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Chicago, IL place to stay
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16282 Lodgings in Chicago, IL

Best family friendly Chicago, IL lodging

Among the 16282 accommodations in Chicago, IL, here are the 4 best for families

2 Bed Apt W/ Office, Free Parking, Near Wrigley - Chicago, IL
9.5 140 reviews

2 Bed Apt W/ Office, Free Parking, Near Wrigley

apartment, Chicago
This two-bedroom Chicago apartment is situated near Wrigleyville, a 15-minute walk from Wrigley Field, and within a 4.8-8 km radius of Lincoln Park Zoo, Water Tower Place, and the United Centre.
The 111 square metre flat offers a fully equipped kitchen, free parking, and amenities including a fireplace and patio, sleeping up to four guests comfortably.
3 Bed 2 Bath Private Fully Furnished Apartment - Chicago, IL
9.6 22 reviews

3 Bed 2 Bath Private Fully Furnished Apartment

apartment, Chicago
This Roscoe Village flat, near the intersection of Hamilton and Addison Streets in Chicago, offers easy access to local shops and restaurants.
The one-bedroom, one-bathroom apartment sleeps eight, features a fully equipped kitchen with dishwasher and in-unit laundry, and benefits from air conditioning and parking.
Lavish Home @ The Belle In Chicago's West Town - Chicago, IL
10 73 reviews

Lavish Home @ The Belle In Chicago's West Town

house, Chicago
This Chicago townhouse, ideally located near the Blue Line, offers easy access to downtown, Fulton Market, Lincoln Park, and Wicker Park.
Sleeping up to 10 guests, the three-bedroom, two-and-a-half-bathroom property boasts a private balcony, patio, attached garage, and fully equipped kitchen including a dishwasher, fridge and freezer, making it perfect for family groups.
Luxury 3br Spacious Suite Sleeps 8 Guests With Patio, Skyline View, Optional Parking And Gym Access Near Mccormick Place And Lakefront - Chicago, IL
9.5 151 reviews

Luxury 3br Spacious Suite Sleeps 8 Guests With Patio, Skyline View, Optional Parking And Gym Access Near Mccormick Place And Lakefront

apartment, Chicago
This apartment is located just 2.4 kilometres from the Field Museum of Natural History, within walking distance of the Art Institute of Chicago and the Chicago Symphony Orchestra, offering easy access to the city's cultural highlights. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment has three bedrooms and two bathrooms, covering 88 square metres, and comfortably accommodates a large group of travellers. It includes a fully equipped kitchen, a terrace with city views, a fitness centre, parking, and an electric vehicle charging station, ensuring a comfortable and convenient stay.

Best Chicago, IL accommodations with a kitchen

Modern Chicago 2br Apartment With Skyline View, Optional Parking & Gym Access Near Mccormick, Museum Campus, Grant Park & Soldier Field - Chicago, IL
9.0 3 reviews

Modern Chicago 2br Apartment With Skyline View, Optional Parking & Gym Access Near Mccormick, Museum Campus, Grant Park & Soldier Field

apartment, Chicago
This McCormick district flat is conveniently located 2.3 km from the Field Museum, 2.7 km from Grant Park, and 2.9 km from the Art Institute of Chicago.
This two-bedroom, two-bathroom Chicago apartment offers 79 square metres of living space, sleeping up to eight guests and boasting a private patio with skyline views, plus access to a fitness centre, parking, and complimentary Wi-Fi.
Quirky Designer Apartment - Steps From Wrigley! - Chicago, IL
9.9 271 reviews

Quirky Designer Apartment - Steps From Wrigley!

apartment, Chicago
This Chicago apartment is located in a peaceful residential area near Wrigleyville, within easy walking distance of the Southport Corridor and a short journey (approximately 1.6km) from Wrigley Field.
The one-bedroom, one-bathroom flat sleeps three guests and offers amenities including air conditioning, free parking (using a pay-by-app system or SpotHero), and free membership to The Metropolitan co-working space in the Willis Tower; it also boasts excellent access to the Brown and Red Line subways.
Newly Rehabbed! 2br With Vintage Charm - Chicago, IL
9.7 330 reviews

Newly Rehabbed! 2br With Vintage Charm

apartment, Chicago
This two-bedroom flat is situated in Ravenswood, a lively northside neighbourhood in Chicago, just a short journey from the city centre by public transport. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The flat comfortably accommodates up to five guests, making it ideal for families or groups of friends. The well-equipped kitchen, along with the laundry facilities and other amenities, offer everything you need for a relaxing and stress-free stay.
Quiet Pilsen Sunlit Apt W/d Queen Near Downtown - Chicago, IL
9.9 57 reviews

Quiet Pilsen Sunlit Apt W/d Queen Near Downtown

apartment, Chicago
This Pilsen flat is conveniently located in Chicago's Mexican-American cultural heartland, within a 24km drive of the city centre.
The one-bedroom apartment, sleeping up to four guests with a queen-size air mattress, offers keyless entry, in-unit laundry, and a fully equipped kitchen; a shared yard provides additional outdoor space.

Frequently asked questions about accommodations in Chicago, IL

  • What are the top attractions and must-see sites in Chicago, IL?

    You can't miss the iconic Willis Tower, formerly known as Sears Tower, offering breathtaking views of the city. The Art Institute of Chicago houses a world-class collection of art, including masterpieces by Monet and Van Gogh. And of course, no trip to Chicago is complete without a stroll along the Magnificent Mile, a vibrant shopping and dining destination.
  • Which cultural festivals and seasonal events should visitors attend in Chicago, IL?

    Chicago is known for its lively festivals, especially during the summer months. The Taste of Chicago, held in Grant Park, is a must-visit for foodies. If you're there in August, check out the Lollapalooza music festival, a major event attracting international artists. And for a truly unique experience, try the Chicago Blues Festival, celebrating the city's rich musical heritage.
  • What are the most convenient modes of transportation within Chicago, IL?

    Chicago's public transport system is excellent, with the 'L' train, a network of elevated and underground lines, being the most convenient way to get around. You can also hop on a bus, which covers a wider area. For shorter distances, consider walking or biking, especially around the downtown area and along the lakefront.
  • What outdoor activities and adventures are popular in and around Chicago, IL?

    Chicago has a beautiful lakefront, perfect for walking, jogging, and cycling along the Lakefront Trail. You can also rent a kayak or paddleboat and explore the waters of Lake Michigan. For a more adventurous experience, head to Lincoln Park Zoo, home to a variety of animals, or visit the Morton Arboretum, a sprawling botanical garden with stunning landscapes.
  • What types of accommodations are available in Chicago, IL?

    Chicago offers a wide range of accommodation options to suit every budget and preference. You can find luxurious hotels in the downtown area, like the Peninsula Chicago, as well as budget-friendly hostels and guesthouses in neighbourhoods like Wicker Park and Logan Square. For a unique experience, consider staying in a historic building or a chic boutique hotel.
  • When is the best time to visit Chicago, IL?

    The best time to visit Chicago is during the shoulder seasons, spring (April-May) and autumn (September-October), when the weather is pleasant and the crowds are smaller. You can enjoy the city's outdoor attractions without the summer heat and humidity. If you're a fan of winter festivities, December and January offer a magical experience with the city's Christmas markets and ice skating rinks.
  • What local dishes and culinary experiences are a must-try in Chicago, IL?

    Chicago is a foodie's paradise, with a diverse culinary scene. You must try a Chicago-style deep-dish pizza, with its thick crust and generous toppings. Also, don't miss the city's famous hot dogs, served on a poppy seed bun with a variety of toppings. For a sweet treat, indulge in a Chicago-style Italian beef sandwich or a slice of deep-fried cheesecake.
  • In which part of Chicago, IL should you consider renting accommodation?

    For easy access to the city's main attractions, consider staying in the downtown area, near the Magnificent Mile and Millennium Park. If you prefer a more local experience, explore neighbourhoods like Wicker Park, known for its trendy shops and restaurants, or Lincoln Park, with its beautiful park and diverse dining options.

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Best Chicago, IL lodging with a pool

Among the 16282 accommodations in Chicago, IL, here are the 4 best ones with a pool

Designer 3br With Resort Amenities And Balcony - Chicago, IL
10 18 reviews

Designer 3br With Resort Amenities And Balcony

apartment, Chicago
This three-bedroom flat is situated in central Chicago, offering excellent access to public transport and entertainment, with the Museum of Contemporary Art a mere 5-minute walk away and the Magnificent Mile 10 minutes away.
This property boasts a fully equipped kitchen, a private balcony with a pool view, and access to communal facilities including a heated lap pool, hot tub, outdoor kitchen, and a rooftop sky club, accommodating up to eight guests.
Prime Loop Apts + Convenience For Groups - Chicago, IL
9.8 367 reviews

Prime Loop Apts + Convenience For Groups

apartment, Chicago
This apartment is situated in Chicago's Financial District, a short walk from Millennium Park and the Chicago River, placing you in the heart of the city's bustling energy. The apartment enjoys excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The apartment spans 115 square metres and features a stylish interior with high-end finishes. You'll have access to a range of amenities including a swimming pool, fitness centre, and a garden, making it easy to relax and enjoy your time in the city.
Stylish 2br With Skyline Views Near Riverwalk - Chicago, IL
10 1 review

Stylish 2br With Skyline Views Near Riverwalk

apartment, Chicago
This two-bedroom, two-bathroom Chicago apartment enjoys a prime downtown location, less than 1km from the Merchandise Mart, State Street, the Chicago Theatre, and the Willis Tower, with easy access to Clark-Lake and Washington-Wells public transport stations.
The self-catering flat offers a fully equipped kitchen, in-unit laundry facilities, a private balcony, an indoor swimming pool, a fitness centre, and sleeps up to four guests, perfect for exploring Chicago's attractions.
Ideal For Groups: Spacious 2br In The Loop - Chicago, IL
No reviews

Ideal For Groups: Spacious 2br In The Loop

apartment, Chicago
This six-bedroom, four-bathroom flat in Chicago's Loop district offers prime positioning, being a mere 400 metres from Millennium Park and 640 metres from the Chicago Theatre, with breathtaking city views from its top-floor setting.
This family-friendly residence accommodates up to 12 guests, featuring a fully equipped chef's kitchen with complimentary Nespresso and tea, high-tech entertainment systems, and access to building amenities including an indoor-outdoor swimming pool, gym, and social room with games and fire pits, with on-site parking available for £40 per night.

Best Chicago, IL accommodations with parking

Spacious & New Industrial Condo Close To Downtown - Chicago, IL
9.8 293 reviews

Spacious & New Industrial Condo Close To Downtown

apartment, Chicago
This West Town/Noble Square flat is centrally located in Chicago, a short distance from the city centre and close to Grand Avenue, offering easy access to local amenities.
Sleeping six guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, garden access, and excellent guest reviews; modern amenities ensure a comfortable stay.
2br Fitness Pad  Private Gym  Sleeps 7 - Chicago, IL
10 3 reviews

2br Fitness Pad Private Gym Sleeps 7

apartment, Chicago
This two-bedroom flat in Chicago's Waveland district offers excellent access to local attractions, managed by LuxuryLodgingSTR for a memorable stay.
This property accommodates up to seven guests and features air conditioning, a full kitchen with a dishwasher, and on-site parking, with a fitness centre also available.
6br/4ba Victorian Greystone Near Downtown Chicago - Chicago, IL
9.5 108 reviews

6br/4ba Victorian Greystone Near Downtown Chicago

apartment, Chicago
This 1895 Victorian greystone property in Chicago is situated 2.1 kilometres from the United Center and 4.8 kilometres from the city centre, offering a unique historical stay.
This 279 square metre residence accommodates up to 16 guests with six bedrooms, four bathrooms, two kitchens, and a substantial garden deck, boasting high-speed internet and on-street parking.
7-bedroom 2-flat Perfect For Groups  Near Train, Expressway, United Center - Chicago, IL
10 4 reviews

7-bedroom 2-flat Perfect For Groups Near Train, Expressway, United Center

apartment, Chicago
This spacious flat in East Garfield Park, Chicago, is situated 800 metres from the United Centre and approximately 1.1 kilometres from the city centre, offering convenient access to the West Loop and downtown.
This seven-bedroom property boasts 334 square metres of living space, accommodating up to 20 guests with multiple living areas, kitchens, and seven beds complemented by additional sleeping options, alongside amenities such as central air conditioning, a garden, and parking, with a 420-friendly policy for outdoor use.
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