park, all within 3 kilometres of your doorstep. This Edgewater flat provides accommodation for up to 5 guests and includes a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, alongside in-unit laundry, air conditioning, and complimentary parking, with a community fitness centre also available for your use.
10 5 reviews
Chicago, IL
01/08 – 15/08
NZ$283/nighttotal: NZ$3962 (14 )
Modern Condo • Safe Chicago Stay Near O’hare
1 2
apartment , Chicago
This one-bedroom flat is located in a secure district near Rosemont, Rivers Casino, and O'Hare Airport, with the Blue Line providing easy access to central Chicago, approximately 25 kilometres away. This apartment offers a Smart TV, electric fireplace, a fully equipped kitchen with modern appliances, complimentary Wi-Fi, and private parking, accommodating up to four guests and their pets.
9.4 46 reviews
Chicago, IL
08/08 – 15/08
NZ$660/nighttotal: NZ$4620 (7 )
Modern 3br & 2ba Near Mccormick & Downtown
3 2
apartment , Chicago
This Bronzeville apartment in Chicago is conveniently located near Lake Michigan and Grant Park, offering easy access to attractions such as the Field Museum and Museum of Science and Industry. The 167 square metre (1800 square foot) property features a spacious three-bedroom, two-bathroom layout sleeping six, a full kitchen with dishwasher, in-unit laundry, and free on-street parking.
