Chicago, IL Holiday Rentals & Airbnb

9.9 31 reviews

Chicago, IL

4 2

SG$357/nighttotal: SG$1785 (5 )

Great Place In The Heart Of Pilsen

apartment - Chicago

This Pilsen flat is located a short walk from CTA transit and Thalia Hall, placing you within easy reach of numerous restaurants and bars.
This 2-bedroom flat comfortably accommodates up to 6 guests and offers a fully equipped kitchen, air conditioning, a private outdoor area, and a dedicated workspace, with a big-screen TV in the living room for entertainment.

10 135 reviews

Chicago, IL

3 2

SG$212/nighttotal: SG$1060 (5 )

Sunny Cozy Spacious Boho-chic Condo In Bridgeport

apartment - Chicago

This two-bedroom Chicago apartment on Morgan Street, Bridgeport, offers easy walking access to local bakeries, restaurants and breweries.
The 2-bathroom flat sleeps five guests and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and excellent guest reviews.

9.4 17 reviews

Chicago, IL

1 1

SG$672/nightfor 1 night

Livn Millennium Park Downtown Chicago Superior 1br

apartment - Chicago

This studio flat is in Downtown Chicago, 600 metres from Millennium Station and 550 metres from DePaul University, with the city centre 800 metres away.
This non-smoking studio offers 42 square metres of space for up to three guests, featuring air conditioning, free WiFi, and a kitchen equipped with a fridge, microwave, and dishwasher.

10 17 reviews

Chicago, IL

1 1

SG$589/nightfor 1 night

Long Term Rental-1 B Pool House-no Pool Parties!

apartment - River Forest

This River Forest pool house, situated approximately 40km from downtown Chicago, offers convenient access to the city's attractions.
The self-contained property features a queen-size bed, custom sofa bed sleeping up to four guests, a private heated pool (open until October), fully equipped kitchen, luxurious bathroom with Kohler fittings, and private parking; enjoy amenities including a barbecue, fire pits, and basketball court.

Chicago, IL

1 1

SG$294/nighttotal: SG$10290 (35 )

Loop 1br W Gym Pool Nr Financial District Chi-233

apartment - Chicago

This Chicago Loop apartment offers a central location, a short walk (less than 1 km) from the Willis Tower and the CIBC Theatre, with Millennium Park and Millennium Station also nearby.
The 88-square-metre (947 sq ft) one-bedroom flat sleeps three, boasting a fully equipped kitchen with dishwasher, in-unit laundry, free Wi-Fi, and access to an on-site swimming pool and fitness centre.

9.9 223 reviews

Chicago, IL

3 3

SG$408/nighttotal: SG$1632 (4 )

️ Lowest Rates! Fun & Stylish 3br In Logan Square

apartment - Chicago

This three-bedroom Chicago apartment is centrally located, details of proximity to specific landmarks omitted for privacy.
The 135-square-metre flat offers three bedrooms with queen-sized beds and convertible sofas, accommodating up to six guests, and features a fully equipped kitchen, private balcony, free Wi-Fi, and on-street parking; pets are welcome for a fee.

9.8 33 reviews

Chicago, IL

2 2

SG$139/nighttotal: SG$1946 (14 )

Cozy Garden Apartment In Chicago

apartment - Chicago

This two-bedroom flat in Noble Square provides excellent access to Wicker Park, the West Loop, and Downtown Chicago, with the Blue Line and Kennedy Expressway nearby.
This garden apartment accommodates up to four guests and features air conditioning, internet, and a kitchen, situated conveniently close to restaurants, bars, shopping, and parks.

9.9 31 reviews

Chicago, IL

1 3

SG$579/nighttotal: SG$1737 (3 )

Shorter Walk To Wrigley Than A Home Run

apartment - Chicago

This three-bedroom flat in Chicago is situated directly opposite Wrigley Stadium, offering unparalleled access to the iconic venue and the surrounding Wrigleyville entertainment district, with restaurants and bars just a stone's throw away.
This recently refurbished condominium accommodates up to six guests, boasting two bathrooms, in-unit laundry, a fully equipped kitchen, and on-site parking, all within a short walk of numerous theatres and event spaces.

9.4 219 reviews

Chicago, IL

1 1

SG$218/nighttotal: SG$654 (3 )

Entire Place Near United Center With Free Parking!

house - Chicago

This Chicago guest suite is situated near the United Centre, a short distance (approximately 0.8 km) from the West Loop and about 1.3 km from the South Loop.
The compact self-contained apartment, sleeping two guests, features a comfortable bed, a small refrigerator, coffee maker and ADT security system; nearby attractions include the United Centre and the West Loop's restaurants.

9.9 141 reviews

Chicago, IL

2 1

SG$119/nighttotal: SG$714 (6 )

Modern 1-bedroom W/ Off-street Parking Space

apartment - Chicago

This one-bedroom flat is located in the Logan Square neighbourhood, just 1.1 kilometres from both the Belmont and Logan Square Blue line stations, making it easy to explore the city. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The flat is ideal for a group of three and comes with a fully-equipped kitchen including a fridge, freezer, microwave oven, and dishwasher. Guests can enjoy modern amenities such as in-unit laundry, high-speed internet, and air conditioning, as well as a peaceful garden.

9.9 63 reviews

Chicago, IL

3 1

SG$202/nighttotal: SG$2626 (13 )

Talman Ave

apartment - Chicago

This one-bedroom Chicago apartment is located in the Lincoln Square/Ravenswood neighbourhood, a short walk (approximately 0.8 km) from the Rockwell Brown Line 'L' station, offering easy access to the city centre in 25 minutes.
The five-room flat, sleeping two guests, includes a kitchen with fridge, microwave, and dishwasher, plus air conditioning, a garden, parking, and is legally registered (R19000042335).

9.7 126 reviews

Chicago, IL

4 3

SG$894/nighttotal: SG$6258 (7 )

Convenient Hip Launching Pad- Easy Street Parking!

apartment - Chicago

This three-bedroom apartment is ideally located in Chicago's West Town neighbourhood, within easy walking distance of Ukrainian Village and the Brewery District, and a short cycle ride via Divvy bike share to Wicker Park, West Loop, and River North.
The spacious flat sleeps six, boasts a well-equipped kitchen with stainless steel appliances, free Wi-Fi, and a shared laundry; free street parking is also provided.

Best family friendly Chicago, IL holiday rentals

Among the 13982 accommodations in Chicago, IL, here are the 4 best family friendly rentals

9.7 59 reviews

Chicago, IL

2 3

SG$369/nighttotal: SG$2583 (7 )

Albany Park Apartment

apartment - Chicago

This Chicago apartment rental is situated near the North Park campus, a short walk from the Brown Line providing direct access to Chicago's city centre.
The two-bedroom, one-bathroom flat sleeps six, features a fully equipped kitchen with washer/dryer, private parking, and a garden, plus is within 3.2km of over 100 restaurants and parks.

9.6 703 reviews

Chicago, IL

9 4

SG$1440/nighttotal: SG$2880 (2 )

4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome

house - Chicago

This four-bedroom holiday home is located in Chicago's Old Town district, just a short walk from Oak Street Beach and Lincoln Park Zoo, offering easy access to the city's attractions and restaurants. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The house is spacious and comfortable, accommodating larger groups with ease. Guests can enjoy a range of amenities, including a fully equipped kitchen, a patio, a garden, a spa, a fitness centre, and a tennis court.

9.0 28 reviews

Chicago, IL

2 2

SG$310/nighttotal: SG$2170 (7 )

Modern, 2-bedroom Apt., 15 Minute Drive To Lake Michigan, Free Parking Spot.

apartment - Chicago

This two-bedroom Chicago apartment rental is situated in the West Ridge neighbourhood, offering convenient access to Lake Michigan and Millennium Park, although precise distances aren't specified.
The family-friendly flat, sleeping four, includes a fully equipped kitchen, designated workspace with high-speed internet, private parking, and on-site host support; nearby attractions include the Field Museum and Wrigley Field.

9.9 59 reviews

Chicago, IL

2 2

SG$410/nighttotal: SG$820 (2 )

Heart Of Lincoln Park

apartment - Chicago

This Lincoln Park flat offers excellent access to North Avenue Beach and Lincoln Park Zoo, both within easy walking distance.
The two-bedroom apartment sleeps five, includes a fully equipped kitchen with dishwasher, in-unit laundry, and fast Wi-Fi, plus parking is available.

Best Chicago, IL holiday rentals with parking

9.7 88 reviews

Chicago, IL

3 3

SG$1085/nighttotal: SG$4340 (4 )

Mccormick Apt 3br Corner Oasis Near Soldier Field

apartment - Chicago

This three-bedroom, two-bathroom Chicago apartment is superbly located in the South Loop, a 0.8 km walk from McCormick Place and a short taxi ride from Soldier Field and the Museum Campus.
Sleeping up to eight guests comfortably, this spacious flat boasts a fully equipped kitchen, in-unit laundry, 4K smart TVs, access to a building gym and EV charging stations, plus optional parking for £24 per day.

9.6 1411 reviews

Chicago, IL

4 2

SG$181/nighttotal: SG$2534 (14 )

Kasa | Walk To Lincoln Park Zoo | Chicago

apartment - Chicago

This two-bedroom, two-bathroom Chicago apartment enjoys a prime downtown location, just south of the Magnificent Mile and steps from Oak Street Beach, offering easy access to Millennium Park and Michigan Avenue.
The 5-guest property boasts a full kitchen with modern appliances, in-unit laundry, and pet-friendly accommodation (fees apply), alongside access to a fitness centre and garden within the building.

10 6 reviews

Chicago, IL

2 1

SG$115/nighttotal: SG$805 (7 )

Horner Park Coach House

house - Chicago

This private coach house is located in Chicago's Horner Park district, offering straightforward access to public transport for journeys to the city centre or the airport, and is within 800 meters of local shops and restaurants.
This one-bedroom accommodation sleeps up to four guests and includes a kitchen with a fridge, air conditioning, and off-street parking, making it suitable for those seeking a quiet base with convenient amenities.

8.4 20 reviews

Chicago, IL

3 1

SG$500/nighttotal: SG$1500 (3 )

Bridgeport Place - Free Parking, Mccormick Place-sox Park

apartment - Chicago

This Bridgeport flat is conveniently located near McCormick Place and Guaranteed Rate Field (2.9km), offering easy access to Union Station (6.1km) and other Chicago attractions.
The 60 square metre one-bedroom apartment sleeps seven, features a fully equipped kitchen, private patio with BBQ, and free on-site parking – a rarity in Chicago.

Frequently asked questions about holiday rentals in Chicago, IL

What should a first-time visitor not miss in Chicago, IL?
You definitely shouldn't miss the iconic Willis Tower, formerly known as the Sears Tower, for panoramic views of the city. A visit to Millennium Park is a must, with the Cloud Gate sculpture, known as 'The Bean', and Crown Fountain. And no trip to Chicago is complete without experiencing the vibrant nightlife and diverse cuisine in the city's many neighbourhoods.
What are the best Airbnb and vacation rentals in Chicago, IL?
2bd/2ba Mag Mile Masterpiece (+Rooftop), Kasa | Walk To Lincoln Park Zoo | Chicago and Charming Chicago-style - Vintage - Tv Nfl Pass are the most popular Airbnb and vacation rentals in Chicago, IL among travelers.
What kind of vacation rentals can you find in Chicago?
There's a wide range of vacation rental choices in Chicago to choose from, from houses to downtown apartments and penthouses.
Which neighborhood in Chicago, IL should you consider for a vacation rental?
For a vibrant, bustling experience, consider staying in the trendy Wicker Park or Bucktown neighbourhoods. If you prefer a more relaxed atmosphere, Lincoln Park or Lakeview offer a mix of residential streets and green spaces. And if you're looking for a historic setting, the Gold Coast or River North are great options.
What are the most popular Airbnbs in Chicago, IL?
Among the Airbnbs in Chicago, IL, Beautiful Corner 2 Bedroom In The Loop | Roof Deck, Kasa | Walk To Lincoln Park Zoo | Chicago and Downtown Mich Ave #20 - Grant Park - Museums 2bd/2ba are the most popular ones.
What's the best one-day itinerary for Chicago?
Kick things off Ferris Bueller style at the Art Institute of Chicago for some culture before heading over to "The Bean" at Millennium Park, making sure you leave the park via the BP Bridge, which will give you stunning views of the city's skyline. On the corner of Michigan Avenue and Randolph street, make sure you check out the Chicago Cultural Center for the stunning interior alone (the largest Tiffany stained-glass dome in the world is so worth it!). Cross through Grant Park and visit the Buckingham Fountain before heading south to the amazing Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium. Head up the Skydeck at Willis Tower (one of the world's tallest buildings) and if you dare, step on the ledge. Head over to the Chicago Riverwalk to find something to eat before hitting one of the famous jazz and blues clubs.
What are the top family-friendly attractions in Chicago, IL?
The Lincoln Park Zoo is a fantastic free attraction with a variety of animals and exhibits. The Shedd Aquarium is a great place to learn about marine life, and the Field Museum offers fascinating exhibits on dinosaurs and other natural history subjects. For a fun day out, consider visiting the Museum of Science and Industry or the Art Institute of Chicago.
What are the best vacation rentals with a pool in Chicago, IL?
Beautiful Corner 2 Bedroom In The Loop | Roof Deck, Amazing Location | Luxury Apt | Rooftop Pool and Whole Flat In Private Club - Walk To L - Dining & Shows are the best vacation rentals with a pool in Chicago, IL.
Where should you book a vacation rental in Chicago?
It really depends on what you want. If you're want to be in the heart of the action, or it's your first visit to the Windy City, then book an apartment or a studio in the Chicago Loop downtown. However, some of the most popular places to book are Lincoln Park and Hyde Park when it comes to vacation rentals.
When is the best time to book a vacation rental in Chicago, IL?
The best time to book a vacation rental is during the shoulder seasons, in spring (April-May) or autumn (September-October), when the weather is pleasant, and the crowds are smaller. However, if you prefer a festive atmosphere, you can book during the summer, when the city hosts various festivals and events.
What are the best rentals for families and kids in Chicago, IL?
The best rentals for families and kids in Chicago, IL are 2bd/2ba Mag Mile Masterpiece (+Rooftop), Downtown Penthouse #2 Vintage 3bd/1ba Family-friendly - Grant Park & Museums and Urban Chicago Loft - 1 Blk To Train W/ 2 Pkg Spots.
What are Chicago's special dishes you should try?
You can't come to Chicago without trying some deep-dish pizza, a Chicago icon. However, there's plenty else to chow down on. Chicago had a large Italian community, so you can try some great Italian-American dishes. If you want something quick to go, grab a spicy Italian beef sandwich from a local street food joint.
What events or festivals should visitors check out in and around Chicago, IL?
Chicago is known for its vibrant festival scene. The Taste of Chicago in July is a great food festival, and the Chicago Blues Festival in June is a must for music lovers. The Lollapalooza music festival in August attracts thousands of music fans, and the Chicago Air and Water Show in August is a spectacular event.
What are the best rentals or Airbnbs with a jacuzzi in Chicago, IL?
The best vacation rentals or Airbnb with a jacuzzi in Chicago, IL are The Neighborhood Hotel Lincoln Park, 4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome and Lincoln Park Single Family Home (4bdrm 3 -5 Bth)-2 Car Garage 4200sqft Sleeps 24.
What is sites are there to see in Chicago?
There's plenty to keep you on your feet on your next trip to Chicago. If you're an art lover, make sure you pay a visit to the Art Institute of Chicago, which is home to more than 300,000 artworks! But if you want a view that's more than paintings, then get yourself to the top of 360 Chicago for panoramas over the city from this 1000-ft-high observation deck. Millennium Park with its futuristic-looking Cloud Gate (AKA the Bean), is great place to explore. And that's just to get you started!
What are the best budget-friendly activities in Chicago, IL?
Take a stroll along the scenic Lakefront Trail, offering stunning views of Lake Michigan. Explore the free exhibits at the Art Institute of Chicago or the Field Museum. Enjoy a picnic lunch in Millennium Park, surrounded by beautiful architecture and public art. And don't forget to check out the free concerts and events happening in various parks and public spaces throughout the city.
What are the best restaurants with local dishes in Chicago, IL?
For a taste of Chicago's iconic deep-dish pizza, head to Lou Malnati's or Pizzeria Bebu. For a classic Chicago hot dog, try Portillo's or The Wiener's Circle. And if you're looking for a more upscale dining experience, Alinea or Next offer innovative and inventive cuisine.
What are the best walking or cycling routes in Chicago, IL?
The Lakefront Trail offers a scenic 18.5-mile path along the shores of Lake Michigan, perfect for walking, running, or cycling. For a more urban experience, explore the Magnificent Mile, a stretch of Michigan Avenue lined with luxury shops and skyscrapers. And for a unique perspective on the city, consider a bike tour through the various neighbourhoods.
Are there pet-friendly attractions in Chicago, IL?
Yes, many attractions in Chicago are pet-friendly. The Lincoln Park Zoo welcomes well-behaved dogs on leash, and the Millennium Park offers designated dog-friendly areas. Many restaurants also have outdoor patios where you can enjoy a meal with your furry friend.
What are the benefits of choosing a vacation rental in Chicago, IL?
Vacation rentals provide more space and privacy than a hotel room, often with a kitchen and laundry facilities. They can also be more affordable, especially for families or groups. And many offer unique locations and charming character, allowing you to experience the city like a local.

Popular destinations

Best Chicago, IL holiday rentals with a balcony

9.4 35 reviews

Chicago, IL

4 2

SG$684/nighttotal: SG$5472 (8 )

Downtown Penthouse - Mich Ave 2bd | +Gym & Views

apartment - Chicago

This penthouse flat is located on Michigan Avenue in Downtown Chicago, just a short walk from Grant Park and Lake Michigan, offering stunning views and easy access to the city's top attractions. The accommodation has received excellent ratings from previous guests.
The flat has two bedrooms and two bathrooms, covering 74 square metres, and can comfortably accommodate up to six guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private laundry, a rooftop deck with panoramic city views, and a fitness centre.

Chicago, IL

8 1

SG$687/nighttotal: SG$2061 (3 )

Fully Equipped 2br Apartment In South Loop With Optional Parking And Gym Access Near Mccormick Place

apartment - Chicago

Vacation rental listing. This accommodation is located in Chicago.
Facilities and services: an elevator, a terrace and a fitness center. Take advantage of the air conditioning in this apartment in Chicago.

9.0 10 reviews

Chicago, IL

9 3

SG$2739/nighttotal: SG$10956 (4 )

Luxury Loft Collection 03 - Terrace - River North

apartment - Chicago

This luxurious River North loft is centrally located in Chicago, offering easy access to Millennium Park and Lake Michigan, both within a few kilometres.
The 223 square metre (2,400 square foot) property boasts three bedrooms, three bathrooms, sleeps fourteen, and includes a private elevator, terrace with cityscape views, secured parking, and a chef's kitchen equipped with Gaggenau appliances.

Chicago, IL

1 1

SG$224/nighttotal: SG$20160 (90 )

Landing | Modern 1bd, Gym, Pool

apartment - Chicago

This Near West Side flat offers convenient access to Millennium Park and Grant Park, situated within easy reach of the Art Institute of Chicago and the Chicago Theatre.
This fully furnished 59 square metre apartment, accommodating two guests, features a dedicated workspace, in-unit laundry, and a well-equipped kitchen, with an on-site fitness centre and 24-hour concierge service enhancing your stay.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

9.6 31 reviews

Chicago, IL

2 1

SG$244/nighttotal: SG$5124 (21 )

The King's Corner | Ground Level | Train Access

apartment - Oak Park

This one-bedroom flat is located a few hundred metres from Historic Downtown Oak Park, providing easy access to its significant landmarks.
This well-appointed residence accommodates two guests and features a king-size bed, a fully equipped kitchen with a microwave and fridge, air conditioning, and complimentary WiFi, with weekly and monthly discounts available.

10 41 reviews

Chicago, IL

4 3

SG$404/nighttotal: SG$808 (2 )

Vibrant 3br Pilsen Stayfree Parkingnear Downtown

apartment - Chicago

This flat is in Chicago's Lower West Side, a short walk from 18th Street and approximately 5 kilometres from Downtown Chicago's Grant Park and Millennium Park.
This 79 square metre residence offers three bedrooms accommodating up to five guests, featuring a full kitchen, air conditioning, complimentary garage parking for one vehicle, and is equipped with 24/7 security cameras.

9.4 39 reviews

Chicago, IL

2 2

SG$301/nighttotal: SG$2107 (7 )

Classy Apt/comfy Beds/25mins To Ord>mdw>dt>hosp

apartment - Berwyn

This two-bedroom flat is situated in Berwyn, just a short drive from the Chicago Zoo, Oak Park, and Little Village, making it a great base for exploring the area. The property has an excellent user rating, so you can be sure of a comfortable stay.
The flat is ideal for families or groups of up to six people. It comes equipped with a kitchen, air conditioning, and a spa, as well as free parking and fast Wi-Fi. You can enjoy easy access to local amenities, including restaurants, public transport, and gambling slots, as well as attractions like Wrigley Field and McCormick Place.

9.9 223 reviews

Chicago, IL

3 2

SG$1073/nighttotal: SG$4292 (4 )

Top Floor Corner Unit With Beautiful Natural Light

apartment - Chicago

This top-floor apartment is situated in Chicago's Arlington-Deming neighbourhood, a short walk from Lincoln Park and its attractions.
The two-bedroom, two-bathroom condo, sleeping up to five guests, boasts a spacious open-plan kitchen, living and dining area with a Juliette balcony offering Lincoln Park and city views; amenities include a dishwasher, coffee maker and Keurig machine, plus free daily parking.

Holiday Rentals in Chicago, IL

Best Holiday rentals and Airbnb offers in Chicago, IL

Great Place In The Heart Of Pilsen

Sunny Cozy Spacious Boho-chic Condo In Bridgeport

Livn Millennium Park Downtown Chicago Superior 1br

Long Term Rental-1 B Pool House-no Pool Parties!

Loop 1br W Gym Pool Nr Financial District Chi-233

️ Lowest Rates! Fun & Stylish 3br In Logan Square

Cozy Garden Apartment In Chicago

Shorter Walk To Wrigley Than A Home Run

Entire Place Near United Center With Free Parking!

Modern 1-bedroom W/ Off-street Parking Space

Talman Ave

Convenient Hip Launching Pad- Easy Street Parking!

Best family friendly Chicago, IL holiday rentals

Albany Park Apartment

4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome

Modern, 2-bedroom Apt., 15 Minute Drive To Lake Michigan, Free Parking Spot.

Heart Of Lincoln Park

Best Chicago, IL holiday rentals with parking

Mccormick Apt 3br Corner Oasis Near Soldier Field

Kasa | Walk To Lincoln Park Zoo | Chicago

Horner Park Coach House

Bridgeport Place - Free Parking, Mccormick Place-sox Park

Frequently asked questions about holiday rentals in Chicago, IL

Popular destinations

Best Chicago, IL holiday rentals with a balcony

Downtown Penthouse - Mich Ave 2bd | +Gym & Views

Fully Equipped 2br Apartment In South Loop With Optional Parking And Gym Access Near Mccormick Place

Luxury Loft Collection 03 - Terrace - River North

Landing | Modern 1bd, Gym, Pool

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

The King's Corner | Ground Level | Train Access

Vibrant 3br Pilsen Stayfree Parkingnear Downtown

Classy Apt/comfy Beds/25mins To Ord>mdw>dt>hosp

Top Floor Corner Unit With Beautiful Natural Light