Best apartment offers in Chicago, IL

13595 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
Chicago, IL apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

13595 Holiday apartments in Chicago, IL

Best family friendly Chicago, IL Holiday Apartments and Self Contained Accommodations

Among the 13595 accommodations in Chicago, IL, here are the 4 best family friendly holiday apartments

Mccormick Place Studio With Optional Parking And Sleeps Up To 4 - Chicago, IL
9.0 1 review

Mccormick Place Studio With Optional Parking And Sleeps Up To 4

studio, Chicago
This McCormick Place studio apartment is conveniently located near Chicago's Museum Campus, approximately 2.3 kilometres from the Field Museum and within 3.2 kilometres of Grant Park and the Art Institute of Chicago.
The 51-square-metre self-catering apartment sleeps up to four guests and features a fully equipped kitchen, fitness centre access, on-site parking, and complimentary Wi-Fi.
Chicago Style Apt/near Hosp/ord/mdw/dt - Chicago, IL
8.4 5 reviews

Chicago Style Apt/near Hosp/ord/mdw/dt

apartment, Berwyn
This Berwyn apartment is situated within 10 kilometres of the Frank Lloyd Wright Home and Studio, Loyola University Medical Center, and Concordia University Chicago, offering easy access to public transport via Berwyn LaVergne and Berwyn stations.
This one-bedroom, one-bathroom flat sleeps four guests and includes free Wi-Fi, a Smart TV, a fully equipped kitchen with oven and microwave, in-unit laundry, and designated parking; nearby parks include Anna and Frederick Douglass Park and Garfield Park.
Walkable Logan! Spa Shower, Dining Destination - Chicago, IL
9.9 500 reviews

Walkable Logan! Spa Shower, Dining Destination

apartment, Chicago
This two-bedroom apartment is situated in the Logan Square district, a short 0.8km walk from the Logan Square Blue Line station, providing easy access to the city centre and O'Hare Airport.
The apartment offers a boutique hotel aesthetic, features a private backyard, and comes equipped with a fully-equipped kitchen, two bathrooms, and a shared laundry facility.
Skyline Views 1br Near * Dunbar Park Lake Meadows - Chicago, IL
No reviews

Skyline Views 1br Near * Dunbar Park Lake Meadows

apartment, Chicago
This Chicago flat offers convenient access to McCormick Place, just a 5-minute drive away, and the city centre, The Loop, within 10-15 minutes, with excellent links to public transport and Lake Shore Drive.
This family-friendly apartment accommodates up to four guests, featuring a fully equipped kitchen, air conditioning, complimentary Wi-Fi, a fitness centre, and secure parking, with a 24/7 virtual concierge service and pet-friendly options available.

Best Chicago, IL holiday apartments with a balcony

Elegant Style Loft Montrose|13 Mins Dt|4 Mins Lake - Chicago, IL
No reviews

Elegant Style Loft Montrose|13 Mins Dt|4 Mins Lake

apartment, Chicago
This one-bedroom flat is situated in Uptown, Chicago, a 4-minute walk from the Lawrence Red Line station, and mere steps from Montrose Beach, Aragon Ballroom, and the Riviera Theatre.
This apartment offers a fully equipped kitchen with quartz countertops, a dedicated workspace, Smart TV, in-unit laundry, and rooftop access with city views, accommodating up to two guests with a queen bed and futon.
Luxury Penthouse Collection Ph1 - Fulton Market - Chicago, IL
No reviews

Luxury Penthouse Collection Ph1 - Fulton Market

apartment, Chicago
This modern penthouse is located in Chicago's Fulton Market district, a 3-kilometre distance from the Art Institute of Chicago and a 2-kilometre distance from the Field Museum of Natural History.
This 111 square metre flat accommodates up to 8 guests with 2 bedrooms, 2 bathrooms, and a pullout sofa, offering a fully equipped kitchen, private parking, and access to a communal rooftop with city views and grilling facilities.
Heart Of Lincoln Park - Chicago, IL
9.4 8 reviews

Heart Of Lincoln Park

apartment, Chicago
This Lincoln Park flat offers a prime Chicago location, within easy walking distance of Lincoln Park itself, North Avenue Beach, and renowned eateries such as Lou Malnati's Pizzeria and Small Cheval.
The two-bedroom, one-bathroom apartment sleeps five, includes in-unit laundry facilities, fast Wi-Fi, and a fully equipped kitchen with a fridge, microwave, and dishwasher; nearby attractions include Lincoln Park Zoo, Wrigley Field, and the United Center.
Little Italy 5br Stay With Optional Parking - Chicago, IL
10 1 review

Little Italy 5br Stay With Optional Parking

apartment, Chicago
This five-bedroom flat in Chicago's Little Italy district is located 13.9 kilometres from Midway International Airport.
Offering space for up to 27 guests, this apartment features five bedrooms, three bathrooms, air conditioning, a kitchen with a fridge, microwave, and dishwasher, and a terrace with city views, with optional paid private parking available.

Frequently asked questions about apartment rentals in Chicago, IL

  • What are the must-see attractions for a 2 days stay in Chicago, IL?

    For a two-day trip, you can't miss the iconic Willis Tower (formerly Sears Tower) for panoramic views of the city. Then, explore Millennium Park, home to Cloud Gate, nicknamed 'The Bean', and the Crown Fountain with its interactive water displays. Finally, stroll along Navy Pier for its Ferris wheel, shops, and restaurants.
  • What are the best apartments in Chicago, IL?

  • Which neighborhoods in Chicago, IL are best for renting an apartment?

    For a vibrant, walkable neighbourhood, consider Lincoln Park with its green spaces and Lake Michigan access. If you prefer a more historic feel, try the Gold Coast, known for its elegant architecture. For a more affordable option with great restaurants and nightlife, check out Wicker Park.
  • What are the best apartments with a pool in Chicago, IL?

  • What are the top cultural and historical sites in Chicago, IL?

    Chicago is brimming with cultural and historical gems. The Art Institute of Chicago houses masterpieces by Monet and Van Gogh, while the Field Museum boasts dinosaur skeletons and ancient Egyptian artefacts. For a taste of history, visit the Chicago Cultural Center, a stunning building with free concerts and exhibitions, or the Museum of Science and Industry.
  • What are the best apartments with a jacuzzi in Chicago, IL?

  • What makes Chicago, IL unique or famous?

    Chicago is known for its stunning architecture, from the towering skyscrapers of the Loop to the charming brownstones of the Gold Coast. It's also a culinary powerhouse, with world-class restaurants and a renowned deep-dish pizza scene. And don't forget the vibrant arts and culture scene, with world-class museums, theatres, and music venues.
  • What are the best apartments for families and kids in Chicago, IL?

  • Where can you find the best local markets and street food in Chicago, IL?

    For a taste of Chicago's diverse food scene, head to Maxwell Street Market on Sundays for a mix of local produce, crafts, and street food. The Wicker Park Farmers Market on Saturdays offers fresh, seasonal produce, while the Green City Market in Lincoln Park has a wide selection of local vendors.
  • What are the best pet friendly apartments in Chicago, IL?

  • How is the public transportation system in Chicago, IL?

    Chicago has a reliable and extensive public transportation system, the 'L', which is a combination of elevated trains and underground subway lines. It's a great way to get around the city, especially during rush hour. You can also use the CTA buses for more local travel.
  • What are the best apartments with parking in Chicago, IL?

  • Which seasonal events or festivals should apartment renters look forward to in Chicago, IL?

    Chicago is a city that comes alive with seasonal events. In the spring, enjoy the Chicago Blues Festival, while summer brings the Taste of Chicago food festival. Autumn is perfect for the Chicago Marathon, and winter offers festive holiday markets and ice skating at Millennium Park.
  • What amenities are typically included in apartments in Chicago, IL?

    Apartments in Chicago typically include central heating and air conditioning, in-building laundry facilities, and sometimes a gym or a rooftop terrace. Some newer buildings may also offer amenities like a swimming pool, a dog park, or a resident lounge.
  • What leisure activities are available for relaxation in Chicago, IL?

    For relaxation, Chicago offers a variety of options. You can stroll along the Lakefront Trail for stunning views of Lake Michigan, visit the Lincoln Park Zoo for a free day out, or take a boat tour on the Chicago River. For a quieter experience, explore the Garfield Park Conservatory, a beautiful greenhouse with exotic plants.

Popular destinations

Best Chicago, IL holiday apartments with parking

Garden Apartment In Historic Pilsen Arts Area - Chicago, IL
9.8 74 reviews

Garden Apartment In Historic Pilsen Arts Area

apartment, Chicago
This Pilsen flat, in Chicago's Mexican heritage neighbourhood, offers convenient access to local taquerias and cultural attractions.
The self-catering apartment features a newly remodelled bathroom, a pull-out sofa accommodating four guests, high-speed Wi-Fi, and a private garden.
Chic Ukrainian Village Home: 4 Bedrooms 2 Bath - Chicago, IL
9.8 139 reviews

Chic Ukrainian Village Home: 4 Bedrooms 2 Bath

apartment, Chicago
This Ukrainian Village flat in Chicago offers easy access to public transport and numerous attractions, including proximity to the city's many museums and parks.
Sleeping up to 10 guests, this self-catering property boasts four bedrooms, two bathrooms, a fully equipped kitchen with modern appliances, in-unit laundry, and ample free street parking.
The Bell House: Apartment #1 - Chicago, IL
10 110 reviews

The Bell House: Apartment #1

apartment, Chicago
This Wicker Park flat, a short walk from the Damen Blue Line station offering easy access to O'Hare International Airport, is situated near Bucktown and numerous restaurants and parks.
The fully renovated two-bedroom apartment, sleeping four guests, boasts a private back deck, shared garden, on-site laundry, and modern amenities including a dedicated workspace, smart TV, and heated bathroom floors.
Welcome To The Wrightwood - Chic & Newly Renovated - Chicago, IL
10 68 reviews

Welcome To The Wrightwood - Chic & Newly Renovated

apartment, Chicago
This Logan Square house, steps from Logan Square's restaurants and bars, offers a prime Chicago location.
The three-story property features two kitchens, four bedrooms sleeping ten, three bathrooms, and a two-car garage; amenities include air conditioning, Wi-Fi, and a garden.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Cabin 105 At 747 Lofts - Chicago, IL
9.1 64 reviews

Cabin 105 At 747 Lofts

apartment, Chicago
This Chicago studio apartment enjoys an excellent location near the Blue Line 'L' train, providing easy access to the city centre and Randolph Street's restaurants in the West Loop.
The self-contained apartment, sleeping two, features a modern kitchen with fridge, microwave, and dishwasher, in-unit laundry, and a spa bath; parking is not guaranteed, but assistance is provided.
Lovely 2-bedroom Apartment In Pilsen - Chicago, IL
9.7 177 reviews

Lovely 2-bedroom Apartment In Pilsen

apartment, Chicago
This two-bedroom apartment is situated in Chicago's Pilsen neighbourhood, a short walk from the Pink Line 'L' train offering easy access to the city centre (approximately 1.6km).
The flat, sleeping up to four guests, boasts a kitchen with fridge, freezer and microwave, air conditioning, a jacuzzi, garden, parking, and is near the Mexican Museum of Art.
Bf - Bright And Cozy 1br Apartment In Logan Square! - Chicago, IL
9.8 290 reviews

Bf - Bright And Cozy 1br Apartment In Logan Square!

apartment, Chicago
This Logan Square flat is conveniently located in Chicago's trendy Logan Square neighbourhood, offering easy access to Chicago's attractions.
The 60-square-metre (646 sq ft) self-catering apartment features one bedroom, one bathroom, sleeps two guests, and includes amenities such as free Wi-Fi, parking, and a fully equipped kitchen.
The Grand Vic: Large 5bd/3ba Home (+Garage) - Chicago, IL
9.9 70 reviews

The Grand Vic: Large 5bd/3ba Home (+Garage)

apartment, Chicago
The Grand Vic, a five-bedroom Chicago house in the North Center neighbourhood, is conveniently located near Lincoln Park Zoo.
This large property sleeps twelve, boasts two kitchens (one themed around early German settlement, the other reflecting later immigrant cultures), a private theatre, a Chicago-style bar lounge, and a formal dining room inspired by the Garfield Park Conservatory and Art Institute, offering foosball and chess for guest entertainment.
©2026 cozycozy.com